Novel deoxy-selenylconduritols: chemoenzymatic synthesis and biological evaluation

被引：10

作者：

Bellomo, Ana ^{[1
]}

Bertucci, Ana ^{[2
]}

Stefani, Helio ^{[3
,4
]}

Vazquez, Alvaro ^{[2
]}

Gonzalez, David ^{[1
]}

机构：

[1] Univ Republica, UdelaR, Fac Quim, Lab Sintesis Organ, Montevideo, Uruguay

[2] Univ Republica, UdelaR, Fac Quim, Lab Farmacognosia & Prod Nat, Montevideo, Uruguay

[3] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo, Brazil

[4] Univ Fed Sao Paulo, Dept Biofis, Sao Paulo, Brazil

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 23期

基金：

巴西圣保罗研究基金会;

关键词：

EFFICIENT SYNTHESIS; (-)-CONDURITOL C; CONDURITOL; CYCLITOLS; SELENIUM; CONDURAMINE; DERIVATIVES; HYDROLYSIS; EPOXIDES; ANALOGS;

D O I：

10.1016/j.tetasy.2009.11.004

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first synthesis of two selenyldeoxycyclitols (4-bromo-2-phenylselenyl conduritol F and 6-phenylselenylconduritol F) is reported via a chemoenzymatic enantioselective route. The key step of the synthesis is the selenolysis of a vinyl epoxide. The new compounds were evaluated for their capacity to inhibit the growth of different microorganisms using a modification of the agar diffusion technique with thin layer chromatography plates as support. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2673 / 2676

页数：4

共 33 条

[11] Synthesis and biological evaluation of conduritol and conduramine analogs [J].

Desjardins, M ;

Lallemand, MC ;

Freeman, S ;

Hudlicky, T ;

Abboud, KA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (05) :621-628

[12] Cyclitols:: Conduritols and related compounds [J].

Gültekin, MS ;

Çelik, M ;

Balci, M .

CURRENT ORGANIC CHEMISTRY, 2004, 8 (13) :1159-1186

[13] STEREOCHEMISTRY OF [2,3]SIGMATROPIC REARRANGEMENTS [J].

HOFFMANN, RW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (08) :563-572

[14]

HOSTETTMAN K, 1994, PURE APPL CHEM, V66, P1234

[15]

Iwaoka M, 2000, TOP CURR CHEM, V208, P55

[16] Synthesis and in vitro anti-bacterial evaluation of tetracyclic-ortho-fused 4H-naphtho[1′,2′-5,6]pyrano[3,4-d](1,2,3)selenadiazole and its derivatives [J].

Karnik, A. V. ;

Kulkarni, A. M. ;

Malviya, N. J. ;

Mourya, B. R. ;

Jadhav, B. L. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (11) :2615-2617

[17] Synthesis of conduritol, conduramine, and validoxylamine analogs from tetrahydronaphthalene-cis-diol. [J].

Lallemand, MC ;

Desjardins, M ;

Freeman, S ;

Hudlicky, T .

TETRAHEDRON LETTERS, 1997, 38 (44) :7693-7696

[18] SYNTHESIS OF (-)-CONDURITOL C (1L-CYCLOHEX-5-ENE-1,2,3/4-TETROL) [J].

LEDRIAN, C ;

VIEIRA, E ;

VOGEL, P .

HELVETICA CHIMICA ACTA, 1989, 72 (02) :338-347

[19] Synthesis of enantiopure cyclitols from (±)-3-bromocyclohexene mediated by intramolecular oxyselenenylation employing (S,S)-hydrobenzoin and (S)-mandelic acid as chiral sources [J].

Lee, YJ ;

Lee, K ;

Jung, SI ;

Jeon, HB ;

Kim, KS .

TETRAHEDRON, 2005, 61 (08) :1987-2001

[20] GLYCOSIDE HYDROLASES - MECHANISTIC INFORMATION FROM STUDIES WITH REVERSIBLE AND IRREVERSIBLE INHIBITORS [J].

LEGLER, G .

ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1990, 48 :319-384

← 1 2 3 4 →