Nitrogen-containing polyhydroxylated aromatics as HIV-1 integrase inhibitors: synthesis, structure-activity relationship analysis, and biological activity

被引：5

作者：

Yu, Shenghui ^{[1
]}

Zhang, Linna ^{[2
]}

Yan, Shifeng ^{[1
]}

Wang, Peng ^{[1
]}

Sanchez, Tino ^{[3
]}

Christ, Frauke ^{[4
,5
]}

Debyser, Zeger ^{[4
,5
]}

Neamati, Nouri ^{[3
]}

Zhao, Guisen ^{[1
]}

机构：

[1] Shandong Univ, Sch Pharmaceut Sci, Dept Med Chem, Jinan 250012, Shandong, Peoples R China

[2] Shandong Univ, Qilu Hosp, Jinan 250012, Shandong, Peoples R China

[3] Univ So Calif, Sch Pharm, Dept Pharmacol & Pharmaceut Sci, Los Angeles, CA 90089 USA

[4] Dept Mol & Cellular Med IRC KULAK, Lab Mol Virol & Gene Therapy, Louvain, Flanders, Belgium

[5] KULeuven, Louvain, Flanders, Belgium

来源：

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY | 2012年 / 27卷 / 05期

基金：

中国国家自然科学基金;

关键词：

HIV-1; integrase inhibitors; polyhydroxylated aromatics; structure-activity relationship; REPLICATION; DERIVATIVES; UPDATE; ACID;

D O I：

10.3109/14756366.2011.604851

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Four series of forty-five nitrogen-containing polyhydroxylated aromatics based on caffeic acid phenethyl ester were designed and synthesized as HIV-1 integrase (IN) inhibitors. Most of these compounds inhibited IN catalytic activities in low micromolar range. Among these new analogues, compounds 9e and 9f were the most potent IN inhibitors with IC50 value of 0.7 mu M against strand transfer reaction. Their key structure-activity relationships were also discussed.

引用

页码：628 / 640

页数：13

共 50 条

[1] Amide-containing diketoacids as HIV-1 integrase inhibitors: Synthesis, structure-activity relationship analysis, and biological activity
Li, Hongcai
Wang, Chao
Sanchez, Tino
Tan, Yanmei
Jiang, Chunying
Neamati, Nouri
Zhao, Guisen
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (07) : 2913 - 2919
[2] Design and synthesis of novel nitrogen-containing polyhydroxylated aromatics as HIV-1 integrase inhibitors from caffeic acid phenethyl ester
Wang, Peng
Liu, Chuan
Sanches, Tino
Zhong, Yuan
Liu, Bo
Xiong, Junlong
Neamati, Nouri
Zhao, Guisen
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (16) : 4574 - 4578
[3] Design, synthesis and structure-activity relationship of HIV-1 integrase inhibitors.
Zhao, H
Neamati, N
Mazumder, A
Pommier, Y
Burke, TR
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 21 - MEDI
[4] Structure-activity relationship study of some inhibitors of HIV-1 integrase
Cyrillo, M
Galvao, DS
[J]. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 1999, 464 (1-3): : 267 - 272
[5] Structure-Activity Relationship Studies of HIV-1 Integrase Oligonucleotide Inhibitors
Agapkina, Julia
Zatsepin, Timofei
Knyazhanskaya, Ekaterina
Mouscadet, Jean-Francois
Gottikh, Marina
[J]. ACS MEDICINAL CHEMISTRY LETTERS, 2011, 2 (07): : 532 - 537
[6] Discovery and structure-activity relationship studies of a unique class of HIV-1 integrase inhibitors
Dayam, Raveendra
Sanchez, Tino
Neamati, Nouri
[J]. CHEMMEDCHEM, 2006, 1 (02) : 238 - 244
[7] Synthesis of polyhydroxylated aromatics having amidation of piperazine nitrogen as HIV-1 integrase inhibitor
Yang, Leifu
Xu, Xuemei
Huang, Yali
Zhang, Bin
Zeng, Chengchu
He, Hongqiu
Wang, Cunxin
Hu, Liming
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (18) : 5469 - 5471
[8] Structure activity relationship of disulfone-containing HIV-1 integrase inhibitors.
Meadows, DC
Gervay-Hague, J
Matthews, TB
North, TW
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U169 - U169
[9] Design, Synthesis and Structure-activity Studies of Rhodanine Derivatives as HIV-1 Integrase Inhibitors
Ramkumar, Kavya
Yarovenko, Vladimir N.
Nikitina, Alexandra S.
Zavarzin, Igor V.
Krayushkin, Mikhail M.
Kovalenko, Leonid V.
Esqueda, Adrian
Odde, Srinivas
Neamati, Nouri
[J]. MOLECULES, 2010, 15 (06) : 3958 - 3992
[10] Quantitative structure-activity relationships of HIV-1 integrase inhibitors of DKAs
Shi Ya-Wei
Liu Zhen-Ming
Jin Hong-Wei
Zhang Liang-Ren
Zhang Li-He
[J]. ACTA PHYSICO-CHIMICA SINICA, 2007, 23 (09) : 1393 - 1398

← 1 2 3 4 5 →