Bioorganic & Medicinal Chemistry Letters 2008-11-01

Piperidine dispiro-1,2,4-trioxane analogues.

Sunil Sabbani, Paul A Stocks, Gemma L Ellis, Jill Davies, Erik Hedenstrom, Stephen A Ward, Paul M O'Neill

Index: Bioorg. Med. Chem. Lett. 18(21) , 5804-8, (2008)

Full Text: HTML

Abstract

Dispiro N-Boc-protected 1,2,4-trioxane 2 was synthesised via Mo(acac)(2) catalysed perhydrolysis of N-Boc spirooxirane followed by condensation of the resulting beta-hydroperoxy alcohol 10 with 2-adamantanone. N-Boc 1,2,4-trioxane 2 was converted to the amine 1,2,4-trioxane hydrochloride salt 3 which was subsequently used to prepare derivatives (4-7). Several of these novel 1,2,4-trioxanes had nanomolar antimalarial activity versus the 3D7 strain of Plasmodium falciparum. Amine intermediate 3 represents a versatile derivative for the preparation of achiral arrays of trioxane analogues with antimalarial activity.

Related Compounds

  • adamantanone

Related Articles:

Effect of adamantanone derivative possessing anti-HIV properties on the redox processes in the cytochrome P-450 system.

2001-01-01

[Dokl. Biochem. Biophys. 378 , 210-3, (2001)]

Conformational relaxation in hemoproteins: the cytochrome P-450cam case.

2000-11-21

[Biochemistry 39(46) , 14219-31, (2000)]

The structural basis for substrate-induced changes in redox potential and spin equilibrium in cytochrome P-450CAM.

1989-01-24

[Biochemistry 28(2) , 917-22, (1989)]

(+/-)-1-(Adamantan-2-yl)-2-propanamine and other amines derived from 2-adamantanone.

1980-05-01

[Farmaco. Sci. 35(5) , 430-40, (1980)]

Synthesis of a silene from 1,1-dilithiosilole and 2-adamantanone.

2004-05-05

[J. Am. Chem. Soc. 126(17) , 5336-7, (2004)]

More Articles...