Category: indole-building-block

An Antimalarial alkaloid from hydrangea. XV. Synthesis of 5-, 6-, 7-, and 8-derivatives with no identical substituents was written by Ablondi, Frank;Gordon, Samuel;Morton, John II;Williams, J. H.. And the article was included in Journal of Organic Chemistry in 1952.Application In Synthesis of 4,7-Dimethylindoline-2,3-dione The following contents are mentioned in the article:

To study the effect of substituents in the C₆H₆ ring on the antimalarial activity and chemotherapeutic index of the DL-form of the hydrangea alkaloid, a series of derivatives with 2 identical substituents in the benzene ring are synthesized by converting, according to Marvel and Hiers (C.A. 20, 193), the appropriate R₂C₆H₃NH₂ into the R₂C₆H₃NHCOCH:NOH (I) (Table F) which, on ring closure with 86% H₂SO₄, give the corresponding isatins (II) (Table G). Oxidation of II with alk. peroxide gives the disubstituted o-H₂NC₆H₄CO₂H (III) (Table H) which, on fusion with HCONH₂ (see preceding abstract), give the corresponding disubstituted 4(3H)-qainazolones (IV) (Table I). Condensation of 1-carbethoxy-2-(3-bromoacetonyl)-3-methoxypiperidine with the appropriate IV gives the disubstituted 3-[2-oxo-3-(1-carbethoxy-3-methoxy-2-piperidyl)propyl]-4(3H)-quinazolones (V) which, hydrolyzed with 6 N HCl, give the corresponding 3-[2-oxo-3 – (3-methoxy-2-piperidyl)propyl]-4(3H)-quinazolones (VI). Demethylation of VI then gives the corresponding 3-hydroxy-2-piperidyl derivatives (VII) (VIa, R = H). The IV, V, VI, and VII are listed in Table I. Cyclization of 55 g. 3,4-Me.₂C₆H₃NHCOCH:NOH with 292 cc. 96% H₂SO₄ and 29 cc. H₂O, solution of the isatin mixture in 1.2 l. H₂O and 310 cc. 10% NaOH, dropwise addition of 12 N HCl to the filtered solution until turbid, and then addition of 4-cc. portions of acid and separation of the precipitate after each addition give 12.6 g. crude 4,5-dimethylisatin. The 4th addition gives no precipitate and strong acidification of the mother liquor gives 23.3 g. 5,6-dimethylisatin. Treating 21.5 g. 4-chloroisatin 4 h. at 50° in 440 cc. AcOH with 20 cc. SO₂Cl₂ and a crystal of iodine gives 60% 4,5-dichloroisatin. In the same way 6-chloroisatin gives 5,6-dichloroisatin. Adding 16.2 g. NaNO₂ in small portions to 25 g. 3,5,2-Me₂(H₂N)C₆H₂NO₂ in 70 cc. 6 N HCl at 0-5° with stirring and adding the diazonium solution to 35.6 g. NaCN and 34.5 g. NiCl₂.H₂O in 230 cc. H₂O with warming on a steam bath 45 min. give 79% 3,5,2-Me₂(NC)C₆H₂NO₂, m. 125-8° which (18.7 g.), heated with 50 cc. 80% H₂SO₄ 5 h. on a steam bath and poured onto ice, gives 52% 4,6,2-Me₂(O₂N)C₆H₂CONH₂; Table F. Disubstituted α-isonitrosoacetanilides (I); Reaction time, Yield, M.p.,;R₂, (min.), %, °C.; 3,4-Di-Me, 2, 84, 179-80^a; 2,5-Di-Me, 5, 33, 151-3; 2,4-Di-Me, 8, 55, 158-9; 2,3-Di-Me, 3, 64, 131-2; 2,5-Di-Cl, 15, 22, 166-8; 3,5-Di-Br, 15, 11, 197-200; 3,4-(CH₂)_4^–, 120, 87, 147-50; (a) Decomposition Table G., Disubstituted isatins (II); Yield, M.p., R₂, Color, %, °C.; 4,5-Di-Me, red, 25, 225-6; 4,7-Di-Me, orange, 75, 260-4; 5,6-Di-Me, red, 46, 214-15; 5,7-Di-Me, orange, 91, 228-31; 6,7-Di-Me, orange, 57, 230-2; 4,5-Di-Cl, red, 60, 243-5; 4,7-Di-Cl, 99, 239-41; 5,6-Di-Cl, orange-red, 68, 264-8^a; 4,6-Di-Br, orange, 88, 254-6; 4,5-(CH₂)_4^–, orange, 32, 188-90^a; 5,6-(CH₂)_4^–, orange, 17, 176-85^a; (a) Decomposition; Table H. Disubstituted anthranilic acids; Yield, M.p.a,; R₂, %, °C.; 5,6-Di-Me, 65, 140-1; 4,6-Di-Me, 91, 160-1; 3,6-Di-Me, 58, 111-13; 4,5-Di-Me, 81, 213-14; 3,5-Di-Me, 65, 188-9; 3,4-Di-Me, 69, 184-6; 5,6-Di-Cl, 59, 165-7; 3,6-Di-Cl, 59, 148-50; 4,5-Di-Cl, 99, 208; 3,5-Di-Cl, 39, 230-1; 4,6-Di-Br, 73, 170-1; 5,6-(CH₂)_4^–, 62, 114; 4,5-(CH₂)_4^–, 86, 171-3; (a) Decomposition (VIII), m. 169-71°. Reduction of 12.9 g. VIII in 100 cc. Methyl Cellosolve 20 min. with 1 g. Pd-charcoal at 2-3 atm. H gives 91% 4,6,2-Me₂(H₂N)C₆H₂CONH₂, m. 160-1°. Adding 25 cc. SO₂Cl₂, over a period of 15 min. to 20 g. o-H₂NC₆H₄CO₂H in 500 cc. AcOH at 40°, stirring the mixture 2 h., and extracting the precipitate with 15% HCl on a steam bath give 39% 3,5,2-Cl₂(H₂N)C₆H₂CO₂H, m.230-1°. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Application In Synthesis of 4,7-Dimethylindoline-2,3-dione).

