1447710-51-1

Basic information

• Product Name: (S)-3-(4-(allyloxy)-3-chlorophenyl)-2-(tert-butoxycarbonylamino)propanoic acid
• Synonyms: (S)-3-(4-(allyloxy)-3-chlorophenyl)-2-(tert-butoxycarbonylamino)propanoic acid
• CAS NO: 1447710-51-1
• Molecular Weight: 355.818
• Mol File: 1447710-51-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-3-(4-(allyloxy)-3-chlorophenyl)-2-(tert-butoxycarbonylamino)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(4-(allyloxy)-3-chlorophenyl)-2-(tert-butoxycarbonylamino)propanoic acid(1447710-51-1)
• EPA Substance Registry System: (S)-3-(4-(allyloxy)-3-chlorophenyl)-2-(tert-butoxycarbonylamino)propanoic acid(1447710-51-1)

Safety Data

• Hazardous Substances Data: 1447710-51-1(Hazardous Substances Data)

Upstream product

• 232277-27-9 methyl (S)-3-(3-chloro-4-hydroxyphenyl)-2-((tert-butoxycarbonyl)amino) propanoate 
• 1447710-21-5 (S)-3-(4-allyloxy-3-chloro-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester 
• 192315-36-9 (S)-2-((tert-butoxycarbonyl)amino)-3-(3-chloro-4-hydroxyphenyl)propanoic acid (N-Boc-3-chlorotyrosine) 

Downstream Products

• 1447710-20-4 [(S)-2-(4-allyloxy-3-chloro-phenyl)-1-(1-cyano-cyclopropylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

Repurposing a Library of Human Cathepsin L Ligands: Identification of Macrocyclic Lactams as Potent Rhodesain and Trypanosoma brucei Inhibitors

Rhodesain (RD) is a parasitic, human cathepsin L (hCatL) like cysteine protease produced by Trypanosoma brucei (T. b.) species and a potential drug target for the treatment of human African trypanosomiasis (HAT). A library of hCatL inhibitors was screened, and macrocyclic lactams were identified as potent RD inhibitors (Ki 50 400 nM). SARs addressing the S2 and S3 pockets of RD were established. Three cocrystal structures with RD revealed a noncovalent binding mode of this ligand class due to oxidation of the catalytic Cys25 to a sulfenic acid (Cys-SOH) during crystallization. The P-glycoprotein efflux ratio was measured and the in vivo brain penetration in rats determined. When tested in vivo in acute HAT model, the compounds permitted up to 16.25 (vs 13.0 for untreated controls) mean days of survival.

CYCLIC AMIDES

The invention relates to a compound of formula (I) wherein A, B, D and R1 to R6 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.