41716-12-5

Usage

1-Methyl-1H-imidazole-5-carbonyl chloride (MICC) properties and specific content

A chemical compound consisting of 6 carbon atoms, 6 hydrogen atoms, 1 chlorine atom, 2 nitrogen atoms, and 1 oxygen atom.

Appearance

White to off-white solid
A solid substance with a pale color, ranging from pure white to a slightly lighter shade of white.

Common uses

Synthesis of pharmaceuticals and agrochemicals
Widely employed as a key component in the production of various drugs and chemicals used in agriculture.

Versatile intermediate

Reagent in organic synthesis and preparation of heterocyclic compounds
Acts as a starting material or mediator in chemical reactions, enabling the formation of a variety of complex organic molecules.

Applications

Production of cationic dyes, UV stabilizers, and catalyst in polymerization reactions
Utilized in the creation of dyes with a positive charge, chemicals that protect materials from UV radiation damage, and substances that accelerate polymer formation.

Potential properties

Anti-inflammatory and antimicrobial
Has been studied for its ability to reduce inflammation and fight against microorganisms, suggesting possible applications in medicine and healthcare.

Industrial and research significance

Diverse chemical reactivity and potential biological activity
The compound's ability to participate in various chemical reactions and its possible biological effects make it valuable in both commercial and scientific contexts.

Upstream product

• 41806-40-0 1-methyl-1H-imidazole-5-carboxylic acid 
• 19485-38-2 1-methyl-1H-imidazole-4,5-dicarboxylic acid 

Downstream Products

• 922706-78-3 N-(2-bromo-4-chlorophenyl)-1-methyl-1H-imidazole-5-carboxamide 
• 1279830-10-2 3-[1-(2,4-difluorobenzyl)-5-(3-methyl-3H-imidazole-4-carbonyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]benzonitrile 
• 1401460-38-5 C₁₉H₁₉N₇OS₂ 
• 1446442-60-9 4-iodo-1-methyl-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-1H-imidazole-5-carboxamide 
• 1446442-90-5 1-methyl-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-1H-imidazole-5-carboxamide 
• 17289-20-2 methyl 1-methyl-1H-imidazole-5-carboxylate 

Relevant academic research and scientific papers

Amide-based xanthine oxidase inhibitors bearing an N-(1-alkyl-3-cyano-1H-indol-5-yl) moiety: Design, synthesis and structure-activity relationship investigation

Our previous work identified a promising isonicotinamide based xanthine oxidase (XO) inhibitor, N-(3-cyano-4-((2-cyanobenzyl)oxy)phenyl)isonicotinamide (1), and concluded that amide is an effective linker in exploring the XO inhibitor chemical space that is completely different from the five-membered ring framework of febuxostat and topiroxostat. Indole, an endogenous bioactive substance and a popular drug construction fragment, was involved in the structural optimization campaign of the present effort. After the installation of some functional groups, N-(1-alkyl-3-cyano-1H-indol-5-yl) was generated and employed to mend the missing H-bond interaction between the 3′-cyano of 1 and Asn768 residue of XO by shortening their distance. In this context, eight kinds of heterocyclic aromatic amide chemotypes were rationally designed and synthesized to investigate the structure-activity relationship (SAR) of amide-based XO inhibitors. The optimized compound a6 (IC50 = 0.018 μM) exhibits 17.2-fold improved potency than the initial compound 1 (IC50 = 0.31 μM). Its potency is comparable to that of topiroxostat (IC50 = 0.013 μM). Molecular docking and molecular dynamics studies proved the existence of the stable H-bond between the cyano group and the Asn768 residue. Moreover, oral administration of a6 (11.8 mg/kg) could effectively reduce serum uric acid levels in an acute hyperuricemia rat model. Liver microsomal stability assay illustrated that compound a6 possesses well metabolic stability in rat liver microsomes. However, the in vivo potency of a6 was much lower than that of topiroxostat, which may be explained by the poor absorption found in the parallel artificial membrane permeability assay (PAMPA). In addition, 6a has non-cytotoxicity against normal cell lines MCF10A and 16HBE. Taken together, this work culminated in the identification of compound 6a as an excellent lead for further exploration of amide-based XO inhibitors.

NEW MALONITRILE DERIVATIVES

The invention relates to a compound of formula (I) wherein R1-R2 are as defined in the description and in the claims. The compound of formula (I) can be used as a medicament.

Cephem Compounds with Latent Reactive Groups

Cephem and penem compounds having a styrylmethylene moiety at the 3-position in the cephem or penem ring to which a positively charged leaving group is bonded and wherein the leaving group contains a vicinal diol or is bonded to a unsubstituted or substituted catechol. The leaving group can be a positively charge nitrogen leaving group. Cephems include cephalosporins, cephamycins, carbacephems, and oxacephems. Penems include penems, carbapenems and oxapenems. Preferred cephems are cephalosporins. Preferred penems are carbapenems. Compounds exhibit antibiotic activity against Gram-negative bacteria and/or Gram-positive bacteria. Compounds exhibit antibiotic activity against bacteria which exhibit multi-drug resistance. Compounds of the invention exhibit antibiotic activity against bacterial strains which produce extended spectrum beta-lactamases (ESBL), which produce AmpC beta-lactamases or which produce a carbapenemase. Pharmaceutical compositions comprising one or more cephems or penems or methods of treatment of bacterial infections with such compounds and compositions.

SUBSTITUTED 2-THIOIMIDAZOLYLCARBOXAMIDES AS PESTICIDES

The present invention relates to compounds of the general formula (I) in which Q, V, T, W, X, Y, n and A have the meanings given in the description—and to a process for their preparation and to their use for controlling animal pests.

Cu(II)-mediated C-H amidation and amination of arenes: Exceptional compatibility with heterocycles

A Cu(OAc)2-mediated C-H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and N-phenylaminobenzoates.

Phenylalanine derivatives as GPR142 agonists for the treatment of Type II diabetes

GPR142 is a novel GPCR that is predominantly expressed in pancreatic β-cells. GPR142 agonists potentiate glucose-dependent insulin secretion, and therefore can reduce the risk of hypoglycemia. Optimization of our lead pyridinone-phenylalanine series led to a proof-of-concept compound 22, which showed in vivo efficacy in mice with dose-dependent increase in insulin secretion and a decrease in glucose levels.

Inhibitors of checkpoint kinases

The instant invention provides for compounds which comprise fused imidazoles that inhibit CHK1 activity. The invention also provides for compositions comprising such inhibitory compounds and methods of inhibiting CHK1 activity by administering the compound to a patient in need of treatment of cancer.

INHIBITORS OF VEGF RECEPTOR AND HGF RECEPTOR SIGNALING

The invention relates to the inhibition of vascular endothelial growth factor (VEGF) receptor signaling and hepatocyte growth factor (HGF) receptor signaling. The invention provides compounds and methods for inhibiting VEGF receptor signaling and HGF receptor signaling. The invention also provides compositions and methods for treating cell proliferative diseases and conditions

Selective Decarboxylation of 1-Methyl-4,5-imidazoledicarboxylic Acid

The selective decarboxylation of 1-methyl-4,5-imidazoledicarboxylic acid was carried out in various solvents. 1-Methyl-5-imidazolecarboxylic acid was obtained by heating in acetic or propionic anhydride, whereas 1-methyl-4-imidazolecarboxylic acid was obtained in N,N-dimethylformamide, N,N-dimethylacetamide, or N-methylpyrrolidone or by pyrolysis.The reaction mechanism is discussed.