Synthesis of Pyrazolyl-Pyrazoles and Pyrazolyl-[1,2,4]-Triazolo[3,4-d][1,5]Benzothiazepines as p53 Activators Using Hydrazonoyl Chlorides
Sobhi M. Gomha
Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613 Egypt
Search for more papers by this authorCorresponding Author
Thoraya A. Farghaly
Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613 Egypt
Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah Almukkarramah, Saudi Arabia
E-mail: [email protected]Search for more papers by this authorAbdelwahed R. Sayed
Department of Chemistry, Faculty of Science, KFU, Saudi Arabia
Department of Chemistry, Faculty of Science, University of Beni Suef, Egypt
Search for more papers by this authorMohamed M. Abdalla
Research Unit, Saco Pharm. Co., 6th October City, Egypt
Search for more papers by this authorSobhi M. Gomha
Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613 Egypt
Search for more papers by this authorCorresponding Author
Thoraya A. Farghaly
Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613 Egypt
Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah Almukkarramah, Saudi Arabia
E-mail: [email protected]Search for more papers by this authorAbdelwahed R. Sayed
Department of Chemistry, Faculty of Science, KFU, Saudi Arabia
Department of Chemistry, Faculty of Science, University of Beni Suef, Egypt
Search for more papers by this authorMohamed M. Abdalla
Research Unit, Saco Pharm. Co., 6th October City, Egypt
Search for more papers by this authorAbstract
Di-pyrazoles, tripyrazoles, and pyrazolyltriazolobenzothiazepines were prepared from α,β-unsaturated ketones and hydrazonoyl chlorides. The structure of all the newly synthesized compounds was established on the bases of their spectral data and elemental analyses. The activity of all products was examined as p53 ubiquitination which showed promising activities.
References and Notes
- 1Saravanan, G.; Alagarsamy, V.; Chanukya, G. Int J Pharma Bio Sci 2010, 1, 1.
- 2Sarma, K. N.; Subha, M. C. S.; Rao, K. Ch. Eur J Chem 2010, 7, 745.
- 3Sahu, S.; Banerjee, M.; Samantray, A.; Behera, C.; Azam, M. A. Trop J Pharm Res 2008, 7, 961.
- 4Sivakumar, K. K.; Rajasekaran, A.; Ponnilavarasan, I.; Somasundaram, A.; Sivasakthi, R.; Kamalaveni, S. Der Pharmacia Lett 2010, 2, 211.
- 5Singh, A.; Rana, A. C. J Chem Pharm Res 2011, 2, 505.
- 6Kalirajan, R.; Rathore, L.; Jubie, S.; Gowramma, B.; Gomathy, S.; Sankar, S.; Elango, K. Indian J. Pharm Educ Res 2010, 44, 358.
- 7Wang, X. H.; Wang, X. K.; Liang, Y. J.; Shi, Z.; Zhang, J. Y.; Chen, L. M.; Fu, L. W. Chinese J. Cancer 2010, 29, 980.
- 8Rostom, S. A. F. Bioorg Med Chem 2010, 18, 2767.
- 9Daidone, G.; Maggio, B.; Raffa, D.; Plescia, S.; Schillaci, D.; Raimondi, M. V. Il Farmaco 2004, 59, 413.
- 10Chou, L.-C.; Huang, L.-J.; Yang, J.-S.; Lee, F.-Y.; Teng, C.-M.; Kuo, S.-C. Bioorg Med Chem 2007, 15, 1732.
- 11Manetti, F.; Brullo, C.; Magnani, M.; Mosci, F.; Chelli, B.; Crespan, E.; Schenone, S.; Naldini, A.; Bruno, O.; Trincavelli, M. L.; Maga, G.; Carraro, F.; Martini, C.; Bondavalli, F.; Botta, M. J Med Chem 2008, 51, 1252.
- 12Li, J.; Zhao, Y. F.; Zhao, X. L.; Yuan, X. Y.; Gong, P. Arch Pharm Chem Life Sci 2006, 339, 593.
- 13Xia, Y.; Dong, Z.-W.; Zhao, B.-X.; Ge, X.; Meng, N.; Shin, D.-S.; Miao, J.-Y. Bioorg Med Chem, 2007, 15, 6893.
- 14Xia, Y.; Fan, Y. C.-D.; Zhao, B.-X.; Zhao, J.; Shin D.-S.; Miao, J.-Y. Eur J Med Chem 2008, 43, 2347.
- 15Farag, A. M.; Mayhoub, A. S.; Barakat, S. E.; Bayomi, A. H. Bioorg Med Chem 2008, 16, 881.
- 16Schenone, S.; Bruno, O.; Ranise, A.; Bondavalli, F.; Brullo, C.; Fossa, P.; Mosti, L.; Menozzi, G.; Carraro, F.; Naldini, A.; Bernini, C.; Manettic F.; Botta, M. Bioorg Med Chem Lett 2004, 14, 2511.
- 17Daidone, G.; Raffa, D.; Maggio, B.; Raimondi, M. V.; Plescia F.; Schillaci, D. Eur J Med Chem 2004, 39, 219.
- 18Ahasan N. B.; Islam, M. R. Bangladesh J Pharmacol 2007, 2, 81.
