MICROWAVE-ASSISTED SYNTHESIS, CHARACTERIZATION, AND BIOLOGICAL EVALUATION OF PHENYLACRYLAMIDE DERIVATIVES OF TRIAZOLES DERIVED FROM OXAZOLONES

Authors

  • Venkat Swamy Puli Department of Chemistry, Koneru Lakshmaiah Education Foundation, Guntur, Andhra Pradesh, India.
  • Vukoti Kiran Kumar Department of Chemistry, Koneru Lakshmaiah Education Foundation, Guntur, Andhra Pradesh, India.
  • Venkata Reddy Regalla Department of Chemistry, Koneru Lakshmaiah Education Foundation, Guntur, Andhra Pradesh, India.
  • Anindita Chatterjee Department of Chemistry, Koneru Lakshmaiah Education Foundation, Guntur, Andhra Pradesh, India.

DOI:

https://doi.org/10.22159/ajpcr.2018.v11i7.25689

Keywords:

Phenyl acrylamides, Triazoles, Oxazolones, Antimicrobial activity, Antioxidant activity

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, 1H NMR, 13C 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.

Downloads

Download data is not yet available.

References

Uchida K. Role of reactive aldehyde in cardiovascular diseases. Free Radical Biol Med 2000;28:1685-96.

Cadenas E, Davies KJ. Mitocondrial free radical generation, oxidative stress, and aging. Free Radical Biol Med 2000;29:222-30.

Kinsella JE, Frankel E, German B, Kanner J, Collin X, Sauleau A, et al. Possible mechanisms for the protective role of antioxidants in wine and plant foods. Med Chem 2003;13:2601-5.

Kinsella JE, Frankel E, German B, Kanner J. Possible mechanisms for the protective role of antioxidants in wine and plant foods. J Food Tech 1993;47:85-9.

Witte CP, Tiller SA, Taylor MA, Davies HV. Leaf urea metabolism in potato. Urease activity profile and patterns of recovery and distribution of (15)N after foliar urea application in wild-type and urease-antisense transgenics. Plant Physiol 2002;128:1129-36.

Ciurli S, Benini S, Rypvniewski WR, Wilson KS, Miletti S, Mangani S. Dibromido{2,4-dichloro-6-[3-dimethylammonio)propyliminomethyl] phenolato}zinc(II). Coord Chem Rev 1999;190:331-5.

Korolkovas A. Essentials of Medicinal Chemistry. Vol. 2. New York: Wiley; 1988. p. 3.

Upadhayaya RS, Kulkarni GM, Vasireddy NR, Vandavasi JK, Dixit SS, Sharma V, et al. Design, synthesis and biological evaluation of novel triazole, urea and thiourea derivatives of Quinoline against Mycobacterium tuberculosis. Bioorg Med Chem 2009;17:4681-92.

Taile V, Hatzade K, Gaidhane P, Ingle V. Synthesis and biological activities of new hydroxy-3-pyrazolyl-4H-chromen-4-ones and their O-glucosides. Turk J Chem 2009;33:295-305.

Pasha MA, Jayashankara VP, Venugopala KN, Rao GK. Zinc oxide (ZnO): An Efficient catalyst for the synthesis of 4-arylmethylidene- 2-phenyl 5(4H)-oxazolones having antimicrobial activity. J Pharm Toxicol 2007;2:264-70.

Tikdari AM, Fozooni S, Hamidian H. Dodecatungstophosphoric acid (H3PW12O40), samarium and ruthenium (ІІІ) chloride catalyzed synthesis of unsaturated 2-phenyl-5(4H)-oxazolone derivatives under solvent-free conditions. Molecules 2008;13:3246-52.

Jiang H, Zhao J, Wang A. An efficient and eco-friendly process for the conversion of carbon dioxide into oxazolones and oxazolidinones under supercritical conditions. J Synth Org Chem 2008;39:763-9.

Cleary T, Brice J, Kennedy N, Chavez F. One-pot process to Z-- benzoylamino-acrylic acid methyl esters via potassium phosphate-catalyzed Erlenmeyer reaction. Tetrahedron Lett 2010;51:625-8.

