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Das, Priyabrata et al. published their research in ACS Medicinal Chemistry Letters in 2013 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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.Formula: C8H3F2NO2

SAR-Based Optimization of a 4-Quinoline Carboxylic Acid Analogue with Potent Antiviral Activity was written by Das, Priyabrata;Deng, Xiaoyi;Zhang, Liang;Roth, Michael G.;Fontoura, Beatriz M. A.;Phillips, Margaret A.;De Brabander, Jef K.. And the article was included in ACS Medicinal Chemistry Letters in 2013.Formula: C8H3F2NO2 This article mentions the following:

It is established that drugs targeting viral proteins are at risk of generating resistant strains. However, drugs targeting host factors can potentially avoid this problem. Herein, we report structure-activity relationship studies leading to the discovery of a very potent lead compound 6-fluoro-2-(5-isopropyl-2-methyl-4-phenoxyphenyl)quinoline-4-carboxylic acid (C44) that inhibits human dihydroorotate dehydrogenase (DHODH) with an IC₅₀ of 1 nM and viral replication of VSV and WSN-Influenza with an EC₅₀ of 2 nM and 41 nM. We also solved the X-ray structure of human DHODH bound to C44, providing structural insight into the potent inhibition of biaryl ether analogs of brequinar. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Formula: C8H3F2NO2).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Shriver, James A. et al. published their research in RSC Advances in 2020 | 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Category: indole-building-block

Exploring an anomaly: the synthesis of 7,7′-diazaindirubin through a 7-azaindoxyl intermediate was written by Shriver, James A.;Wang, Katelyn R.;Patterson, Andrew C.;DeYoung, James R.;Lipsius, Richard J.. And the article was included in RSC Advances in 2020.Category: indole-building-block This article mentions the following:

Two independent methods generating 7-azaindoxyl as an intermediate verified that 7,7′-diazaindirubin was formed exclusively over 7,7′-diazaindigo. This contrasted with long-standing knowledge related to the reactivity of indoxyl, which proceeded via a radical-initiated homodimerization process, leading to indigo. A series of experiments confirmed 7-azaindoxyl as an intermediate with resulted suggesting a condensation pathway followed by oxidation In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Category: indole-building-block).

Chen, Chou-Hsiung et al. published their research in Organic & Biomolecular Chemistry in 2014 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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). Reference of 827-01-0

A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues was written by Chen, Chou-Hsiung;Genapathy, Sivaneswary;Fischer, Peter M.;Chan, Weng C.. And the article was included in Organic & Biomolecular Chemistry in 2014.Reference of 827-01-0 This article mentions the following:

A facile route has been established for the synthesis of indole-substituted (S)-tryptophans from corresponding indoles, which utilizes a chiral auxiliary-facilitated Strecker amino acid synthesis strategy. The chiral auxiliary reagents evaluated were (S)-methylbenzylamine and related derivatives To illustrate the robustness of the method, eight optically pure (S)-tryptophan analogs were synthesized, which were subsequently used for the convergent synthesis of a potent antibacterial agent, argyrin A, and its analogs. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Reference of 827-01-0).

Zhang, Xing-Long et al. published their research in Organic Letters in 2021 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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). Product Details of 4769-96-4

Palladium-Catalyzed Three-Component Regioselective Dehydrogenative Coupling of Indoles, 2-Methylbut-2-ene, and Carboxylic Acids was written by Zhang, Xing-Long;Guo, Rui-Li;Wang, Meng-Yue;Zhao, Bao-Yin;Jia, Qiong;Yang, Jin-Hui;Wang, Yong-Qiang. And the article was included in Organic Letters in 2021.Product Details of 4769-96-4 This article mentions the following:

An unprecedented palladium-catalyzed three-component dehydrogenative cascade coupling of indoles, 2-methylbut-2-ene, and carboxylic acids or methanol has been developed. The approach enables the straightforward introduction of a C3′-bonded five-carbon structural unit with a tertiary alc. quaternary carbon center giving access to functionalized indoles I (R¹ = H, 5-Me, 6-Br, 6-NO₂, etc.; R² = Me, n-pentyl, Ph, 2-thienyl, etc.; R³ = Me, MeCO, cyclopropylcarbonyl, ClCHMeCO, etc.). The protocol employs 2-methylbut-2-ene as the C5 source and features a broad substrate scope, atom and step economies, and high chemo- and regioselectivies. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Product Details of 4769-96-4).

