Synthesis and cytotoxic evaluation of novel symmetrical taspine derivatives as anticancer agents

Medicinal Chemistry

Volumn 7, Issue 4, 2011, Pages 286-294

  Zhang, Jie ^a   Zhang, Yanmin ^a   Pan, Xiaoyan ^a   Wang, Sicen ^a   He, Langchong ^a  

^a XI'AN JIAOTONG UNIVERSITY   (China)

Author keywords

Antiangiogenic agents; Anticancer agents; Antiproliferative activity; Cytotoxicity; Symmetrical taspine derivatives; VEGFR 2

Indexed keywords

2 BROMO 3 HYDROXY 4 METHOXYBENZALDEHYDE; 3 (BENZYLOXY) 2 BROMO 4 METHOXY N METHYLBENZAMIDE; 3 (BENZYLOXY) 2 BROMO 4 METHOXYBENZALDEHYDE; 3 (BENZYLOXY) 2 BROMO 4 METHOXYBENZOIC ACID; 5,5' DIMETHOXY 6,6' BIS[2 [(4 METHOXYPHENYL)AMINO] 2 OXOETHOXY] N,N' DIMETHYLBIPHENYL 2,2' DICARBOXAMIDE; 5,5' DIMETHOXY N,N' DIMETHYL 6,6' BIS[2 OXO 2 [[3 (TRIFLUOROMETHYL)PHENYL]AMINO]ETHOXY]BIPHENYL 2,2' DICARBOXAMIDE; 6,6' BIS(2 ANILINO 2 OXOETHOXY) 5,5' DIMETHOXY N,N' DIMETHYLBIPHENYL 2,2' DICARBOXAMIDE; 6,6' BIS(BENZYLOXY) 5,5' DIMETHOXY N,N' DIMETHYLBIPHENYL 2,2' DICARBOXAMIDE; 6,6' BIS[2 (ISOPROPYLAMINO) 2 OXOETHOXY] 5,5' DIMETHOXY N,N' DIMETHYLBIPHENYL 2,2' DICARBOXAMIDE; 6,6' BIS[2 [(3 CHLORO 4 FLUOROPHENYL)AMINO] 2 OXOETHOXY] 5,5' DIMETHOXY N,N' DIMETHYLBIPHENYL 2,2' DICARBOXAMIDE; 6,6' BIS[2 [(3 CHLORO 4 FLUOROPHENYL)AMINO] 2 OXOETHOXY] N,N' DIISOPROPYL 5,5' DIMETHOXYBIPHENYL 2,2' DICARBOXAMIDE; 6,6' BIS[2 [(3 CHLORO 4 FLUOROPHENYL)AMINO] 2 OXOETHOXY] N,N,N',N' TETRAETHYL 5,5' DIMETHOXYBIPHENYL 2,2' DICARBOXAMIDE; 6,6' BIS[2 [(3 FLUOROPHENYL)AMINO] 2 OXOETHOXY] 5,5' DIMETHOXY N,N' DIMETHYLBIPHENYL 2,2' DICARBOXAMIDE; 6,6' BIS[2 [(3,4 DICHLOROPHENYL)AMINO] 2 OXOETHOXY] 5,5' DIMETHOXY N,N' DIMETHYLBIPHENYL 2,2' DICARBOXAMIDE; 6,6' BIS[2 [(4 BROMOPHENYL)AMINO] 2 OXOETHOXY] 5,5' DIMETHOXY N,N' DIMETHYLBIPHENYL 2,2' DICARBOXAMIDE; 6,6' BIS[2 [(4 BROMOPHENYL)AMINO] 2 OXOETHOXY] N,N' DIISOPROPYL 5,5' DIMETHOXYBIPHENYL 2,2' DICARBOXAMIDE; 6,6' BIS[2 [(6 FLUOROPYRIDIN 3 YL)AMINO] 2 OXOETHOXY] 5,5' DIMETHOXY N,N' DIMETHYLBIPHENYL 2,2' DICARBOXAMIDE; 6,6' BIS[2 [(6 FLUOROPYRIDIN 3 YL)AMINO] 2 OXOETHOXY] N,N' DIISOPROPYL 5,5' DIMETHOXYBIPHENYL 2,2' DICARBOXAMIDE; 6,6' DIHYDROXY 5,5' DIMETHOXY N,N' DIMETHYLBIPHENYL 2,2' DICARBOXAMIDE; ANGIOGENESIS INHIBITOR; ANTINEOPLASTIC AGENT; BIPHENYL DERIVATIVE; N,N' DIISOPROPYL 5,5' DIMETHOXY 6,6' BIS[2 [(4 METHOXYPHENYL)AMINO] 2 OXOETHOXY]BIPHENYL 2,2' DICARBOXAMIDE; TASPINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; CYTOPATHOGENIC EFFECT; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; MITOSIS INHIBITION; MOLECULAR DOCKING; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ALKALOIDS; ANGIOGENESIS INHIBITORS; ANTINEOPLASTIC AGENTS; BIPHENYL COMPOUNDS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; HYDROCARBONS, HALOGENATED; INHIBITORY CONCENTRATION 50; MOLECULAR TARGETED THERAPY; NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79959362677     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/157340611796150914     Document Type: Article

