indole-building-block | - Page 91 of 1434

Mino, Takashi et al. published their research in Organic & Biomolecular Chemistry in 2019 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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.Quality Control of 6-Nitro-1H-indole

Synthesis and application of P,olefin type axially chiral ligands with sec-alkyl groups was written by Mino, Takashi;Yamaguchi, Daiki;Masuda, Chihiro;Youda, Junpei;Ebisawa, Toshibumi;Yoshida, Yasushi;Sakamoto, Masami. And the article was included in Organic & Biomolecular Chemistry in 2019.Quality Control of 6-Nitro-1H-indole This article mentions the following:

We synthesized N-trans-cinnamyl-N-cyclohexylaniline type aminophosphine 2 and a series of N-2-adamantyl-N-trans-cinnamylaniline type aminophosphines 3. Although aminophosphine 2 failed to find the existence of axial chirality, aminophosphines 3, which exist in the axial chirality in a C(aryl)-N(amine) bond by chiral HPLC anal. as 1-adamantyl type chiral ligands 1. Enantiomeric isomers of 3b, 3c, and 3d were obtained in an enantiomerically pure form. We also identified the palladium-catalyzed asym. allylic substitution of 1,3-diphenyl-2-propenyl acetate with indoles using aminophosphines 3b–d as effective chiral ligands in high enantioselectivities (up to 96% ee). In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Quality Control of 6-Nitro-1H-indole).

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

Smith, Keith et al. published their research in Synthesis in 2003 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 5-Isopropylindoline-2,3-dione

Carbonylation of doubly lithiated N’-aryl-N,N-dimethylureas: A novel approach to isatins via intramolecular trapping of acyllithiums was written by Smith, Keith;El-Hiti, Gamal A.;Hawes, Anthony C.. And the article was included in Synthesis in 2003.Name: 5-Isopropylindoline-2,3-dione This article mentions the following:

Lithiation of N’-(2-bromoaryl)-N,N-dimethylureas with methyllithium and tert-butyllithium under nitrogen in anhydrous THF at 0 °C gave doubly lithiated arylurea derivatives, which react with carbon monoxide at 0 °C to give isatins in good yields. The scope of the reaction has been demonstrated by application to the synthesis of isatin itself and four substituted isatins bearing alkyl, chloro or fluoro groups. Double lithiation and quenching with ammonium chloride of N‘-(2-bromophenyl)-N,N-dimethylurea gave N‘-(2-bromophenyl)-N,N-dimethylurea. Lithiation of N‘-(2-bromophenyl)-N,N-dimethylurea with methyllithium was followed by addition of (1,1-dimethylethyl)lithium, effecting an bromine-lithium exchange. Sequential carbonylation with carbon monoxide and quenching gave 1H-indole-2,3-dione (isatin). In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Name: 5-Isopropylindoline-2,3-dione).

Marasek-Ciolakowska, Agnieszka et al. published their research in International Journal of Molecular Sciences in 2020 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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). Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid

Formation of the secondary abscission zone induced by the interaction of methyl jasmonate and auxin in Bryophyllum calycinum: relevance to auxin status and histology was written by Marasek-Ciolakowska, Agnieszka;Saniewski, Marian;Dziurka, Michal;Kowalska, Urszula;Goraj-Koniarska, Justyna;Ueda, Junichi;Miyamoto, Kensuke. And the article was included in International Journal of Molecular Sciences in 2020.Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

The interaction of Me jasmonate (JA-Me) and indole-3-acetic acid (IAA) to induce the formation of the secondary abscission zone in the middle of internode segments of Bryophyllum calycinum was investigated in relation to auxin status and histol. When IAA at 0.1% (weight/weight, in lanolin) was applied to the segments, the formation of the secondary abscission zone at a few mm above the treatment in the apical direction was observed On the contrary, IAA at 0.5% (weight/weight, in lanolin) did not induce the formation of the secondary abscission zone. JA-Me at 0.5% (weight/weight, in lanolin) applied to the middle of internode segments kept in the normal (natural) or inverted positions also induced the formation of the secondary abscission zone below and above parts of the treatment. Comprehensive analyses of plant hormones revealed that the balance of the endogenous levels of IAA in both sides adjacent to the abscission zone was significantly disturbed when the secondary abscission formation was induced by the application of IAA. These results strongly suggest that an auxin gradient is important in the formation of the secondary abscission zone in the internode segments of B. calycinum, and IAA gradient results from polar IAA transport from the application site. Further possible mechanisms of the formation of the secondary abscission zone in the internode segments of B. calycinum are also discussed in the interaction of JA-Me and IAA. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid).

