Affiliation:
1. Heilongjiang Provincial Key Laboratory of Drug Prevention and Treatment for Senile Diseases, College of Pharmacy, Harbin University of Commerce, Harbin 150076, China
2. College of Pharmacy, Chosun University, Kwangju 501-759, Korea
Abstract
The syntheses of acyclic nucleoside phosphonate (ANP) analogs linked with cyclic systems
are described in the present review. The purpose of the review is to report the methodology of
ANP analogs and to give an idea on the synthesis of a therapeutic structural feature of such analogs.
The cyclopropane systems were mainly prepared by diazomethane cyclopropanation catalyzed by
Pd(OAc)2, intramolecular alkylation, Kulinkovich cyclopropanation, and use of difluorocyclopropane,
and so forth. The preparation of methylenecyclopropane system was made by diazoacetate
cyclopropanation catalyzed by Rhodium followed by addition-elimination reactions. For the preparation
of a variety of tethered 1,2,3-triazole systems, 1,3-dipolar cycloaddition between azidealkylphosphonates
and propargylated nucleobases was mainly applied. The formation of various
phosphonate moieties was achieved via phosphonylation of alkoxide, cross-coupling between
BrZnCF2P (O)(OEt)2 with iodoalkens catalyzed by CuBr, Michaelis-Arbuzov reaction with phosphite,
and Rh(II)-catalyzed O-H insertion, and so forth.
Publisher
Bentham Science Publishers Ltd.
Subject
Pharmacology,Molecular Medicine,Drug Discovery,Biochemistry,Organic Chemistry