Yamada S, Yoshihara Y, Kawahara Y. DL-α-alkyl-α-amino Acid and Intermediates Therefore, United States Patent, Patent No: US 3422135, Jan. 14, 1969.

Burckhalter JH, Edgerton WH. A new type of 8-quinolinol amebacidal agent. J Am Chem Soc 1951;73:4837-9.

Sztanke K, Tuzimski T, Rzymowska J, Pasternak K, Kandefer-Szerszeń M. Synthesis, determination of the lipophilicity, anticancer and antimicrobial properties of some fused 1,2,4-triazole derivatives. Eur J Med Chem 2008;43:404-19.

Wilkinson BL, Long H, Sim E, Fairbanks AJ. Synthesis of arabino glycosyl triazoles as potential inhibitors of mycobacterial cell wall biosynthesis. Bioorg Med Chem Lett 2008;18:62-5.

Chattopadhyaya J. Design, synthesis and biological evaluation of novel triazole, urea and thiourea derivatives of quinoline against Mycobacterium tuberculosis. Bioorg Med Chem 2009;17:4681-92.

Jordao AA, Afonso PP, Ferreira VF, Desouza MC, Almeida MC, Beltrame CO, et al. Synthesis, antitubercular activity, and SAR study of N–substituted-phenylamino-5-methyl-1H-1, 2, 3-triazoles-4- carbohydrazides. Eur J Med Chem 2009;44:37-77.

Jordao AK, Ferreira VF, Lima ES, Desouza MC, Carlos EC, Castro HC, et al. Synthesis and anti-HSV-1 activity of new 1,2,3-triazole derivatives. Bioorg Med Chem 2009;17:3713.

Crotty S, Maag D, Arnold JJ, Zhong W, Lau JY, Hong Z, et al. The broad-spectrum antiviral ribonucleotide, ribavirin, is an RNA virus mutagen. Nat Med 2000;6:1375-9.

Williamson DJ, Hill RG, Shepheard SI, Hargreaves RJ. Role of opioid receptors in neurogenic dural vasodilation and sensitization of trigeminal neurones in anaesthetized rats. J Br J Pharmacol 2001;133:1029.

Torres HA, Hachem RY, Chemaly RF, Kontoyiannis DP. Detection of Pneumocystis jirovecii by quantitative PCR to differentiate colonization and pneumonia in immunocompromised HIV-positive and HIV-negative patients. Lancet Infect Dis 2005;5:774-5.

Bektas H, Demirbas A, Demirbas N, Karaoglu SA. Design and synthesis of new 1,2,4-triazole derivatives containing morpholine moiety as antimicrobial agents. Turk J Chem 2010;34:65.

Jadhav HP, Pathare DB. Separation and determination of the s-isomer of (10-camphorsulfonyl) oxaziridine in a bulk drug substance by normal-phase liquid chromatography. Int J Pharm Pharm Sci 2015;7:66-9.

Furniss BS, Hannafurd AJ, Smith PW, Tatchell AL. Vogel, Arthur Israel. Vogel’s Textbook of Practical Organic Chemistry, Including Qualitative Organic Analysis. 111. Title. QD261.Vol. 63. London: The School of Chemistry, Thames Polytechnic; 1989.

Abhinit M, Ghodke M, Pratima NA. Exploring potential of 4-thiazolidinone: A brief review. Int J Pharm Pharm Sci 2009;1:

Published

07-07-2018

How to Cite

Puli, V. S., V. K. Kumar, V. R. Regalla, and A. Chatterjee. “MICROWAVE-ASSISTED SYNTHESIS, CHARACTERIZATION, AND BIOLOGICAL EVALUATION OF PHENYLACRYLAMIDE DERIVATIVES OF TRIAZOLES DERIVED FROM OXAZOLONES”. Asian Journal of Pharmaceutical and Clinical Research, vol. 11, no. 7, July 2018, pp. 285-90, doi:10.22159/ajpcr.2018.v11i7.25689.

Issue

Section

Original Article(s)

Most read articles by the same author(s)