05/01/2023 - Page 6 of 11 - Indole Building Blocks

Zou, Zirong et al. published their research in Journal of Organic Chemistry in 2021 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Reference of 5388-42-1

Metal-Free Cascade Formation of Intermolecular C-N Bonds Accessing Substituted Isoindolinones under Cathodic Reduction was written by Zou, Zirong;Cai, Genuo;Chen, Weihao;Zou, Canlin;Li, Yamei;Wu, Hongting;Chen, Lu;Hu, Jinhui;Li, Yibiao;Huang, Yubing. And the article was included in Journal of Organic Chemistry in 2021.Reference of 5388-42-1 This article mentions the following:

An electrochem. protocol for the construction of substituted isoindolinones I (R¹ = H, 5-Me, 6-Cl, etc.; R² = Ph, c-hexyl, 2-furyl, etc.) via reduction/amidation of 2-carboxybenzaldehydes and amines has been realized. Under metal-free and external-reductant-free electrolytic conditions, the reaction achieves the cascade formation of intermol. C-N bonds and provides a series of isoindolinones in moderate to good yields. The deuterium-labeling experiment proves that the hydrogen in the methylene of the product is mainly provided by H2O in the system. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

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

Khalafy, Jabbar et al. published their research in Australian Journal of Chemistry in 1998 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.HPLC of Formula: 5388-42-1

Flash vacuum pyrolysis of some N-benzylbenzotriazoles and N-benzylbenzisoxazolones was written by Khalafy, Jabbar;Prager, Rolf H.. And the article was included in Australian Journal of Chemistry in 1998.HPLC of Formula: 5388-42-1 This article mentions the following:

The flash vacuum pyrolysis products of 2-(benzotriazol-1-ylmethyl)benzonitrile, Me 2-(benzotriazol-1-ylmethyl)benzoate, and the corresponding benzisoxazolones have been characterized. The benzotriazoles lose nitrogen to give diradicals, which undergo intramol. hydrogen-atom transfer or cyclization, while the benzisoxazolones rearrange initially to the corresponding benzaldehyde N-(2-carboxyphenyl)imines, which undergo subsequent intramol. addition reactions. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1HPLC of Formula: 5388-42-1).

Barltrop, J. A. et al. published their research in Journal of the Chemical Society in 1954 | CAS: 16732-64-2

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Category: indole-building-block

Synthesis of lysergic acid. I. Derivatives of indole was written by Barltrop, J. A.;Taylor, D. A. H.. And the article was included in Journal of the Chemical Society in 1954.Category: indole-building-block This article mentions the following:

