21216-80-8

Usage

InChI:InChI=1/C19H37NO/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-19(21)4-2/h4H,2-3,5-18H2,1H3,(H,20,21)

Upstream product

• 143-27-1 hexadecylamine 
• 814-68-6 acryloyl chloride 
• 4860-03-1 1-Chlorohexadecan 
• 79-06-1 2-propenamide 

Downstream Products

• 274904-27-7 (E)-3-(4-{2-[4-((E)-2-Hexadecylcarbamoyl-vinyl)-phenyl]-2-oxo-acetyl}-phenyl)-acrylic acid tert-butyl ester 
• 274903-80-9 (E)-3-(4-{5-[4-((E)-2-hexadecylcarbamoyl-vinyl)phenyl]-1H-imidazol-4-yl}phenyl)-aceylic acid tert-butyl ester 
• 274903-84-3 3-(4-{4-[4-((E)-2-Carboxy-vinyl)-phenyl]-5-[4-((E)-2-hexadecylcarbamoyl-vinyl)-phenyl]-1H-imidazol-2-yl}-phenyl)-4,5-dihydro-isoxazole-5-carboxylic acid 
• 274904-58-4 3-(4-{4-[4-((E)-2-tert-butoxycarbonyl-vinyl)phenyl]-5-[4-(2-hexadecylcarbamoyl-vinyl)phenyl]-1H-imidazol-2-yl}phenyl)-isoxazole-5-carboxylic acid ethyl ester 
• 274903-83-2 3-(4-{4-[4-((E)-2-tert-butoxycarbonyl-vinyl)phenyl]-5-[4-(2-hexadecylcarbamoyl-vinyl)phenyl]-1H-imidazol-2-yl}phenyl)-4,5-dihydroisoxazole-5-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Process for the preparation of N-substituted acrylamides

The present invention relates to a process for the preparation of N-substituted acrylamides of the general formula CH2=CH—CONHR, wherein, R is alkyl group having carbon 1 to 22 or acyl group having carbon 1 to 18. The process for the preparation of the N-substituted acrylamides comprises reacting acrylamide with alkyl acyl chloride in the presence of Lewis acid catalyst in an organic solvent at a temperature ranging between room temperature to 50° C. for a period ranging between 1 hour to 24 hours.

Development of potent non-carbohydrate imidazole-based small molecule selectin inhibitors with antiinflammatory activity

A novel series of non-carbohydrate imidazole-based selectin inhibitors has been discovered via high-throughput screening using a P-selectin ELISA-based assay system. The initial lead 1 had an IC50 of 17 μM in the P-selectin ELISA; this potency was significantly improved via an extensive SAR exploration. One of the current lead compounds (29) has an IC50 of 300 nM in a P-selectin ELISA; it also has good activity in P- and E-selectin cell adhesion assays and shows efficacy in vivo. These compounds represent a novel series of sLeX mimetics with antiinflammatory activity. Their unique profile supports our interest in their further evaluation as drug candidates for the treatment of inflammation. Herein we describe the syntheses, optimization, and SAR of this series of novel potent selectin antagonists.