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Isotope labeled ‘HEA/HEE’ moiety in the synthesis of labeled HIV‐protease inhibitors—Part II
Author(s) -
Ekhato I. Victor,
Liao Yuan,
Plesescu Mihaela
Publication year - 2005
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.913
Subject(s) - indinavir , chemistry , amprenavir , saquinavir , moiety , protease , protease inhibitor (pharmacology) , darunavir , enzyme , stereochemistry , human immunodeficiency virus (hiv) , organic chemistry , hiv 1 protease , sida , virology , antiretroviral therapy , viral load , biology , viral disease
[ 2 H 5 ]‐Amprenavir and [ 2 H 5 ]‐saquinavir have been prepared from a common labeled precursor (1S, 2S)‐(1‐oxiranyl‐2‐[ 2 H 5 ]phenylethyl)‐carbamic acid tert‐ butyl ester, 1 . Both of these compounds are in the ‘HEA’ class of HIV protease inhibitors. [ 2 H 5 ]‐Indinavir, a representative of the ‘HEE’ group of protease inhibitors, has also been synthesized. In the case of indinavir, 1S‐(2,2‐dimethyl‐8, 8a‐dihydro‐3aH‐indeno‐[1,2‐d]‐oxazol‐3R‐yl)‐2‐oxiranylmethyl‐3‐[ 2 H 5 ]phenylpropan‐1‐one, 11 , provided the [phenyl‐ 2 H 5 ]‐HEE core structure for synthesis of the desired labeled compound. Copyright © 2005 John Wiley & Sons, Ltd.