As a model for the synthesis of lysergic acid, 2-methyl-3(2-oxocyclohexylidenemethyl)indole (I), prepared by condensing 2-methylindole (II) with formylcyclohexanone (III), was reduced to 2-methyl-3-(2-oxocyclohexylmethyl)indole (IV) and cyclized in small yield to a tetracyclic system (V), 4,6,6a,7,8,9-or 4,6,7,8,9,10-hexahydro-5-methyldibenz[cd,f] isoindole. An alternative, involving the cyclization of 4-bromo-3(2-oxocyclohexylmethyl)indole by an intramol. Grignard reaction, failed since the essential intermediate, 4-bromoindole (VI), could not be prepared II (9.5 g.) and 20 g. III in EtOH refluxed 2 h. gave 10 g. I, yellow prisms, m. 126° (from EtOH); dinitrophenylhydrazone, orange needles, m. 234°. I (0.67 g.) in EtOH hydrogenated at room temperature and pressure over Pd-C 1 h. gave IV, a colorless oil; picrate, m. 135° (from C₆H₆); semicarbazone, plates, m. 199-200° (decomposition). Indole (2 g.) and 4 g. III refluxed 2 h. in EtOH also gave 3-(2-oxocyclohexylidenemethyl)indole, needles, m. 232°. 2-Phenylindole and III in EtOH gave a blue substance, m. 200°, which is apparently of complex structure. IV (1 g.) was stirred 2 min. at 130° in 4 g. P₂O₅ and 3 cc. sirupy H₃PO₄, the insoluble residue dissolved in MeOH, the solution brought to pH 6, 2 g. Girard’s reagent “P” added, and the solution refluxed 20 min. The residue yielded the picrate of V, red needles, m. 144°. When 9.3 g. IV in 50 cc. PhMe was refluxed 1 h. with P₂O₅ no ketone fraction could be isolated. 2,6-Br(O₂N)C₆H₃Me (VII) (1 kg. crude), recrystallized, yielded 400 g. pure VII, m. 42°, and 500 g. 4,2-Br(O₂N)C₆H₃Me (VIII), m. 47°. VII (216 g.) and 143 g. (CO₂Et)₂, refluxed 45 min. with NaOEt in EtOH give 119 g. 2,6-Br(O₂N)C₆H₃CH₂COCO₂H (IX), m. 117° (from C₆H₆); semicarbazone, m. 216°. From the steam distillate was recovered 115 g. VII. Similarly VIII gave 40% 4,2-Br(O₂N)C₆H₃CH₂COCO₂H (X), needles, m. 144°, and 51% unchanged VIII. IX (28 g.) reduced in a refluxing solution of 150 g. FeSO₄.7H₂O and 60 cc. NH₄OH in 600 cc. H₂O 5 min. gave 18 g. 4-bromo-2-indolecarboxylic acid (XI), m. 266° (from EtOH). IX (28 g.) and 45 cc. 10% NaOH in 100 cc. H₂O treated during 1 h. with 53 g. Na₂S₂O₄, and the solution acidified with HCl and heated 2 h. gives 22 g. XI. Similarly X gave the 6-Br isomer of XI, needles, m. 223° (from aqueous EtOH). VII (21.6 g.) suspended in 50 cc. EtOH, hydrogenated with Raney Ni at room temperature and 3 atm. pressure, gave 17 g. 6,2-Br(H₂N)C₆H₃Me (XII), b₁₆ 130°. XII (9.3 g.) heated overnight in 20 cc. anhydrous HCO₂H gave 10 g. N-formyl derivative, (XIII), leaflets, m. 116°. 4,2-Br(HCONH)C₆H₃Me, needles, m. 137°, was similarly prepared from VIII. XIII (16 g.) added to 2.9 g. K in 100 cc. tert-BuOH, the alc. distilled, and the residue heated 0.5 h. to 270° did not form any VI. 6,2-Br(AcNH)C₆H₃Me (34 g.) warmed under N with 14 g. NaNH₂ until evolution of NH₃ ceased, then heated 15 min. at 240°, did not afford 4-bromo-2-methylindole. Me 2-bromocinnamate (11.4 g.) in concentrated H₂SO₄ treated during 0.5 h. at 0° with 3.5 g. HNO₃ (d. 1.48) in 10 cc. H₂SO₄ gave 13.7 g. crude product which, triturated with MeOH, yielded 9.5 g. Me 2-bromo-5-nitrocinnamate (XIV), yellow needles, m. 169° (from MeOH). XIV (6 g.) suspended in 50% H₂SO₄ and refluxed a few min. with a saturated solution of 7 g. KMnO₄ gave 2.4 g. 2,5-Br(O₂N)C₆H₃Me, needles, m. 178° (from aqueous EtOH). In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Category: indole-building-block).

Grimm, Sebastian H. et al. published their research in Bioorganic & Medicinal Chemistry in 2019 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.SDS of cas: 754214-56-7

Comprehensive structure-activity-relationship of azaindoles as highly potent FLT3 inhibitors was written by Grimm, Sebastian H.;Gagestein, Berend;Keijzer, Jordi F.;Liu, Nora;Wijdeven, Ruud H.;Lenselink, Eelke B.;Tuin, Adriaan W.;van den Nieuwendijk, Adrianus M. C. H.;van Westen, Gerard J. P.;van Boeckel, Constant A. A.;Overkleeft, Herman S.;Neefjes, Jacques;van der Stelt, Mario. And the article was included in Bioorganic & Medicinal Chemistry in 2019.SDS of cas: 754214-56-7 This article mentions the following:

Acute myeloid leukemia (AML) is characterized by fast progression and low survival rates, in which Fms-like tyrosine kinase 3 (FLT3) receptor mutations have been identified as a driver mutation in cancer progression in a subgroup of AML patients. Clin. trials have shown emergence of drug resistant mutants, emphasizing the ongoing need for new chem. matter to enable the treatment of this disease. Here, we present the discovery and topol. structure-activity relationship (SAR) study of analogs of isoquinolinesulfonamide H-89, a well-known PKA inhibitor, as FLT3 inhibitors. Surprisingly, we found that the SAR was not consistent with the observed binding mode of H-89 in PKA. Matched mol. pair anal. resulted in the identification of highly active sub-nanomolar azaindoles as novel FLT3-inhibitors. Structure based modeling using the FLT3 crystal structure suggested an alternative, flipped binding orientation of the new inhibitors. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7SDS of cas: 754214-56-7).

