Synthesis of pyridazino[3,4-b][1,5]benzodiazepin-5-ones and their biological evaluation as non-nucleoside HIV reverse transcriptase inhibitors

被引：16
|
作者：
Heinisch, G
Huber, E
Matuszczak, B
Maurer, A
Prillinger, U
机构：
[1] Inst. of Pharmaceutical Chemistry, University of Innsbruck, Innrain 52a
来源：
ARCHIV DER PHARMAZIE | 1997年 / 330卷 / 1-2期
关键词：
HIV-1 reverse transcriptase inhibition; pyridazino[3,4-b][1,5]benzodiazepin-5-ones; non-nucleoside reverse transcriptase inhibitors;
D O I：
10.1002/ardp.19973300108
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Starting from 3,6-dichloro-N-(2-chIoro-5-nitrophenyl)-pyridazine-4-carboxamide (7) a series of 6,11-dialkylated pyridazino-[3,4-b][1,5]benzodiazepin-5-ones with a 3-chloro-8-nitro, 8-amino, 8-acetylamino, or 8-chloro substitution pattern was prepared via N-alkyl-3-alkylamino-6-chloro-N-(2-chloro-5-nitrophenyl)-pyridazine-4-carboxamides. The new compounds were screened as non-nucleoside reverse transcriptase inhibitors. The influence of the substitution pattern in compounds 10-13 on inhibitory potency is discussed.
引用
收藏
页码：29 / 34
页数：6
相关论文
共 50 条
  • [21] Optimization of 5-Aryloxyimidazole Non-Nucleoside Reverse Transcriptase Inhibitors
    Jones, Lyn H.
    Allan, Gill
    Corbau, Romuald
    Hay, Duncan
    Middleton, Donald S.
    Mowbray, Charles E.
    Newman, Sandra D.
    Perros, Manos
    Randall, Amy
    Vuong, Hannah
    Webster, Rob
    Westby, Mike
    Williams, David
    CHEMMEDCHEM, 2008, 3 (11) : 1756 - 1762
  • [22] Synthesis and biological evaluation of alkenyldiarylmethane HIV-1 non-nucleoside reverse transcriptase inhibitors that possess increased hydrolytic stability
    Cullen, Matthew D.
    Deng, Bo-Liang
    Hartman, Tracy L.
    Watson, Karen M.
    Buckheit, Robert W., Jr.
    Pannecouque, Christophe
    De Clercq, Erik
    Cushman, Mark
    JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (20) : 4854 - 4867
  • [23] Synthesis and Biological Evaluation of Aryl-phospho-indole as Novel HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors
    Alexandre, Francois-Rene
    Amador, Agnes
    Bot, Stephanie
    Caillet, Catherine
    Convard, Thierry
    Jakubik, Jocelyn
    Musiu, Chiara
    Poddesu, Barbara
    Vargiu, Luana
    Liuzzi, Michel
    Roland, Arlene
    Seifer, Maria
    Standring, David
    Storer, Richard
    Dousson, Cyril B.
    JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (01) : 392 - 395
  • [24] Synthesis and biological evaluation of piperidine-substituted triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors
    Chen, Xuwang
    Zhan, Peng
    Pannecouque, Christophe
    Balzarini, Jan
    De Clercq, Erik
    Liu, Xinyong
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 51 : 60 - 66
  • [25] 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
  • [26] 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
  • [27] Mechanisms of resistance of HIV-1 reverse transcriptase to nucleoside and non-nucleoside inhibitors
    Boyer, PL
    Tantillo, C
    Ding, J
    Ferris, AL
    Clark, P
    Arnold, E
    Hughes, SH
    JOURNAL OF ACQUIRED IMMUNE DEFICIENCY SYNDROMES AND HUMAN RETROVIROLOGY, 1995, 10 : 6 - 6
  • [28] Design, Synthesis, and Evaluation of Diarylpyridines and Diarylanilines as Potent Non-nucleoside HIV-1 Reverse Transcriptase Inhibitors
    Tian, Xingtao
    Qin, Bingjie
    Wu, Zhiyuan
    Wang, Xiaofeng
    Lu, Hong
    Morris-Natschke, Susan L.
    Chen, Chin Ho
    Jiang, Shibo
    Lee, Kuo-Hsiung
    Xie, Lan
    JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (23) : 8287 - 8297
  • [29] SYNTHESIS AND REACTION OF DIHYDROFURO[3,4-B][1,5]BENZODIAZEPINONES AND DIHYDROPYRROLO[3,4-B][1,5]BENZODIAZEPINONES
    MATSUO, K
    TAKADA, S
    INOUE, J
    TANAKA, K
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1986, 106 (08): : 715 - 720
  • [30] Synthesis and Biological Evaluation of Novel 2-Arylalkylthio-5-iodine-6-substituted-benzyl-pyrimidine-4(3H)-ones as Potent HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors
    Zhang, Liang
    Tang, Xiaowan
    Cao, Yuanyuan
    Wu, Shaotong
    Zhang, Yu
    Zhao, Jianxiong
    Guo, Ying
    Tian, Chao
    Zhang, Zhili
    Liu, Junyi
    Wang, Xiaowei
    MOLECULES, 2014, 19 (06) : 7104 - 7121
12345