Uses of cyanoacetylhydrazine in heterocyclic synthesis: Novel synthesis of pyrazole derivatives with anti-tumor activities

Molecules

Volumn 17, Issue 7, 2012, Pages 8449-8463

  Mohareb, Rafat M ^a,b   El Sayed, Nahed N E ^c,d   Abdelaziz, Mahmoud A ^e,f  

^a CAIRO UNIVERSITY   (Egypt)

^b October University for Modern Sciences and Arts   (Egypt)

^c NATIONAL ORGANIZATION FOR DRUG CONTROL AND RESEARCH NODCAR   (Egypt)

^d KING SAUD UNIVERSITY   (Saudi Arabia)

^e Al Ghad International Colleges for Applied Medical Sciences   (Saudi Arabia)

^f Modern Academy for Engineering and Technology in Maadi   (Egypt)

Author keywords

Antitumor; Pyrazole; Thiazole; Thiophene

Indexed keywords

ANTINEOPLASTIC AGENT; HETEROCYCLIC COMPOUND; HYDRAZINE DERIVATIVE; PYRAZOLE; PYRAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; DRUG SCREENING; HUMAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HETEROCYCLIC COMPOUNDS; HUMANS; HYDRAZINES; PYRAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84864585922     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17078449     Document Type: Article

References (29)

