Microwave-assisted solvent free efficient synthesis of 1,3,4-oxadiazole-2(3H)-thiones and their potent in vitro urease inhibition activity

Sohail Anjum Shahzad; Muhammad Yar; Zulfiqar Ali Khan; Islam Ullah Khan; Syed Ali Raza Naqvi; Nasir Mahmood; Khalid Mohammed Khan

doi:10.5155/eurjchem.3.2.143-146.551

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Published: Jun 30, 2012

DOI: https://doi.org/10.5155/eurjchem.3.2.143-146.551

Keywords:

High yield, Hydrazides, Solvent free, Urease inhibition, Microwave-irradiation, Substituted-1, 3, 4-oxadiazole

Section

Research Article

Issue

Vol. 3 No. 2 (2012): June 2012

Dates

Received 2011-11-18
Accepted 2012-02-03
Published 2012-06-30

Sohail Anjum Shahzad

Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad, 22060, Pakistan

Muhammad Yar

Interdisciplinary Research Center in Biomedical Materials, COMSATS Institute of Information Technology, Lahore, 54000, Pakistan

Zulfiqar Ali Khan

Department of Chemistry, Government College University, Faisalabad, 38000, Pakistan

Islam Ullah Khan

Department of Chemistry, Government College University, Lahore, 54000, Pakistan

Syed Ali Raza Naqvi

Department of Chemistry, Government College University, Faisalabad, 38000, Pakistan

Nasir Mahmood

Department of Allied Sciences and Chemical Pathology, University of Health Sciences, Lahore, 54600, Pakistan

Khalid Mohammed Khan

Hussain Ibrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan

Abstract

An efficient solvent free microwave assisted synthesis of 5-substituted-1,3,4-oxadiazole-2(3H)-thiones (2a-2r) from hydrazides and carbon disulfide has been accomplished in good to excellent yield. The urease inhibition activity of the resulting compounds was investigated. Preliminary bioassay indicated that the compound 2j bearing 2-bromo substituent is the most active inhibitor exhibiting IC₅₀12.60 ± 0.92 μM.

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How to Cite

(1)

Shahzad, S. A.; Yar, M.; Khan, Z. A.; Khan, I. U.; Naqvi, S. A. R.; Mahmood, N.; Khan, K. M. Microwave-Assisted Solvent Free Efficient Synthesis of 1,3,4-Oxadiazole-2(3H)-Thiones and Their Potent in Vitro Urease Inhibition Activity. Eur. J. Chem. 2012, 3, 143-146.

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References

[1]. Dixon, N. E.; Gazzola, C.; Watters, J. J.; Blakeley, R. L.; Zerner, B. J. Am. Chem. Soc. 1975, 97, 4130-4131.
http://dx.doi.org/10.1021/ja00847a044
PMid:1159215

[2]. Amtul, Z.; Atta-ur-Rahman; Siddiqui, R. A.; Choudhary, M. I. Curr. Med. Chem. 2002, 9, 1323-1348.
PMid:12132990

[3]. Andrews, R. K.; Dexter, A.; Blakeley, R. L.; Zerner, B. J. Am. Chem. Soc. 1986, 108, 7124-7125.
http://dx.doi.org/10.1021/ja00282a059

[4]. Faraci, W. S.; Yang, B. V.; O’Rourke, D.; Spencer, R. W. Bioorg. Med. Chem. 1995, 3, 605-610.
http://dx.doi.org/10.1016/0968-0896(95)00043-G

[5]. Kot, M.; Zaborska, W.; Orlinska, K. J. Enzym. Inhib. Med. Chem. 2001, 16, 507-516.
http://dx.doi.org/10.1080/14756360127569

[6]. Collier, J. L.; Brahamsha, B.; Palenik, B. Microbiology 1999, 145, 447-459.
http://dx.doi.org/10.1099/13500872-145-2-447
PMid:10075427

[7]. Krajewska, B. J. Mol. Catal. B: Enzym. 2009, 59, 9-21.
http://dx.doi.org/10.1016/j.molcatb.2009.01.003

