561324-07-0

Basic information

• Product Name: [(S)-((1S,2S)-2-Azidomethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester
• Synonyms: [(S)-((1S,2S)-2-Azidomethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester
• CAS NO: 561324-07-0
• Molecular Weight: 388.423
• Mol File: 561324-07-0.mol

Chemical Properties

• CAS DataBase Reference: [(S)-((1S,2S)-2-Azidomethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [(S)-((1S,2S)-2-Azidomethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester(561324-07-0)
• EPA Substance Registry System: [(S)-((1S,2S)-2-Azidomethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester(561324-07-0)

Safety Data

• Hazardous Substances Data: 561324-07-0(Hazardous Substances Data)

Upstream product

• 420130-97-8 [(S)-((1S,2S)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester 

Downstream Products

• 561326-86-1 [(S)-((1S,2S)-2-Aminomethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester 

Relevant articles and documents

Synthesis and evaluation of trans 3,4-cyclopropyl L-arginine analogues as isoform selective inhibitors of nitric oxide synthase

Four optically pure conformationally restricted L-arginine analogues syn- 1 and anti- 2 trans-3,4-cyclopropyl L-arginine, and syn- 3 and anti-trans-3,4-cyclopropyl N-(1-iminoethyl) L-ornithine 4 were synthesized. These compounds were tested as potential inhibitors against the three isoforms of nitric oxide synthase (NOS). Compound 1 was determined to be a poor substrate of NOS, while compound 2 was determined to be a poor mixed type inhibitor and did not exhibit any isoform selectivity. Syn- 3 and anti-trans-3,4-cyclopropyl N-(1-iminoethyl) L-ornithine 4 were found to be competitive inhibitors of NOS. These compounds were time dependent inhibitors of inducible NOS (iNOS), but not of neuronal NOS (nNOS) or endothelial NOS (eNOS). Compound 3 was 10- to 100-fold more potent an inhibitor than 4, exhibited a 5-fold increase in nNOS/iNOS and eNOS/iNOS selectivity over 4, and displayed tight binding characteristics against iNOS. These results indicate that the relative configuration of the cyclopropyl ring in the L-arginine analogues significantly affects their inhibitory potential and NOS isoform selectivity.