Synthesis and HPLC-Analysis of N-(2-Phenyl-cyclopropyl)-Substituted Chain Elongated Nucleoside Analogues

Abstract

A novel class of nucleoside analogues containing adenine, uracil, thymine and 5-fluorouracil as the heterocyclic moieties have been prepared from 2-phenylcyclopropane carboxylic acid. These compounds showed weak antitum or activity. The resolution of the racemates on an analytical and semipreparative scale was perform ed by HPLC using chiral stationary phases.

General and Efficient α‐Oxygenation of Carbonyl Compounds by TEMPO Induced by Single‐Electron‐Transfer Oxidation of Their Enolates

“…(2‐Phenylcyclopropyl)acetic acid was prepared according to the literature 32. The analytical data are in agreement with those published previously.…”

“…They were synthesized in a straightforward manner by a Simmons–Smith cyclopropanation of cinnamic alcohol ( 20 ),30 followed by the bromination of 21 31. Kolbe nitrile synthesis furnished 22 ,32 which was transformed by hydrolysis and alkylation into (2‐phenylcyclopropyl)acetate 23 in good overall yield. The oxygenation of 23 indeed exclusively provided ring‐opened products 24 and 25 .…”

Enantioselective Gas Chromatographic Analysis of Cyclopropane Derivatives

“…Naturally-occurring and synthetic cyclopropanes bearing simple functionalities are endowed with a large spectrum of biological properties ranging from enzyme inhibitions to insecticidal, antifungal, herbicidal, antimicrobial, antibiotic, antibacterial, antitumor and antiviral activities [1,2]. Thus, they constitute a common structure motif in pyrethroids [3], the antidepressant tranylcyclopromine [4], papain and cystein protease inhibitors [5], the potential anti-psychotic substances [6], anti-HIV agents [7,8], and marine lactones [9]. Accordingly, a great deal of effort has been developed over the last two decades to make the stereo-controlled synthesis of substituted cyclopropanes more appealing to organic chemists [10][11][12][13].…”

Rhodium(II)-Catalyzed Inter- and Intramolecular Cyclopropanations with Diazo Compounds and Phenyliodonium Ylides: Synthesis and Chiral Analysis

“…Naturally occurring and synthetic cyclopropanes bearing simple or complex functionalities are endowed with a large spectrum of biological properties ranging from enzyme inhibitions to insecticidal, antifungal, herbicidal, antimicrobial, antibiotic, antibacterial, antitumor, and antiviral activities [1]. Thus, they constitute a common structural motif in pyrethroids [2], the antidepressant tranylcyclopromine [3], papain and cystein protease inhibitors [4], potentially antipsychotic substances [5], anti-HIV agents [6], and marine lactones [7]. Accordingly, a great deal of effort has been developed over the last two decades to make the stereochemically controlled synthesis of substituted cyclopropanes more appealing to organic chemists [8].…”