European Journal of Chemistry

Synthesis and antimicrobial activity of some new 1,3-thiazoles, 1,3,4-thiadiazoles, 1,2,4-triazoles and 1,3-thiazines incorporating acridine and 1,2,3,4-tetrahydroacridine moieties



Main Article Content

Tarik El-Sayed Ali
Azza Mohammed El-Kazak

Abstract

Some new sulfur-nitrogen heterocyclic systems such as 1,3-thiazoles, 1,3,4-thiadiazoles, 1,2,4-triazoles and 1,3-thiazines incorporating acridine and 1,2,3,4-tetrahydroacridine moieties were synthesized via heterocyclization of the key intermediate 4-(acridin-9-yl)-1-(1,2,3,4-tetrahydroacridin-9-ylcarbonyl)thiosemicarbazide. Structures of the new comp-ounds were established by elemental analyses and spectral data. All the products were also screened in vitro for their antimicrobial activity.

1_1_6_11_800


icon graph This Abstract was viewed 11848 times | icon graph Article PDF downloaded 1935 times

How to Cite
(1)
Ali, T. E.-S.; El-Kazak, A. M. Synthesis and Antimicrobial Activity of Some New 1,3-Thiazoles, 1,3,4-Thiadiazoles, 1,2,4-Triazoles and 1,3-Thiazines Incorporating Acridine and 1,2,3,4-Tetrahydroacridine Moieties. Eur. J. Chem. 2010, 1, 6-11.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Bouffier, L.; Demeunynck, M.; Milet, A.; Dumy, P. J. Org. Chem. 2004, 69, 8144-8147.
doi:10.1021/jo0487855
PMid:15527309

[2]. Chiron, J.; Galy, J. P. Synthesis 2004, 313-327.
doi:10.1055/s-2003-44379

[3]. Chen, H. Huaxue Yanjiu Yu Yingyong 2000, 12, 164-168.

[4]. Sivan, S.; Tuchman, S.; Lotan, N. Biosystems 2003, 70, 21-33.
doi:10.1016/S0303-2647(03)00039-X

[5]. Flock, S.; Bailly, F.; Bailly, C.; Waring, M. J.; Henichart, J. P.; Colson, P.; Houssier, C. J. Biomol. Struct. Dyn. 1994, 11, 881-886.

[6]. Gooch, B. D.; Beal, P. A. J. Am. Chem. Soc. 2004, 126, 10603-10610.
doi:10.1021/ja047818v
PMid:15327318

[7]. Stefanska, B.; Bontemps-Gracz, M. M.; Antonini, I.; Martelli, S.; Arciemiuk, M.; Piwkowska, A.; Rogacka, D.; Borowski, E. Bioorg. Med. Chem. 2005, 13, 1969-1975.
doi:10.1016/j.bmc.2005.01.023

[8]. Demeunynck, M. Expert Opin. Ther. Patents 2004, 14, 55-70.

[9]. Abdel-Halim, A. M.; Tawfik, A. M.; Ibrahim, S. S.; El-Kazak, A. M. Indian J. Heterocyclic. Chem. 1994, 3, 165-170.

[10]. Chen, Y. L.; Lu, C. M.; Chen, I. L.; Tsao, L. T.; Wang, J. P. J. Med. Chem. 2002, 45, 4689-4694.
doi:10.1021/jm020102v
PMid:12361395

[11]. Chen, Y. L.; Chen, I. L.; Lu, C. M.; Treng, C. C.; Tsao, L. T.; Wang, J. P. Bioorg. Med. Chem. 2003, 11, 3921-3927.
doi:10.1016/S0968-0896(03)00439-5

[12]. Skotnicki, J. S.; Gilman, S. C.; US 851536; Chem.Abstr. 1990, 112, 118672.

[13]. Cai, S.; Li, Q. S.; Borchardt, R. T.; Kuczera, K.; Schowen, R. L. Bioorg. Med. Chem. 2007, 15, 7281-7287.
doi:10.1016/j.bmc.2007.08.029

[14]. Rao, B. M.; Sangaraju, S.; Srinivasu, M. K.; Madhavan, P.; Devi, M. L.; Kumar, P. R.; Candrasekhar, K. B.; Arpitha, Ch.; Balaji, T. S. J. Pharm. Biomed. Anal. 2006, 41, 1146-1151.
doi:10.1016/j.jpba.2006.01.011
PMid:16473490

[15]. Hancu, G.; Gaspar, A.; Gyeresi, A. J. Biochem. Biophys. Methods 2007, 69, 251-259.
doi:10.1016/j.jbbm.2006.02.003
PMid:16563516

[16]. Bajetti, E.; Zilembo, N.; Bichisao, E.; Pozzi, P.; Toffolatti, L. Crit. Rev. Oncol. Hematol. 2000, 33, 137-142.
doi:10.1016/S1040-8428(99)00062-1

[17]. Demirbas, A.; Ceylan, S.; Demirbas, N. J. Heterocycl. Chem. 2007, 44, 1271-1280.
doi:10.1002/jhet.5570440608

[18]. Guirgis, F. K.; Ghanem, M. H.; Abdel-Hay, M. M. Arzneim.-Forsch. 1976, 26, 435-440.
PMid:134717

[19]. Bashir, Y.; Kann, M.; Stradling, J. R. Pulm. Pharmacol. 1990, 3, 151-154.
doi:10.1016/0952-0600(90)90046-L

[20]. Cohen, S. M.; Erturk, E.; Von Esch, A. M.; Crovetti, A. J.; Bryan, G. T. J. Natl. Cancer Inst. 1975, 54, 841-849.

