Browse > Article
http://dx.doi.org/10.5012/jkcs.2013.57.2.221

Synthesis and Screening of Some Novel 2-[5-(Substituted phenyl)-[1,3,4]oxadiazol-2-yl]-benzoxazoles as Potential Antimicrobial Agents  

Gadegoni, Hemalatha (Jayamukhi College of Pharmacy)
Manda, Sarangapani (University College of Pharmaceutical Sciences, Kakatiya University)
Rangu, Shivaprasad (Department of Chemistry, Kakatiya University)
Publication Information
Abstract
A series of some novel 2-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-yl]-benzoxazoles were synthesized by using benzoxazole-2-carboxylic acid on reaction with thionyl chloride in presence of ethanol solvent at room temperature gave benzoxazole-2-carbonyl chloride, which is turned into benzoxazole-2-carboxylic acid hydrazide on reaction with hydrazine hydrate in ethanol solvent under reflux. The subsequent treatment of benzoxazole-2-carboxylic acid hydrazide with an appropriate aromatic carboxylic acid in presence of polyphosparic acid under reflux afforded the title compounds. The chemical structures of the newly synthesized compounds were elucidated by their IR, $^1H$ NMR and Mass spectral data analysis. Further the compounds are used to find out their ability towards anti microbial and nematicidal activity.
Keywords
1,3,4-Oxadiazole; Benzoxazole; Antimicrobial activity; Antifungal activity; Nematicidal activity;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Denny, W. A.; Rewcastle, G. W.; Baguley, B. J. Med. Chem. 1990, 33, 814.   DOI
2 Kondo, J.; Suzuki, N.; Imaoka, T.; Kawasaki, T.; Nakanishi, A.; Kawahara, Y. Anal. Sci. 1994, 10, 17.   DOI   ScienceOn
3 Song, X.; Vig, B. S.; Lorenzi, P. L.; Drach, J. C.; Townsend, L. B.; Amidon, G. L. J. Med. Chem. 2005, 48, 1274.   DOI   ScienceOn
4 Yildiz-Oren, I.; Yalcin, I.; Aki-Sener, E.; Carturk, N. Eur. J. Med. Chem. 2004, 39, 291.   DOI   ScienceOn
5 Yamato, M. J. Pharm. Soc. Jpn. 1992, 112, 81.
6 Benazzouz, A.; Boraud, T.; Dubedat, P.; Boireau, A.; Stutzmann, J. M.; Gross, C. Eur. J.Tharmacol. 1995, 284, 299.   DOI   ScienceOn
7 Kumar, D.; Jacob, M. R.; Reynolds, M. B.; Kerwin, S. M. Bioorg. Med. Chem. 2002, 10, 3997.   DOI   ScienceOn
8 Evans, D. A.; Sacks, C. E.; Kleschick, W. A.; Taber, T. R. J. Am. Chem. Soc. 1979, 101, 6789.   DOI
9 Figge, A.; Altenbach, H. J.; Brauer, D. J.; Tielmann, P. Tetrahedron: Asymmetry 2002, 13, 137.   DOI   ScienceOn
10 So, Y. H.; Heeschen, J. P. J. Org. Chem. 1997, 62, 3552.   DOI   ScienceOn
11 Villemin, D.; Hammadi, M.; Martin, B. Synth. Commun. 1996, 26, 2895.   DOI   ScienceOn
12 Doise, M.; Dennin, F.; Blondeau, D.; Sliwa, H. Tetrahedron Lett. 1990, 31, 1155.   DOI   ScienceOn
13 Jenkins, G. L.; Knevel, A. M.; Davis, C. S. J. Org. Chem. 1961, 26, 274.
14 Bezerra, N. M. M.; De-Oliveira, S. P.; Srivastava, R. M.; Silva, D. Farmaco 2005, 60, 955.   DOI   ScienceOn
15 Zareef, M.; Iqbal, R.; De Dominguez, N. G.; Rodrigues, J.; Zaidi, J. H.; Arfan, M.; Supuran, C. T. J. Enzyme Inhib. Med. Chem. 2007, 22, 301.   DOI   ScienceOn
