European Journal of Chemistry 2013, 4(3), 277-284 | doi: https://doi.org/10.5155/eurjchem.4.3.277-284.837 | Get rights and content

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Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives


Kamal Mohamed Dawood (1,*) , Hussein Khalaf-Allah Abu-Deif (2)

(1) Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt
(2) Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt
(*) Corresponding Author

Received: 26 May 2013 | Revised: 12 Jun 2013 | Accepted: 12 Jun 2013 | Published: 30 Sep 2013 | Issue Date: September 2013

Abstract


1,2-Bis-(2-(phenylimino)-4-oxo-1,3-thiazolidin-3-yl)ethane (4) was synthesized and its reaction with various aldehydes afforded the novel 5-arylidene derivatives 5a-e and 7. Reaction of compound 4 with phenyl isothiocyanate in the presence of potassium hydroxide, followed by addition of two equivalents of α-halo ketones furnished the corresponding 1,2-bis-[5-(thiazolidin-2-ylidene)thiazolidin-3-yl]ethane derivatives 10, 14a-c, and 17a,b. The structures of the newly synthesized compounds were established by elemental and spectral analyses. Compounds 5a-e, 7, 10, 14a-c and 17a were screened for their antimicrobial activity against eight microorganisms. All compounds showed high antibacterial and antifungal activities against all the test microorganisms except E. coli and C. albicans. The MIC of the active compounds was also evaluated, where; compounds 10 and 17a were more potent active (minimum inhibitory concentration 0.49 and 0.98 μg/mL, respectively) against S. racemosum than Amphotericin B (MIC 1.95 μg/mL).

4_3_277_284

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Keywords


Antifungal; Bis-thiourea; Antibacterial; Alfa-Halo ketones; Bis-thiazolidinones; 1,3-Thiazolidin-4-one

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DOI: 10.5155/eurjchem.4.3.277-284.837

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Funding information


Faculty of Science, Cairo University, Giza 12613, Egypt

Citations

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[1]. Kamal M. Dawood
Bis‐thiourea Derivatives and Their Utility in Synthesis of Mono‐heterocyclic, Bis‐heterocyclic, and Fused Heterocyclic Systems
Journal of Heterocyclic Chemistry  56(6), 1701, 2019
DOI: 10.1002/jhet.3540
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[2]. Tapan Kumar Jena, Faiz Ahmed Khan
Acid mediated synthesis of thiazolines, thiazoles and enamide derivatives from methyl enol ethers: Application towards synthesis of wilsoniamine B
Tetrahedron Letters  61(13), 151675, 2020
DOI: 10.1016/j.tetlet.2020.151675
/


[3]. Amer A. Amer, Antar A. Abdelhamid, Amany Sh. Elnakeeb, Hanan A. Salah
One‐pot multicomponent designing of novel 2‐imino‐4‐arylidene‐1,3‐thiazolidin‐4‐one
Journal of Heterocyclic Chemistry  60(3), 489, 2023
DOI: 10.1002/jhet.4604
/


[4]. Kamal M. DAWOOD, Eman A. RAGAB, Korany A. ALI
Synthetic access to some new benzothiazole-based 1,3,4-thiadiazole and 1,3-thiazole derivatives
TURKISH JOURNAL OF CHEMISTRY  40, 277, 2016
DOI: 10.3906/kim-1503-75
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[5]. Ashraf A. Abbas, Kamal M. Dawood
Benzofuran as a promising scaffold for the synthesis of novel antimicrobial agents
Expert Opinion on Drug Discovery  17(12), 1357, 2022
DOI: 10.1080/17460441.2023.2157400
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[6]. Javad Safaei-Ghomi, Seyed Hadi Nazemzadeh, Hossein Shahbazi-Alavi
Nano-colloidal silica-tethered polyhedral oligomeric silsesquioxanes with eight branches of 3-aminopropyltriethoxysilane as high-performance catalyst for the preparation of bis-thiazolidinones under ultrasonic conditions
Zeitschrift für Naturforschung B  72(12), 927, 2017
DOI: 10.1515/znb-2017-0091
/