[8]. Karplus, P. A.; Pearson, M. A.; Hausinger, R. P. Acc. Chem. Res. 1997, 30, 330-337.
http://dx.doi.org/10.1021/ar960022j

[9]. Dixon, N. E.; Gazzola, C.; Blakeley, R. L.; Zerner, B. J. Am. Chem. Soc. 1975, 97, 4131-4133.
http://dx.doi.org/10.1021/ja00847a045
PMid:1159216

[10]. Ermler, U.; Grabarse, W.; Shima, S.; Goubeaud, M.; Thauer, R. K. Curr. Opin. Struct. Biol. 1998, 8, 749-758.
http://dx.doi.org/10.1016/S0959-440X(98)80095-X

[11]. Jabri, E.; Carr, M. B.; Hausinger, R. P.; Karplus, P. A. Science 1995, 268, 998-1004.
http://dx.doi.org/10.1126/science.7754395
PMid:7754395

[12]. Benini, S.; Rypniewski, W. R.; Wilson, K. S.; Ciurli, S.; Mangani, S. J. Biol. Inorg. Chem. 1998, 3, 268-273.
http://dx.doi.org/10.1007/s007750050231

[13]. Witte, C. P.; Tiller, S. A.; Taylor, M. A.; Davies, H. V. Plant Physiol. 2002, 128, 1129-1136.
http://dx.doi.org/10.1104/pp.010506
PMid:11891267 PMCid:152224

[14]. Mobley, H. L. T.; Hausinger, R. P. Microbiol. Rev. 1989, 53, 85-100.
PMid:2651866 PMCid:372718

[15]. Zonia, L. E.; Stebbins, N. E.; Polacco, J. C. Plant Physiol. 1995, 107, 1097-1103.
http://dx.doi.org/10.1104/pp.107.4.1097
PMid:7770520 PMCid:157242

[16]. Mulvaney, R. L.; Bremner, J. M. Soil Biochemistry, Paul, E. A.; Ladd, J. N.; Eds., Marcel Dekker, Inc., New York, 1981, 153-196.

[17]. Mobley, H. L. T.; Island, M. D.; Hausinger, R. P. Microbiol. Rev. 1995, 59, 451-480.
PMid:7565414 PMCid:239369

[18]. Williamson, J. S. Curr. Pharm. Des. 2001, 7, 355-392.
http://dx.doi.org/10.2174/1381612013397979
PMid:11254894

[19]. Estiu G.; Merz, Jr. K. M. J. Am. Chem. Soc. 2004, 126, 6932-6944.
http://dx.doi.org/10.1021/ja049327g
PMid:15174863

[20]. Burne, R. A.; Chen, Y. Y. M. Microbes Infect. 2000, 2, 533-542.
http://dx.doi.org/10.1016/S1286-4579(00)00312-9

[21]. Bayerdorffer, E.; Ottenjhan, R. Scand. J. Gastroenterol. 1988, 23, 93-100.
http://dx.doi.org/10.3109/00365528809091721

[22]. Shingalapur, R. V.; Hosamani, K. M.; Keri, R. S.; Hugar, M. H. Eur. J. Med. Chem. 2010, 45, 1753-1759.
http://dx.doi.org/10.1016/j.ejmech.2010.01.007
PMid:20122763

[23]. Ahmed, S. A.; Hamdy, M. A. -R.; Nadia, M. M.; Mahmoud, A. E. -G. Bioorg. Med. Chem. 2006, 14, 1236-1246.
http://dx.doi.org/10.1016/j.bmc.2006.08.033

[24]. Saitoh, M.; Kunitomo, J.; Kimura, E.; Hayase, Y.; Kobayashi, H.; Uchiyama, N.; Kawamoto, T.; Tanaka, T.; Mol, C. D.; Dougan, D. R.; Textor, G. S.; Snell, G. P.; Itoh, F. Bioorg. & Med. Chem. 2009, 17, 2017-2029.
http://dx.doi.org/10.1016/j.bmc.2009.01.019

[25]. Sen Gupta, A. K.; Garg, M.; Chandra, U. J. Indian Chem. Soc. 1979, 56, 1230-1232.