Denmark, Scott E. et al. published their research in Journal of Organic Chemistry in 2017 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.Related Products of 14204-27-4

Catalytic, Enantioselective, Intramolecular Sulfenofunctionalization of Alkenes with Phenols was written by Denmark, Scott E.;Kornfilt, David J. P.. And the article was included in Journal of Organic Chemistry in 2017.Related Products of 14204-27-4 This article mentions the following:

The catalytic, enantioselective, cyclization of phenols with electrophilic sulfenophthalimides onto isolated or conjugated alkenes affords 2,3-disubstituted benzopyrans, e.g., I, and benzoxepins. The reaction is catalyzed by a BINAM-based phosphoramide Lewis base catalyst which assists in the highly enantioselective formation of a thiiranium ion intermediate. The influence of nucleophile electron d., alkene substitution pattern, tether length and Lewis base functional groups on the rate, enantio- and site-selectivity for the cyclization is investigated. The reaction is not affected by the presence of substituents on the phenol ring. In contrast, substitutions around the alkene strongly affect the reaction outcome. Sequential lengthening of the tether results in decreased reactivity, which necessitated increased temperatures for reaction to occur. Sterically bulky aryl groups on the sulfenyl moiety prevented erosion of enantiomeric composition at these elevated temperatures Alcs. and carboxylic acids preferentially captured thiiranium ions in competition with phenolic hydroxyl groups. An improved method for the selective C(2) allylation of phenols is also described. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Related Products of 14204-27-4).

Gudipati, Rajyalakshmi et al. published their research in Journal of Enzyme Inhibition and Medicinal Chemistry in 2011 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Recommanded Product: 7-Nitroindoline-2,3-dione

Synthesis, anticancer and antioxidant activities of some novel N-(benzo[d]oxazol-2-yl)-2-(7- or 5-substituted-2-oxoindolin-3-ylidene) hydrazinecarboxamide derivatives was written by Gudipati, Rajyalakshmi;Anreddy, Rama Narsimha Reddy;Manda, Saranagapani. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2011.Recommanded Product: 7-Nitroindoline-2,3-dione This article mentions the following:

N-(benzo[d]oxazol-2-yl)-2-(7- or 5-substituted-2-oxoindolin-3-ylidene)hydrazinecarboxamides were synthesized by treating N-(benzoxazol-2-yl)hydrazinecarboxamide with different isatin derivatives The newly synthesized compounds were characterized on the basis of spectral analyses. All the synthesized derivatives were screened for anticancer and antioxidant activities. The results showed the anticancer activity of test compounds against HeLa, IMR-32 and MCF-7 cancer cell lines using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. All the synthetic compounds produced a dose-dependent inhibition of growth of the cells. The IC₅₀ values of some compounds were comparable with standard anticancer agent, cisplatin. All the title compounds effectively scavenged the free radical, α,α-diphenyl-β-picryl hydrazyl. The test compounds having substitution with different halides (electron withdrawing groups) at C5 position showed more potent anticancer and antioxidant activities than those at C7 position. These results indicate that C5-substituted derivatives may be useful for developing antioxidant agents that play a protective role in many pathol. conditions such as cancer, diabetes and so on. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Recommanded Product: 7-Nitroindoline-2,3-dione).

Lin, Cai et al. published their research in Journal of Medicinal Chemistry in 2019 | CAS: 1000340-39-5

3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Safety of 3-Bromo-4-chloro-7-azaindole

Discovery of Pyrrolo[2,3-b]pyridine (1,7-Dideazapurine) Nucleoside Analogues as Anti-Trypanosoma cruzi Agents was written by Lin, Cai;Hulpia, Fabian;da Silva, Cristiane Franca;Batista, Denise da Gama Jaen;Van Hecke, Kristof;Maes, Louis;Caljon, Guy;Soeiro, Maria de Nazare C.;Van Calenbergh, Serge. And the article was included in Journal of Medicinal Chemistry in 2019.Safety of 3-Bromo-4-chloro-7-azaindole This article mentions the following:

Trypanosoma cruzi is the causative pathogen of Chagas disease and the main culprit for cardiac-related mortality in Latin-America triggered by an infective agent. Incapable of synthesizing purines de novo, this parasite depends on acquisition and processing of host-derived purines, making purine (nucleoside) analogs a potential source of antitrypanosomal agents. In this respect, hitherto 7-deazaadenosine (tubercidin) analogs attracted most attention. Here, we investigated analogs with an addnl. nitrogen (N1) removed. Structure-activity relationship investigation showed that C7 modification afforded analogs with potent antitrypanosomal activity. Halogens and small, linear carbon-based substituents were preferred. Compound 11 proved most potent in vitro, showed full suppression of parasitemia in a mouse model of acute infection, and elicited 100% animal survival after oral dosing at 25 mg/kg b.i.d. for 5 and 15 days. Cyclophosphamide-induced immunosuppression led to recrudescence. Washout experiments demonstrated a lack of complete clearance of infected cell cultures, potentially explaining the in vivo results. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5Safety of 3-Bromo-4-chloro-7-azaindole).

