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Synthetic Studies of Bioactive Marine Alkaloids Based on Nitroso-Ene Reaction

Research Project

Project/Area Number 13672232
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionTokyo University of Pharmacy & Life Science

Principal Investigator

AOYAGI Sakae  Tokyo University of Pharmacy & Life Science School of Pharmacy, associate professor, 薬学部, 助教授 (30212385)

Project Period (FY) 2001 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 2002: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 2001: ¥1,600,000 (Direct Cost: ¥1,600,000)
Keywordsmarine alkaloids / halichlorine / pinnaic acid / acylnitroso compounds / ene reaction / ピンナ酸類
Research Abstract

Halichlorine and pinnaic acid are novel marine natural products isolated from the marine sponge and the Okinawan bivalve, respectively. Halichlorine is shown to inhibit the induction of VCAM-1 (vascular cell adhension molecule-1), a potent target for the treatment and coronary heart disease. Pinnaic acid is an inhibitor of phospholipase A2 that has potential for treatment of inflammatory disease. The investigator has developed the synthesis of the spirocyclic core of halichlorine and pinnaic acid. The key steps in the synthetic approach are the preparation of the unique azaspiro[4.5]decan skeleton through the application of the intramolecular enereacton of the N-acylnitroso compound, stereoselective introduction of the tert-butyldimethylsilyloxy)ethyl moiety to the 7-position of the azaspiro[4.5]decan skeleton through a stereoselective introduction of the ethynyl group, and construction of the 2-hydroxy-1-methylethyl moiety onto the 1-position

Report

(3 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report

URL: 

Published: 2001-04-01   Modified: 2016-04-21  

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