Design, synthesis and spectroscopic and crystallographic characterisation of novel functionalized pyrazole derivatives: biological evaluation for their cytotoxic, angiogenic and antioxidant activities
The current study presents the synthesis of functionalized pyrazoles (18–29) through 3 + 2 annulation reaction of ethyl 2-(arylidene)-3-oxobutanoates (8–13) with phenylhydrazine hydrochlorides (14–17) in acetic acid under reflux conditions. Structures of the synthesized new compounds were characterized by spectral and single-crystal X-ray diffraction studies. Preliminary assessment on their biological activities showed that compounds 19, 23 and 28 have anticancer and antiangiogenic properties and compounds 20, 24 and 26 have excellent diphenylpicrylhydrazyl (DPPH) radical scavenging activities. Detailed quantitative structure–activity relationship (QSAR) analysis provided insights into the molecular features that might have contributed towards increasing potency of inhibition. In summary, we present a study that has successfully demonstrated the synthesis of novel pyrazole analogues that display anticancer, antiangiogenic and DPPH free radical scavenging activities, making them lead molecules of choice for further development.
KeywordsAntiangiogenic Antioxidant Citotoxic Condensation Pyrazoles
The authors are grateful to the IOE Instrumentation Facility, Vijnana Bhavana, University of Mysore, for recording spectra and X-ray diffraction studies, and JSS College of Pharmacy, Mysuru, for providing cell lines.
Compliance with ethical standards
Conflict of interest
All authors declare no conflict of interest including financial, personal or other relationships with other people or organizations for this article.
- 1.S. Eckhardt, Curr. Med. Chem. 3, 419 (2002)Google Scholar
- 10.A.D. Prasanna, R.J. Sonali, Int. J. Med. Chem. 2015, 670181 (2015)Google Scholar
- 16.P. Jayaroopa, K. Ajay Kumar, Int. J. Pharm. Pharm. Sci. 5(4), 431 (2013)Google Scholar
- 24.A. Dileep Kumar, K. Kumara, N.K. Lokanath, K. Ajay Kumar, M. Prabhuswamy, Chem. Data Collect. 5–6, 68 (2016)Google Scholar