1381810-27-0

Basic information

• Product Name: (S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid
• Synonyms: (S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid
• CAS NO: 1381810-27-0
• Molecular Weight: 606.835
• Mol File: 1381810-27-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid(1381810-27-0)
• EPA Substance Registry System: (S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid(1381810-27-0)

Safety Data

• Hazardous Substances Data: 1381810-27-0(Hazardous Substances Data)

Upstream product

• 247186-22-7 (tert-butoxycarbonyl)-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester 

Downstream Products

• 1381808-45-2 (E)-(5S,11S,14S,17R,18R,19S,20S)-11-(3-hydroxy-benzyl)-14-isopropyl-18,20-dimethoxy-17,19-dimethyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone 
• 1381811-24-0 (S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyl}-hexahydro-pyridazine-3-carboxylic acid 3-iodo-benzyl ester 
• 1381811-30-8 (S)-1-{(S)-3-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-[(S)-2-((E)-(2R,3R,4R,5R)-3,5-dimethoxy-2,4-dimethyl-7-tributylstannanyl-hept-6-enoylamino)-3-methylbutyrylamino]-propionyl}-hexahydro-pyridazine-3-carboxylic acid 3-iodo-benzyl ester 
• 1381808-56-5 (E)-(8S,14S,17S,20R,21S)-21-hydroxy-14-(3-hydroxy-benzyl)-17-isopropyl-20-methyl-6-oxa-12,15,18,27-tetraaza-tricyclo[20.2.2.1*8,12*]heptacosa-1⁽²⁵⁾,2,22⁽²⁶⁾,23-tetraene-7,13,16,19-tetraone 
• 1381811-81-9 (S)-1-{(S)-2-{(S)-2-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3-(4-vinyl-phenyl)-propionylamino]-3-methyl-butyrylamino}-3-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyl}-hexahydro-pyridazine-3-carboxylic acid but-3-enyl ester 
• 1381811-86-4 (E)-(8S,14S,17S,20R,21S)-21-(t-butyl-dimethyl-silanyloxy)-14-[3-(t-butyl-dimethyl-silanyloxy)-benzyl]-17-isopropyl-20-methyl-6-oxa-12,15,18,27-tetraaza-tricyclo[20.2.2.1*8,12*]heptacosa-1⁽²⁵⁾,2,22⁽²⁶⁾,23-tetraene-7,13,16,19-tetraone 
• 1381808-66-7 (8S,14S,17S,20R,21S)-21-hydroxy-14-(3-hydroxy-benzyl)-17-isopropyl-20-methyl-6-oxa-12,15,18,27-tetraaza-tricyclo[20.2.2.1*8,12*]heptacosa-1⁽²⁵⁾,22⁽²⁶⁾,23-triene-7,13,16,19-tetraone 
• 1381810-40-7 (S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]propionyl}hexahydropyridazine-3-carboxylic acid but-3-enyl ester 
• 1381814-47-6 (S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyl}-hexahydro-pyridazine-3-carboxylic acid (R)-6-vinyl-indan-1-yl ester 
• 1381808-85-0 (13E,15E)-(3S,6S,9R,10R,21S)-3-(3-hydroxybenzyl)-6-isopropyl-10-methoxy-9-methyl-19-oxa-1,4,7,25-tetraazabicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone 
• 1381812-52-7 (13E,15E)-(3S,6S,9R,10R,21S)-3-[3-(tert-butyldimethylsilanyloxy)benzyl]-6-isopropyl-10-methoxy-9-methyl-19-oxa-1,4,7,25-tetraazabicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone 
• 1381808-22-5 (13E,15E)-(3S,6S,9R,10R,11S,12S,21S)-3-(3-hydroxybenzyl)-6-isopropyl-10,12-dimethoxy-9,11-dimethyl-19-oxa-1,4,7,25-tetraazabicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone 
• 1381810-47-4 (S)-1-{(S)-3-[3-(tert-butyldimethylsilanyloxy)phenyl]-2-[(S)-2-((E)-(2R,3R,4S,5S)-3,5-dimethoxy-2,4-dimethylnona-6,8-dienoylamino)-3-methylbutyrylamino]propionyl}hexahydropyridazine-3-carboxylic acid but-3-enyl ester 
• 1381815-52-6 (E)-(2R,5S,11S,14S,18R)-11-[3-(tert-butyl-dimethyl-silanyloxy)-benzyl]-14-isopropyl-18-methoxy-2-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁶⁾,21,23⁽²⁷⁾,24-tetraene-4,10,13,16-tetraone 

Relevant articles and documents

Discovery of Potent Cyclophilin Inhibitors Based on the Structural Simplification of Sanglifehrin A

Cyclophilin inhibition has been a target for the treatment of hepatitis C and other diseases, but the generation of potent, drug-like molecules through chemical synthesis has been challenging. In this study, a set of macrocyclic cyclophilin inhibitors was synthesized based on the core structure of the natural product sanglifehrin A. Initial compound optimization identified the valine-m-tyrosine-piperazic acid tripeptide (Val-m-Tyr-Pip) in the sanglifehrin core, stereocenters at C14 and C15, and the hydroxyl group of the m-tyrosine (m-Tyr) residue as key contributors to compound potency. Replacing the C18-C21 diene unit of sanglifehrin with a styryl group led to potent compounds that displayed a novel binding mode in which the styrene moiety engaged in a π-stacking interaction with Arg55 of cyclophilin A (Cyp A), and the m-Tyr residue was displaced into solvent. This observation allowed further simplifications of the scaffold to generate new lead compounds in the search for orally bioavailable cyclophilin inhibitors.