An efficient stereoselective synthesis of [3S(1S,9S)]-3-[[[9-(benzoylamino) octahydro-6,10-dioxo-6H-pyridazino-(1,2-a)(1,2)-diazepin-1-yl]-carbonyl ]amino]-4-oxobutanoic acid, an interleukin converting enzyme (ICE) inhibitor

M H Chen; O P Goel; J W Hyun; J Magano; J R Rubin

doi:10.1016/s0960-894x(99)00236-x

An efficient stereoselective synthesis of [3S(1S,9S)]-3-[[[9-(benzoylamino) octahydro-6,10-dioxo-6H-pyridazino-(1,2-a)(1,2)-diazepin-1-yl]-carbonyl ]amino]-4-oxobutanoic acid, an interleukin converting enzyme (ICE) inhibitor

Bioorg Med Chem Lett. 1999 Jun 7;9(11):1587-92. doi: 10.1016/s0960-894x(99)00236-x.

Authors

M H Chen¹, O P Goel, J W Hyun, J Magano, J R Rubin

Affiliation

¹ Parke-Davis Pharmaceutical Research Division, Warner-Lambert Company, Ann Arbor, MI 48105, USA.

PMID: 10386941
DOI: 10.1016/s0960-894x(99)00236-x

Abstract

The title compound 1 is a potent interleukin-1beta-converting enzyme (ICE) inhibitor. Recently, an efficient chiral synthesis of compound 1 has been accomplished in our labs. The overall yield of this 18-step stereoselective synthesis was 9.8%.

MeSH terms

Azepines / chemical synthesis*
Butyrates / chemical synthesis*
Models, Chemical
Models, Molecular
Oxaloacetates*
Oxaloacetic Acid / chemical synthesis
Pyridazines / chemical synthesis
Serpins / chemical synthesis*
Viral Proteins*

Substances

Azepines
Butyrates
Oxaloacetates
PD 194035
Pyridazines
Serpins
Viral Proteins
Oxaloacetic Acid
piperazic acid
interleukin-1beta-converting enzyme inhibitor