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application In Synthesis of 4,7-Dimethylindoline-2,3-dione

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Isonitrosoacetanilides and their condensation to form isatin derivatives was written by Sandmeyer, T.. And the article was included in Helvetica Chimica Acta in 1919.Product Details of 15540-90-6 The following contents are mentioned in the article:

Hydroxylaminesulfonic acid solution (A) was prepared by adding rapidly with stirring 627 g. NaHSO₃ to 84 g. NaNO₂ in 500 cc. H₂O containing 300 g. ice. After 1.5 hrs. a cold solution of 66 g. concentrated H₂SO₄ in 66 g. H₂O is added during the course of 2 hrs. until the solution is acid to congo paper; after 2 days the reaction is completed. Isonitrosoacetanilide (B) is prepared by boiling 3-4 hrs. under reflux 450 g. of A, adding 10 g. PhNH₂, 350 g. H₂O, 16.5 g. CCl₃CHO.H₂O and continuing the boiling for 1 hr. longer. On cooling rapidly the light yellow crystals of B sep., are filtered and washed with H₂O; they m. 175° (decomposition), are readily soluble in Et₂O or EtOH, slightly in cold H₂O or PhH; acids precipitate it unchanged from alk. solutions Isonitrosoacet-p-chloroanilide (C) is prepared by boiling under reflux for several hrs. 450 g. of A, mixing a 100-50 g. portion into a paste with 12.75 g. p-ClC₆H₄NH₂, adding the paste to the remainder of A, diluting with 300 g. H₂O and then boiling for 0.75 hr. with 16.5 g. CCl₃CHO.H₂O. The crystals of C which sep. on cooling are dissolved in dilute NaOH, dilute HCl is added nearly to neutralization and the solution filtered. C is obtained on the addition of acid as a white, crystalline precipitate which is filtered and washed with H₂O; it m. 165°, is slightly soluble in H₂O, fairly in Et₂O and readily in EtOH; yield, 14.3 g. The following derivatives were obtained in the same way from the corresponding aromatic amines and the m. p. refers to the uncrystd. reaction product: o-toluide, 121°; m-toluide, 146°; p-toluide, 162°; m-xylide, 161°; p-xylide, 151°; o-aniside, 140°; p-phenetide, 195°; methylanilide, 145°; ethylanilide, 160°; benzylanilide, 142°; o-chloroanilide, 150°; m-chloroanilide, 154°; 2,5-dichloroanilide, 163°; 3,4-dichloroanilide, 158°; 3,5-dichloroanilide, 185°; 5-chloro-2-toluide (Me = 1), 167°; 4-chloro-2-toluide, 148°; 6-chloro-3-toluide, 187°; 4-chloro-3-toluide, 134°; 2-chloro-4-toluide, 177°; 3-chloro-4-toluide, 188°; 4-chloro-2-aniside (MeO = 1), 182°; p-bromoanilide, 167°; 2,4-dibromoanilide, 215°; anthranilic acid, 208°. Isatin (D) was prepared by adding gradually with stirring 10 g. B to 50 g. of concentrated H₂SO₄ at 60° and keeping the temperature at all times below 65°; after B has been added and is in solution, the temperature, is raised to 75° for 10-5 min.; the solution is cooled and immediately diluted with 160 g. cold H₂O; the yellow-red crystals of D which sep. are filtered and washed with H₂O; these crystals show all the characteristic tests for D and m. 197°. In the same way by modifying the temperature the following isonitrosoacetanilides were converted into isatin derivatives; at 55-60° during addition and at 65-70° at completion, methyl and ethylanilides; at 60-5° and subsequently at 70-5°, o- and p- toluides and o- and p-xylides; at 80-5° and subsequently at 95°, o- and m-chloroanilides, 4-chloro-2-toluide, 4-chloro-3-toluide, 2-chloro-4-toluide, 4-chloro-2-aniside; at 90-5° subsequently 105°, 3-chloro-4-toluide, 5-chloro-2-toluide, 6-chloro-3-toluide, p-chloro-anilide, 2,5-and 3,5-dichloroanilides; at 95-100°, subsequently 110°, 3,4-dichloro-anilide, p-bromoanilide, anthranilic acid. The isatin derivatives from o-aniside, p-phenitide and 2,4-dibromoanilide could not be prepared by this reaction; a mixture of two isomers is obtained when both free o-positions are not the same, e. g., m-toluide or 3,4-dichloroanilide. The following were prepared by this reaction and the m. p. refers to the uncrystd. material; mixture of 4- and 6-methylisatins, orange-yellow, 143°; 4,7-dimethylisatin, orange-yellow, 250°; 7-chloroisatin, red-brown, 175°; mixture of 4- and 6-chloroisatins, orange-yellow, 212°; mixture of 4-chloro-7-methylisatin, orange-yellow, 4,5- and. 5,6-dichloroisatins, yellow-red 200°; 4,6-dichloroisatin, citron-yellow, 250°; 273°; 5-chloro-7-methylisatin, yellow-brown, 265°; mixture of 4-chloro-5-methyl- and 5-methyl-6-chloroisatins, red, 205°; 4-methyl-7-chloroisatin, orange-yellow, 252°; 4-chloro-7-methoxyisatin, red, 240°; isatin-7-carboxylic acid, brown-yellow, 235°. Many of the yields were quant. Application for patents has been made. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Product Details of 15540-90-6).

