Intramolecular 1,3-dipolar cycloaddition as a route to triazolobenzodiazepines and pyrrolobenzodiazepines

被引：23

作者：

Chambers, Christopher S. ^{[1
]}

Patel, Nilesh ^{[1
]}

Hemming, Karl ^{[1
]}

机构：

[1] Univ Huddersfield, Dept Chem & Biol Sci, Huddersfield HD1 3DH, W Yorkshire, England

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 37期

基金：

英国工程与自然科学研究理事会;

关键词：

Benzodiazepine; Benzothiadiazepine; Pyrrolobenzodiazepine; Alkyne; Azide; 1,3-Dipolar cycloaddition; SULFONAMIDE ANALOGS; AZIDE; DERIVATIVES; FLUMAZENIL; 1,2,5-BENZOTHIADIAZEPINE; BENZOTHIADIAZEPINES; BENZODIAZEPINES; DESIGN; PBTDS;

D O I：

10.1016/j.tetlet.2010.07.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular 1,3-dipolar cycloaddition between an alkyne and an azide leads to a series of 1,2,3-triazolo-fused 1,4-benzodiazepines,1,2,5-benzothiadiazepines, pyrrolobenzodiazepines and pyrrolobenzothiadiazepines (eight examples). The products are privileged structures in medicinal chemistry. The precursor azido alkynes are obtained, usually as transient intermediates, by treatment of the corresponding aldehydes (derived from a-amino acids) with the Bestmann-Ohira reagent. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4859 / 4861

页数：3

共 35 条

[11] Pyrrolo[2,1-c][1,4]benzodiazepine as a Scaffold for the Design and Synthesis of Anti-Tumour Drugs [J].

Cipolla, Laura ;

Araujo, Ana C. ;

Airoldi, Cristina ;

Bini, Davide .

ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2009, 9 (01) :1-31

[12] 1,2,5-Benzothiadiazepine and pyrrolo[2,1-d][1,2,5]benzothiadiazepine derivatives with specific anti-human immunodeficiency virus type 1 activity [J].

Di Santo, R ;

Costi, R ;

Artico, M ;

Massa, S ;

Marongiu, ME ;

Loi, AG ;

De Montis, A ;

La Colla, P .

ANTIVIRAL CHEMISTRY & CHEMOTHERAPY, 1998, 9 (02) :127-137

[13] A concise and efficient synthesis of flumazenil and its precursor for radiolabeling with fluorine-18 [J].

Donohue, Sean R. ;

Dannals, Robert F. .

TETRAHEDRON LETTERS, 2009, 50 (52) :7271-7273

[14]

Ghosh AK, 2003, EUR J ORG CHEM, V2003, P821, DOI 10.1002/ejoc.200390125

[15] Synthesis of a benzodiazepine-derived rhodium NHC complex by C-H bond activation [J].

Gribble, Michael W., Jr. ;

Ellman, Jonathan A. ;

Bergman, Robert G. .

ORGANOMETALLICS, 2008, 27 (10) :2152-2155

[16] SYNTHESIS AND EVALUATION OF IMIDAZO[1,5-A][1,4]BENZODIAZEPINE ESTERS WITH HIGH AFFINITIES AND SELECTIVITIES AT DIAZEPAM-INSENSITIVE BENZODIAZEPINE RECEPTORS [J].

GU, ZQ ;

WONG, G ;

DOMINGUEZ, C ;

DECOSTA, BR ;

RICE, KC ;

SKOLNICK, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (08) :1001-1006

[17]

Hemming K, 2005, J CHEM RES-S, P1

[18] The synthesis of pyrrolo[1,2-b][1,2,5]benzothiadiazepines from 1,2-thiazine 1-oxides -: sulfonamide analogues of the pyrrolobenzodiazepine antitumour natural products [J].

Hemming, K ;

Patel, N .

TETRAHEDRON LETTERS, 2004, 45 (41) :7553-7556

[19] The synthesis of bicyclic 1,2,3,4-tetrahydro-1,4-benzodiazepin-5-ones from 2-(o-nitrobenzoyl)-1,2-thiazine-1-oxide precursors [J].

Hemming, K ;

Loukou, C .

TETRAHEDRON, 2004, 60 (15) :3349-3357

[20]

HUNKELER W, 1993, CHIMIA, V47, P141

← 1 2 3 4 →