118959-44-7

Usage

Uses

Used in Pharmaceutical Industry:
1-methyl-1H-Indole-3-carboxamide is used as an intermediate in the synthesis of pharmaceuticals for its potential anti-inflammatory and anticancer properties, contributing to the development of new drugs that can address these health concerns.
Used in Chemical Industry:
As a starting material, 1-methyl-1H-Indole-3-carboxamide is used in the synthesis of a wide range of organic compounds, highlighting its importance in the creation of various chemical products.
Used in Dye and Pigment Production:
1-methyl-1H-Indole-3-carboxamide is utilized in the production of various dyes and pigments, owing to its chemical properties that lend themselves to color creation and application in different industries.
Used in Biochemical Synthesis:
1-methyl-1H-Indole-3-carboxamide serves as a starting material for the synthesis of a broad spectrum of biochemicals, further expanding its applications in the field of chemistry and beyond.

Upstream product

• 603-76-9 1-methylindole 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 24662-37-1 1-methyl-1H-indole-3-carbonitrile 
• 32387-21-6 1-methyl-3-indolecarboxylic acid 
• 390799-61-8 1-methylindole-3-carboxamidine E-oxime 
• 228566-47-0 C₁₀H₉Cl₂N₂O₂P 
• 942-24-5 3-methoxycarbonylindole 
• 108438-43-3 methyl 1-methyl-1H-indole-3-carboxylate 
• 24666-30-6 1-methyl-1H-indole-3-carbaldehyde oxime 
• 120-72-9 indole 
• 19012-03-4 N-methyl-3-formylindole 
• 5457-28-3 3-cyano-1H-indole 
• 571151-09-2 (1-methyl-1H-indole-3-carbonyl)-phosphoramidic acid 
• 125818-09-9 methyl 1-methyl-1H-indole-3-carboxamidate hydrochloride 

Relevant academic research and scientific papers

Synthesis and antitumor activity of new thiazole nortopsentin analogs

New thiazole nortopsentin analogs in which one of the two indole units was replaced by a naphthyl and/or 7-azaindolyl portion, were conveniently synthesized. Among these, three derivatives showed good antiproliferative activity, in particular against MCF7 cell line, with GI50 values in the micromolar range. Their cytotoxic effect on MCF7 cells was further investigated in order to elucidate their mode of action. Results showed that the three compounds act as pro-apoptotic agents inducing a clear shift of viable cells towards early apoptosis, while not exerting necrotic effects. They also caused cell cycle perturbation with significant decrease in the percentage of cells in the G0/G1 and S phases, accompanied by a concomitant percentage increase of cells in the G2/M phase, and appearance of a subG1-cell population.

Synthesis and antiproliferative activity of thiazolyl-bis-pyrrolo[2,3-b]pyridines and indolyl-thiazolyl-pyrrolo[2,3-c]pyridines, nortopsentin analogues

Two new series of nortopsentin analogues, in which the imidazole ring of the natural product was replaced by thiazole and indole units were both substituted by 7-azaindole moieties or one indole unit was replaced by a 6-azaindole portion, were efficiently synthesized. Compounds belonging to both series inhibited the growth of HCT-116 colorectal cancer cells at low micromolar concentrations, whereas they did not affect the viability of normal-like intestinal cells. A compound of the former series induced apoptosis, evident as externalization of plasma membrane phosphatidylserine (PS), and changes of mitochondrial trans-membrane potential, while blocking the cell cycle in G2/M phase. In contrast, a derivative of the latter series elicited distinct responses in accordance with the dose. Thus, low concentrations (GI30) induced morphological changes characteristic of autophagic death with massive formation of cytoplasmic acid vacuoles without apparent loss of nuclear material, and with arrest of cell cycle at the G1 phase, whereas higher concentrations (GI70) induced apoptosis with arrest of cell cycle at the G1 phase.

Synthesis and antiproliferative activity of substituted 3[2-(1h-indol-3-yl)- 1,3-thiazol-4-yl]-1h-pyrrolo[3,2-b]pyridines, marine alkaloid nortopsentin analogues

A large number of indolyl-4-azaindolyl thiazoles, nortopsentin analogues, were conveniently synthesized. The antiproliferative activity of the new derivatives was examined against four human tumor cell lines with different histologic origin. Seven derivatives consistently reduced the growth of the experimental models independently of TP53 gene status and exhibited the highest activity against the malignant peritoneal mesothelioma (STO) cell line. The most active compound of this series acts as a CDK1 inhibitor, and was found to cause cell cycle arrest at G2/M phase, to induce apoptosis by preventing the phosphorylation of survivin in Thr34 and to increase the cytotoxic activity of paclitaxel in STO cells.

Novel 1H-pyrrolo[2,3-b]pyridine derivative nortopsentin analogues: Synthesis and antitumor activity in peritoneal mesothelioma experimental models

In this study, we describe the synthesis of new nortopsentin analogues, 1H-pyrrolo[2,3-b]pyridine derivatives and their biological effects in experimental models of diffuse malignant peritoneal mesothelioma (DMPM), a rare and rapidly fatal disease, poorly responsive to conventional therapies. The three most active compounds, 1f (3-[2-(5-fluoro-1-methyl-1H-indol-3-yl)-1,3- thiazol-4-yl]-1H-pyrrolo[2,3-b]pyridine), 3f (3-[2-(1H-indol-3-yl)-1,3-thiazol- 4-yl]-1-methyl-1H-pyrrolo[2,3-b]pyridine), and 1l (3-[2-(5-fluoro-1-methyl-1H- indol-3-yl)-1,3-thiazol-4-yl]-1-methyl-1H-pyrrolo[2,3-b] pyridine), which were shown to act as cyclin-dependent kinase 1 inhibitors, consistently reduced DMPM cell proliferation and induced a caspase-dependent apoptotic response, with a concomitant reduction of the expression of the active Thr34- phosphorylated form of the antiapoptotic protein survivin. Moreover, the combined treatment of DMPM cells with 3f derivative and paclitaxel produced a synergistic cytotoxic effect, which was paralleled by an enhanced apoptotic response. In the mouse model, i.p. administration of 1f, 3f, and 1l derivatives was effective, resulting in a significant tumor volume inhibition of DMPM xenografts (range, 58-75%) at well-tolerated doses, and two complete responses were observed in each treatment group.

Au/Ag-cocatalyzed aldoximes to amides rearrangement under solvent- and acid-free conditions

(Chemical Equation Presented) The gold/silver-cocatalyzed conversion of aldoximes into primary amides is reported. The reaction, which proceeds under neat and acid-free conditions, allows for the conversion of a range of aldoximes, and is a rare example of cooperative catalysis involving well-defined gold species.

Low molecular weight indole fragments as IMPDH inhibitors

The study of non-oxazole containing indole fragments as inhibitors of inosine monophosphate dehydrogenase (IMPDH) is described. The synthesis and in vitro inhibitory values for IMPDH II are discussed.

Isocyanatophosphoryl Dichloride as Reagent for Introduction of Carbamoyl Group into Molecules of π-Excessive Heterocycles and Enamines

A study on the stepwise hydrolysis of hetarene- and cycloalkenecarboxamidophosphoryl dichlorides afforded the synthesis of hitherto unknown hetarene- and cycloalkene-carboxamidophosphoric acids as well as allowing the introduction of unsubstituted carbamoyl group in the molecules of pyrroles, indoles, indolizines, and some enamines.

Iminoxyl radicals and stable products from the one-electron oxidation of 1-methylindole-3-carbaldehyde oximes

The radical intermediates and the stable products formed on one-electron oxidation of 1-methylindole-3-carbaldehyde oxime 2a were compared with those of 1-methylindole-3-carboxamidine oxime 4a in aqueous solution. The dibromide radical anion generated radiolytically by pulse radiolysis reacted with both 2a and 4a >C=NOH to yield the radical cations [>C=NOH]·+, which exist in prototropic equilibria with the neutral iminoxyl radicals [>C=NO]· (pKa = 3.53 ? 0.03 and 5.01 ± 0.01 at ionic strength 0.05 M, respectively). This was confirmed by the observed primary salt-effect which accelerated the decay of the radical cations but not the iminoxyl radicals. Methylation of the N-hydroxyimino function in both 2a and 4a precluded deprotonation of the corresponding radical cations [>C=NOCH3]·+. At low concentrations of 2a and high dose rates the 2a radicals [>C=NO]· decayed bimolecularly via unstable dimers to the aldehyde >C=O, with higher concentrations and lower dose rates favouring the chain-catalysed isomerisation of the N-hydroxyimino moiety. Radicals from 4a decay bimolecularly to form unstable dimers which degrade to produce an amide, nitrile and carboxylic acid. The observed differences in the oxidation chemistry of 2a and 4a probably reflect the enhanced stabilisation of iminoxyl radicals through α-amino substitution.

Novel 5-HT3 antagonists. Indole oxadiazoles.

The synthesis and biochemical evaluation of a series of indole oxadiazole 5-HT3 antagonists are described. The key pharmacophoric elements have been defined as a basic nitrogen, a linking group capable of H-bonding interactions, and an aromatic moiety. Th

FIRST REACTIONS OF VINYLINDOLES WITH DIETHYL MESOXALATE, NITROSOBENZENE, AND CHLOROSULFONYL ISOCYANATE: NEW FUNCTIONALIZED AND ANNELLATED INDOLES

Diethyl mesoxalate reacts with 2- and 3-vinylindoles via electrophilic substitution to give new, functionalized and annellated indoles in high regioselectivities.Regio-controlled dimerization processes occur in the reactions of the vinylindoles 5a and 8a.Nitrosobenzene reacts with 2- and 3-vinylindoles in a multi-stage sequence including regiospecific tandem hetero-Diels-Alder reactions to give the new, 2,3-difunctionalized indoles 11 and 12 which are conformationally stabilized by proton chelation.The heterocumulenechlorosulfonyl isocyanate reacts as a simple electrophile (like diethyl mesoxalate) with 2-vinylindole 5b to give the indole-3-carboxamide 14.In addition, analogous reactions of N-methylindole were also studied and, in most cases, gave comparable reactivity patterns.