References (31)

1. Printz, C. BATTLE to personalize lung cancer treatment. Novel clinical trial design and tissue gathering procedures drive biomarker discovery. Cancer, 2010, 116, 3307-3308.
2. Yang, A.S.; Chapman, P.B. The history and future of chemotherapy for melanoma. Hematol. Oncol. Clin. North. Am., 2009, 23, 583-597.
3. Ozkay, Y.; Işikdaǧ, I.; Incesu, Z.; Akalin, G. Synthesis of 2- substituted-N- [4-(1-methyl-4,5-diphenyl-1H-imidazole-2- yl)phenyl]acetamide derivatives and evaluation of their anticancer activity. Eur. J. Med. Chem., 2010, 45, 3320-3328.
4. Wu, G.; Guo, H.F.; Gao, K.; Liu, Y.N.; Bastow, K.F.; Morris-Natschke, S.L.; Lee, K.H.; Xie, L. Synthesis of unsymmetrical biphenyls as potent cytotoxic agents. Bioorg. Med. Chem. Lett., 2008, 18, 5272-5276.
5. Li, Y.; Hu, Z.; He, L. An approach to develop binary chromatographic fingerprints of the total alkaloids from Caulophyllum robustum by high performance liquid chromatography/diode array detector and gas chromatography/mass spectrometry. J. Pharm. Biomed. Anal., 2007, 43, 1667-1672. (Pubitemid 46453083)
6. Perdue, G.P.; Blomster, R.N.; Blake, D.A.; Farnsworth, N.R. South American plants II: taspine isolation and anti-inflammatory activity. J. Pharm. Sci., 1979, 68, 124-126. (Pubitemid 9100643)
7. Zhao, J.; Zhao, L.; Chen, W.; He, L.C.; Li, X. Taspine downregulates VEGF expression and inhibits proliferation of vascular endothelial cells through PI3 kinase and MAP kinase signaling pathways. Biomed. Pharmacother., 2008, 62, 383-389. (Pubitemid 351899096)
8. Zhang, Y.; He, L.; Zhou, Y. Taspine isolated from Radix et Rhizoma Leonticis inhibits growth of human umbilical vein endothelial cell (HUVEC) by inducing its apoptosis. Phytomedicine., 2008, 15, 112-119.
9. Zhang, J.; Zhang, Y.; Zhang, S.; Wang, S.; He, L. Discovery of novel taspine derivatives as antiangiogenic agents. Bioorg. Med. Chem. Lett., 2010, 20, 718-721.
10. Zhang, J.; Zhang, Y.; Shan, Y.; Li, N.; Ma, W.; He, L. Synthesis and preliminary biological evaluation of novel taspine derivatives as anticancer agents. Eur. J. Med. Chem., 2010, 45, 2798-2805.
11. Pizzirani, D.; Roberti, M.; Grimaudo, S.; Di Cristina, A.; Pipitone, R.M.; Tolomeo, M.; Recanatini, M. Identification of biphenylbased hybrid molecules able to decrease the intracellular level of Bcl-2 protein in Bcl-2 overexpressing leukemia cells. J. Med. Chem., 2009, 52, 6936-6940.
12. Daly, J.W.; Guroff, G.; Udenfriend, S.; Witkop, B. Hydroxylation of alkyl and halogen substituted anilines and acetanilides by microsomal hydroxylases. Biochem. Pharmacol., 1968, 17, 31-36.
