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

[21] FAT NUCLEOSIDES AND NUCLEOTIDES, CONTINUED - SYNTHESIS OF SEVERAL RING-EXPANDED XANTHINE AND XANTHOSINE ANALOGS CONTAINING THE NOVEL IMIDAZO[4,5-E][1,2,4] TRIAZEPINE RING-SYSTEM
BHADTI, VS
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HOSMANE, RS
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 200 : 324 - ORGN
[22] Synthesis of a novel heterocyclic ring system:: 2-thia-3,5,6,7,9-pentaazabenz[cd]azulenes
Tumkevicius, S
Agrofoglio, LA
Kaminskas, A
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TETRAHEDRON LETTERS, 2002, 43 (04) : 695 - 697
[23] Synthesis of a novel ring-expanded nucleoside analog containing the imidazo[4,5-e][1,3]diazepine ring system with a guanidinocarbamoyl-substituted cyclopropylidene group in place of a sugar moiety.
Chen, HM
Hosmane, RS
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U61 - U61
[24] THE SYNTHESIS OF SUBSTITUTED IMIDAZO[4,5-D]ISOTHIAZOLES VIA THE RING ANNULATION OF ISOTHIAZOLE DIAMINES - AN INVESTIGATION OF THE CHEMICAL, PHYSICAL, AND BIOLOGICAL PROPERTIES OF SEVERAL NOVEL 5/5 FUSED ANALOGS OF THE PURINE RING-SYSTEM
SWAYZE, EE
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JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) : 6309 - 6317
[25] A unique ring-expanded acyclic nucleoside analogue that inhibits both adenosine deaminase (ADA) and guanine deaminase (GDA; guanase):: Synthesis and enzyme inhibition studies of 4,6-diamino-8H-1-hydroxyethoxymethyl-8-iminoimidazo[4,5-e][1,3]diazepine
Wang, LJ
Hosmane, RS
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (22) : 2893 - 2896
[26] THE SYNTHESIS OF THE NOVEL HETEROCYCLIC RING-SYSTEM NAPHTHO[1',2'-4,5]THIENO[3,2-A][4,7]PHENANTHROLINE
MUSMAR, MJ
ZEKTZER, AS
CASTLE, RN
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 59 - ORGN
[27] Inhibition of adenosine deaminase by novel 5:7 fused heterocycles containing the imidazo[4,5-e][1,2,4]triazepine ring system:: A structure-activity relationship study
Reayi, A
Hosmane, RS
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (04) : 1044 - 1050
[28] SYNTHESIS OF 1,1'-DIBENZYL-5,5'-7,7'-BIS(HEXANO)BIS[6(1H)-CYCLOHEPTATRIAZOLONE], A NOVEL HETEROCYCLIC RING-SYSTEM
ABUORABI, ST
HARMON, RE
JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1986, 31 (04) : 504 - 505
[29] SYNTHETIC APPROACHES TO 5/8-FUSED HETEROCYCLIC-SYSTEMS - A NOVEL REARRANGEMENT DURING THE SYNTHESIS OF IMIDAZO[4,5-E][L,2,4]TRIAZOCINE RING-SYSTEM
BURNETT, FN
HOSMANE, RS
NUCLEOSIDES & NUCLEOTIDES, 1995, 14 (3-5): : 325 - 328
[30] Synthesis of a novel purine-containing heterocyclic ring system:: 8,10-dimethylindolo[2′,3′:5,6][1,2,4]triazino[4,3-f]purine-9,11(8H,10H,13H)-dione
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Primofiore, G
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JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (02) : 373 - 377

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