IKHLASS ABBAS, SOBHI GOMHA, MOHAMED ELNEAIRY, MAHMOUD ELAASSER, BAZADA MABROUK

Synthesis and biological evaluation of novel fused triazolo[4,3-$a$] pyrimidinones

The reaction of thione 3 or its 2-methylthio derivative 4 with hydrazonoyl halides 5a-l, in the presence of triethylamine, yielded the corresponding triazolo[4,3-$a$]pyrimidin-5(1$H)$-ones 8a-l. The structure of compounds 8a-l was further confirmed by the reaction of 3 with the appropriate active chloromethylenes 11a-c followed by coupling of the products with benzenediazonium chloride to afford the azo-coupling products 6b, f, and j, which were converted in situ to 8b, f, and j. 2-Hydrazinyl-pyrido[3',2':4,5]thieno[3,2-$d$]pyrimidin-4(3$H)$-one (13) was prepared and condensed with different aldehydes 14a-f to give the corresponding hydrazone derivatives 15a-f. Oxidative cyclization of the hydrazones 15a-f give the corresponding triazolo[4,3-$a$] pyrimidin-5(1$H)$-one derivatives 16a-f.

Anahtar Kelimeler:

The antimicrobial activity of the products was evaluated and the results revealed that compounds 8f and 15f showed strong activity against gram-positive bacteria while compound 15d showed the highest activity against gram-negative bacteria. Moreover, co

Synthesis and biological evaluation of novel fused triazolo[4,3-$a$] pyrimidinones

Keywords:

The antimicrobial activity of the products was evaluated and the results revealed that compounds 8f and 15f showed strong activity against gram-positive bacteria while compound 15d showed the highest activity against gram-negative bacteria. Moreover, co,

