Open AccessSynthesis and anti-HIV-1 screening of novel N′-(1-(aryl)ethylidene)-2-(5,5-dioxido-3-phenylbenzo[e]pyrazolo[4,3-c][1,2]thiazin-4(1H)-yl)acetohydrazides
Author(s) -
Sana Aslam,
Matloob Ahmad,
Muhammad ZiaurRehman,
Catherine Montero,
Mervi Detorio,
Masood Parvez,
Raymond F. Schinazi
Publication year - 2013
Publication title -
archives of pharmacal research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.855
H-Index - 87
eISSN - 1976-3786
pISSN - 0253-6269
DOI - 10.1007/s12272-013-0200-9
Subject(s) - ec50 , human immunodeficiency virus (hiv) , aryl , chemistry , stereochemistry , cytotoxic t cell , in vitro , virology , organic chemistry , biology , biochemistry , alkyl
A novel series of N'-(1-(aryl)ethylidene)-2-(5,5-dioxido-3-phenylbenzo[e]pyrazolo[4,3-c][1,2]thiazin-4(1H)-yl)acetohydrazides was synthesized. The synthesis was carried out by thermal method as well as ultrasonic bath to reduce reaction time and to enhance product yields. The synthesized compounds were characterized by spectroscopic techniques like NMR, infrared and EIMS. The structure of compound 5w was elucidated by X-ray crystallography. The titled compounds were evaluated for anti-human immunodeficiency virus type 1 (anti-HIV-1) and cytotoxic activities. Biological studies indicated that amongst these compounds, 5a, b, j, h and i showed the activity with median effective concentration (EC50) values less than 20 μM. Compound 5i exhibited the most potent anti-HIV-1 activity (EC50 = 3.2 μM) while 5h showed anti-HIV-1 activity (EC50 = 3.8 μM) with no toxicity at all in primary human lymphocytes, CEM and VERO cells.