Cele, Zamani E. D. et al. published their research in European Journal of Organic Chemistry in 2015 | CAS: 14204-27-4

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

Applied Enantioselective Aminocatalysis: α-Heteroatom Functionalization Reactions on the Carbapenem (β-Lactam Antibiotic) Core was written by Cele, Zamani E. D.;Arvidsson, Per I.;Kruger, Hendrik G.;Govender, Thavendran;Naicker, Tricia. And the article was included in European Journal of Organic Chemistry in 2015.Product Details of 14204-27-4 This article mentions the following:

The carbapenem (β-lactam antibiotic) scaffold serves as a useful nucleophile in organocatalytic diarylprolinol trimethylsilyl ether mediated α-heterofunctionalization reactions leading to the formation of diverse products that bear multiple stereocenters in high diastereoselectivity and moderate to good yields. Under optimized conditions the synthesis of the target compounds was achieved using (2S)-2-[diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine (chiral prolinol-silyl ether) as a catalyst. Starting materials included (5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (4-nitrophenyl)methyl ester, 1,2-diazenedicarboxylic acid, 1,2-bis(1,1-dimethylethyl) ester, N-(hydroxy)carbamic acid ester, (nitros)benzene,2-(phenylthio)-1H-isoindole-1,3(2H)-dione, 2-(phenylseleno)-1H-i-Isoindole-1,3(2H)-dione. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Product Details of 14204-27-4).

Zhang, Guangji et al. published their research in ACS Sustainable Chemistry & Engineering in 2020 | CAS: 4769-96-4

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

Co,N-Codoped Porous Carbon-Supported Co_yZnS with Superior Activity for Nitroarene Hydrogenation was written by Zhang, Guangji;Tang, Feiying;Wang, Xiaoying;An, Ping;Wang, Liqiang;Liu, You-Nian. And the article was included in ACS Sustainable Chemistry & Engineering in 2020.Synthetic Route of C8H6N2O2 This article mentions the following:

Preparation of chemoselective hydrogenation catalyst containing both CoNx and CoyZnS supported on N-doped porous carbon (CoN_x-Co_yZnS@NPC-Z) was reported. The CoN_x-Co_yZnS@NPC-Z catalyst were prepared by pyrolyzing the protein-metal-ion networks, followed by treatment with acid. The CoN_x-Co_yZnS@NPC-Z-3 catalyst delivered high catalytic activity and selectivity in chemoselective hydrogenation of nitroarenes afforded aryl amines R-NH₂ [R = Ph, 4-ClC₆H₄, 2-naphthyl, etc.] with almost full conversion and >98% selectivity in water/methanol mixture solvents at 90掳C under 5 bar of H₂ pressure for 3h of reaction. Also Schiff-base derivatives R¹CH=NR² [R¹ = Ph, 4-ClC₆H₄, 4-MeOC₆H₄, etc.; R² = Ph, 2-MeC₆H₄, 4-ClC₆H₄, etc.] were prepared via one-pot reductive amination of aryl aldehydes with aromatic nitro compounds using CoN_x-Co_yZnS@NPC-3 catalyst. Notably, the catalytic hydrogenation could work even under 1 bar of H₂ pressure and at room temperature with high conversion and selectivity. Besides, CoN_x-Co_yZnS@NPC-Z-3 exhibited remarkable tolerance to CO or H₂S poisoning and acid erosion. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Synthetic Route of C8H6N2O2).

