232277-27-9

Basic information

• Product Name: methyl (S)-3-(3-chloro-4-hydroxyphenyl)-2-((tert-butoxycarbonyl)amino) propanoate
• Synonyms: methyl (S)-3-(3-chloro-4-hydroxyphenyl)-2-((tert-butoxycarbonyl)amino) propanoate
• CAS NO: 232277-27-9
• Molecular Weight: 329.781
• Mol File: 232277-27-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: methyl (S)-3-(3-chloro-4-hydroxyphenyl)-2-((tert-butoxycarbonyl)amino) propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (S)-3-(3-chloro-4-hydroxyphenyl)-2-((tert-butoxycarbonyl)amino) propanoate(232277-27-9)
• EPA Substance Registry System: methyl (S)-3-(3-chloro-4-hydroxyphenyl)-2-((tert-butoxycarbonyl)amino) propanoate(232277-27-9)

Safety Data

• Hazardous Substances Data: 232277-27-9(Hazardous Substances Data)

Upstream product

• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 3417-91-2 L-tyrosine methyl ester HCl 
• 60-18-4 L-tyrosine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 782440-99-7 3-chloro-L-tyrosine methyl ester 
• 1447710-67-9 (S)-2-(tert-butoxycarbonylamino)-3-(3-chloro-4-hydroxyphenyl)propanoate dicyclohexylammonium salt 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1447710-21-5 (S)-3-(4-allyloxy-3-chloro-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester 
• 1447710-23-7 (S)-3-(4-allyloxy-3-chloro-phenyl)-2-amino-propionic acid methyl ester 
• 1447710-25-9 (S)-2-(2-allyloxy-benzoylamino)-3-(4-allyloxy-3-chloro-phenyl)-propionic acid methyl ester 
• 1447710-36-2 (S)-2-[(S)-2-(4-allyloxy-3-chloro-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1447710-38-4 (S)-3-(4-allyloxy-3-chloro-phenyl)-2-[((S)-pyrrolidine-2-carbonyl)-amino]-propionic acid methyl ester 
• 1447710-40-8 (S)-3-(4-allyloxy-3-chloro-phenyl)-2-[((S)-1-but-3-enyl-pyrrolidine-2-carbonyl)-amino]-propionic acid methyl ester 
• 1447710-51-1 (S)-3-(4-(allyloxy)-3-chlorophenyl)-2-(tert-butoxycarbonylamino)propanoic acid 
• 1447710-53-3 (S)-3-(4-allyloxy-3-chloro-phenyl)-2-amino-N-(1-cyano-cyclopropyl)-propionamide 
• 7423-93-0 (S)-2-amino-3-(3-chloro-4-hydroxyphenyl)propanoic acid 
• 782440-99-7 3-chloro-L-tyrosine methyl ester 
• 192315-37-0 (S)-methyl 3-(3-chloro-4-methoxyphenyl)-2-(tert-butoxycarbonylamino)propanoate 
• 1447710-20-4 [(S)-2-(4-allyloxy-3-chloro-phenyl)-1-(1-cyano-cyclopropylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 232275-06-8 N-(2,6-Dichlorobenzoyl)-3-chloro-4-(2-methoxyphenyl)-L-phenylalanine 

Relevant articles and documents

Chemical investigations into the biosynthesis of the gymnastatin and dankastatin alkaloids

Electrophilic natural products have provided fertile ground for understanding how nature inhibits protein function using covalent bond formation. The fungal strainGymnascella dankaliensishas provided an especially interesting collection of halogenated cytotoxic agents derived from tyrosine which feature an array of reactive functional groups. Herein we explore chemical and potentially biosynthetic relationships between architecturally complex gymnastatin and dankastatin members, finding conditions that favor formation of a given scaffold from a common intermediate. Additionally, we find that multiple natural products can also be formed from aranorosin, a non-halogenated natural product also produced byGymnascellasp. fungi, using simple chloride salts thus offering an alternative hypothesis for the origins of these compounds in nature. Finally, growth inhibitory activity of multiple members against human triple negative breast cancer cells is reported.

Synthesis and trypanocide activity of chloro-l-tyrosine and bromo-l-tyrosine derivatives

Twenty-two halogenated l-tyrosine derivatives were synthesized to examine new substances for the treatment of Chagas disease. The synthesis of these derivatives with different degree of substitution in the amino group with methyl iodide, giving primary, tertiary, and quaternary amino acids. All compounds were tested in vitro against intracellular amastigotes of Trypanosoma cruzi, and the cytotoxicity were evaluated over monocytic cell line U-937. Compound 25 was the most active against T. cruzi with a EC50 of 75.52 μM compared with benznidazole with a EC50 of 58.79 μM. Compounds 3, 4, 7, and 15 were the derivatives with the best selectivity index (SI) with values of 7.5, 8.3,12.1, and 8.6, respectively. Finally, compound 7 was the safer and the more promising derivative against T. cruzi.

MACROCYCLIC AMIDES AS PROTEASE INHIBITORS

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.