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. 2014 Nov;37(11):1380-93.
doi: 10.1007/s12272-013-0200-9. Epub 2013 Jul 10.

Synthesis 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

Sana Aslam  1 , Matloob Ahmad, Muhammad Zia-Ur-Rehman, Catherine Montero, Mervi Detorio, Masood Parvez, Raymond F Schinazi
Affiliations

Synthesis 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

Sana Aslam et al. Arch Pharm Res. 2014 Nov.

Erratum in

  • Arch Pharm Res. 2014 Nov;37(11):1504

Abstract

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.

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Conflict of interest statement

Conflict of Interest The authors declare no conflicts of interest.

Figures

Fig. 1
Fig. 1
Potent anti-inflammatory drugs based on benzothiazine and pyrazole pharmacophores, respectively
Fig. 2
Fig. 2
ORTEP-3 drawing of 2-(5,5-dioxido-3-phenylbenzo[e]pyrazolo[4,3-c][1,2]thiazin-4(1H)-yl)-N′-(thiophen-2-ylmethylene)acetohydrazide (5w)
Scheme 1
Scheme 1
Synthetic route for novel series of N′-(1-arylethylidene)-2-(5,5-dioxido-3-phenylbenzo[e]pyrazolo[4,3-c][1,2]thiazin-4(1H)-yl)acetohydrazides (5a–w)
See this image and copyright information in PMC

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References

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