Facile and efficient solid-phase synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines

被引：19

作者：

Kamal, A ^{[1
]}

Reddy, KL ^{[1
]}

Devaiah, V ^{[1
]}

Shankaraiah, N ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Biotransformat Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNLETT | 2004年 / 10期

关键词：

pyrrolo[2,1-c][1,4]benzodiazepines; solid-phase synthesis; chloromethyl Wang resin; isatoic anhydrides;

D O I：

10.1055/s-2004-829096

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The solid-phase synthesis of pyrrolo[2,1-c] [1,4]benzodiazepines is described. Isatoic anhydrides attached to chloromethyl Wang resin are coupled with proline and the polymer-bound tricyclic compounds are reduced using very mild conditions, and successively cleaved from the resin to afford the desired imine-containing heterocyclic compounds. Reactions were monitored by FT-IR spectroscopy on the resin beads.

引用

收藏

页码：1841 / 1843

页数：3

相关论文

共 25 条

[1] Solid-phase synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines [J].

Berry, JM ;

Howard, PW ;

Thurston, DE .

TETRAHEDRON LETTERS, 2000, 41 (32) :6171-6174

[2] Traceless solid-phase organic synthesis [J].

Blaney, P ;

Grigg, R ;

Sridharan, V .

CHEMICAL REVIEWS, 2002, 102 (07) :2607-2624

[3] Solid-phase organic reactions III: A review of the literature Nov 96 Dec 97 [J].

Booth, S ;

Hermkens, PHH ;

Ottenheijm, HCJ ;

Rees, DC .

TETRAHEDRON, 1998, 54 (51) :15385-15443

[4]

CARABATEAS PM, 1973, Patent No. 3732212

[5] Recent advances in the preparation of heterocycles on solid support:: A review of the literature [J].

Franzén, RG .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (03) :195-214

[6] APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .2. COMBINATORIAL ORGANIC-SYNTHESIS, LIBRARY SCREENING STRATEGIES, AND FUTURE-DIRECTIONS [J].

GORDON, EM ;

BARRETT, RW ;

DOWER, WJ ;

FODOR, SPA ;

GALLOP, MA .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (10) :1385-1401

[7] Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity [J].

Gregson, SJ ;

Howard, PW ;

Hartley, JA ;

Brooks, NA ;

Adams, LJ ;

Jenkins, TC ;

Kelland, LR ;

Thurston, DE .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (05) :737-748

[8] An efficient synthesis of pyrrolo[2,1-c][1,4]benzodiazepine.: Synthesis of the antibiotic DC-81 [J].

Hu, WP ;

Wang, JJ ;

Lin, FL ;

Lin, YC ;

Lin, SR ;

Hsu, MH .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2881-2883

[9]

JUNG G, 1998, COMBINATORIAL CHEM

[10]

Kamal A, 1999, SYNLETT, P1251