Liu, Yungen et al. published their research in Chemistry – An Asian Journal in 2015 | 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 167631-84-7

[Fe(F₂₀TPP)Cl]-Catalyzed Amination with Arylamines and {[Fe(F₂₀TPP)(NAr)](PhI=NAr)}⁺. Intermediate Assessed by High-Resolution ESI-MS and DFT Calculations was written by Liu, Yungen;Chen, Guo-Qiang;Tse, Chun-Wai;Guan, Xianguo;Xu, Zheng-Jiang;Huang, Jie-Sheng;Che, Chi-Ming. And the article was included in Chemistry – An Asian Journal in 2015.Recommanded Product: 167631-84-7 This article mentions the following:

Amination of C-H bonds catalyzed by transition metal complexes via nitrene/imide insertion is an appealing strategy for C-N bond formation, and the use of iminoiodinanes, or their in situ generated forms from PhI(OAc)₂+primary amides (such as sulfonamides, sulfamates, and carbamates), as nitrogen sources for the amination reaction was well documented. A metal catalyst+PhI(OAc)₂+primary arylamines amination protocol was developed using [Fe(F₂₀TPP)Cl] (H₂F₂₀TPP=meso-tetrakis(pentafluorophenyl)porphyrin) as a catalyst. This catalytic method is applicable for both intra- and intermol. amination of sp² and sp³ C-H bonds (>27 examples), affording the amination products, including natural products such as rutaecarpine, in moderate-to-good yields. ESI-MS anal. and DFT calculations lend support for the involvement of {[Fe(F₂₀TPP)(NC₆H₄-p-NO₂)](PhI=NC₆H₄-p-NO₂)}^+. intermediate in the catalysis. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Recommanded Product: 167631-84-7).

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

Zhang, Bing et al. published their research in European Journal of Medicinal Chemistry in 2022 | 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C8H6N2O2

Design, synthesis, and biological evaluation of N-(3-cyano-1H-indol-5/6-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxamides and 5-(6-oxo-1,6-dihydropyrimidin-2-yl)-1H-indole-3-carbonitriles as novel xanthine oxidase inhibitors was written by Zhang, Bing;Duan, Yulin;Yang, Yuwei;Mao, Qing;Lin, Fengwei;Gao, Jun;Dai, Xiwen;Zhang, Peng;Li, Qiuhua;Li, Jinxin;Dai, Ronghua;Wang, Shaojie. And the article was included in European Journal of Medicinal Chemistry in 2022.Formula: C8H6N2O2 This article mentions the following:

Xanthine oxidase (XO) has been an important target for the treatment of hyperuricemia and gout. The anal. of potential interactions of pyrimidinone and 3-cyano indole pharmacophores present in the corresponding reported XO inhibitors with parts of the XO active pocket indicated that they both can be used as effective fragments for the fragment-based design of nonpurine XO inhibitors. In this paper, we adopted the fragment-based drug design strategy to link the two fragments with an amide bond to design the type 1 compounds 13a-13w,14c, 14d, 14f, 14g, 14j, 14k, and 15g. Compound 13g displayed an evident XO inhibitory potency (IC₅₀ = 0.16 娓璏), which was 52.3-fold higher than that of allopurinol (IC₅₀ = 8.37 娓璏). For comparison, type 2 compounds 5-(6-oxo-1,6-dihydropyrimidin-2-yl)-1H-indole-3-carbonitriles (25c-25g) were also designed by linking the two fragments with a single bond directly. The results showed that compound 25c from the latter series displayed the best inhibitory potency (IC₅₀ = 0.085 娓璏), and it was 98.5-fold stronger than that of allopurinol (IC₅₀ = 8.37 娓璏). These results suggested that amide and single bonds were applicable for linking the two fragments together to obtain potent nonpurine XO inhibitors. The structure-activity relationship results revealed that hydrophobic groups at N-atom of the indole moiety were indispensable for the improvement of the inhibitory potency in vitro against XO. In addition, enzyme kinetics studies suggested that compounds 13g and 25c, as the most promising XO inhibitors for the two types of target compounds, acted as mixed-type inhibitors for XO. Moreover, mol. modeling studies suggested that the pyrimidinone and indole moieties of the target compounds could interact well with key amino acid residues in the active pocket of XO. Furthermore, in vivo hypouricemic effect demonstrated that compounds 13g and 25c could effectively reduce serum uric acid levels at an oral dose of 10 mg/kg. Therefore, compounds 13g and 25c could be potential and efficacious agents for the treatment of hyperuricemia and gout. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Formula: C8H6N2O2).

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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C8H6N2O2

Devi, N. Saritha et al. published their research in International Journal of Pharmacy and Biological Sciences in 2018 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.SDS of cas: 112656-95-8

Synthesis and screening of 2-hydroxy-N-(2,41-dioxospiro [indoline-3,21-thiazolidin]-31-yl) benzamides for antiinflammatory activity was written by Devi, N. Saritha;Sarangapani, Manda. And the article was included in International Journal of Pharmacy and Biological Sciences in 2018.SDS of cas: 112656-95-8 This article mentions the following:

A novel synthesis of 2-hydroxy-N-(2,4′-dioxospiro[indoline-3,2′-thiazolidin]-3′-yl)benzamide derivatives I [R = H, 5-F, 5,6-dichloro, etc.] was synthesized by cyclization of isatin hydrazones with thioglycollic acid. The synthesized compounds I were characterized by spectral data (IR, ¹H-NMR, MASS) and evaluated for in-vitro, in-vivo anti-inflammatory activity. The test compounds I exhibited significant potency to inhibit COX-2 enzyme values between 46.23 鍗?0.38 to 73.24 鍗?0.35, Among the tested compounds compounds I [R = 5,6-dichloro, 5-F, 5-Cl] were considered to possess more potent anti-inflammatory activity when compared to standard drug indomethacin. By in-vitro anti-inflammatory activity the compounds I [R = 5,6-dichloro, 5-F, 5-Cl, 5-Br] were considered to possess more potent anti-inflammatory activity when compared to standard drug indomethacin. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8SDS of cas: 112656-95-8).

Dandia, Anshu et al. published their research in Synthetic Communications in 2001 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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). Synthetic Route of C8H4N2O4

Improved synthesis of 3-spiro indolines in dry media under microwave irradiation was written by Dandia, Anshu;Sachdeva, Harshita;Singh, Ruby. And the article was included in Synthetic Communications in 2001.Synthetic Route of C8H4N2O4 This article mentions the following:

The spiro[indole-dipyrrolopyridines] I (X = NH; R = H, Me; R¹, R² = F, H; H, NO₂; Me, Me; NO₂, H; H, NO₂) were prepared in an efficient, one-pot synthesis using microwave irradiation by reaction of spiro[indole-dipyrrolopyrans] I (X = O) with ammonium acetate in the presence of acetic acid. I (X = O) were prepared in situ by microwave induced reaction of indole-2,3-diones and 2-pyrrolidones in a 1:2 molar ratio. Comparative studies were made between microwave irradiation of reactants in the absence of any solvent and catalyzed reactions in the presence of o-dichlorobenzene and classical heating. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Synthetic Route of C8H4N2O4).

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).

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

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 鎺矯 gave doubly lithiated arylurea derivatives, which react with carbon monoxide at 0 鎺矯 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).