Anti-malarial activity of N6-substituted adenosine derivatives.: Part I

被引：31

作者：

Golisade, A

Wiesner, J

Herforth, C

Jomaa, H

Link, A

机构：

[1] Univ Hamburg, Inst Pharm, D-20146 Hamburg, Germany

[2] Jomaa Pharmaka GmbH, D-35392 Giessen, Germany

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2002年 / 10卷 / 03期

关键词：

D O I：

10.1016/S0968-0896(01)00331-5

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis and biological evaluation of novel N-6-substituted adenosine derivatives is reported. The first series of compounds was obtained using an established procedure for the nucleophilic substitution of a 1-(6-chloro-purin-9-yl)-beta-D-1-deoxyribofuranose with various amines. In addition, attachment of two different amino-functionalised spacer arms at the N-6-position of adenosine enabled derivatisation by an innovative polymer-assisted protocol. Thus, we were able to prepare three series of substituted derivatives that displayed activity versus the multiresistant Plasmodium falciparum strain Dd2 in cell culture experiments. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：769 / 777

页数：9

相关论文

共 18 条

[1] Antimalarial activity of 77 phospholipid polar head analogs:: Close correlation between inhibition of phospholipid metabolism and in vitro Plasmodium falciparum growth [J].

Ancelin, ML ;

Calas, M ;

Bompart, J ;

Cordina, G ;

Martin, D ;

Ben Bari, M ;

Jei, T ;

Druilhe, P ;

Vial, HJ .

BLOOD, 1998, 91 (04) :1426-1437

[2] DOUBLY AND TRIPLY BRIDGED POLYOXAPOLYAZAHETEROPHANES DERIVED FROM 2,4,6-TRICHLORO-S-TRIAZINE [J].

ANELLI, PL ;

LUNAZZI, L ;

MONTANARI, F ;

QUICI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) :4197-4203

[3] Activation method to prepare a highly reactive acylsulfonamide ''safety-catch'' linker for solid-phase synthesis [J].

Backes, BJ ;

Virgilio, AA ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :3055-3056

[4] An alkanesulfonamide "safety-catch" linker for solid-phase synthesis [J].

Backes, BJ ;

Ellman, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2322-2330

[5] Isolation and functional characterization of the PfNT1 nucleoside transporter gene from Plasmodium falciparum [J].

Carter, NS ;

Ben Mamoun, C ;

Liu, W ;

Silva, EO ;

Landfear, SM ;

Goldberg, DE ;

Ullman, B .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (14) :10683-10691

[6] The first preparation of α-functionalized benzylamine [J].

Cho, SD ;

Kim, HJ ;

Ahn, CJ ;

Falck, JR ;

Shin, DS .

TETRAHEDRON LETTERS, 1999, 40 (47) :8215-8217

[7] QUANTITATIVE ASSESSMENT OF ANTI-MALARIAL ACTIVITY INVITRO BY A SEMIAUTOMATED MICRODILUTION TECHNIQUE [J].

DESJARDINS, RE ;

CANFIELD, CJ ;

HAYNES, JD ;

CHULAY, JD .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 16 (06) :710-718

[8] Polymer-assisted solution-phase synthesis of 2′-amido-2′-deoxyadenosine derivatives targeted at the NAD+-binding sites of parasite enzymes [J].

Golisade, A ;

Bressi, JC ;

Van Calenbergh, S ;

Gelb, MH ;

Link, A .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (05) :537-544

[9] SAFETY CATCH PRINCIPLE IN SOLID PHASE PEPTIDE SYNTHESIS [J].

KENNER, GW ;

MCDERMOT.JR ;

SHEPPARD, RC .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (12) :636-&

[10]

Kirschning A, 2001, ANGEW CHEM INT EDIT, V40, P650, DOI 10.1002/1521-3773(20010216)40:4<650::AID-ANIE6500>3.0.CO