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Product Details of 15540-90-6

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Reactivity of the carbonyl group and of dehydrogenation activity of isatin compounds. II was written by Giovannini, E.;Portmann, P.;Johl, A.;Schnyder, K.;Knecht, B.;Zen-Ruffinen, H. P.. And the article was included in Helvetica Chimica Acta in 1957.Name: 4,7-Dimethylindoline-2,3-dione The following contents are mentioned in the article:

The dehydrogenation activity of many mono- and disubstituted derivatives of isatin (I) expressed as time of decolorization of a methylene blue (II) solution according to Langenbeck (C.A. 21, 2126) have been measured and tabulated as relative activities to that of I (100), using 10^-4 or 2 × 10^-5 mole compound in 5 cc. pyridine and 2 cc. standard aqueous solution [2 g. DL-MeCH(NH₂)CO₂H (III), 0.3737 g. II, and 10 cc. AcOH made up to 100 cc.] (isatin substituent, m.p., decoloration time (min.) with 10^-4 and 2 × 10^-5 mole, relative dehydrogenation activity given): H, 200°, 10, 50, 100; 4-Me, 190-2°, > 1320, -, < 0.75; 5-Me, 186-7°, 11, 50, 95; 6-Me, 190-1°, 19, 72, 61; 7-Me, 266°, -, 31, 161; 4-Cl, 259-60°, 113, -, 8.8; 5-Cl, 251-3°, 7, 42, 131; 6-Cl, 263°, 8, -, -; 7-Cl, 188-90°, 6, 33, 159; 4-NO₂, 245°, > 900, -, < 1.1; 5-NO₂, 253°, 12, 68, 88; 6-NO₂, 288-90°, 7, 48, 123; 7-NO₂, 237°, -, 42, 119; 4-NH₂, 254-5°, > 900, -, < 1.1; 5-NH₂, above 330°, 12, 65, 80; 7-NH₂, above 330°, -, 52, 96; 4-HO, 260° (decomposition), 73, -, 13.7; 5-HO, above 290° (decomposition), 9, -, 111; 6-HO, above 325° (decomposition), 127, -, 7.8; 5-MeO, 201-2°, 9, 43, 114; 6-MeO, 229-30°, 69, -, 14.4; 7-MeO, 240-2°, 7, 33, 147; 4-CO₂H, 285°, -, 1.5, 3300; 5-CO₂H, 295°, 7, 32, 150; 6-CO₂H, 328-30°, -, 28, 178; 7-CO₂H, 277°, -, 32, 156; 4-SO₃H, 183° (decomposition), 4, -, 250; 5-SO₃H, 145-7°, 19, -, 52; 6-SO₃H, above 290° (decomposition), 15, -, 67; 7-SO₃H, m. above 350° (decomposition), 19, -, 52. Substituents in the 4-position have a great influence, in one sense or another, on the dehydrogenation activity of I and probably on the activity of the 3-CO group. The effect of the 4-CO₂H group is not due to its acid character as shown by the relative dehydrogenation activities of the 4-HO and 4-SO₃H substituted compounds The effect of double substitution was examined: 4,6-Me₂, 241-3°, > 900, -, < 1.1; 4,7-Me₂, -, > 900, -, < 1.1; 5,6-Me₂, 212-13°, 20, -, 50; 4,7-Me(CO₂H), 258-60°, > 900, -, < 1.1; 7,4-Me(CO₂H), 295°, -, 1.5, 3300; 4,7-(CO₂H)₂, 303-5°, -, 3.5, 1430; 4,7-Cl₂, 246°, 89, -, 11.2; 5,6-(HO)₂, 290° (decomposition), 230, -, 4.3; 5,6-Cl(HO), 284-6°, 236, -, 4.2; 5.6-(MeO)₂, 252°, 75, -, 13.3; 5,6-CH₂O₂, 284°, 60, -, 16.6. The inactivation caused by the 4-Me group persists. The effect of 2 activating groups is not additive but groups with contrary effects may give an intermediate value. Since the inactivation caused by some 4-substituents might be attributable to steric effects, the dehydrogenation activities with H₂NCH₂CO₂H (IV) have been compared with those with III [isatin substituent, times (min.) of decolorization with III and IV, ratios of activity (III/IV) given]: H, 10, 4, 2.5; 4-Me, > 1310, 108, > 13; 5-Me, 11, 4, 2.7; 6-Me, 18, 7, 2.5; 4,6-Me₂, > 900, 205, > 4.4; 4,7-Me₂, > 900, 131, > 6.9; 4-Cl, 113, 12, 9.4; 4-NO₂, > 900, 280, > 3.2; 4-CO₂H, 1.5, 0.75, 2. The activity of 4-methylisatin is less than that of the other isomers against IV and no explanation is offered for the activity of 4-carboxyisatin. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Name: 4,7-Dimethylindoline-2,3-dione).

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Name: 4,7-Dimethylindoline-2,3-dione

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Organic catalysts. XL. Synthetic dehydrogenases. 8 was written by Mix, Hermann;Krause, Hans Walter. And the article was included in Chemische Berichte in 1956.Application of 15540-90-6 The following contents are mentioned in the article:

Some isatins, CMe:CH.CH:CR.C:C.NH.CO.CO (I), and N-(7-methylisatin-4-carbonyl)amino acid Et esters (II), substituted in the 4-position, are prepared and tested for their dehydrogenase activity. Treating p-MeC₆H₄CO₂H with fuming HNO₃ yields 4,3-Me(O₂N)C₆H₃CO₂H, m. 188-9°, which, reduced with Raney Ni in dioxane at 120° and 100 atm., gives 90% 4,3-Me(H₂N)C₆H₃CO₂H (III), m. 162°. Heating 5 g. III in 150 cc. H₂O containing 2 cc. concentrated H₂SO₄ with 5.5 g. CCl₃CHO.H₂O (IV) and 6.5 g. (HONH₂)₂.H₂SO₄ (V) yields 3-isonitrosoacetamido-4-methylbenzoic acid which (10 g.), heated in 22 cc. concentrated H₂SO₄ at 85-90° and kept 0.5 hr. at 95-100°, gives 72% I (R = CO₂H) (VI), yellow-red needles, m. 278-80°; Et ester, prepared by heating 5 g. VI in 150 cc. EtOH-HCl 0.5 hr. on a water bath and chromatographing over Al₂O₃, orange rods, m. 205°. Heating 5 g. 4,3-Me(H₂N)C₆H₃CN, m. 81°, 6.3 g. IV, and 7.5 g. V in 430 cc. H₂O and 3 cc. concentrated H₂SO₄ gives 2-2.5 g. isonitroso compound which, heated with concentrated H₂SO₄, yields I (R = CONH₂), brick-red crystals, decompose above 270°. Adding 0.94 cc. ClCO₂Et dropwise to a solution of 2 g. VI and 2.28 g. Bu₃N in 20 cc. CHCl₃ at -5°, stirring the mixture 0.5 hr. at -5°, then adding 900 mg. PhNH₂, and stirring the mixture 12 hrs. give I (R = CONHPh), small red rods, m. 308°; I (R = CONEt₂), light red leaflets, m. 192°. The following II are prepared (amino acid given): alanine, light red rods, m. 254°; norvaline, light red leaflets, m. 220°; α-aminobutyric acid, red leaflets, m. 218-19°; glutamic di-Et ester, red needles, m. 171-2°; glutamic mono-Et ester, long red needles, m. 186-7°; phenylalanine, red needles, m. 225-6°; tryptophan Me ester, purple crystals, m. 254°. Treating 1.2 g. 2,4-Me₂C₆H₃NH₂ in 30 cc. H₂O and 1.16 g. concentrated H₂SO₄ with 1.7 g. IV and 1.9 g. V yields isonitrosoacetamido-p-xylene which, added to 10 cc. concentrated H₂SO₄ at 65-7° and the mixture heated 20 min. at 65-70°, gives 4,7-dimethylisatin, yellow-red precipitate, m. 261°. Reduction of 4,3-Me(O₂N)C₆H₃NHAc with Raney Ni at 120° and 100 atm. gives 100% 3,4-Me(H₂N)C₆H₃NHAc, m. 159°, which (6 g.), stirred 4-5 hrs. at 36-40° with 6 g. IV and 7.2 g. V, yields 3-isonitrosoacetamido-4-methylacetanilide. Heating the latter 45 min. in 10 cc. concentrated H₂SO₄ at 95-100° gives 4-amino-7-methylisatin, light red needles, charring above 310°. The dehydrogenase activity of these compounds has been tested by measuring the time required to decolorize a solution of 2 × 10^-5 moles methylene blue and 2.25 × 10^-4 moles DL-alanine in 71% HCONMe₂ at 40°. The results, given in a table, show that V is the most active catalyst. The introduction of the Me group at the 7-position has no effect on the dehydrogenation velocity. For the calculation of the partial velocities of the catalysis the P_S curves of some of the compounds are given. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Application of 15540-90-6).