16 Ram, V. J.; Pandey, H. N. Eur. J. Med. Chem. 1990, 25, 541.   DOI   ScienceOn
17 Shirote, P. J.; Bhatia, M. S. Arab. J. Chem. 2010, 145.
18 Padmavathi, V.; Reddy, G. S.; Padmaja, A.; Kondaiah, P.; Shazia, A. Eur. J. Med. Chem. 2009, 44, 2106.   DOI   ScienceOn
19 Jayashankar, B.; Rai, K. M. L.; Baskaran, N.; Shazia, H. S. S. Eur. J. Med. Chem. 2009, 44, 3898.   DOI   ScienceOn
20 Shashikan, D.; Bhandari, V.; Bothara, K. G.; Raut, M. K.; Patil, A. A.; Sarkate, A. P.; Mokale, V. J. Bioorg. Med. Chem. Lett. 2008, 16, 1822.   DOI   ScienceOn
21 Omar, F. A.; Mahfouz, N. M.; Rahman, M. A. Eur. J. Med. Chem. 1996, 31, 819.   DOI   ScienceOn
22 Seely, H. W.; Van, D. P. J. Microbes in Action: A Laboratory Manual of Microbiology; D. B. Taraporevala Sons & Co. Pvt. Ltd.: Bomay, 1975; p 55.
23 Barry, A. I. The Antimicrobial Suspectibility Test, Principles of Practices, 4th ed.; ELBS: 1976; p 80.
24 Horsfall, J. G. Bot. Rev. 1945, 11, 357.   DOI
25 Mc Beth, C. W.; Bergeson, G. B. Phytopathology 1953, 43, 264.
26 Chakraborti, A. K.; Rudrawar, S.; Kaur, G.; Sharma, L. Synlett. 2004, 1533.
27 Hein, D. W.; Alheim, R. J.; Leavitt, J. J. Am. Chem. Soc. 1957, 79, 427.   DOI
28 Terashima, M.; Ishii, M. Synthesis 1982, 484.
29 Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Otokesh, S.; Baghbanzadeh, M. Tetrahedron Lett. 2006, 47, 2557.   DOI   ScienceOn
30 Bhawal, B. M.; Mayabhate, S. P.; Likhite, A. P.; Deshmukh, A. R. Synth. Commun. 1995, 25, 3315.   DOI   ScienceOn
31 Chen, Y.; Zeng, D. X. J. Org. Chem. 2004, 69, 5037.   DOI   ScienceOn
32 Preston, P. N. The Chemistry of Heterocyclic Compounds; Wiley: New York, 1981; p 5.
33 Terashima, M.; Ishii, M. Synthesis 1982, 1484.
34 Andotra, C. S.; Manhas, B. S. Acta Cienc. Indica Chem. 1992, 18, 99.
35 Hutt, M. P.; Elstager, E. F.; Werbet, L. M. J. Heterocycl. Chem. 1970, 7, 511.   DOI
36 Silvestrini, B.; Pagatti, C. Br. J. Pharmacol. 1961, 16, 209.
37 Sharma, R. S.; Bahel, C. S. J. Indian Chem. Soc. 1982, 59, 877.
38 Omar, A.; Mohsen, M. E.; Aboul Wafa, O. M. J. Heterocycl. Chem. 1984, 21, 1415.   DOI
39 Narayana, B.; Vijayaraj, K. K.; Ashalatha, B. V.; Kumari, N. S. Arch. Pharm. 2008, 338.
40 Gaonkar, S. L.; Rai, K. M. Eur. J. Med. Chem. 2006, 41, 841.   DOI   ScienceOn
41 Ali, M. A.; Yar, M. S. Bioorg. Med. Chem. Lett. 2007, 17, 3314.   DOI   ScienceOn
42 Zarghi, A.; Tabatabai, S. A.; Faizi, M.; Ahadian, A.; Navabi, P.; Zanganeh, V.; Shafiee, A. Bioorg. Med. Chem. Lett. 2005, 15, 1863.   DOI   ScienceOn