Synthesis and biological evaluation of some N 4 -aryl-substituted 5-fluoroisatin-3-thiosemicarbazones
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Med Chem Res DOI 10.1007/s00044-013-0575-7
ORIGINAL RESEARCH
Synthesis and biological evaluation of some N4-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones Humayun Pervez • Naveeda Saira • Mohammad Saeed Iqbal Muhammad Yaqub • Khalid Mohammed Khan
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Received: 20 December 2012 / Accepted: 5 March 2013 Ó Springer Science+Business Media New York 2013
Abstract A series of N4-aryl-substituted 5-fluoroisatin-3thiosemicarbazones 3a–3l was synthesized and evaluated for selected biological activities. The brine shrimp lethality bioassay was carried out to study their in vitro cytotoxicity potential and besides, their antifungal, phytotoxic and urease inhibitory effects were also investigated. Seven compounds i.e. 3a, 3d, 3f, 3g, 3h, 3j and 3k proved to be active in the brine shrimp assay, displaying promising cytotoxicity (LD50 = 6.89 9 10-5–2.79 9 10-4 M). Amongst these, 3a and 3h were found to be the most active ones (LD50 = 6.89 9 10-5 and 9.79 9 10-5 M, respectively). Compounds 3i, 3j and 3 k displayed moderate (40 %) antifungal activity against one or two fungal strains i.e. A. flavus and/or M. canis. In phytotoxicity assay, all the synthesized compounds, including the reference point 2m showed weak-to-moderate (15–70 %) activity at the highest tested concentration (500 lg/mL). In urease inhibition assay, compounds 3f, 3g and 3j proved to be the most potent inhibitors, demonstrating relatively a higher degree of enzymatic inhibition with IC50 values ranging from 37.7 to 47.3 lM.
H. Pervez (&) N. Saira M. Yaqub Organic Chemistry Division, Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan e-mail: [email protected] M. S. Iqbal Department of Chemistry, FC College, Lahore 54600, Pakistan K. M. Khan H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Keywords: Antifungal Cytotoxicity 5-Fluoroisatin Phytotoxicity Thiosemicarbazones Urease inhibitors
Introduction It is evident from the literature that isatin and its derivatives are associated with a wide variety of biological activities like analgesic, anticonvulsant, antimicrobial, anti-inflammatory, antiglycation, antineoplastic, antiplasmodial, antituberculosis and antiviral (Aboul-Fadl and Bin-Jubair, 2010; Bal et al., 2005; Banerjee et al., 2011; Beauchard et al., 2006; Chen et al., 2005; Chiyanzu et al., 2005, 2003; Da Silva et al., 2001; Guzel et al., 2008; Hall et al., 2011, 2009; Hyatt et al., 2007; Jarrahpour et al., 2007; Karali et al., 2007; Khan et al., 2009; Pandeya et al., 2005; Patel et al., 2006; Pirrung et al., 2005; Quenelle et al., 2006; Ravichandran et al., 2007; Singh et al., 2010; Smitha et al., 2008; Terzioglu et al., 2006; Vine et al., 2009). Among isatin derivatives, isatin-derived thiosemicarbazones have been reported to exhibit diverse chemotherapeutic activities, including antimicrobial, antituberculosis, antiulcer, cytotoxicity and enzymatic inhibition (Aboul-Fadl and Bin-Jubair, 2010; Bal
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