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Application of 15540-90-6

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

New isatins was written by Buu-Hoi;Guettier, Haniel. And the article was included in Bulletin de la Societe Chimique de France in 1946.Synthetic Route of C10H9NO2 The following contents are mentioned in the article:

New halogenated or nitrated compounds are prepared from homologs of isatin. The starting materials were prepared by the Sandmeyer reaction (of. C.A. 13, 1840). Thus, 9-tert-butylindophenazine, m. 230°, results from heating o-C₆H₄(NH₂)₂ with the product of the Sandmeyer reaction (apparently 5-tert-butylisatin) in AcOH and crystallizing from alc. 5-Methylisatin (I) suspended in H₂O containing a few grains of iodine and treated with a slow current of Cl several hours at a tepid temperature gives 5-methyl-7-chloroisatin, m. 180° (from alc.). I (10 g.) in 100 cc. cold H₂SO₄, treated with 6 g. KNO₃ and poured into ice, gives about 1 g. 5-methyl-7-nitroisatin, m. 202-3° after reprecipitation from aqueous NaNO₃ by HCl and recrystallization from boiling alc. Likewise, 2 g. 6-methylisatin in suspension, treated with 1 cc. Br 2 hrs., yields 5-bromo-6-methylisatin, m. about 200° (softens above 190°) after recrystallization from AcOH. 7-Methylisatin with Br gives 5-bromo-7-methylisatin, m. about 287°. Treating 5 g. 4,7-dimethylisatin (II) suspended in 500 cc. H₂O with a slow stream of Cl gives about 3 g. 4,7-dimethyl-5-chloroisatin, m. 270-1° (from AcOH). Similarly, 10 g. II treated with Br 24 hrs. gives about 7 g. 4,7-dimethyl-5-bromoisatin, m. 298°. II with KNO₃ in H₂SO₄ gives 4, 7-dimethyl-5-nitroisatin, m. 255°. A series of indophenazines was prepared by heating together in AcOH the isatin and o-C₆H₄(NH₂)₂ and recrystallizing from glacial AcOH or PhNO₂. Empirical formulas and m.p. are: C₁₅H₁₀N₃Br, m. 261°; C₁₅H₁₀N₃Cl, m. 285°; C₁₅H₁₀O₂N₄, m. 319°; C₁₆H₁₃N₃, m. 315° (sublimes above 290°); C₁₅H₁₁N₃, m. 313° (sublimes above 260°); C₁₅H₁₀N₃Br, m. 310-15°; C₁₅H₁₁N₃, m. 313°; C₁₅H₁₀N₃Br, m. 312°; C₁₆H₁₃N₃, m. 309°; C₁₅H₁₂N₃Cl, m. 319°; C₁₀H₁₂N₃Br, m. 321°; C₁₆H₁₂O₂N₄, m. above 340°. A series of isatin 3-hydrazones are prepared by treating the isatin with excess N₂H₄.H₂O in dilute alc. Empirical formulas are: C₉H₈ON₃Br, m. 246° (decomposition); C₉H₈ON₃Br, m. 256° (decomposition); C₉H₈ON₃Br, decompose 220°; C₉H₃ON₃Cl, decompose 198°. A series of isatin 3-phenylhydrazones results from adding PhNHNH₂. dropwise to a saturated alc. solution of the isatin, boiling, cooling, and crystallizing from alc. Empirical formulas: C₁₅H₁₂ON₃Br, decompose 287°; C₁₅H₁₂ON₃Br, decompose 269-70°; C₁₅H₁₂ON₃Br, 280°; C₁₅H₁₂ON₃Cl, decompose 259-60°. N-Mercuric derivatives, prepared from all the above isatins by treating them in alc. with aqueous Hg(OAc)₂ and crystallized from HOAc, m. above 350°. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Synthetic Route of C10H9NO2).