[26]. Chiyomaru, I.; Takita, K.; Ito, H.; Kumiai Chem. Ind. Co. Ltd., Jap. Pat. 1972, 72 07, 549. Chem. Abstr. 1972, 77, 549.

[27]. ONeal, J. B.; Rosen, H.; Russel, P. B.; Adams, A. C.; Blumenthal, A. J. Med. Pharm. Chem. 1962, 5, 617-626.
http://dx.doi.org/10.1021/jm01238a019

[28]. Thomas, J. Ger. Pat. 2, 403, 357/1974 Chem. Abstr. 1974, 81, 136153g.

[29]. Yale, H. L.; Losee, K. J. Med. Chem. 1966, 9, 478-483.
http://dx.doi.org/10.1021/jm00322a007
PMid:5968010

[30]. Turner, S.; Reckitt and Colman Products Ltd., Ger. Pat. 1978, 2, 727, 146 Chem. Abstr., 1978, 88, 105357s.

[31]. Hodogaya Chemical Co. Ltd., Jap. Pat. 1980, 80 27024 Chem. Abstr., 1980, 93, 232719q.

[32]. Hakko Chem. Ind. Co. Ltd., Brit. Pat. 1, 266, 542/1972 Chem. Abstr., 1972, 77, 5474g.

[33]. Singh, H.; Yadav, L. D. S. Agric. Biol. Chem. 1976, 40, 759-764.
http://dx.doi.org/10.1271/bbb1961.40.759

[34]. Misato, T.; Ko, K.; Honma, Y.; Konno, K.; Taniyama, E. Inst. Phys. Chem. Res., Jap. Pat. 1977, 772 508 Chem. Abstr. 1977, 87, 147054

[35]. Vassiliou, S.; Kosikowska, P.; Grabowiecka, A.; Yiotakis, A.; Kafarski, P.; Berlicki, L. J. Med. Chem. 2010, 53, 5597-5606.
http://dx.doi.org/10.1021/jm100340m
PMid:20684601

[36]. Vassiliou, S.; Grabowiecka, A.; Kosikowska, P.; Yiotakis, A.; Kafarski, P.; Berlicki, L. J. Med. Chem. 2008, 51, 5736-5744.
http://dx.doi.org/10.1021/jm800570q
PMid:18717581

[37]. Rauf, A.; Ahmed, F.; Qureshi, A. M.; Aziz-ur-Rehman, K. A.; Qadir, M. I.; Choudhary, M. I.; Chohan, Z. H.; Youssoufi, M. H.; Hadda, T. B. J. Chin. Chem. Soc. 2011, 58, 528-537.
http://dx.doi.org/10.1002/jccs.201190017

[38]. Muri, E. M. F.; Mishra, H.; Stein, S. M.; Williamson, J. S. Lett. Drug Des. Discov. 2004, 1, 30-34.
http://dx.doi.org/10.2174/1570180043485680

[39]. Khan, M. H., Hameed, S.; Yasin, K. A.; Akhtar, T.; Khan, K. M. Monatsh Chem. 2010, 141, 479-484.
http://dx.doi.org/10.1007/s00706-010-0276-6

[40]. Serwar, M.; Akhtar, T.; Hameed, S.; Khan, K. M. Arkivoc 2009, 7, 210-221.

[41]. Amtul, Z.; Rasheed, M.; Choudhary, M. I.; Rosanna, S.; Khan, K. M.; Atta-ur-Rahman, Biochem. Biophys. Res. Commun. 2004, 319, 1053-1063.
http://dx.doi.org/10.1016/j.bbrc.2004.05.036
PMid:15184088

[42]. Weatherburn, M. W. Anal. Chem. 1967, 39, 971-1974.
http://dx.doi.org/10.1021/ac60252a045

[43]. Khan, K. M.; Shahzad, S. A.; Rani, M.; Ali, M.; Perveen, S.; Anwar, A.; Voelter, W. Lett. Org. Chem. 2006, 3, 286-288.
http://dx.doi.org/10.2174/157017806776114522

Supporting Agencies

The Organisation for the Prohibition of Chemical Weapons (OPCW), Netherland and Higher Education Commission (HEC) Pakistan (Project No. 1910 and under IPFP)

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