European Journal of Chemistry

Utility of thiocarbamoyl moiety in synthesis of some new sulphur containing heterocyclic compounds and evaluation of their antimicrobial activity



Main Article Content

Ahmed Fadda
Hala Refat
Shimaa Kamal

Abstract

The reaction of N,N'-(1,4-phenylene)bis(2-cyanoacetamide) (1) with phenyl isothiocyanate gave thiocarbamoyl derivative 3, which reacted with α-halocarbonyl compounds in a mixture of ethanol:N,N-dimethylformamide in the presence of triethylamineto afford thiazoles 4, 7, 10 and thiophene12 derivatives. While, when the same reaction was refluxed in a mixture of ethanol:N,N-dimethylformamide only afforded the acyclic compounds 5, 6, 8, 9 and 11, which when refluxed in N,N-dimethylformamide in presence of triethylamine gave the corresponding above thiazole and thiophene derivatives. Moreover, the reaction of compound 3 with dihalo compounds afforded cyclic dithio derivatives 13a, 13b and 14. The newly synthesized compounds were characterized by analytical, spectral data and evaluation of their antimicrobial activities of 4, 7, 14 and 15 have a high antimicrobial activity.


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Fadda, A.; Refat, H.; Kamal, S. Utility of Thiocarbamoyl Moiety in Synthesis of Some New Sulphur Containing Heterocyclic Compounds and Evaluation of Their Antimicrobial Activity. Eur. J. Chem. 2014, 5, 296-304.

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References

[1]. Mukerjee, A. K.; Ashare, R. Chem. Rev. 1991, 91, 1-24.
http://dx.doi.org/10.1021/cr00001a001

[2]. Ead, H. A.; Abdellah, S. O.; Kassab, N. A.; Metwalli, N. H.; Saleh, H. Arch. Pharm. (Weinheim) 1997, 320, 1227-1232.

[3]. Misra, N. C.; Patnaik, K. K.; Indian J. Appl. Chem. 1971, 34, 148-155.

[4]. Rao, R. B.; Singh, S. R. J. IndianChem. Soc. 1973, 50, 492-498.

[5]. Parmer, S. S.; Chaudhari, D. A.; Gupta, T. K. J. Med. Chem. 1972, 15, 99-101.
http://dx.doi.org/10.1021/jm00271a030

[6]. Pavlenko, A. F.; Moshchitiskii, S. D. Chem. Heterocyc. Compd. 3; 1968. Chem. Abst. 1967, 68, 114479.

[7]. Tisler, M.; Andolsek, A.; Stanovnik, B.; Likar, M.; Schauer, P. J. Med. Chem. 1971, 14, 53-54.
http://dx.doi.org/10.1021/jm00283a014

[8]. Singh, S. R. J. Indian Chem. Soc. 1975, 52, 734-741.

[9]. Chaudhary, H. S.; Pujari, H. K. Indian J. Chem. 1972, 10, 766-771.

[10]. Dhal, P. N.; Achary, T. E.; Nayak, A. Indian J. Chem. 1975, 13, 46-52.

[11]. Mallick, S. K.; Martin, A. R.; Lingard, R. G. J. Med. Chem. 1971, 14, 528-532.
http://dx.doi.org/10.1021/jm00288a017

[12]. Burton, W. H.; Budde, W. L.; Cheng, J. J. Med. Chem. 1970, 13, 1009-1012.
http://dx.doi.org/10.1021/jm00299a061

[13]. Fadda, A. A.; Refat, M. H.; Zaki, M. E. A. Molecules 1999, 5, 701-709.
http://dx.doi.org/10.3390/50500701

[14]. Fadda, A. A.; Metwally, M. A.; Bondock, S. B.; El-Desoky, S. I.; Etman, H. A. Sulfur Lett. 2002, 25, 199-205.
http://dx.doi.org/10.1080/02786110214496

[15]. Fadda, A. A.; Metwally, M. A.; Bondock, S. B.; El-Desoky, S. I.; Etman, H. A. Sulfur Lett. 2003, 26, 127-135.
http://dx.doi.org/10.1080/0278611031000095331

[16]. Bondock, S.; Fadda, A. A. Eur. J. Med. Chem. 2011, 46(6), 2555-2561
http://dx.doi.org/10.1016/j.ejmech.2011.03.045

[17]. Bondock, S.; Fadaly, W.; Metwally, M. A. Eur. J. Med. Chem. 2010, 45(9), 3692-701
http://dx.doi.org/10.1016/j.ejmech.2010.05.018

[18]. Fadda, A. A.; Etman, H. A.; Sarhan, A. A.; El-Hadidy, S. A. Phosphorus Sulfur 2010, 185, 526-536.
http://dx.doi.org/10.1080/10426500902839863

[19]. El-Shafei, A.; Fadda, A. A.; Khalil, A. M.; Ameen, T. A. E.; Badria, F. A. Bioorg. Med. Chem. 2009, 17, 5096-5105.
http://dx.doi.org/10.1016/j.bmc.2009.05.053

[20]. Fadda, A. A.; Abdel-Latif, E.; El-Mekawy, R. E. Phosphorus Sulfur 2008, 183, 1940-1953.
http://dx.doi.org/10.1080/10426500701839536

[21]. Fadda, A. A.; Abdel-Latif, E.; El-Mekawy, R. E. Pharmacol. Pharm. 2012, 3, 148-157.
http://dx.doi.org/10.4236/pp.2012.32022

[22]. Fadda, A. A.; Abdel-Latif, E.; El-Mekawy, R. E. Eur. J. Med. Chem. 2009, 44, 1250-1256.
http://dx.doi.org/10.1016/j.ejmech.2008.09.006

[23]. Hantzsch, A.; Weber, H. Chem. Ber. 1887, 20, 3118-3132.
http://dx.doi.org/10.1002/cber.188702002200

[24]. Fadda, A. A.; Afsah, E. S. M.; Awad, R. S. Eur. J. Med. Chem. 2013, 60, 421-430.
http://dx.doi.org/10.1016/j.ejmech.2012.11.017

[25]. Abou-Melha, H.; Fadda, A. A. Spectrochim. Acta A 2012, 89, 123-128.
http://dx.doi.org/10.1016/j.saa.2011.12.054

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