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Patrick, G. L. An Introduction to Medicinal Chemistry ; 4th edition. Oxford University Press: Oxford, UK, 2008.
D¨ur¨ust, Y.; Karaku¸s, H.; Yavuz, M. Z.; Gepdiremen, A. A., Turk. J. Chem. 2014, 38, 739–755.
Gomha, S. M.; Riyadh, S. M.; Abbas, I. M.; Bauomi, M. A. Heterocycles 2013, 87, 341–356.
Badrey, M. G.; Gomha, S. M. Molecules 2012, 17, 11538–11553.
Riyadh, S.M.; Farghaly, T. A.; Gomha, S. M. Arch. Pharm. Res. 2010, 33, 1721–1728.
Bekircan, O.; Kahveci, B.; K¨u¸c¨uk, M. Turk. J. Chem. 2006, 30, 29–40.
Huang, L. H.; Zheng, Y. F.; Lu, Y. Z.; Song, C. J.; Wang, Y. G.; Yu, B.; Hong- Liu, M. Steroids 2012, 77, 710–715.
Zhang, N.; Ayral-Kaloustian, S.; Nguyen, T. H.; Wu, Y.; Tong, W. U.S. patent WO 20, 0503, 0775, 2005.
Zhang, N.; Semiramis, A.; Thai, N. J. Med. Chem. 2007 , 50, 319–327.
Havlicek, L.; Fuksova, K.; Krystof, V. Bioorg. Med. Chem. 2005, 13, 5399–5407.
Zhao, X.; Zhao, Y.; Guo, S.; Song, H.; Wang, D.; Gong, P. Molecules 2007, 12, 1136–1146.
Iwona, L.; Marzena, F.; Tadeusz, M.; Tadeusz, S.; Julia, J. Dalton Trans. 2013, 42, 6219–6226.
Marwaha, A.; White, J.; El Mazouni, F.; Creason, S.; Kokkonda, S.; Buckner, F.; Rathod, P. J. Med. Chem. 2012, 55, 7425–7437.
Yin, L.; Shuai, Z.; Zhi-Jun, L.; Hai-Liang, Z. Eur. J. Med. Chem. 2013, 64, 54–61.
Abd El-Wahab, H. A. Pharmaceuticals 2012, 5, 745–757.
Abdel-Aziem, A.; El-Gendy, M. S.; Abdelhamid A. O. Eur. J. Chem. 2012, 3, 455–460.
Khera, M.; Cliffe, I.; Mathur, T.; Prakash, O. Bioorg. Med. Chem. Lett. 2011, 21, 2887–2889.
Ashour, H.; Shaaban, O.; Rizk, O.; El-Ashmawy, I. Eur. J. Med. Chem. 2013, 62, 341–351.
Fraley, M.; Hoffman, W.; Rubino, R. Bioorg. Med. Chem. Lett. 2002, 12, 2767–2770.
Chen, Q.; Zhu, X.; Liu, Z. Eur. J. Med. Chem. 2008, 43, 595–603.
Uryu, S.; Tokuhiro, S.; Murasugi, T. Brain Res. 2002, 946, 298–306.
Ram, V. J.; Upadhyay, D. N. Indian J. Chem. 1999, 38B, 1173–1177.
Barthelemy, G.; Hallot, A.; Vallat, J. N. Fr. Pat. 2, 459, 834, 1985, Chem. Abstr. 1985, 103, 71335u.
Ram, V. J.; Singha, U. K.; Guru, P. Y. Eur. J. Med. Chem. 1990, 25, 533–538.
Nakamura, H.; Hosoi, Y.; Fukawa, J. Jpn. Kokai Pat. 03, 10, 245, 1991, Chem. Abstr. 1991, 115, 266657f.
Gomha, S. M.; Abdulla, M. M.; Abou-Seri, S. M. Eur. J. Med. Chem. 2015, 92, 459–470.
Gomha, S. M.; Abdel-Aziz, H. A. Heterocycles 2012, 85, 2291–2330.
Gomha, S. M.; Ahmed, S. A.; Abdelhamid, A. O. Molecules 2015, 20, 1357–1376 .
Gomha, S. M.; Abdel-Aziz, H. A. Bull. Korean Chem. Soc. 2012, 33, 2985–2990.
Gomha, S. M.; Eldebss, T. M. A.; Abdulla, M. M.; Mayhoub, A. S. Eur. J. Med. Chem. 2014, 82, 472–479.
Gomha, S. M. Monatsh. Chem. 2009, 140, 213–220.
Gomha, S. M.; Shawali, A. S.; Abdelhamid, A. O. Turk. J. Chem. 2014, 38, 865– 879.
Gad-Elkareem, M. A. M.; Elneairy, M. A. A.; Taha, A. M. Heteroat. Chem. 2007, 18, 405–413.
Elgemeie, G. E. H. Heterocycles 1990, 31, 123–127.
Shawali, S. A.; Elghandour, H.; Sayed, A. R. Synthetic Commun. 2001, 31, 731–740.
Shaban, M. A. E.; Taha, M. A. M.; Nasr, A. Z.; Morgaan, A. E. A. Pharmazie 1995, 50, 784–788.
Ishii, K.; Hatanaka, M.; Ueda, I. Pharm. Bull. 1991, 39, 3331–3334.
Abarca, B.; Jimenez, M.; Jones, G.; Soriano, C. J. Chem. Res. (M) 1986, 3358–3367.
Abdel-Aziz, S. A.; Allimony, H. A.; ElShaar, H. M.; Usama, F. A.; Abdel-Rahman R. M. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 113, 67–77.
Abdelfattah, M.; Negm, A. M.; Gaafar, A. E. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 72, 145–156.
Rashed, N.; Mousaad, A.; Saleh, A. J. Chin. Chem. Soc. 1993, 40, 393–397.
Van Oosterom, T.; Judson, I.; Verweij, J.; Stroobants, S.; Di Paola, E. D.; Dimitrijevic, S.. The Lancet 2001, 358, 1421–1423.
Dieckmann, W.; Platz, O. Ber. Dtsch. Chem. Ges. 1906, 38, 2989–2995.
Hassaneen, H. M.; Shawali, A. S.; Abunada, N. M. Org. Prep. Proc. Int. 1992, 24, 171–175.
Farag, M.; Algharib. M. S. Org. Prep. Proc. Int. 1988, 20, 521–526.
Hegarty, F.; Cashman, M. P.; Scott. F. L. J. Chem. Soc. Perkin Trans. II 1972, 1381–1386.
Pfaller, M. A.; Burmeister, L.; Bartlett, M. A.; Ghorab, M. A.; Rinaldi, M. G. J. Clin. Microbiol. 1988, 26, 1437–1441.
Wayne, P. A. CLSI, Clinical and Laboratory Standards Institute, Twentieth informational supplement, 2012, M100-S22.
Wayne, P. A., National Committee for Clinical Laboratory Standards, NCCLS Document, 2002, M38-A; USA.
Klanˇcnik, S.; Piskernik, B.; Jerˇsek, S.; Moˇzina, S. J. Microbiol. Methods 2010, 81, 121–126.
Gangadevi, V.; Muthumary, J. Afr. J. Biotechnol. 2007, 6, 1382–1386.
Mosmann, T. J. Immunol. Methods 1983, 65, 55–63.