13. Knesl, P.; Röseling, D.; Jordis, U. Improved synthesis of substituted 6,7-dihydroxy-4-quinazolineamines: tandutinib, erlotinib and gefitinib. Molecules., 2006, 11, 286-297. (Pubitemid 43684791)
14. Bermejo, A.; Andreu, I.; Suvire, F.; Leonce, S.; Caignard, D.H.; Renard, P.; Pierre, A.; Enriz, R.D.; Cortes, D.; Cabedo, N. Syntheses and antitumor targeting G1 phase of the cell cycle of benzoyldihydroisoquinolines and related 1-substituted isoquinolines. J. Med. Chem., 2002, 45, 5058-5068. (Pubitemid 35278702)
15. Wang, J.Q.; Gao, M.; Miller, K.D.; Sledge, G.W.; Zheng, Q.H. Synthesis of [11C]Iressa as a new potential PET cancer imaging agent for epidermal growth factor receptor tyrosine kinase. Bioorg. Med. Chem. Lett., 2006, 16, 4102-4106. (Pubitemid 44425196)
16. Palmer, B.D.; Wilson, W.R.; Atwell, G.J.; Schultz, D.; Xu, X.Z.; Denny, W.A. Hypoxia-selective antitumor agents. 9. Structureactivity relationships for hypoxia-selective cytotoxicity among analogues of 5- [N,N-bis(2-chloroethyl) amino]-2,4-dinitrobenzamide. J. Med. Chem., 1994, 37, 2175-2184. (Pubitemid 24228445)
17. Montoya-Pelaez, P.J.; Uh, Y.S.; Lata, C.; Thompson, M.P.; Lemieux, R.P.; Crudden, C.M. The synthesis and resolution of 2,2'-, 4,4'-, and 6,6'-substituted chiral biphenyl derivatives for application in the preparation of chiral materials. J. Org. Chem., 2006, 71, 5921-5929. (Pubitemid 44200259)
18. Svenson, S.; Thompson, D.H. Facile and Efficient Synthesis of Bolaamphiphilic Tetraether Phosphocholines. J. Org. Chem., 1998, 63, 7180-7182. (Pubitemid 128722945)
19. Wu, Y.; Yang, Y.Q.; Hu, Q. A facile access to chiral 4-isopropyl-, 4-benzyl-, and 4-phenyloxazolidine-2-thione. J. Org. Chem., 2004, 69, 3990-3992. (Pubitemid 38668268)
20. Naruse, I.; Ohmori, T.; Ao, Y.; Fukumoto, H.; Kuroki, T.; Mori, M.; Saijo, N.; Nishio, K. Antitumor activity of the selective epidermal growth factor receptor-tyrosine kinase inhibitor (EGFRTKI) Iressa (ZD1839) in an EGFR-expressing multidrug-resistant cell line in vitro and in vivo. Int. J. Cancer., 2002, 98, 310-315. (Pubitemid 34150818)
21. Lipinski, C.A.; Lombardo, F.; Dominy, B.W.; Feeney, P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settingsof outstanding interest. Adv. Drug. Deliv. Rev., 1997, 23, 3-25. (Pubitemid 27046991)