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

Kumar, Dalip et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2011 | CAS: 90271-86-6

5-Bromo-3-cyanoindole (cas: 90271-86-6) 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.Computed Properties of C9H5BrN2

Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles was written by Kumar, Dalip;Kumar, N. Maruthi;Chang, Kuei-Hua;Gupta, Ritika;Shah, Kavita. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Computed Properties of C9H5BrN2 This article mentions the following:

A series of 3,5-bis(indolyl)-1,2,4-thiadiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. Indole-3-thiocarboxamides, e.g., I, reacted with iodobenzene diacetate via oxidative dimerization to give 3,5-bis(indolyl)-1,2,4-thiadiazoles, e.g., II. Among the synthesized bis(indolyl)-1,2,4-thiadiazoles, the compound II with 4-chlorobenzyl and methoxy substituents showed the most potent activity. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Computed Properties of C9H5BrN2).

Takemoto, Masumi et al. published their research in Heterocycles in 2007 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application of 4583-55-5

Oxidative cleavage reaction of substituted indoles catalyzed by plant cell cultures was written by Takemoto, Masumi;Iwakiri, Yasutaka;Tanaka, Kiyoshi. And the article was included in Heterocycles in 2007.Application of 4583-55-5 This article mentions the following:

We have developed a novel method for the oxidative cleavage of indole carbon double bonds in the presence of H₂O₂ using plant cell cultures as peroxidase. The oxidative method has some advantage, as features such as mild reactions, good yields, easy work-up, and safety. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Application of 4583-55-5).

Nishiyama, Takashi et al. published their research in European Journal of Medicinal Chemistry in 2016 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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.Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate

Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells was written by Nishiyama, Takashi;Hatae, Noriyuki;Yoshimura, Teruki;Takaki, Sawa;Abe, Takumi;Ishikura, Minoru;Hibino, Satoshi;Choshi, Tominari. And the article was included in European Journal of Medicinal Chemistry in 2016.Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

A convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O₂ atmosphere as an important step is reported. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions I (R¹ = R² = H, CH₃; R³ = H, 6-OCH₃, 5,6-(OCH₃)₂, 7-CH₃, 6-NO₂, etc.; R⁴ = H, MOM) have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate).

Zhang, Deliang et al. published their research in Organic Letters in 2020 | 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.Formula: C8H6N2O2

Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine was written by Zhang, Deliang;Iwai, Tomohiro;Sawamura, Masaya. And the article was included in Organic Letters in 2020.Formula: C8H6N2O2 This article mentions the following:

In the presence of a catalyst generated from [Ir(cod)Cl]₂ and the crosslinked polystyrene-bound diphosphine PS-DPPBz, indolines and selected partially saturated five- and six-membered nitrogen heterocycles underwent reversible acceptorless dehydrogenation to give aromatic nitrogen heterocycles. The method was used for the dehydrogenation of N-substituted indolines with various nitrogen substituents and substituents with various electronic and steric effects. Under 40 atm. of H₂, indoles and a quinoline, isoquinoline, and quinoxaline underwent hydrogenation in the presence of the resin-bound iridium catalyst to yield partially saturated nitrogen heterocycles. A reaction pathway involving oxidative addition of an N-adjacent C(sp³)-H bond to a bisphosphine-coordinated Ir(I) center is proposed for the dehydrogenation of N-substituted substrates. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Formula: C8H6N2O2).

Parham, William E. et al. published their research in Journal of Organic Chemistry in 1976 | 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. 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

Selective halogen-lithium exchange in bromophenylalkyl halides was written by Parham, William E.;Jones, Lawrence D.;Sayed, Yousry A.. And the article was included in Journal of Organic Chemistry in 1976.Reference of 5388-42-1 This article mentions the following:

Exchange of the aryl halide atom in o-BrC6H4CH2Cl, o-BrC6H4(CH2)2Br, and o-BrC6H4(CH2)3Cl for Li was carried out with BuLi in THF-hexane at -100掳. The stable lithio derivatives reacted with a variety of electrophiles; e.g., o-LiC6H4CH2Cl (I) with H2O, cyclohexanone, or PhNCO at low temperature gave, resp., PhCH2Cl, II, and III. I with H2O at room temperature gave 9,10-dihydroanthracene (not benzocyclopropene). Benzocyclobutene was formed from o-LiC6H4(CH2)2Br under similar conditions. O-halobenzyl bromides were lithiated at the benzyl bromine atom and underwent subsequent coupling to bibenzyl. O-BrC6H4(CH2)3Br with BuLi underwent intramol. coupling to indan. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).