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Synthetic Route of C10H9NO2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Optically active bithienyls. VIII. Synthesis of 3,3′,6,6′-tetramethyldiphenic acid was written by Gronowitz, Salo;Hansen, Gunnar. And the article was included in Arkiv foer Kemi in 1967.Formula: C10H9NO2 The following contents are mentioned in the article:

cf. CA 62: 11757d. The title compound (I) was prepared for comparison of its racemization rate with that of its bithienyl analog (II) (G. and Beselin, CA 59: 15241g). The procedure for condensation of 2,5-Me2C6H3NH2 with CCl3CHO.H2O and NH2OH.HCl (Baker, et al., CA 46: 10176h) was modified and yielded 78% 2,5-Me2C6H3NHCOCH:NOH (III), m. 153-6°. III cyclized with 86% H2SO4 yielded 76% 4,7-dimethylisatin decomposing at 270° which on oxidation with alk. H2O2 yielded 68% 3,6-dimethylanthranilic acid (IV), m. 119-20°. The diazonium salt of IV (Atkinson and Lawler: Organic Syntheses. Collective Volume 1 Wiley: New York 1941. p. 222) yielded 56% I, m. 290-306°. Three other routes to I failed but produced new compounds 2,3-Dibromo-5-nitro-p-xylene (from nitration of 2-bromo-p-xylene with fuming HNO3 and bromination at 0° of the 5-nitro derivative in concentrated H2SO4 in the presence of Ag2SO4) was reduced in 90% EtOH with Fe powder and HCl yielding 94% 5-amino-2,3-dibromo-p-xylene (V), m. 87-9° (EtOH-H2O). V diazotized at 0°, reduced with 50% H3PO2 (added dropwise at -2°), left 18 hrs. in a refrigerator, and the oil which separated taken up in C6H6 and fractionated, yielded 85% 2,3-dibromo-p-xylene (VI), b16 139-44°, m. 16-17°. Since VI with BuLi and CO2 failed to give the corresponding carboxylic acid, apparently a stable Li compound could not be formed for a synthesis of I parallel to that of II. 2-Acetamido-p-xylene nitrated, refluxed with concentrated HCl, and steam distilled yielded 10% 2-amino-3-nitro-p-xylene (VII), m. 29-32°, from the distillate and 52% 5-nitro isomer (VIII), m. 142-3°, from the residue. The structures of VII and VIII are evident from their N.M.R. spectra. VIII brominated in AcOH at 40° yielded 75% 2-amino-3-bromo-5-nitro-p-xylene (Blanksma CA 7: 1492) which was diazotized by Schoutissen’s method (CA 28: 1215), treated with KI in H2O, warmed to 45°, NaHSO3 added, and the product recrystallized from EtOH-H2O yielding 85% 3-bromo-2-iodo-5-nitro-p-xylene (IX), m. 107-8°. A biphenyl derivative could not be obtained from IX by Ullman coupling. 3,6-Dimethylphthalic anhydride (from the Diels-Alder adduct between 2,5-dimethylfuran and maleic anhydride) heated 2-3 hrs. over a free flame with concentrated NH4OH yielded 97% 3,6-dimethylphathalimide (X), m. 227-8° (MeOH-H2O). X should give IV with NaOH solution and hypobromite, but only the anhydride resulted. N.M.R. values are recorded for all compounds This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Formula: C10H9NO2).