References


[1]. Dhooghe, M.; De Kime, N. Tetrahedron 2006, 62, 513-535.
http://dx.doi.org/10.1016/j.tet.2005.09.028

[2]. Hunter, R.; Younis, Y.; Muhanji, C. I.; Curtin, T. L.; Naidoo, K. J.; Petersen, M.; Bailey C. M.; Basavapathruni, A.; Anderson, K. S. Bioorg. Med. Chem. 2008, 16, 10270-10280.
http://dx.doi.org/10.1016/j.bmc.2008.10.048
PMid:18996020 PMCid:PMC2639753

[3]. Kang, I. J.; Wang, L. W.; Yeh, T. K.; Lee, C. C.; Lee, Y. C.; Hsu, S. J.; Wu, Y. S.; Wang, J. C.; Chao, Y. S.; Yueh, A.; Chern, J. H. Bioorg. Med. Chem. 2010, 18, 6414-6421.
http://dx.doi.org/10.1016/j.bmc.2010.07.002
PMid:20675142

[4]. Lee, J.; Kim, S. Y.; Lee, J.; Kang, M.; Kil, M. J.; Choi, H. K.; Jin, M. K.; Wang, Y.; Toth, A.; Pearce, L. V.; Lundberg, D. J.; Tran, R.; Blumberg, P. M. Bioorg. Med. Chem. 2004, 12, 3411-3420.
http://dx.doi.org/10.1016/j.bmc.2004.04.040
PMid:15186827

[5]. Zhang, H. J.; Qin, X.; Liu, K.; Zhu, D. D.; Wang, X. M.; Zhu, H. L. Bioorg. Med. Chem. 2011, 19, 5708-5715.
http://dx.doi.org/10.1016/j.bmc.2011.06.077
PMid:21872479

[6]. Abdel‐Aziem, A.; El‐Gendy, M. S.; Abdelhamid, A. O. Eur. J. Chem. 2012, 3, 455‐460.
http://dx.doi.org/10.5155/eurjchem.3.4.455-460.683

[7]. Faidallah, H. M.; Khan, H. H.; Asiri, A. M. Eur. J. Chem. 2011, 2, 243‐250.
http://dx.doi.org/10.5155/eurjchem.2.2.243-250.257

[8]. Saeed, S.; Rashid, N.; Ali, M.; Hussain, R.; Jones, P. Eur. J. Chem. 2010, 1, 221‐227
http://dx.doi.org/10.5155/eurjchem.1.3.221-227.124

[9]. Lv, P. C.; Li, H. Q.; Sun, J.; Zhou, Y.; Zhu, H. L. Bioorg. Med. Chem. 2010, 18, 4606-4614.
http://dx.doi.org/10.1016/j.bmc.2010.05.034
PMid:20627597

[10]. Venkatachalam, T. K.; Qazi, S.; Samuel, P.; Uckun, F. M. Bioorg. Med. Chem. 2003, 11, 1095-1105.
http://dx.doi.org/10.1016/S0968-0896(02)00531-X

[11]. Sohtome, Y.; Hashimoto, Y.; Nagasawa, K. Adv. Synth. Catal. 2005, 347, 1643-1648.
http://dx.doi.org/10.1002/adsc.200505148

[12]. Berkessel, A.; Roland, K.; Neudçrfl, J. M. Org. Lett. 2006, 8, 4195-4198.
http://dx.doi.org/10.1021/ol061298m
PMid:16956185

[13]. Fleming, E. M.; McCabe, T.; Connon, S. J. Tetrahedron Lett. 2006, 47, 7037-7042.
http://dx.doi.org/10.1016/j.tetlet.2006.07.112

[14]. Martin, N. J. A.; Ozores, L.; List, B. J. Am. Chem. Soc. 2007, 129, 8976-8977.
http://dx.doi.org/10.1021/ja074045c
PMid:17602561

[15]. Rampalakos, C.; Wulffa, W. D. Adv. Synth. Catal. 2008, 350, 1785-1790.
http://dx.doi.org/10.1002/adsc.200800214
PMid:23795151 PMCid:PMC3686523

