Category: indole-building-block

Relation of chemical structure to plant growth-regulator activity in the pineapple plant. V. Post-harvest delay of senescence of pineapple fruit was written by Gortner, Willis A.;Leeper, Robert W.. And the article was included in Botanical Gazette (Chicago) in 1969.Formula: C11H11NO2 This article mentions the following:

The effects of 369 compounds, including 94 phenoxyacetic acids, 43 other phenoxy acids, 23 phenylacetic acids, 15 hydrocinnamic acids, 9 benzoic acids, 7 salicylic acids, 48 naphthalene derivatives, 22 indole acids, 5 hydrazine derivatives, and 8 cinnamic acids, for postharvest delay of senescence of pineapple fruit (Ananas comosus) were determined Seventy-six of the compounds were active, and 27 were highly active in delaying senescence. In the phenoxyacetic acid series, high activity was obtained from some halogen-substituted acids but not generally from Me-substituted acids. In the phenoxy-α-propionic acid series, high activity was not observed for a number of halogen- and Me-substituted acids. None of the substituted phenoxy acids other than HOAc and α- propionic showed even moderate activity. An appreciable number of Cl-substituted phenylacetic acids and several benzoic acids showed activity. None of the phenylalkylcarboxylic acids other than HOAc showed even moderate activity. None of the salicylic acid, phthalic acids, or phthalamic acids showed any activity. All hydrazine derivatives were inactive. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Formula: C11H11NO2).

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Formula: C11H11NO2

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

Photoredox Imino Functionalizations of Olefins was written by Davies, Jacob;Sheikh, Nadeem S.;Leonori, Daniele. And the article was included in Angewandte Chemie, International Edition in 2017.HPLC of Formula: 14204-27-4 This article mentions the following:

Shown herein is that polyfunctionalized nitrogen heterocycles can be easily prepared by a visible-light-mediated radical cascade process. This divergent strategy features the oxidative generation of iminyl radicals and subsequent cyclization/radical trapping, which allows the effective construction of highly functionalized heterocycles. The reactions proceed efficiently at room temperature, utilize an organic photocatalyst, use simple and readily available materials, and generate, in a single step, valuable building blocks that would be difficult to prepare by other methods. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4HPLC of Formula: 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. 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.HPLC of Formula: 14204-27-4

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

Discovery of Aminopiperidine Indoles That Activate the Guanine Nucleotide Exchange Factor SOS1 and Modulate RAS Signaling was written by Abbott, Jason R.;Hodges, Timothy R.;Daniels, R. Nathan;Patel, Pratiq A.;Kennedy, J. Phillip;Howes, Jennifer E.;Akan, Denis T.;Burns, Michael C.;Sai, Jiqing;Sobolik, Tammy;Beesetty, Yugandhar;Lee, Taekyu;Rossanese, Olivia W.;Phan, Jason;Waterson, Alex G.;Fesik, Stephen W.. And the article was included in Journal of Medicinal Chemistry in 2018.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Indole-substituted tryptophan amides such as I were prepared through optimization of aminopiperidine-substituted indoles as activators of the guanine nucleotide exchange factor (GEF) son of sevenless homolog 1 (SOS1) for use in modulating RAS signaling and thus as potential antitumor agents. Substitution patterns on the indole nucleus, the pendant amino acid moiety, and the linker unit connecting these two fragments were modified to determine structure-activity relations for the SOS1-mediated activation of nucleotide exchange. Effective compounds such as I activated the nucleotide exchange process at sub-micromolar concentrations in vitro (IC₅₀ for I = 0.8 ± 0.36 μM), increased levels of active RAS-GTP in HeLa cells, and elicited signaling changes in the mitogen-activated protein kinase/extracellular regulated kinase (MAPK/ERK) pathway, resulting in a decrease in pERK1/2^T202/Y204 protein levels at higher compound concentrations The structures of selected compounds bound to the ternary complex of RAS, SOS1, and RAS were determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Safety of 5-Chloroindole-3-carboxaldehyde

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

H-β zeolite, an efficient reusable catalyst for one-pot synthesis of isatins from anilines was written by Raj, I. Victor Paul;Shaikh, Tanveer Mahamadali;Sudalai, Arumugam. And the article was included in Acta Chimica Slovenica in 2010.Recommanded Product: 150560-58-0 This article mentions the following:

The authors described a simple and highly efficient procedure for the single-step preparation of isatins from the com. available anilines using H-β zeolite as a truly heterogeneous catalyst. H-β zeolite is readily separated from the reaction mixture by simple filtration and was reused several times without considerable loss of activity. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Recommanded Product: 150560-58-0).

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 150560-58-0

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

Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131) was written by See, Cheng Shang;Kitagawa, Mayumi;Liao, Pei-Ju;Lee, Kyung Hee;Wong, Jasmine;Lee, Sang Hyun;Dymock, Brian W.. And the article was included in European Journal of Medicinal Chemistry in 2018.Electric Literature of C9H6ClNO This article mentions the following:

Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI₅₀ 1.5μM). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20mg/kg IP twice a day. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Electric Literature of C9H6ClNO).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Electric Literature of C9H6ClNO

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

Silver Mediated Banert Cascade with Carbon Nucleophiles was written by Alexander, Juliana R.;Kevorkian, Paul V.;Topczewski, Joseph J.. And the article was included in Organic Letters in 2021.Safety of 2-Methyl-6-nitro-1H-indole This article mentions the following:

The Banert cascade of propargylic azides was promoted by simple silver salts and the triazafulvene intermediate can be intercepted by carbon nucleophiles. Various indoles (>25 examples, up to 92% yield) and electron-rich heterocycles were effective. The Mayr nucleophilicity parameter (N) was found to correlate to the reaction efficiency, which enabled the formation of Csp³-Csp² and Csp³-Csp³ bonds under otherwise identical conditions from structurally dissimilar nucleophiles. In the experiment, the researchers used many compounds, for example, 2-Methyl-6-nitro-1H-indole (cas: 3484-23-9Safety of 2-Methyl-6-nitro-1H-indole).

2-Methyl-6-nitro-1H-indole (cas: 3484-23-9) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Safety of 2-Methyl-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

Facile synthesis of monofunctional pentamethine carbocyanine fluorophores was written by Shao, Fangwei;Yuan, Hushan;Josephson, Lee;Weissleder, Ralph;Hilderbrand, Scott A.. And the article was included in Dyes and Pigments in 2011.Category: indole-building-block This article mentions the following:

A high-yield route to sym., conjugatable pentamethine carbocyanine dyes with far-red/near IR (NIR) emission between 650 and 700 nm is reported. The dyes are prepared via condensation of indolium or benz[e]indolium inner salts with an alkyl carboxylic acid derivatized malonaldehyde dianil or alternatively in a one-pot reaction without isolation of the malonaldehyde intermediate. The fluorophores are water-soluble, have bright fluorescence emission, are easily prepared in good yield, and are promising candidates for use in a variety of biochem. and in vivo imaging applications. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Category: indole-building-block).

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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). Category: indole-building-block

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

Fluorine-containing quinoline and quinoxaline styryl derivatives: synthesis and photophysical properties was written by Nosova, E. V.;Trashakhova, T. V.;Ustyugov, V. S.;Mochul’skaya, N. N.;Valova, M. S.;Lipunova, G. N.;Charushin, V. N.. And the article was included in Russian Chemical Bulletin in 2011.Recommanded Product: 774-47-0 This article mentions the following:

(E)-2-Styryl-substituted 6,7-difluoroquinolines, e.g., I, and quinoxalines, e.g., II, were synthesized by the condensation of the corresponding 2-methylbenzazines with aromatic aldehydes. Photoluminescence of the synthesized 6,7-difluoro-2-styrylbenzazines was studied. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Recommanded Product: 774-47-0).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 774-47-0

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 3-Formylindoles via Electrochemical Decarboxylation of Glyoxylic Acid with an Amine as a Dual Function Organocatalyst was written by Lin, Dian-Zhao;Huang, Jing-Mei. And the article was included in Organic Letters in 2019.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A method for 3-formylation of indoles has been developed through electrochem. decarboxylation of glyoxylic acid with the amine as a dual function organocatalyst. The amine facilitated both the electrochem. decarboxylation and the nucleophilic reaction efficiently, whose loading can be as low as 1 mol %. This protocol has a broad range of functional group tolerance under ambient conditions. The gram-scale experiment has shown great potential in the synthetic application of this strategy. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Application In Synthesis of 5-Chloroindole-3-carboxaldehyde).

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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde

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

One-pot total synthesis of streptindole, arsindoline B and their congeners through tandem decarboxylative deaminative dual-coupling reaction of amino acids with indoles was written by Xiang, Jiachen;Wang, Jungang;Wang, Miao;Meng, Xianggao;Wu, Anxin. And the article was included in Organic & Biomolecular Chemistry in 2015.Safety of 6-Nitro-1H-indole This article mentions the following:

This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM (bis(indolyl)methane) scaffolds and its further application to the one-pot total synthesis of natural products. This method featured a stimulating example of activating amino acids in one pot as multi-carbon building blocks for transformation into final targets which are equipped with amino acid side chain backbones. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Safety of 6-Nitro-1H-indole).

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