Synthesis and guanase inhibition studies of a novel ring-expanded purine analogue containing a 5:7-fused, planar, aromatic heterocyclic ring system

被引：11

作者：

Rajappan, V ^{[1
]}

Hosmane, RS ^{[1
]}

机构：

[1] Univ Maryland Baltimore Cty, Dept Chem & Biochem, Lab Drug Design & Synth, Baltimore, MD 21250 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1998年 / 8卷 / 24期

关键词：

D O I：

10.1016/S0960-894X(98)00672-6

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis of a novel planar, potentially aromatic, ring-expanded xanthine analogue (1), containing the 5:7-fused imidazo[4,5-e][1,4]diazepine ring system, along with guanase inhibition studies are reported. The compound was synthesized in six steps, starting from 1-benzyl-5-nitroimidazole-4-carboxylic acid (2), and was biochemically screened against rabbit liver guanase. Compound 1 is a moderate competitive inhibitor of the enzyme with a K-i of 2.27 +/- 0.66 x 10(-4) M. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3649 / 3652

页数：4

共 31 条

[1] An efficient, short synthesis and potent anti-hepatitis B viral activity of a novel ring-expanded purine nucleoside analogue containing a 5:7-fused, planar, aromatic, imidazo [4,5-E][1,3]diazepine ring system
Chen, HM
Sood, R
Hosmane, RS
NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (03): : 331 - 335
[2] THE SYNTHESIS OF NOVEL REGIOISOMERIC RING-EXPANDED XANTHINE NUCLEOSIDES CONTAINING THE 5/7-FUSED IMIDAZO[4,5-E][1,2,4]TRIAZEPINE RING-SYSTEM
BHADTI, VS
BHAN, A
HOSMANE, RS
HULCE, M
NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (06): : 1137 - 1149
[3] Synthesis and potent anticancer activity of a series of ring-expanded heterocyclic bases, nuleosides, and nucleotides containing the 5:7-fused imidazo[4,5-e][1,3]diazepine ring system
Xie, Min
Hosmane, Ramachandra S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[4] Synthesis of ring-expanded heterocyclic bases, nucleosides, and nucleotides containing the 5:7-fused imidazo[4,5-e][1,4]diazepine ring system as potential antiviral compounds against flaviviridae
Shukla, Brahmi
Hosmane, Ramachandra
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[5] Synthesis of a novel ring-expanded purine analogue containing a 5:8-fused imidazo[4,5-e][1,2,4]triazocine ring system amidst opportunistic rearrangements and ring transformations
Burnett, FN
Hosmane, RS
TETRAHEDRON, 2002, 58 (47) : 9567 - 9578
[6] Synthesis and biological activity of a series of ring-expanded heterocyclic bases containing the 5:7-fused imidazo[4,5-e][1,3]diazepine ring system as potent anti-cancer agents
Xie, Min
Ramanchandra, Hosmane S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[7] Dual inhibition of HCV and HIV by ring-expanded nucleosides containing the 5: 7-fused imidazo[4,5-e][1,3] diazepine ring system. In vitro results and implications
Zhang, Ning
Zhang, Peng
Baier, Andrea
Cova, Lucyna
Hosmane, Ramachandra S.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (04) : 1154 - 1157
[8] THE SYNTHESIS AND BIOPHYSICAL INVESTIGATIONS OF NOVEL RING-EXPANDED NUCLEOSIDES, NUCLEOTIDES, AND HOMOPOLYMERS CONTAINING THE 5-7-FUSED HETEROCYCLIC RING-SYSTEM IMIDAZO[4,5-E][1,4]DIAZEPINE
HOSMANE, RS
BHAN, A
KARPEL, RL
SIRIWARDANE, U
HOSMANE, NS
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23): : 5882 - 5890
[9] Synthesis of a novel ring-expanded ("fat") nucleotide analogue of phosphonomethoxyethylguanine (PMEG) containing the imidazo[4,5-e][1,3]diazepine ring system
Chen, HM
Hosmane, RS
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (06) : 1313 - 1315
[10] SYNTHESIS OF A NOVEL RING-EXPANDED XANTHINE ANALOG AND SEVERAL METHYL OR BENZYL DERIVATIVES CONTAINING THE 5-7-FUSED IMIDAZO[4,5-E][1,2,4]TRIAZEPINE RING-SYSTEM
HOSMANE, RS
BHADTI, VS
LIM, BB
SYNTHESIS-STUTTGART, 1990, (11): : 1095 - 1100

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