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Formula: C10H9NO2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Improved superaugmented eccentric connectivity indices – Part II: Application in development of models for prediction of hiCE and hCE1 inhibitory activities of isatins was written by Dutt, Rohit;Singh, Monika;Madan, A. K.. And the article was included in Medicinal Chemistry Research in 2012.Formula: C10H9NO2 The following contents are mentioned in the article:

Topochem. versions of all the four superaugmented eccentric connectivity indexes (denoted by: ^SAcξ₄^c, ^SAcξ₅^c, ^SAcξ₆^c, and ^SAcξ₇^c) were utilized for the development of models for prediction of hiCE and hCE1 inhibitory activities. The values of these topochem. indexes were computed for each of the 65 analogs constituting the data set using an inhouse computer program. Resulting data was analyzed and suitable models were developed after identification of the active ranges by maximization of moving average with regard to active derivatives Subsequently, two biol. activities were assigned to each analog using proposed models, which were then compared with the reported hiCE and hCE1 inhibitory activities. Statistical significance of topol. indexes/models was investigated through sensitivity, specificity, and Matthews correlation coefficient (MCC). The overall accuracy of prediction varied from a min. of 81% for a model based upon ^SAcξ₄^c to a maximum of 92% in case of a model based upon ^SAcξ₅^c with regard to hiCE inhibitory activity and from a min. of 85% for a model based upon ^SAcξ₄^c to a maximum of 94% in case of a model based upon ^SAcξ₇^c with regard to hCE1 inhibitory activity. An excellent relationship between new generation superaugmented eccentric connectivity topochem. indexes (^SAcξ₄^c, ^SAcξ₅^c, ^SAcξ₆^c, and ^SAcξ₇^c) and hiCE and hCE1 inhibitory activities can be attributed to the sensitivity of the proposed topol. indexes toward nature, number, and relative position of heteroatom. High predictability amalgamated with high potency of the active ranges offer proposed models a vast potential for providing lead structures for development of potent and selective hiCE and hCE1 inhibitors. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Formula: C10H9NO2).

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Formula: C10H9NO2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis of novel 4,5-dihydropyrrolo[1,2-a]quinoxalines, spiro[dihydroindolone-pyrrolo[1,2-a]quinoxaline] derivatives and their antituberculosis and anticancer activity was written by Makane, Vitthal B.;Vamshi Krishna, Eruva;Karale, Uattam B.;Babar, Dattatraya A.;Kalari, Saradhi;Rekha, Estharla M.;Shukla, Manjulika;Kaul, Grace;Sriram, Dharmarajan;Chopra, Sidharth;Misra, Sunil;Rode, Haridas B.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2020.Synthetic Route of C10H9NO2 The following contents are mentioned in the article:

A facile strategy was developed for the synthesis of biol. important 4,5-dihydropyrrolo[1,2-a]quinoxalines I (R = H, F; R¹ = 4-Me, 2-Br, 4-Cl; R² = H, Cl, Me) and spiro derivatives II (R³ = H, Me, Bn; R⁴ = H, Me; R⁵ = H, Me, Cl, F, I, OCF₃; R⁶ = H, Me) by treating 2-(1H-pyrrol-1-yl)anilines 4-R-2-(1H-pyrrol-1-yl)C₆H₃NH₂ such as with imidazo[1,2-a]pyridine-3-carbaldehydes III or isatins IV, using amidosulfonic acid (NH₃SO₃) as a solid catalyst in water at room temperature The protocol has been extended to electrophile ninhydrin. The catalyst could be recycled for six times without the loss of activity. The compounds I, II, V were evaluated for their antituberculosis, antibacterial, and anticancer activities. It is worth noting that compounds I (R = H, R¹ = 2-Br, R² = Cl, Me) demonstrated a min. inhibitory concentration value of 6.25μM against Mycobacterium tuberculosis H37Rv, whereas compounds I (R = H, R¹ = 2-Br, R² = Cl; R = F, R¹ = 2-Br, R² = H), II (R = H, R³ = H, R⁴ = H, R⁵ = I, OCF₃, R⁶ = H; R = H, R³ = Bn, R⁴ = H, R⁵ = H, R⁶ = H) showed a remarkable inhibition of A549, DU145, HeLa, HepG2, MCF-7, and B16-F10 cell lines, resp. Staphylococcus aureus was inhibited by compounds II (R = H, R³ = H, R⁴ = H, R⁵ = Cl, I, OCF₃, R⁶ = H; R = H, F, R³ = H, R⁴ = Me, R⁵ = H, R⁶ = Me) at 32μg/mL. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Synthetic Route of C10H9NO2).

