Synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines by employing polymer-supported reagents:: Preparation of DC-81

被引：29

作者：

Kamal, A ^{[1
]}

Reddy, KL ^{[1
]}

Devaiah, V ^{[1
]}

Shankaraiah, N ^{[1
]}

机构：

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

来源：

SYNLETT | 2004年 / 14期

关键词：

polymer-supported reagents; combinatorial library; pyrrolo[2.1-c][1.4] benzodiazepines;

D O I：

10.1055/s-2004-834821

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polymer-supported reagents have been utilized for the generation of combinatorial library of substituted pyrrolo[2,1-c][1.4]benzodiazepine derivatives that provides a clean and efficient preparation and does not require conventional purification techniques like chromatography. This methodology involves intra molecular azn-Wittig reaction and has been extended for the synthesis of the natural product DC-81 in good overall yields.

引用

页码：2533 / 2536

页数：4

共 44 条

[1]

Baxendale IR, 2002, ANGEW CHEM INT EDIT, V41, P2194, DOI 10.1002/1521-3773(20020617)41:12<2194::AID-ANIE2194>3.0.CO

[2]

2-4

[3]

Baxendale IR, 2001, SYNLETT, P1482

[4] Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents [J].

Caldarelli, M ;

Habermann, J ;

Ley, SV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (02) :107-110

[5]

CARABATEAS PM, 1973, Patent No. 3732212

[6] Linker length modulates DNA cross-linking reactivity and cytotoxic potency of C8/C8′ ether-linked C2-exo-unsaturated pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimers [J].

Gregson, SJ ;

Howard, PW ;

Gullick, DR ;

Hamaguchi, A ;

Corcoran, KE ;

Brooks, NA ;

Hartley, JA ;

Jenkins, TC ;

Patel, S ;

Guille, MJ ;

Thurston, DE .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (05) :1161-1174

[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]

Grieder A, 2003, SYNTHESIS-STUTTGART, P1707

[9] Polymer supported perruthenate (PSP): A new oxidant for clean organic synthesis [J].

Hinzen, B ;

Ley, SV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (13) :1907-1908

[10] 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

← 1 2 3 4 5 →