1. Liu, X.H.; Cui, P.; Song, B.A.; Bhadury, P.S.; Zhu, H.L.; Wang, S.F. Synthesis, structure and antibacterial activity of novel 1-(5-substituted-3- substituted-4, 5-dihydropyrazol-1-yl)ethanone oxime ester derivatives. Bioorgan. Med. Chem. 2008, 16, 4075-4082. (Pubitemid 351484019)
2. Ouyang, G.; Chen, Z.; Cai, X.J.; Song, B.A.; Bhadury, P.S.; Yang, S.; Jin, L.H.; Xue, W.; Hu, D.Y.; Zeng, S. Synthesis and antiviral activity of novel pyrazole derivatives containing oxime esters group. Bioorgan. Med. Chem. 2008, 16, 9699-9707.
3. Abdel-Hafez, E.M.N.; Rahma, G.E.A.A.; Aziz, M.A.; Radwan, M.F.; Farag, H.H. Design, synthesis and biological investigation of certain pyrazole-3-carboxylic acid derivatives as novel carriers for nitric oxide. Bioorgan. Med. Chem. 2009, 17, 3829-3837.
4. Park, H.J.; Lee, K.; Park, S.J.; Ahn, B.; Lee, J.C.; Cho, H.Y.; Lee, K.I. Identification of antitumor activity of pyrazole oxime ethers. Bioorgan. Med. Chem. Lett. 2005, 15, 3307-3312. (Pubitemid 40799080)
5. Ouyang, G.; Cai, X.J.; Chen, Z.; Song, B.A.; Bhadury, P.S.; Yang, S.; Jin, L.H.; Xue, W.; Hu, D.Y.; Zeng, S. Synthesis and antiviral activities of pyrazole derivatives containing an oxime moiety. J. Agric. Food Chem. 2008, 56, 101601-102607.
6. Dai, H.; Li, Y.Q.; Du, D.; Qin, X.; Zhang, X.; Yu, H.B.; Fang, J.X. Synthesis and biological activities of novel pyrazole oxime derivatives containing a 2-chloro-5-thiazolyl moiety. Food Chem. 2008, 56, 10805-10810.
7. Riyadh, S.M.; Farghaly, T.A.; Abdallah, M.A.; Abdalla, M.M.; El-Aziz, M.R.A. New pyrazoles incorporating pyrazolylpyrazole moiety: Synthesis, anti-HCV and antitumor activity. Eur. J. Med. Chem. 2010, 45, 1042-1050.
8. Anzaldi, M.; Maccio, C.; Mazzei, M.; Bertolotto, M.; Ottonello, L.; Dallegri, F.; Balbi, A. Antiproliferative and proapoptotic activities of a new class of pyrazole derivatives in HL-60 cells. Chem. Biodivers. 2009, 6, 1674-1684.
9. El-Shafei, A.; Fadda, A.A.; Khalil, A.M.; Ameen, T.A.E.; Badria, F.A. Synthesis, antitumor evaluation, molecular modeling and quantitative structure-activity relationship (QSAR) of some novel arylazopyrazolodiazine and triazine analogs. Bioorgan. Med. Chem. 2009, 17, 5096-5105.
10. Huang, K.H.; Veal, J.M.; Fadden, P.R.; Rice, J.W.; Eaves, J.; Strachan, J.P.; Barabasz, A.F.; Foley, B.E.; Barta, T.E.; Ma, W.; et al. Discovery of Novel 2-Aminobenzamide Inhibitors of Heat Shock Protein 90 as Potent, Selective and Orally Active Antitumor Agents. J. Med. Chem. 2009, 52, 4288-4305.
11. Chandanshive, J.Z.; Bonini, B.F.; Tiznado, W.; Escobar, C.A.; Caballero, J.; Femoni, C.; Fochi, M.; Franchini, M.C. 1, 3-Dipolar Cycloaddition of Nitrile Imines with Cyclic α-β-Unsaturated Ketones: A Regiochemical Route to Ring-Fused Pyrazoles. Eur. J. Org. Chem. 2011, 4806-4811.
12. Chandanshive, J.Z.; Bonini, B.F.; Gentili, D.; Fochi, M.; Bernardi, L.; Franchini, M.C. Regiocontrolled Synthesis of Ring-Fused Thieno[2, 3-c]pyrazoles through 1, 3-Dipolar Cycloaddition of Nitrile Imines with Sulfur-Based Acetylenes. Eur. J. Org. Chem. 2010, 33, 6440-6447.
13. Bondock, S.; Fadaly, W.; Metwally, M.A. Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. Eur. J. Med. Chem. 2010, 45, 3692-3701.
14. Mohareb, R.M.; Samir, E.M. The Reaction of cyanoacetylhydrazine with chloroacetone: Synthesis of 1, 2, 4-triazine, 1, 3, 4-oxadiazine and their fused derivatives with antitumor activities. Open J. Med. Chem. 2012, 2, 1-9.
15. Mohareb, R.M.; Ibrahim, R.A.; Moustafa, H.E. Hydrazide-hydrazones in the synthesis of 1, 3, 4-oxadiazine, 1, 2, 4-triazine and pyrazole derivatives with anti-tumor activities. Open Org. Chem. J. 2010, 4, 8-14.
16. Mohareb, R.M.; Schatz, J. Anti-tumor and anti-leishmanial evaluations of 1, 3, 4-oxadiazine, pyran derivatives derived from cross-coupling reactions of β-bromo-6H-1, 3, 4- oxadiazine derivatives. Bioorgan. Med. Chem. 2011, 19, 2707-2713.
17. Khalil, A.M.; Berghot, M.A.; Gouda, M.A. Synthesis and antibacterial activity of some new thiazole and thiophene derivatives. Eur. J. Med. Chem. 2009, 44, 4434-4440.
18. McKibben, B.P.; Cartwright, C.H.; Castelhano, A.L. Practical synthesis of tetrasubstituted thiophenes for use in compound libraies. Tetrahedron 1999, 40, 5471-5474. (Pubitemid 29325186)
19. Balamurugan, K.; Perumal, S.; Sunil, A.; Reddy, A.S.K.; Yogeeswari, P.; Sriram, D.A. facile domino protocol for the regioselective synthesis and discovery of novel 2-amino-5-arylthieno [2, 3-b] thiophene as antimycobacterial agents. Tetrahedron Lett. 2009, 50, 6191-6195.
20. Ye, D.; Zhang, Y.; Wang, F.; Zheng, M.; Zhang, X.; Luo, X.; Shen, X.; Jiang, H.; Liu, H. Novel thiophene derivatives as PTP1B inhibitors with selectivity and cellular activity. Bioorgan. Med. Chem. 2010, 18, 1773-1782.
21. Mansour, S.A.; Mahmoud, S.B.; Saleh, I.A.; Mostafa, M.G. Ant-breast cancer activity of some novel 1, 2-dihydropyridine, thiophene and thiazole derivatives. Eur. J. Med. Chem. 2011, 46, 137-141.
22. Scrowston, R.M. Recent advances in the chemistry of benzo [b]-thiophene. Adv. Heterocycl. Chem. 1981, 29, 171-249.
23. Parida, K.M.; Rath, D. Amine functionalized MCM-41: An active and reusable catalyst for Knoevenagel condensation reaction. J. Mol. Catal. A: Chem. 2009, 310, 93-100.
24. Jain, D.; Mishra, M.; Rani, A. Synthesis and characterization of novel aminopropylated fly ash catalyst and its beneficial application in base catalyzed Knoevenagel condensation reaction. Fuel Process. Technol. 2012, 95, 119-126.
25. Tisseh, Z.N.; Dabiri, M.; Nobahar, M.; Khavasi, H.R.; Bazgir, A. Catalyst-free, aqueous and highly diastereoselective synthesis of new 5-substituted 1H-tetrazoles via a muti-component domino Knoevenagel condensation/1, 3- dipolar cycloaddition reaction. Tetrahedron 2012, 68, 1769-1773.
26. Atamanyuk, D.V.; Ostapiuk, Y.V.; Kryshchyshyn, A.P. A new domino-Knoevenagel-hetero- Diels-Alder reaction. Tetrahedron Lett. 2008, 49, 4648-4651.
27. Cateni, F.; Zilic, J.; Zacchigna, M.; Bonivento, P.; Frausin, F.; Scarcia, V. Synthesis and biological properties of new α-methylene- butyrolactones and α, β-unsaturated γ-butyrolactones. Eur. J. Med. Chem. 2006, 41, 192-200.
28. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J.T.; Bokesch, H.; Kenne, S.; Boyd, M.R. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 1990, 82, 1107-1112. (Pubitemid 20213250)
29. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paul, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A.; et al. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J. Natl. Cancer Inst. 1991, 83, 757-766.