Copyright (c) 2016 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Antitumor Activity of Some Methyl N-(5-Phenylthien-3-yl)amidrazone-2-carboxylates
Corresponding Author(s) : Mohammed M. Abadleh
Asian Journal of Chemistry,
Vol. 28 No. 5 (2016): Vol 28 Issue 5
Abstract
A series of new N-(5-phenylthien-3-yl)amidrazone-2-carboxylates (7a-n), incorporating N-substituted piperazines and related congeners, were prepared by reacting the hydrazonoyl chloride (5) (derived from 3-amino-5-phenyl-2-carboxylate) with the appropriate sec-cyclic amine. The in vitro antitumor activity screening of these amidrazones was performed against colon (RKO), breast (MCF-7) and cervical (HeLa) cancer cells. The N-alkylpiperazine derivatives 7e-g alone exhibited good to moderate activity (IC50 = 5-22 μM), while the rest compounds were, however, inactive at £ 100 μM.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- M.M. Abadleh, M.M. El-Abadelah, S.S. Sabri and H.H. Mohammed, Z. Naturforsch, 69b, 811 (2014).
- M.N. Abu-Aisheh, M.S. Mustafa, M.M. El-Abadelah, R.G. Naffa, S.I. Ismail, M.A. Zihlif, M.O. Taha and M.S. Mubarak, Eur. J. Med. Chem., 54, 65 (2012); doi:10.1016/j.ejmech.2012.04.028.
- T. Mosmann, J. Immunol. Methods, 65, 55 (1983); doi:10.1016/0022-1759(83)90303-4.
- R.R. Phillips, Org. React., 10, 143 (1959).
- H.C. Yao and P. Resnick, J. Am. Chem. Soc., 84, 3514 (1962); doi:10.1021/ja00877a018.
- G.C. Barrett, M.M. El-Abadelah and M.K. Hargreaves, J. Chem. Soc. C, 1986 (1970); doi:10.1039/j39700001986.
- V.M. Neplyuev, I.M. Bazavova and M.O. Lozinskii, Zh. Org. Khim., 25, 2225 (1989).
- R.N. Butler and F.L. Scott, Chem. Ind. (London), 1216 (1970).
- A.F. Hegarty, J.B. Aylward and F.L. Scott, J. Chem. Soc. C, 2587 (1967); doi:10.1039/j39670002587.
- V.A. Galishev, V.N. Chistokletov and A.A. Petrov, Zh. Obshch. Khim., 45, 1695 (1975).
- A.S. Shawali and C. Párkanyi, J. Heterocycl. Chem., 17, 833 (1980); doi:10.1002/jhet.5570170501.
- H.M. Hassaneen, H.A.H. Mousa, N.M. Abed and A.S. Shawali, Heterocycles, 27, 695 (1988); doi:10.3987/COM-87-4381.
- T. Benincori and F. Sannicolo, J. Org. Chem., 53, 1309 (1988); doi:10.1021/jo00241a035.
- R.J. Abdel-Jalil, E.Q. El-Momani, M. Hamad, W. Voelter, M.S. Mubarak, B.H. Smith and D.G. Peters, Monatsh. Chem., 141, 251 (2010); doi:10.1007/s00706-009-0241-4.
- E.D. Awad, M.M. El-Abadelah, S. Matar, M.A. Zihlif, R.G. Naffa, E.Q. Al-Momani and M.S. Mubarak, Molecules, 17, 227 (2012); doi:10.3390/molecules17010227.
- M.M. Abadleh, M.M. El-Abadelah, S.S. Sabri, Q.M.A. Abdallah, A. Nasr and M.F. El-Badawy, Lett. Org. Chem., 11, 664 (2014); doi:10.2174/1570178611666140807004701.
- A.Y. Habashneh, M.M. El-Abadelah, M.A. Zihlif, A. Imraish and M.O. Taha, Pharm. Chem. Life Sci., 347, 415 (2014); doi:10.1002/ardp.201300326.
References
M.M. Abadleh, M.M. El-Abadelah, S.S. Sabri and H.H. Mohammed, Z. Naturforsch, 69b, 811 (2014).
M.N. Abu-Aisheh, M.S. Mustafa, M.M. El-Abadelah, R.G. Naffa, S.I. Ismail, M.A. Zihlif, M.O. Taha and M.S. Mubarak, Eur. J. Med. Chem., 54, 65 (2012); doi:10.1016/j.ejmech.2012.04.028.
T. Mosmann, J. Immunol. Methods, 65, 55 (1983); doi:10.1016/0022-1759(83)90303-4.
R.R. Phillips, Org. React., 10, 143 (1959).
H.C. Yao and P. Resnick, J. Am. Chem. Soc., 84, 3514 (1962); doi:10.1021/ja00877a018.
G.C. Barrett, M.M. El-Abadelah and M.K. Hargreaves, J. Chem. Soc. C, 1986 (1970); doi:10.1039/j39700001986.
V.M. Neplyuev, I.M. Bazavova and M.O. Lozinskii, Zh. Org. Khim., 25, 2225 (1989).
R.N. Butler and F.L. Scott, Chem. Ind. (London), 1216 (1970).
A.F. Hegarty, J.B. Aylward and F.L. Scott, J. Chem. Soc. C, 2587 (1967); doi:10.1039/j39670002587.
V.A. Galishev, V.N. Chistokletov and A.A. Petrov, Zh. Obshch. Khim., 45, 1695 (1975).
A.S. Shawali and C. Párkanyi, J. Heterocycl. Chem., 17, 833 (1980); doi:10.1002/jhet.5570170501.
H.M. Hassaneen, H.A.H. Mousa, N.M. Abed and A.S. Shawali, Heterocycles, 27, 695 (1988); doi:10.3987/COM-87-4381.
T. Benincori and F. Sannicolo, J. Org. Chem., 53, 1309 (1988); doi:10.1021/jo00241a035.
R.J. Abdel-Jalil, E.Q. El-Momani, M. Hamad, W. Voelter, M.S. Mubarak, B.H. Smith and D.G. Peters, Monatsh. Chem., 141, 251 (2010); doi:10.1007/s00706-009-0241-4.
E.D. Awad, M.M. El-Abadelah, S. Matar, M.A. Zihlif, R.G. Naffa, E.Q. Al-Momani and M.S. Mubarak, Molecules, 17, 227 (2012); doi:10.3390/molecules17010227.
M.M. Abadleh, M.M. El-Abadelah, S.S. Sabri, Q.M.A. Abdallah, A. Nasr and M.F. El-Badawy, Lett. Org. Chem., 11, 664 (2014); doi:10.2174/1570178611666140807004701.
A.Y. Habashneh, M.M. El-Abadelah, M.A. Zihlif, A. Imraish and M.O. Taha, Pharm. Chem. Life Sci., 347, 415 (2014); doi:10.1002/ardp.201300326.