Vol 11, Issue 7, 2018 Online - 2455-3891 Print - 0974-2441 MICROWAVE-ASSISTED SYNTHESIS, CHARACTERIZATION, AND BIOLOGICAL EVALUATION OF PHENYLACRYLAMIDE DERIVATIVES OF TRIAZOLES DERIVED FROM OXAZOLONES VENKAT SWAMY PULI, 1,2 VUKOTI KIRAN KUMAR, 1,2 VENKATA REDDY REGALLA, 1,2 ANINDITA CHATTERJEE 1 * 1 Department of Chemistry, Koneru Lakshmaiah Education Foundation, Guntur, Andhra Pradesh, India. 2 Department of Medicinal Chemistry, GVK Biosciences Private Limited, Hyderabad, Telangana, India. Email: anindita@kluniversity.in Received: 07 March 2018, Revised and Accepted: 12 April 2018 ABSTRACT Objective: The aim of the present study is to synthesize novel phenylacrylamide derivatives as potent bioactive agents. Methods: Novel N-(3-(4H-1,2,4-triazol-4-ylamino)-3-oxo-1-arylidene prop-2-yl) benzimidic acids (7a-c) have been synthesized by the reaction of 4-(arylidene)-2-phenyloxazol-5(4H)-ones (5a-c) with 4-amino-1, 2, 4-triazole (6) in the presence of anhydrous sodium acetate in glacial acetic acid. Titled compounds (7a-c) were obtained in good yields using microwave technology which resulted in dramatic reductions in reaction times leading to the formation of phenylacrylamide derivatives (7a-c) at a faster rate. Results: The structures of the newly synthesized compounds were characterized by Fourier-transform infrared, 1 H NMR, 13 C NMR, and mass spectral studies. This method can be an efficient method for the synthesis of phenylacrylamide derivatives (7a-c). Conclusion: All the final compounds were screened for their antimicrobial and antioxidant activities and found to be biologically active. Among all the compounds, 7b was found to be potent antimicrobial and antioxidant. Keywords: Phenyl acrylamides, Triazoles, Oxazolones, Antimicrobial activity, Antioxidant activity. INTRODUCTION Infectious diseases are one of the leading causes of death worldwide. Treatment of infectious disease is an important and challenging problem. Some of azole derivatives used as common antibiotics such as amphotericin B possess a toxic effect on humans as well as on microbes. Besides this, although there are antimicrobial agents having different structures frequently used in the treatment of microbial infections, there is increasing resistance to these drugs [1]. To overcome the development of resistance, it is crucial to synthesize a new class of antibiotics. Antioxidants and scavenging free radicals are critical for maintaining optimal cellular and systemic health. Hence, in this area also, research is required for the development of new drugs [2-6]. The remarkable ability of heterocyclic nuclei to serve both as biomimetics and reactive pharmacophores has largely contributed to their unique value as traditional key elements of numerous drugs [7,8]. Among these heterocyclic compounds, oxazolone, phenyl acrylamides [9,10], and triazoles are having a wide variety of biological importance. Oxazolone plays very vital role in the development of various biologically active agents such as analgesic, anti-inflammatory, antidepressant, anticancer, antimicrobial, and antidiabetic. Oxazol- 5-ones contain numerous reactive sites allowing for a diverse set of possible modifications. This diverse activity makes them excellent substrates for their use in diversity-oriented synthesis. Triazole moiety may be considered as a bioisostere of imidazole, which is a part of the azole group of antifungal drug (i.e., fluconazole). The 1, 2, 4-triazole nucleus has been incorporated into a wide variety of therapeutically important agents such as ribavirin (antiviral), rizatriptan (antimigraine), alprazolam (anxiolytic), vorozole, letrozole, and anastrozole (antitumoral) [11-23]. In the past few years, the use of microwave irradiation in organic synthesis has become increasingly popular within the theme in the scientific community because it is a new enabling technology for drug discovery and development. Microwave-assisted organic synthesis has been shown to dramatically reduce reaction times, increase product yields, and enhance product purities by reducing unwanted side reactions compared to conventional heating methods. In the present study, our main objective was to use the microwave technology [13,24,25] and the final molecules were designed to combine both oxazolone and 1, 2, 4-triazole moieties that were expected to have synergistic antimicrobial and antioxidant activities. In view of the above facts and in continuation of our efforts, we here in report the synthesis and biological activity of N-(3-(4H-1,2,4-triazol-4-ylamino)-3-oxo-1- arylidene prop-2-yl) benzimidic acids (7a-c). The synthetic approach is outlined in Scheme-I. METHODS All the chemicals were of LR grade and were obtained from SD Fine Chemicals and Avra Chemicals. Melting points (MP) were determined in open capillaries on Sheetal precision MP apparatus. Each reaction was monitored by thin-layer chromatography (TLC) using appropriate solvent system, which was selected by trial and error method. Pre- coated TLC plates (0.25 mm silica gel) were obtained from E. Merck. Mass spectral analysis using electrospray ionization (ESI) using a quadrupole time-of-flight mass analyzer (QSTAR XL, Applied Biosystems/MDS Sciex, Foster City, CA, USA) equipped with an ESI source and mass spectra were reported in m/z value as molecular ion peak. The instruments used for obtaining the spectroscopic data were as follows: Infrared (IR) spectra were recorded on Fourier-transform IR spectrophotometer SHIMADZU-435instrument by KBr, dilated cardiomyopathy disc method. Ultraviolet (UV) spectra were recorded on OPTIZEN3220 UV-visible spectrophotometer instrument. All 1 HNMR spectra were recorded on 1 H NMR (CDCl 3 , avance300 MHz) instrument, and the samples were made in dimethyl sulfoxide (DMSO)-d 6 using tetramethylsilane as the internal standard. © 2018 The Authors. Published by Innovare Academic Sciences Pvt Ltd. This is an open access article under the CC BY license (http://creativecommons. org/licenses/by/4. 0/) DOI: http://dx.doi.org/10.22159/ajpcr.2018.v11i7.25689 Research Article