[16]. Jain, A. K.; Vaidya, A.; Ravichandran, V.; Kashaw, S. K.; Agrawal, R. K. Bioorg. Med. Chem. 2012, 20, 3378-3395.
http://dx.doi.org/10.1016/j.bmc.2012.03.069
PMid:22546204

[17]. Liu, X. F.; Zheng, C. J.; Sun, L. P.; Liu, X. K.; Piao, H. R. Eur. J. Med. Chem. 2011, 46, 3469-3473.
http://dx.doi.org/10.1016/j.ejmech.2011.05.012
PMid:21624712

[18]. Turan-Zitouni G.; Kaplancikli, Z. A.; Ozdemir, A. Eur. J. Med. Chem. 2010, 45, 2085-2088.
http://dx.doi.org/10.1016/j.ejmech.2010.01.017
PMid:20149489

[19]. Wang, S.; Zhao, Y.; Zhang, G.; Lv, Y.; Zhang, N.; Gong, P. Eur. J. Med. Chem. 2011, 46, 3509-3518.
http://dx.doi.org/10.1016/j.ejmech.2011.05.017
PMid:21621880

[20]. Bekhit, A. A.; Fahmy, H. T. Y.; Rostom, S. A. F.; Bekhit, A. A. Eur. J. Med. Chem. 2010, 45, 6027-6038.
http://dx.doi.org/10.1016/j.ejmech.2010.10.001
PMid:20970223

[21]. Kaur, H.; Kumar, S.; Vishwakarma, P.; Sharma, M.; Saxena, K. K.; Kumar, A. Eur. J. Med. Chem. 2010, 45, 2777-2783.
http://dx.doi.org/10.1016/j.ejmech.2010.02.060
PMid:20392546

[22]. Maccari, R.; Corso, A. D.; Giglio, M.; Moschini, R.; Mura, U.; Ottana, R. Bioorg. Med. Chem. Lett. 2011, 21, 200-203.
http://dx.doi.org/10.1016/j.bmcl.2010.11.041
PMid:21129963

[23]. Ottana, R.; Maccari, R.; Giglio, M.; Del Corso, A.; Cappiello, M.; Mura, U.; Cosconati, S.; Marinelli, L.; Novellino, E.; Sartini, S.; La-Motta, C.; Da Settimo, F. Eur. J. Med. Chem. 2011, 46, 2797-2806.
http://dx.doi.org/10.1016/j.ejmech.2011.03.068
PMid:21531055

[24]. Vigorita, M. G.; Ottana, R.; Monforte F.; Maccari R.; Monforte, M. T.; Trovato, A.; Taviano, M. F.; Miceli, N.; De Luca, G.; Alcaro, S.; Ortuso, F. Bioorg. Med. Chem. 2003, 11, 999-1006.
http://dx.doi.org/10.1016/S0968-0896(02)00518-7

[25]. Dawood, K. M.; Abdel-Gawad, H.; Mohamed, H. A.; Badria, F. A. Med. Chem. Res. 2011, 20, 912-919.
http://dx.doi.org/10.1007/s00044-010-9420-4

[26]. Abdel-Aziz, H. A.; El-Zahabi, H. S. A.; Dawood, K. M. Eur. J. Med. Chem. 2010, 45, 2427-2432.
http://dx.doi.org/10.1016/j.ejmech.2010.02.026
PMid:20207452

[27]. Hegazi, B.; Mohamed, H. A.; Dawood, K. M.; Badria, F. A. Chem. Pharm. Bull. 2010, 58, 479-483.
http://dx.doi.org/10.1248/cpb.58.479

[28]. Abdel-Aziz, H. A. I.; Mekawey, A. A.; Dawood, K. M. Eur J. Med. Chem. 2009, 44, 3637-3644.
http://dx.doi.org/10.1016/j.ejmech.2009.02.020
PMid:19321238

[29]. Dawood, K. M.; Abdel-Gawad, H.; Rageb, E. A.; Ellithey, M.; Mohamed, H. A. Bioorg. Med. Chem. 2006, 14, 3672-3680.
http://dx.doi.org/10.1016/j.bmc.2006.01.033
PMid:16464601

[30]. Dawood, K. M.; Abdel-Gawad, H.; Ellithey, M.; Mohamed, H. A.; Hegazi, B. Arch. Pharm. Chem. Life Sci. 2006, 339, 133-140.
http://dx.doi.org/10.1002/ardp.200500176
PMid:16528794

[31]. Dawood, K. M. J. Heterocycl. Chem. 2005, 42, 221-225.
http://dx.doi.org/10.1002/jhet.5570420207

[32]. Cowper, R. M.; Davidson, L. H. Org. Synth. 1943, 2, 840-840.

[33]. Czerney, P.; Hartmann, H. J. Prakt. Chem. 1983, 325, 551-560.
http://dx.doi.org/10.1002/prac.19833250405

[34]. Kira, M. A; Abdel-Rahman, M. O.; Gadalla, K. Z. Tetrahedron Lett. 1969, 10, 109-110.
http://dx.doi.org/10.1016/S0040-4039(01)88217-4

[35]. Holder, I. A.; Boyce, S. T. Burns 1994, 20, 426-429.
http://dx.doi.org/10.1016/0305-4179(94)90035-3

[36]. Agwa, H.; Aly, M. M.; Bonaly, R. J. Union Arab Biol, 2000, 7, 62-82.

[37]. Doughari, J. H; Trop. J. Pharm. Res. 2006, 5, 597-603.

[38]. Midgley, G.; Clayton, Y.; Hay, J. Diagnosis in color medical mycology, international, UK. 1997, pp. 14-17.

[39]. Shiriling, E. M.; Gottlieb, D. Int. J. Syst. Bact. 1966, 16, 313-340.
http://dx.doi.org/10.1099/00207713-16-3-313

[40]. Dangeli, F.; Bandel, A.; Giormani, V. J. Org. Chem. 1963, 28, 1596-1600.
http://dx.doi.org/10.1021/jo01041a040

[41]. Ottana, R.; Maccari, R.; Barreca, M. L.; Bruno, G.; Rotondo, A.; Rossi, A.; Chiricosta, G.; Paola, R. D.; Sautebin, L.; Cuzzocrea, S.; Vigorita, M. G. Bioorg. Med. Chem. 2005, 13, 4243-4252.
http://dx.doi.org/10.1016/j.bmc.2005.04.058
PMid:15905093

[42]. Dhal, P. N.; Achary, T. E.; Nayak, A. Indian J. Chem. 1975, 13, 753-755.

[43]. Momose, Y.; Meguro, K.; Ikeda, H.; Hatanaka, C.; Oi, S.; Sohda, T. Chem. Pharm. Bull. 1991, 39, 1440-1445.
http://dx.doi.org/10.1248/cpb.39.1440

[44]. Kempegowda; Kumar, G. P. S.; Prakash, D.; Mani, T. T. Der Pharma Chem. 2011, 3, 330-341.

[45]. Karigar, A.; Himaja, M.; Mali, V. S.; Prathap, K. J.; Sikarwar, S. M. Internat. Res. J. Pharm. 2011, 2, 153-158.


How to cite


Dawood, K.; Abu-Deif, H. Eur. J. Chem. 2013, 4(3), 277-284. doi:10.5155/eurjchem.4.3.277-284.837
Dawood, K.; Abu-Deif, H. Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives. Eur. J. Chem. 2013, 4(3), 277-284. doi:10.5155/eurjchem.4.3.277-284.837
Dawood, K., & Abu-Deif, H. (2013). Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives. European Journal of Chemistry, 4(3), 277-284. doi:10.5155/eurjchem.4.3.277-284.837
Dawood, Kamal, & Hussein Khalaf-Allah Abu-Deif. "Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives." European Journal of Chemistry [Online], 4.3 (2013): 277-284. Web. 30 May. 2023
Dawood, Kamal, AND Abu-Deif, Hussein. "Synthesis and antimicrobial activity of some new 1,2-bis-[1,3-thiazolidin-3-yl]ethane derivatives" European Journal of Chemistry [Online], Volume 4 Number 3 (30 September 2013)

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