European Journal of Chemistry 2015, 6(2), 157-162 | doi: https://doi.org/10.5155/eurjchem.6.2.157-162.1219 | Get rights and content






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Design, synthesis, antimicrobial activity and anticancer screening of some new 1,3-thiazolidin-4-ones derivatives


Wesam Saber Shehab (1,*) , Samar Mohamed Mouneir (2)

(1) Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44511, Egypt
(2) Department of Pharmacology, Faculty of Veterinary Medicine, Cairo University, Cairo, 12211, Egypt
(*) Corresponding Author

Received: 17 Nov 2014 | Accepted: 01 Feb 2015 | Published: 30 Jun 2015 | Issue Date: June 2015

Abstract


A series of new thiazolidin-4-ones have been synthesized by the reaction of 3-acetylindole with thiourea to yield 2-amino-arylthiazole (1) which, reacted with 2-chloroacetyl chloride to produce 2-chloroacetamido-4-arylthiazoles (2). The later was treated with potassium thiocyanate to afford the related 2-amino-3-(4-arylthiazol-2-yl) thiazolidin-4-ones (3). Condensation of compounds 1 and 3 with different aromatic aldehydes give Schiff’s bases (4a-c) and (5a-c) reaction of compound 5a-c with thioglycollic acids furnishes the target thiazolidin-4-one molecules (6a-c). Further, condensation of compound 6a with benzaldehyde affords benzylidenethiazolo derivative (7) which on refluxing with malononitrile, acetylacetone afforded thiazolopyridine derivatives (8,9). Structure elucidation of the products has been accomplished on the basis of elemental analysis, IR, 1H NMR data. Compound 3exhibited the most potent antibacterial and anticancer activity.


Keywords


Anticancer; Schiff’s bases; 3-Acetylindol; Antimicrobial; 1,3-Thiazolidin-4-ones; Thiazolopyridine derivatives

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DOI: 10.5155/eurjchem.6.2.157-162.1219

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References

[1]. Agarwal, O. P. Textbook of Organic Chemistry, 4th edition, Goel Publisher, p730, 2006.

[2]. Bama, K. G.; Rajani, K. B. Indian J. Chem. B. 1988, 27, 1157-1158.

[3]. Mahd, A. K.; Zaman, M. S. Indian J. Chem. B. 2004, 43, 2189-2194.

[4]. Verma, L.; Wakode, S. Pharma Innov. J. 2013, 2, 41-50.

[5]. Raghuram, R. A.; Rajan, K. S.; Devsingh, S.; Bhagavan, R. M. Indian J. Chem. B 2001, 40, 813-816 .

[6]. Reddy, P. S. N.; Manmahan, R.; Pradap, R. P. Indian J. Chem. B 2003, 40, 2119-2120.

[7]. Mulwad, W.; Choudhari, B. Indian. J. Chem. B 2005, 42, 1074-1078.

[8]. Mhogale, V. A. Indian J. Chem. Sci. 1990, 102(4), 535-540.

[9]. Sharshira, E. M.; Hamada, N. M. M. Am. J. Org. Chem. 2012, 2(3), 69-73.
http://dx.doi.org/10.5923/j.ajoc.20120203.06

[10]. Brown, F. C. Chem. Rev. 1961, 61, 463-463.
http://dx.doi.org/10.1021/cr60213a002

[11]. Singh, S. P.; Parmar, S. S.; Raman, K.; Stenberg, V. I. Chjem. Rev. 1981, 61, 175-203.
http://dx.doi.org/10.1021/cr00042a003

[12]. Doran, W. J.; Shonle, H. A. J. Org. Chem. 1938, 3, 193-197.
http://dx.doi.org/10.1021/jo01220a001

[13]. Troutman, H. D.; Long, L. M. J. Am. Chem. Soc. 1948, 70, 3436-3439.
http://dx.doi.org/10.1021/ja01190a064

[14]. Rout, M. K.; Mahapatra; G. N. J. Am. Chem. Soc. 1955, 77, 2427-2428.
http://dx.doi.org/10.1021/ja01614a020

[15]. Gaikwad, N. J.; Trupude, R. N. Indian Drugs 1994, 31, 593-594.

[16]. El-Gendy, Z.; Abdel-Rahman, R. M.; Fawzy, M. M; Mahmoud, M. B. J. Ind. Chem. Soc. 1994, 67, 927-929.

[17]. Diumo, M. V.; Mazzoni, O.; Piscopo, E.; Calignano, A.; Giordano, F.; Bolognese, A. J. Med. Chem. 1992, 35, 2190-2912.

[18]. Shah, V.; Pant, C. K.; Joshi, P. C. Asian J. Chem. 1993, 5, 83-88.

[19]. Mukhatar, S.; Majeebar, R. V. P.; Ansari, W. H.; Lemiere, G.; De Groot, A.; Dommisse, R. J. Ind. Chem. Soc. 1999, 4, 232-237.

