Synthesis and Biological Evaluation of Aryl-phospho-indole as Novel HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors

被引：164

作者：

Alexandre, Francois-Rene ^{[1
]}

Amador, Agnes ^{[1
]}

Bot, Stephanie ^{[1
]}

Caillet, Catherine ^{[1
]}

Convard, Thierry ^{[1
]}

Jakubik, Jocelyn ^{[3
]}

Musiu, Chiara ^{[2
]}

Poddesu, Barbara ^{[2
]}

Vargiu, Luana ^{[2
]}

Liuzzi, Michel ^{[2
]}

Roland, Arlene ^{[1
]}

Seifer, Maria ^{[3
]}

Standring, David ^{[3
]}

Storer, Richard ^{[1
]}

Dousson, Cyril B. ^{[1
]}

机构：

[1] Labs Idenix, Dept Chim Med, F-34189 Montpellier 4, France

[2] Univ Cagliari, Cooperat Lab Idenix, Zona Ind Macchiareddu UTA, Idenix Pharmaceut, I-09010 Cagliari, Italy

[3] Idenix Pharmaceut, Cambridge, MA 02139 USA

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2011年 / 54卷 / 01期

关键词：

ANALOGS; DESIGN; POTENT;

D O I：

10.1021/jm101142k

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A novel series of 3-aryl-phospho-indole (API) non-nucleoside reverse transcriptase inhibitors of HIV-1 was developed Chemical variation in the phosphorus linker led to the discovery of 3-phenyl-methyl-phosphinate-2-carboxamide 14, which possessed excellent potency against wild-type HIV-1 as well as viruses bearing K103N and Y181C single mutants in the reverse transcriptase gene Chiral separation of the enantiomers showed that only R enantiomer retained the activity The pharmacokinetic, solubility, and metabolic properties of 14 were assessed

引用

页码：392 / 395

页数：4

共 50 条

[1] Synthesis and biological evaluation of imidazole thioacetanilides as novel non-nucleoside HIV-1 reverse transcriptase inhibitors
Zhan, Peng
Liu, Xinyong
Zhu, Junjie
Fang, Zengjun
Li, Zhenyu
Pannecouque, Christophe
De Clercq, Erik
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (16) : 5775 - 5781
[2] Synthesis and biological evaluations of sulfanyltriazoles as novel HIV-1 non-nucleoside reverse transcriptase inhibitors
Wang, Zhiwei
Wu, Baogen
Kuhen, Kelli L.
Bursulaya, Badry
Nguyen, Truc N.
Nguyen, Deborah G.
He, Yun
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (16) : 4174 - 4177
[3] Non-nucleoside inhibitors of HIV-1 reverse transcriptase
Proudfoot, JR
EXPERT OPINION ON THERAPEUTIC PATENTS, 1998, 8 (08) : 971 - 982
[4] HIV-1 non-nucleoside reverse transcriptase inhibitors
Högberg, M
Morrison, I
EXPERT OPINION ON THERAPEUTIC PATENTS, 2000, 10 (08) : 1189 - 1199
[5] Synthesis and biological evaluation of (±)-benzhydrol derivatives as potent non-nucleoside HIV-1 reverse transcriptase inhibitors
Ma, Xiao-Dong
Zhang, Xuan
Yang, Shi-Qiong
Dai, Hui-Fang
Yang, Liu-Meng
Gu, Shuang-Xi
Zheng, Yong-Tang
He, Qiu-Qin
Chen, Fen-Er
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (16) : 4704 - 4709
[6] Synthesis and biological evaluation of CHX-DAPYs as HIV-1 non-nucleoside reverse transcriptase inhibitors
Yan, Zi-Hong
Wu, Hai-Qiu
Chen, Wen-Xue
Wu, Yan
Piao, Hu-Ri
He, Qiu-Qin
Chen, Fen-Er
De Clercq, Erik
Pannecouque, Christophe
BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (12) : 3220 - 3226
[7] Design, synthesis, and biological evaluations of novel quinolones as HIV-1 non-nucleoside reverse transcriptase inhibitors
Ellis, David
Kuhen, Kelli L.
Anaclerio, Beth
Wu, Baogen
Wolff, Karen
Yin, Hong
Bursulaya, Badry
Caldwell, Jeremy
Karanewsky, Donald
He, Yun
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (16) : 4246 - 4251
[8] Novel benzophenones as non-nucleoside reverse transcriptase inhibitors of HIV-1
Chan, JH
Freeman, GA
Tidwell, JH
Romines, KR
Schaller, LT
Cowan, JR
Gonzales, SS
Lowell, GS
Andrews, CW
Reynolds, DJ
St Clair, M
Hazen, RJ
Ferris, RG
Creech, KL
Roberts, GB
Short, SA
Weaver, K
Koszalka, GW
Boone, LR
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (05) : 1175 - 1182
[9] Non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis and biological evaluation of novel quinoxalinylethylpyridylthioureas as potent antiviral agents
Campiani, G
Fabbrini, M
Morelli, E
Nacci, V
Greco, G
Novellino, E
Maga, G
Spadari, S
Bergamini, A
Faggioli, E
Uccella, I
Bolacchi, F
Marini, S
Coletta, M
Fracasso, C
Caccia, S
ANTIVIRAL CHEMISTRY & CHEMOTHERAPY, 2000, 11 (02): : 141 - 155
[10] Discovery of the Aryl-phospho-indole IDX899, a Highly Potent Anti-HIV Non-nucleoside Reverse Transcriptase Inhibitor
Dousson, Cyril
Alexandre, Francois-Rene
Amador, Agnes
Bonaric, Severine
Bot, Stephanie
Caillet, Catherine
Convard, Thierry
da Costa, Daniel
Lioure, Marie-Pierre
Roland, Arlene
Rosinovsky, Elodie
Maldonado, Sebastien
Parsy, Christophe
Trochet, Christophe
Storer, Richard
Stewart, Alistair
Wang, Jingyang
Mayes, Benjamin A.
Musiu, Chiara
Poddesul, Barbara
Vargiu, Luana
Liuzzi, Michel
Moussa, Adel
Jakubik, Jocelyn
Hubbard, Luke
Seifer, Maria
Standring, David
JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (05) : 1891 - 1898

← 1 2 3 4 5 →