Morzyk-Ociepa, Barbara et al. published their research in Journal of Molecular Structure in 2018 | CAS: 1000340-39-5

3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C7H4BrClN2

Crystal structures, vibrational spectra and DFT calculations of five halogeno-derivatives of 7-azaindole (3Br7AI, 4Br7AI, 4Cl7AI, 3Br4Cl7AI and 5Br3Cl7AI): a comparative study was written by Morzyk-Ociepa, Barbara;Dysz, Karolina;Turowska-Tyrk, Ilona;Michalska, Danuta. And the article was included in Journal of Molecular Structure in 2018.Formula: C7H4BrClN2 This article mentions the following:

Structures and vibrational spectra of 3-bromo-7-azaindole (3Br7AI), 4-bromo-7-azaindole (4Br7AI), 4-chloro-7-azaindole (4Cl7AI), 5-bromo-3-chloro-7-azaindole (5Br3Cl7AI) and 3-bromo-4-chloro-7-azaindole (3Br4Cl7AI) have been investigated. For the first time a single crystal anal. is reported for the three compounds: 3Br7AI (P2₁/n space group; a = 12.6586(3), b = 3.98664(12), c = 14.1189(4)Å, β = 100.901(2)°, Z = 4); 4Br7AI (P21/n space group; a = 5.38136 (13), b = 9.2262 (2), c = 13.9806 (4)Å, β = 90.052 (2)°, Z = 4); and 5Br3Cl7AI (C2/c space group; a = 22.9444(10), b = 3.91953(12), c = 17.8500(6)Å, β = 102.621(4)o, Z = 8). In the crystal structure, a pair of mols. forms a centrosym. dimer connected by dual nearly linear N-H···N hydrogen bonds between the pyrrole and pyridine rings. In addition, the structures of 4Br7AI and 5Br3Cl7AI are stabilized by C2-H2···Br hydrogen bonds. The IR and Raman spectra of all compounds and their N-deuterated derivatives were recorded in the solid state. The theor. mol. structures and vibrational spectra of the centrosym. dimers of five investigated compounds were calculated using the B3LYP method with the 6-311G++(d,p) basis set. The optimized structural parameters and the calculated vibrational spectra reproduce well the experiment Detailed vibrational assignments for all these compounds have been made on the basis of the calculated potential energy distributions (PEDs). The characteristic marker bands for the chloro- and bromo-derivativeds of 7-azaindoles are reported. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5Formula: C7H4BrClN2).

Li, Butong et al. published their research in Polycyclic Aromatic Compounds in 2022 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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 C8H6N2O2

Theoretical Calculations about the Nitro-Substituted Derivatives of Indole as Potential High-Energy-Density Compounds was written by Li, Butong;Li, Lulin;Zhu, Junjie. And the article was included in Polycyclic Aromatic Compounds in 2022.Computed Properties of C8H6N2O2 This article mentions the following:

Nitro-substituted derivatives of indole were designed by substituting the hydrogen atoms of indole one by one. To explore the thermal stability, the heats of formation were calculated by using the isodesmic reaction and pos. values are confirmed for all of them, which indicated their energetic nature. To explore the kinetic stability, the bond dissociation energies are calculated accompanied by the bond orders, and enough kinetic stability is evaluated. To detect the potential application as high-energy-d. compounds, the detonation velocity (D), the detonation pressure (P), the explosive heats (Q), and the mol. d. (ρ) is calculated further according to the famous Kamlet-Jacobs equation. Based on our calculation, hex-substituted indole has excellent detonation characters (D = 8.80 km/s, P = 35.88 GPa) and can be regarded as high-energy-d. compounds for further research. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Computed Properties of C8H6N2O2).

Hu, Zhang et al. published their research in International Journal of Chemistry (Toronto, ON, Canada) in 2010 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Electric Literature of C14H9NO2S

Quaternized chitosan as an efficient catalyst for synthesis of N-alkylthio-phthalimides was written by Hu, Zhang;Li, Sidong. And the article was included in International Journal of Chemistry (Toronto, ON, Canada) in 2010.Electric Literature of C14H9NO2S This article mentions the following:

A practical and efficient synthesis of N-alkylthio-phthalimides by the reaction of N-chlorophthalimide with thiols catalyzed by quaternized chitosan was described. The reactions were carried out in relatively mild conditions, and a variety of N-alkylthio-phthalimides were efficiently prepared with moderate to good yields. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Electric Literature of C14H9NO2S).