22. Falcó, J.L.; Lloveras, M.; Buira, I.; Teixidó, J.; Borrell, J.I.; Méndez, E.; Terencio, J.; Palomer, A.; Guglietta, A. Design, synthesis and biological activity of acyl substituted 3-amino-5-methyl- 1,4,5,7-tetrahydropyrazolo [3,4-b]pyridin-6-ones as potential hypnotic drugs. Eur. J. Med. Chem., 2005, 40, 1179-1187. (Pubitemid 41446291)
23. Chen, L.; Zhang, Y.; Kong, X.; Peng, S.; Tian, J. Synthesis and biological evaluation of nitric oxide-releasing derivatives of oleanolic acid as inhibitors of HepG2 cell apoptosis. Bioorg. Med. Chem. Lett., 2007, 17, 2979-2982. (Pubitemid 46702645)
24. Zhang, Y.; He, L.; Meng, L.; Luo, W. Taspine isolated from Radix et Rhizoma Leonticis inhibits proliferation and migration of endothelial cells as well as chicken chorioallantoic membrane neovascularisation. Vascul. Pharmacol., 2008, 48, 129-137.
25. Schulz, P.; Scholz, A.; Rexin, A.; Hauff, P.; Schirner, M.; Wiedenmann, B.; Detjen, K. Inducible re-expression of p16 in an orthotopic mouse model of pancreatic cancer inhibits lymphangiogenesis and lymphatic metastasis. Br. J. Cancer., 2008, 99, 110-117. (Pubitemid 351920244)
26. Staehler, M.; Rohrmann, K.; Haseke, N.; Stief, C.G.; Siebels, M. Targeted agents for the treatment of advanced renal cell carcinoma. Curr. Drug. Targets., 2005, 6, 835-846. (Pubitemid 41472497)
27. Usui, T.; Ban, H.S.; Kawada, J.; Hirokawa, T.; Nakamura, H. Discovery of indenopyrazoles as EGFR and VEGFR-2 tyrosine kinase inhibitors by in silico high-throughput screening. Bioorg. Med. Chem. Lett., 2008, 18, 285-288.
28. Harris, P.A.; Boloor, A.; Cheung, M.; Kumar, R.; Crosby, R.M.; Davis-Ward, R.G.; Epperly, A.H.; Hinkle, K.W.; Hunter 3rd, R.N.; Johnson, J.H.; Knick, V.B.; Laudeman, C.P.; Luttrell, D.K.; Mook, R.A.; Nolte, R.T.; SRudolph, K.; Szewczyk, J.P.; Truesdale, A.T.; Veal, J.M.; Wang, L.; Stafford, J.A. Discovery of 5- [ [4- [(2,3- dimethyl-2H-indazol-6-yl)methylamino]-2- pyrimidinyl]amino]-2- methyl-benzenesulfonamide (Pazopanib), a novel and potent vascular endothelial growth factor receptor inhibitor. J. Med. Chem., 2008, 51, 4632-4640.
29. Kiss, T.; Fenyvesi, F.; Bácskay, I.; Váradi, J.; Fenyvesi, F.; Iványi, R.; Szente, L.; Tósaki, A.; Vecsernyés, M. Evaluation of the cytotoxicity of beta-cyclodextrin derivatives: evidence for the role of cholesterol extraction. Eur. J. Pharm. Sci., 2010, 40, 376-380.
30. Sivan, S.K.; Manga, V. Molecular docking and 3D-QSAR studies on triazolinone and pyridazinone, non-nucleoside inhibitor of HIV- 1 reverse transcriptase. J. Mol. Model., 2010, 16, 1169-1178.
31. Gupta, P.; Roy, N.; Garg, P. Docking-based 3D-QSAR study of HIV-1 integrase inhibitors. Eur. J. Med. Chem., 2009, 44, 4276-4287.