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新型N'-(1-(芳基)亚乙基)-2-(5,5-二氧代-3-苯基苯并[e]吡唑并[4,3-c][1,2]噻嗪-4(1H)-基)乙酰肼的合成及抗HIV-1筛选

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.

作者信息

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

机构信息

Institute of Chemistry, University of the Punjab, Lahore, 54590, Pakistan.

出版信息

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

DOI:10.1007/s12272-013-0200-9
PMID:23835833
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7732025/
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.

摘要

合成了一系列新型的N'-(1-(芳基)亚乙基)-2-(5,5-二氧化-3-苯基苯并[e]吡唑并[4,3-c][1,2]噻嗪-4(1H)-基)乙酰肼。采用热法以及超声浴进行合成，以缩短反应时间并提高产物收率。通过核磁共振、红外光谱和电子轰击质谱等光谱技术对合成的化合物进行了表征。通过X射线晶体学阐明了化合物5w的结构。对标题化合物进行了抗1型人类免疫缺陷病毒(抗HIV-1)和细胞毒性活性评估。生物学研究表明，在这些化合物中，5a、b、j、h和i表现出活性，其半数有效浓度(EC50)值小于20μM。化合物5i表现出最有效的抗HIV-1活性(EC50 = 3.2μM)，而5h表现出抗HIV-1活性(EC50 = 3.8μM)，在原代人淋巴细胞、CEM和VERO细胞中完全没有毒性。

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