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

被引：17

作者：

Zhang, Ning ^{[1
]}

Zhang, Peng ^{[1
]}

Baier, Andrea ^{[2
]}

Cova, Lucyna ^{[3
]}

Hosmane, Ramachandra S. ^{[1
]}

机构：

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

[2] John Paul II Catholic Univ Lublin, Dept Mol Biol, Lublin, Poland

[3] INSERM, U871, F-69003 Lyon 03, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 04期

基金：

美国国家卫生研究院;

关键词：

Ring-expanded nucleosides; Imidazo[4,5-e][1,3] diazepines; Organic synthesis; Antiviral compounds; In vitro screening; Hepatitis C virus (HCV); Human immunodeficiency virus (HIV); Dual inhibitors of HCV and HIV; Inhibition of HCV NTPase/helicase; Inhibition of RNA helicase DDX3; HEPATITIS-C VIRUS; HUMAN-IMMUNODEFICIENCY-VIRUS; WEST-NILE VIRUS; INFECTED PATIENTS; HIV/HCV COINFECTION; FAT NUCLEOSIDE; LIVER FIBROSIS; RNA HELICASE; INTERFERON; UPDATE;

D O I：

10.1016/j.bmcl.2013.12.121

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Examples of ring-expanded nucleosides (RENs), represented by general structures 1 and 2, exhibited dual anti-HCV and anti-HIV activities in both cell culture systems and the respective target enzyme assays, including HCV NTPase/helicase and human RNA helicase DDX3. Since HCV is a leading co-infection in late stage HIV AIDS patients, often leading to liver cirrhosis and death, the observed dual inhibition of HCV and HIV by the target nucleoside analogues has potentially beneficial implications in treating HIV patients infected with HCV. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1154 / 1157

页数：4

共 41 条

[21] A novel, broad-spectrum anticancer compound containing the imidazo[4,5-e][1,3]diazepine ring system
Xie, Min
Ujjinamatada, Ravi K.
Sadowska, Mariola
Lapidus, Rena G.
Edelman, Martin J.
Hosmane, Ramachandra S.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (15) : 4386 - 4389
[22] Synthesis and in vitro anti-hepatitis B and C virus activities of ring-expanded ('fat') nucleobase analogues containing the imidazo[4,5-e][1,3]diazepine-4,8-dione ring system
Zhang, P
Zhang, N
Korba, BE
Hosmane, RS
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (24) : 5397 - 5401
[23] 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
[24] 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
[25] SYNTHESIS OF RING EXPANDED XANTHINES AND XANTHOSINES CONTAINING THE IMIDAZO[4,5-D][1,3]DIAZEPINE RING-SYSTEM
HOSMANE, RS
VAIDYA, VP
CHUNG, MK
SIRIWARDANE, U
ZHANG, HM
HOSMANE, NS
NUCLEOSIDES & NUCLEOTIDES, 1991, 10 (08): : 1693 - 1706
[26] 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
LIM, BB
HOSMANE, RS
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 200 : 324 - ORGN
[27] Synthesis of a novel ring-expanded nucleoside analogue containing the imidazo[4,5-e][1,3]diazepine ring system with a guanidinocarbamoyl-substituted cyclopropylidene group in place of a sugar moiety (vol 37, pg 951, 2000)
Chen, HM
Hosmane, RS
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (06) : 1469 - 1469
[28] Chemical and biological effects of substitution of the 2-position of ring-expanded ('fat') nucleosides containing the imidazo[4,5-e][1,3]diazepine-4,8-dione ring system:: The role of electronic and steric factors on glycosidic bond stability and anti-HCV activity
Zhang, Peng
Zhang, Ning
Buckwold, Victor E.
Hosmane, Ramachandra S.
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (14) : 4933 - 4945
[29] STUDIES ON FAT NUCLEOSIDES AND NUCLEOTIDES, CONTINUED - SYNTHETIC, STRUCTURAL, AND CONFORMATIONAL INVESTIGATIONS OF SEVERAL RING EXPANDED XANTHINE, XANTHOSINE, AND XANTHYLIC ACID ANALOGS, CONTAINING THE NOVEL IMIDAZO[4,5-E][1,4]DIAZEPINE AND IMIDAZO[4,5-D][1,3]DIAZEPINE RING-SYSTEMS
BHAN, A
VAIDYA, VP
HOSMANE, RS
CHUNG, MK
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 200 : 43 - ORGN
[30] Synthesis and guanase inhibition studies of a novel ring-expanded purine analogue containing a 5:7-fused, planar, aromatic heterocyclic ring system
Rajappan, V
Hosmane, RS
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (24) : 3649 - 3652

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