[21]. Patt, W. C.; Hamilton, H. W.; Taylor, M. D.; Ryan, M. J.; Taylor, D. G.; Connolly, C. J. C.; Doherty, A. M.; Klutchko, S. R.; Sircar, I.; Steinbaugh, B. A.; Batley, B. L.; Painchaud, C. A.; Rapundalo, S. T.; Michniewicz, B. M.; Olson, S. C. J. J. Med. Chem. 1992, 35, 2562-2572.
doi:10.1021/jm00092a006
PMid:1635057

[22]. Jaen, J. C.; Wise, L. D.; Caprathe, B. W.; Tecle, H.; Bergmeier, S.; Humblet, C. C.; Heffner, T. G.; Meltzner, L. T.; Pugsley, T. A. J. Med. Chem. 1990, 33, 311-317.
doi:10.1021/jm00163a051
PMid:1967314

[23]. Bell, F. W.; Cantrell, A. S.; Hogberg, M.; Jaskunas, S. R.; Johansson, N. G.; Jordon, C. L.; Kinnick, M. D.; Lind, P.; Morin Jr., J. M.; Noreen, R.; Oberg, B.; Palkowitz, J. A.; Parrish, C. A.; Pranc, P.; Sahlberg, C.; Ternansky, R. J.; Vasileff, R. T.; Vrang, L.; West, S. J.; Zhang, H.; Zhou, X. X. J. Med. Chem. 1995, 38, 4929-4936.
doi:10.1021/jm00025a010
PMid:8523406

[24]. Rudolph, J.; Theis, H.; Hanke, R.; Endermann, R.; Johannsen, L.; Geschke, F. U. J. Med. Chem. 2001, 44, 619-626.
doi:10.1021/jm0010623
PMid:11170652

[25]. Cecchetti, V.; Cruciani, G.; Filipponi, E.; Fravolini, A.; Tabarrini, O.; Xin, T. Bioorg. Med. Chem. 1997, 5, 1339-1344.
doi:10.1016/S0968-0896(97)00084-9

[26]. Kai, H.; Morioka, Y.; Tomida, M.; Takahashi, T.; Hattori, M.; Hanasaki, K.; Koike, K.; Chiba, H.; Shinohara, S.; Kanemasa, T.; Iwamoto, Y.; Takahashi, K.; Yamaguchi, Y.; Baba, T.; Yoshikawa, T.; Takenaka, H. Bioorg. Med. Chem. Lett. 2007, 17, 3925-3929.
doi:10.1016/j.bmcl.2007.04.099

[27]. Ali, T. E. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 1717-1726.
doi:10.1080/10426500701313896

[28]. Ali, T. E.; Abdel-Aziz, S. A.; El-Shaaer, H. M.; Hanafy, F. I.; El-Fauomy, A. Z.; Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 2139-2160.
doi:10.1080/10426500701851291

[29]. Ali, T. E.; Ibrahim, M. A.; Abdel-Karim, S. M. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 2358-2392.
doi:10.1080/10426500802473094

[30]. Alberti, A.; Ritiche, B. Org. Synth. 1960, 3, 53-54.

[31]. Kristian, P.; Baletova, E.; Bernat, J.; Imrich, J.; Sedlak, E.; Danihel, I.; Bohm, S.; Pronayova, N.; Klika, K. D.; Pihlaja, K.; Baranova, J. Chem. Pap. 2004, 58, 268-275.

[32]. Popp, F. D. J. Org. Chem. 1962, 27, 2658-2659.
doi:10.1021/jo01054a518

[33]. Kilka, K. D.; Balentova, E.; Bernat, J.; Imrich, J.; Vavrusova, M.; Kleinpeter, E.; Pihlaja, K.; Koch, A. J. Heterocyclic. Chem. 2006, 43, 633-643.
doi:10.1002/jhet.5570430317

[34]. Kilka, K. D.; Imrich, J.; Vilkova, M.; Bernat, J.; Pihlaja, K. J. Heterocyclic. Chem. 2006, 43, 739-743.
doi:10.1002/jhet.5570430331

[35]. Balentova, E.; Imrich, J.; Bernat, J.; Sucha, L.; Vilkova, M.; Pronayova, N.; Kristian, P.; Kilka, K. D. J. Heterocyclic. Chem. 2006, 43, 645-656.
doi:10.1002/jhet.5570430318

[36]. Tomaščiková, J.; Imrich, J.; Danihel, I.; Böhm, S.; Kristian, P.; Pisarčíková, J.; Sabol, M.; Klika, K.D. Molecules 2008, 13, 501-518.
doi:10.3390/molecules13030501

[37]. Liszkiewicz, H. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 1402-1409.
doi:10.1080/10426500701648077

[38]. Keshk, E. M.; El-Desoky, S. I.; Hammouda, M. A. A.; Abdel-Rahman, A. H.; Hegazi, A. G. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 1323-1343.
doi:10.1080/10426500701641304

[39]. Junjappa, H.; Ila, H.; Asokan, C.V. Tetrahedron 1990, 46, 5423-5450.
doi:10.1016/S0040-4020(01)87748-6

[40]. Rahman, A. U.; Choudhary, M. I.; Thomsen, W.J. Bioassay Techniques for drug development, 16 the Netherlands: Harwood Academic Publishers 2001.

[41]. Khan, K. M.; Saify, Z. S.; Zeesha, A. K.; Ahmed, M.; Saeed, M.; Schick, M.; Bkohlbau, H.J.; Voelter, W. Arzneim-Forsch/Drug Res. 2000, 50, 915-922.

[42]. Mishra, D.; Patnaik, S.; Rath, C. C.; Dash, S. K.; Mishra, R. K.; Patnaik, U. Indian J. Pharm. Sci. 2002, 64, 256-259.

Supporting Agencies

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).