- 19Warshakoon, N. C.; Wu, S.; Boyer, A.; Kawamoto, R.; Renock, S.; Xu, K.; Pokross, M.; Evdokimov, A. G.; Zhou, S.; Winter, C.; Walter R.; Mekel, M. Bioorg Med Chem Lett 2006, 16, 5687.
- 20Huang, S.; Lin, R.; Yu, Y.; Lu, Y.; Connolly, P. J.; Chiu, G.; Li, S.; Emanuel S. L.; Middleton, S. A. Bioorg Med Chem Lett 2007, 17, 1243.
- 21Zhu, G.-D.; Gong, J.; Gandhi, V. B.; Woods, K.; Luo, Y.; Liu, X.; Guan, R.; Klinghofer, V.; Johnson, E. F.; Stoll, V. S.; Mamo, M.; Li, Q.; Rosenberg, S. H.; Giranda, V. L. Bioorg Med Chem 2007, 15, 2441.
- 22Krystof, V.; Cankar, P.; Frysova, I.; Slouka, J.; Kontopidis, G.; Dzubak, P.; Hajduch, M.; Srovnal, J.; Walter, F. d. A. J.; Orsag, M.; Paprskarova, M.; Rolcık, J.; Latr, A.; Fischer, P. M.; Strnad, M. J Med Chem 2006, 49, 6500.
- 23Hopenwasser, J.; Mozayani, A.; Danielson, T. J.; Harbin, A.; Narula, H. S.; Posey, D. H.; Shrode, P. W.; Wilson, S. K.; Li, R.; Sanchez, L. J Anal Toxicol 2004, 28, 264.
- 24Kawakita, S.; Kinoshita, M.; Ishikawa, H.; Kagoshima, T.; Katori, R.; Ishikawa, K.; Hirota, Y. Clin Cardiol 1991, 14, 53.
- 25Arya, K.; Dandi, A. Bioorg Med Chem Lett 2008, 18, 114.
- 26Farghaly, T. A.; Mahmoud, H. K. Arch Pharm Chem Life Sci 2013, 346, 392.
- 27Riyadh, S. M.; Farghaly, T. A.; Abdallah, M. A.; Abdalla, M. M.; Abdel-Aziz, M. R. Eur J Med Chem 2010, 45, 1042.
- 28El-Gamel, N. E. A.; Farghaly, T. A. Spectrochim Acta A Mol Biomol Spectrosc 2013, 115, 469.
- 29Sayed, A. R.; Al-Shihry, S. S.; Gomaa, M. A. M. Eur J Chem 2014, 5, 267.
- 30Sayed, A. R. Tetrahedron, 2013 69, 5293.
- 31Hassaneen, H. M.; Mousa, H. A. H.; Shawali, A. S. J Heterocycl Chem 1987, 24, 1665.
- 32Thonon, D.; Goukens, E.; Kaisin, G.; Paris, J.; Flagothier, J.; Luxen, A. Tetrahedron 2011, 67, 5572.
- 33Mernyak, E.; Kozma, E.; Hetenyi, A.; Mark, L.; Schneider, G.; Wolfling, J. Steroids 2009, 74, 520.
- 34Yıldırım, M.; Dürüst, Y. Tetrahedron 2011, 67, 3209.
- 35Oida, T.; Shimizu, T.; Hayashi, Y.; Teramura, K. Bull Chem Soc Jpn 1981, 54, 1429.
- 36Huisgen, R.; Knupfer, H.; Sustmann, R.; Wallbillich, G.; Weberndorfer, V. Tetrahedron 1962, 17, 3.
- 37Abunada, N. M.; Hassaneen, H. M.; Kandile, N. G.; Miqdad, O. A. Molecules 2008, 13, 1011.
- 38Kumar, R. R.; Perumal, S. Tetrahedron 2007, 63, 7850
- 39Ferwanah, A. S.; Awadallah, A. M.; Khafaja, N. A. Asian J Chem 2001. 13, 1203.
- 40Ferwanah, A. S.; Kandile, N. G.; Awadallah, A. M.; Miqdad, O. A. Synthetic Commun 2002. 32, 2017.
- 41Awadallah, A. M.; Ferwanah, A. S.; Elsawi, E. A.; Dalloul, H. M. Asian J. Chem 2002, 14, 1230.
- 42Elwan, N. M.; Abdelhadi, H. A.; Abdallah, T. A.; Hassaneen, H. M. Tetrahedron 1996. 52, 3451.
- 43Hussein, A. Q.; El-Abadelah, M. M.; Aladhami, K. H.; Abushmla, A. Heterocycles 1989, 29, 1163.
- 44Dong, Z. Q.; Liu, F. M.; Xu, F.; Yuan, Z. L. Mol Divers 2001, 15, 963.
- 45Gomha, S. M.; Eldebss, T. M. A.; Abdulla, M. M.; Mayhoub, A. S. Eur J Med Chem 2014, 82, 472.
- 46Gomha, S. M.; Abdel-aziz, H. M. J Chem Res 2013, 2, 298.
- 47Li-Rong, W.; Shu-Wen, W.; Ming, L.; Hua-Zheng, Y. Chin J Chem 2005, 23, 1231.
- 48Breitmaier, E.; Structure Elucidation by NMR in Organic Chemistry, A Practical Guide; John Wiley: Chichester, UK, 1993; p 27.