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Synthetic Route of C10H9NO2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Further Studies on Triazinoindoles as Potential Novel Multitarget-Directed Anti-Alzheimer’s Agents was written by Patel, Dushyant V.;Patel, Nirav R.;Kanhed, Ashish M.;Teli, Divya M.;Patel, Kishan B.;Gandhi, Pallav M.;Patel, Sagar P.;Chaudhary, Bharat N.;Shah, Dharti B.;Prajapati, Navnit K.;Patel, Kirti V.;Yadav, Mange Ram. And the article was included in ACS Chemical Neuroscience in 2020.Computed Properties of C10H9NO2 The following contents are mentioned in the article:

The inadequate clin. efficacy of the present anti-Alzheimer’s disease (AD) drugs and their low impact on the progression of Alzheimer’s disease in patients have revised the research focus from single targets to multitarget-directed ligands. A novel series of substituted triazinoindole derivatives were obtained by introducing various substituents on the indole ring for the development of multitarget-directed ligands as anti-AD agents. The exptl. data indicated that some of these compounds exhibited significant anti-AD properties. Among them, 8-(piperidin-1-yl)-N-(6-(pyrrolidin-1-yl)hexyl)-5H-[1,2,4]triazino[5,6-b]indol-3-amine (60), the most potent cholinesterase inhibitor (AChE, IC₅₀ value of 0.32μM; BuChE, IC₅₀ value of 0.21μM), was also found to possess significant self-mediated Aβ_1-42 aggregation inhibitory activity (54% at 25μM concentration). Addnl., compound 60 showed strong antioxidant activity. In the PAMPA assay, compound 60 exhibited blood-brain barrier penetrating ability. An acute toxicity study in rats demonstrated no sign of toxicity at doses up to 2000 mg/kg. Furthermore, compound 60 significantly restored the cognitive deficits in the scopolamine-induced mice model and Aβ_1-42-induced rat model. In the in silico ADMET prediction studies, the compound satisfied all the parameters of CNS acting drugs. These results highlighted the potential of compound 60 to be a promising multitarget-directed ligand for the development of potential anti-AD drugs. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Computed Properties of C10H9NO2).

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Computed Properties of C10H9NO2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Application of a spin-labeled spin-trap to the detection of nitric oxide (NO) was written by Marx, Lucien;Rassat, Andre. And the article was included in Angewandte Chemie, International Edition in 2000.Safety of 2-Benzyl-5-bromoisoindoline-1,3-dione The following contents are mentioned in the article:

We suggest a new use of diradicals as spin-labeled spin-traps. These reagents would combine a stable radical (R_T), designed to trap selectively the radical to be detected and to yield diamagnetic products, and another radical (R_L), unreactive during this reaction, at a distance such that the diradical EPR spectrum would be a single line. In this way, as R_T reacts, the signal of the R_T moiety would be detected at the very beginning of the reaction, with both the concentration of spin trap and of spin adduct being monitored on the same spectrum. Furthermore, the rate of the trapping reaction (usually bimol.) could easily be increased by increasing the biradical concentration As an example of this method, we have studied the trapping of NO by a new diradical that was designed to combine two aminoxy groups on an isoindoline backbone. The diradical was prepared in six steps from phthalic anhydride. When nitric oxide was bubbled into a deoxygenated solution of the synthesized aminoxy-isoindoline derivative in ethanol, samples were taken after 10,30, 60, and 90 min and analyzed by thin layer chromatog. and EPR; a three-line spectrum, not apparent in the spectrum of the sample taken after 10 min, appeared superimposed on the diradical spectrum of the sample taken after 30 min. Four new nitroxides were then detected : they all displayed the same typical isoindolidinyloxyl(radical) 3-line EPR spectrum (toluene, a_N = 1.37 mT). This study involved multiple reactions and reactants, such as 2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1Safety of 2-Benzyl-5-bromoisoindoline-1,3-dione).

2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Safety of 2-Benzyl-5-bromoisoindoline-1,3-dione

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles