279226-70-9

Basic information

• Product Name: 1H-Benzimidazole-5-carboxaldehyde,1-methyl-
• Synonyms: 1H-Benzimidazole-5-carboxaldehyde,1-methyl-;1H-Benzimidazole-5-carboxaldehyde, 1-methyl- (9CI);1-Methylbenzimidazole-5-carboxaldehyde;1-Methyl-1H-benzimidazole-5-carboxaldehyde;1-Methyl-1H-1,3-benzodiazole-5-carbaldehyde
• CAS NO: 279226-70-9
• Molecular Formula: C9H8N2O
• Molecular Weight: 160.17262
• Product Categories: ALDEHYDE;BENZIMIDAZOLE;AMINETERTIARY
• Mol File: 279226-70-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 336.9 °C at 760 mmHg
• Flash Point: 157.5 °C
• Appearance: /
• Density: 1.21 g/cm³
• Vapor Pressure: 0.000109mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 1H-Benzimidazole-5-carboxaldehyde,1-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole-5-carboxaldehyde,1-methyl-(279226-70-9)
• EPA Substance Registry System: 1H-Benzimidazole-5-carboxaldehyde,1-methyl-(279226-70-9)

Safety Data

• Hazardous Substances Data: 279226-70-9(Hazardous Substances Data)

Usage

General Description

1-Methyl-1H-Benzimidazole-5-carboxaldehyde is a chemical compound classified under the class of organic compounds known as benzimidazoles. Its systematic name is 1-methyl-1H-benzimidazole-5-carbaldehyde, as per IUPAC guidelines. Benzimidazoles are compounds containing a benzene ring fused to an imidazole ring. 1H-Benzimidazole-5-carboxaldehyde,1-methyl- can be identified by its chemical formula C9H8N2O. The various properties such as weight, melting and boiling points, solubility, and polarity depend on the specific physical and chemical conditions. Benzimidazoles, including 1-methyl-1H-benzimidazole-5-carboxaldehyde, are known in medicinal chemistry for their various pharmacological properties and are used in the synthesis of a wide range of therapeutic agents.

InChI:InChI=1/C9H8N2O/c1-11-6-10-8-4-7(5-12)2-3-9(8)11/h2-6H,1H3

Upstream product

• 106429-29-2 5-(hydroxymethyl)-benzimidazole 
• 15788-16-6 5-benzimidazolecarboxylic acid 
• 58442-17-4 1H-benzo[d]imidazole-5-carbaldehyde 
• 74-88-4 methyl iodide 
• 115576-91-5 (1-methyl-1H-benzimidazol-5-yl)methanol 

Relevant articles and documents

Substitution at the indole 3 position yields highly potent indolecombretastatins against human tumor cells

Resistance to combretastatin A-4 is mediated by metabolic modification of the phenolic hydroxyl and ether groups of the 3-hydroxy-4-methoxyphenyl (B ring). Replacement of the B ring of combretastatin A-4 by a N-methyl-5-indolyl reduces tubulin polymerization inhibition (TPI) and cytotoxicity against human cancer cell lines but cyano, methoxycarbonyl, formyl, and hydroxyiminomethyl substitutions at the indole 3-position restores potent TPI and cytotoxicity against sensitive human cancer cell lines. These highly potent substituted derivatives displayed low nanomolar cytotoxicity against several human cancer cell lines due to tubulin inhibition, as shown by cell cycle analysis, confocal microscopy, and tubulin polymerization inhibitory activity studies, and promoted cell killing mediated by caspase-3 activation. Binding at the colchicine site was suggested by molecular modeling studies. Substituted combretastatins displayed higher potencies than the isomeric isocombretastatins and the highest potencies were achieved for the hydroxyiminomethyl (21) and cyano (23) groups, with TPI values in the submicromolar range and cytotoxicities in the nanomolar and subnanomolar range. Dose-response and time-course studies showed that drug concentrations as low as 1 nM (23) or 10 nM (21) led to a complete G2/M cell cycle arrest after 15 h treatment followed by a high apoptosis-like cell response after 48–72 h treatment. The P-glycoprotein antagonist verapamil increased 21 and 23 cytotoxicity to IC50 values of 10?10 M, and highly potentiated the cytotoxic activity in 100-fold of the CHO derivative (17), in A-549 human non-small cell lung cancer cells. The cyano substituted indolecombretastatin 23 is by itself highly potent against rather resistant HT-29 and A-549 cell lines. A 3,4,5-trimethoxyphenyl ring always afforded more potent derivatives than a 2,3,4-trimethoxyphenyl ring.