Indole‐3‐Aldehyde

James, Philip N.; Snyder, H. R.

doi:10.1002/0471264180.os039.11

Cited by 14 publications

(17 citation statements)

References 8 publications

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“…5‐(3′‐Indolyl)‐3‐substituted‐1,2,4‐triazoles 6a‐g and 7a‐o were prepared as described in the Scheme 1. The indole‐3‐carboxaldehyde 2 and N ‐methylindole‐3‐carboxaldehyde 3 were prepared according to the literature procedures (32,33). Indole‐3‐carbonitriles ( 4 and 5 ) were synthesized in good yields from the corresponding indole‐3‐carboxaldehydes ( 2 and 3 ) by reacting with hydroxylamine hydrochloride in the presence of sodium formate and formic acid at reflux temperature.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Novel Indolyl-1,2,4-triazoles as Potent and Selective Anticancer Agents

Kumar

Narayanam

Chang

et al. 2011

Chemical Biology &Amp; Drug Design

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A diverse series of 22 indolyl-1,2,4-triazole congeners (6 and 7) have been synthesized from the reaction of indole-3-carbonitrile (4) or (5) with appropriate acid hydrazides in the presence of potassium carbonate. Synthesized compounds were evaluated for their cytotoxicity against six human cancer cell lines, and some of the compounds displayed promising activity. In particular, 3-(3',4',5'-trimethoxyphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole (7i) and 3-(4'-piperidinyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole (7n) were the most promising and broadly active compounds against the tested cell lines. It was interesting to note that the trimethoxyphenyl analog 7i showed twofold selective cytotoxicity against PaCa2 cell line (IC(50) 0.8 μm), whereas piperidinyl analog 7n was found to be selectively cytotoxic against MCF7 cell line (IC(50) 1.6 μm). Notably, the 4-fluorophenyl derivative 7c exhibited selective cytotoxicity against PC3 cell line (IC(50) 4 μm). The structure-activity relationship study revealed that substituents including 3,4,5-trimethoxyphenyl, 3,4-dimethoxyphenyl, 4-benzyloxy-3-methoxyphenyl, 4-piperidinyl, 4-fluorophenyl and N-methylindole are beneficial for the activity of indolyl-1,2,4-triazoles (6 and 7).

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Section: Resultsmentioning

confidence: 99%

“…Indole‐3‐carboxaldehyde ( 2 ) was synthesized from commercially available indole as described in the literature (32,33). The N‐methylation of 2 was carried out using dimethylcarbonate in the presence of potassium carbonate (32,33).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Novel Indolyl-1,2,4-triazoles as Potent and Selective Anticancer Agents

Kumar

Narayanam

Chang

et al. 2011

Chemical Biology &Amp; Drug Design

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“…Unless otherwise noted, all solvents and reagents were commercially available and used without further purification. Compounds 2 22 , 4a–f 23 , 24 , 6a–f 23 , 24 , 7a 25 , 8a,b 26 , 27 and 9a 28 were prepared according to the reported procedures.…”

Section: Methodsmentioning

confidence: 99%

Inhibition studies on a panel of human carbonic anhydrases withN1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails

Awadallah

Bua

Mahmoud

et al. 2018

Journal of Enzyme Inhibition and Medicinal Chemistry

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Being the primary sulfonamide among the most efficient zinc binding group (ZBG) to design inhibitors for the metallo-enzymes carbonic anhydrases (CA, EC 4.2.1.1), herein, we propose an investigation on four physiologically important human (h) CAs (hCA I, II, IV, and IX) with N1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails. The effect of the functionalisation of the sulfonamide group with five different substitution patterns, namely acetyl, pyridine, thiazole, pyrimidine, and carbamimidoyl, was evaluated in relation to the inhibition profile of the corresponding primary sulfonamide analogues. With most of these latter being nanomolar inhibitors of all four considered isoforms, a totally counterproductive effect on the inhibition potency can be ascribed to N1-functionalisations of the ZBG primary sulfonamide structure with pyridine, thiazole, and pyrimidine moieties. On the other hand, incorporation of less hindered groups, such as sulfonylacetamides and sulfonylguanidines, maintained a certain degree of activity dependent on the tailing moiety, with KIs spanning in the low micromolar range.

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“…Conversion of 1-benzyl indole to 1-benzyl indole-3-aldehyde followed previously outlined procedure for formylation of indole [40]. Under very dry conditions, phosphorous oxychloride (2.6 mL, 0.028 mole) was added to 8.7 mL freshly distilled dimethylformamide in a 3-neck flask while stirring on an ice bath under a drying column and purged with nitrogen gas.…”

Section: Methodsmentioning

confidence: 99%

1-Benzyl-indole-3-carbinol is a novel indole-3-carbinol derivative with significantly enhanced potency of anti-proliferative and anti-estrogenic properties in human breast cancer cells

Nguyen

Лавренов

Sundar

et al. 2010

Chemico-Biological Interactions

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Indole-3-carbinol (I3C), a natural autolysis product of a gluccosinolate present in Brassica vegetables such as broccoli and cabbage, has anti-proliferative and anti-estrogenic activities in human breast cancer cells. A new and significantly more potent I3C analogue, 1-benzyl-I3C was synthesized, and in comparison to I3C, this novel derivative displayed an approximate 1000-fold enhanced potency in suppressing the growth of both estrogen responsive (MCF-7) and estrogen independent (MDA-MB-231) human breast cancer cells (I3C IC50 of 52 μM, and 1-benzyl-I3C IC50 of 0.05 μM). At significantly lower concentrations, 1-benzyl-I3C induced a robust G1 cell cycle arrest and elicited the key I3C-specific effects on expression and activity of G1 acting cell cycle genes including the disruption of endogenous interactions of the Sp1 transcription factor with the CDK6 promoter. Furthermore, in estrogen responsive MCF-7 cells, with enhanced potency 1-benzyl-I3C down regulated production of estrogen receptor-alpha protein, acts with tamoxifen to arrest breast cancer cell growth more effectively than either compound alone, and inhibited the in vivo growth of human breast cancer cell-derived tumor xenografts in athymic mice. Our results implicate 1-benzyl-I3C as a novel, potent inhibitor of human breast cancer proliferation and estrogen responsiveness that could potentially be developed into a promising therapeutic agent for the treatment of indole-sensitive cancers.

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Indole‐3‐Aldehyde

Abstract: Indole‐3‐aldehyde reactant: 288 ml. (274 g., 3.74 moles) of freshly distilled dimethylformamide catalyst: 86 ml. (144 g., 0.94 mole) of freshly distilled phosphorus oxychloride reactant: 100 g. (0.85 mole) of indole product: indole‐3‐aldehyde

Cited by 14 publications

References 8 publications

Synthesis of Novel Indolyl-1,2,4-triazoles as Potent and Selective Anticancer Agents

Synthesis of Novel Indolyl-1,2,4-triazoles as Potent and Selective Anticancer Agents

Inhibition studies on a panel of human carbonic anhydrases withN1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails

1-Benzyl-indole-3-carbinol is a novel indole-3-carbinol derivative with significantly enhanced potency of anti-proliferative and anti-estrogenic properties in human breast cancer cells

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