[20]. Radwan, M. A. A.; Ragab, E. A.; Nermien, M. Bioorg. Med. Chem. 2007, 15, 3832-3841.
http://dx.doi.org/10.1016/j.bmc.2007.03.024

[21]. Singh, P.; Mittal, A.; Kaur, S. Bioorg. Med. Chem. Lett. 2008, 18, 85-89.
http://dx.doi.org/10.1016/j.bmcl.2007.11.010

[22]. Ryu, C. K. K.; Lee, J. Y.; Park, R.; Ma, N. Bioorg. Med. Chem. Lett. 2007, 5, 127-31.
http://dx.doi.org/10.1016/j.bmcl.2006.09.076

[23]. Liu, K.; Sun, J.; Lou, H.; Dai, S., Xu, H. Phytochem. 2008, 69, 1405-1410.
http://dx.doi.org/10.1016/j.phytochem.2008.01.008

[24]. Abdel-Rahman, A. A. H.; Abdel-Megied, A. E. S.; Hawata, M. A. M.; Kasem, E. R.; Shaaban, M. T. Monatsh. Chem. 2007, 138, 889-897.
http://dx.doi.org/10.1007/s00706-007-0700-8

[25]. Geroge, S.; Waran, M. P.; Chakraborty, A.; Ravi, T. K. Acta. Pharm. 2008, 58, 119-129.

[26]. Metawally, M. A.; Shaaban, S.; Abdel-Wahab, B. F.; Gamal, A. Curr. Org. Chem. 2009, 13, 1475-1495.
http://dx.doi.org/10.2174/138527209789055063

[27]. Winter, C. A.; Risley, E. A.; Nuss, G. W. Soc. Exp. Biol. Med. 1962, 111, 544-547.
http://dx.doi.org/10.3181/00379727-111-27849

[28]. Loveleen, V.; Sharad, W. Pharma Innov. J. 2013, 2(5), 41-50

[29]. Bauer, A. W.; Kirby, W. M.; Sherris, C.; Turck, M. Am. J. Clin. Path. 1966, 45, 493-496.

[30]. Pfaller, M. A.; Burmeister, L.; Bartlett, M. A.; Rinaldi, M. G. J. Clin. Microbiol. 1988, 26, 1437-1441.

[31]. National Committee for Clinical Laboratory Standards. Performance Vol. 41, Antimicrobial susceptibility of Flavobacteria, 1997.

[32]. National Committee for Clinical Laboratory Standards. Methods for dilutionantimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard M7-A3. National Committee for Clinical Laboratory Standards, Villanova, PA, USA, 1997.

[33]. National Committee for Clinical Laboratory Standards, Reference Methodfor Broth Dilution Antifungal Susceptibility Testing of Conidium-Forming Filamentous Fungi: Proposed Standard M38-A, NCCLS, Wayne, PA, USA, 2002.

[34]. National Committee for Clinical Laboratory Standards, Method forAntifungal Disk Diffusion Susceptibility Testing of Yeast: Proposed Guideline M44-P, NCCLS, Wayne, PA, USA, 2003.

[35]. Liebowitz, L. D.; Ashbee, H. R.; Evans, E. G. V.; Chong, Y.; Mallatova, N.; Zaidi, M.; Gibbs, M. Diagn. Microbiol. Infect. Dis. 2002, 4, 27-33.

[36]. Matar, M. J.; Ostrosky-Zeichner, L.; Paetznick, V. L.; Rodriguez, J. R.; Chen, E.; Rex, J. H. Antimicrob. Agents Chemother. 2003, 47, 1647-1651.
http://dx.doi.org/10.1128/AAC.47.5.1647-1651.2003

[37]. Skhen, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Oyd, M. R. J. Nat. Cancer Inst. 1990, 82, 1107-1112.
http://dx.doi.org/10.1093/jnci/82.13.1107

How to cite


Shehab, W.; Mouneir, S. Eur. J. Chem. 2015, 6(2), 157-162. doi:10.5155/eurjchem.6.2.157-162.1219
Shehab, W.; Mouneir, S. Design, synthesis, antimicrobial activity and anticancer screening of some new 1,3-thiazolidin-4-ones derivatives. Eur. J. Chem. 2015, 6(2), 157-162. doi:10.5155/eurjchem.6.2.157-162.1219
Shehab, W., & Mouneir, S. (2015). Design, synthesis, antimicrobial activity and anticancer screening of some new 1,3-thiazolidin-4-ones derivatives. European Journal of Chemistry, 6(2), 157-162. doi:10.5155/eurjchem.6.2.157-162.1219
Shehab, Wesam, & Samar Mohamed Mouneir. "Design, synthesis, antimicrobial activity and anticancer screening of some new 1,3-thiazolidin-4-ones derivatives." European Journal of Chemistry [Online], 6.2 (2015): 157-162. Web. 23 Jan. 2020
Shehab, Wesam, AND Mouneir, Samar. "Design, synthesis, antimicrobial activity and anticancer screening of some new 1,3-thiazolidin-4-ones derivatives" European Journal of Chemistry [Online], Volume 6 Number 2 (30 June 2015)

DOI Link: https://doi.org/10.5155/eurjchem.6.2.157-162.1219

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