Synthesis and preliminary biological evaluation of 1,2,3-triazole-Jaspine B hybrids as potential cytotoxic agents

European Journal of Medicinal Chemistry

Volumn 80, Issue , 2014, Pages 593-604

  Xu, Jin Mei ^a   Zhang, En ^a   Shi, Xiao Jing ^a   Wang, Yan Chao ^a   Yu, Bin ^a   Jiao, Wei Wei ^a   Guo, Ya Zhuo ^a   Liu, Hong Min ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

1,2,3 Triazole; Apoptosis; Cell cycle arrest; Cytotoxicity; Jaspine B

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 1,2,3 TRIAZOLE JASPINE B HYBRID; 4 AMINO 2 [[(1 DECYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 OL; 4 AMINO 2 [[(1 DODECYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 OL; 4 AMINO 2 [[(1 HEPTYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 OL; 4 AMINO 2 [[(1 NONYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 OL; 4 AMINO 2 [[(1 OCTADECYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 OL; 4 AMINO 2 [[(1 OCTYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 OL; 4 AMINO 2 [[(1 TETRADECYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 OL; CYTOTOXIC AGENT; FLUOROURACIL; JASPINE B; TERT BUTYL [4 (BENZYLOXY) 5 [[(1 DECYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 YL] CARBAMATE; TERT BUTYL [4 (BENZYLOXY) 5 [[(1 DODECYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 YL] CARBAMATE; TERT BUTYL [4 (BENZYLOXY) 5 [[(1 HEPTYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 YL] CARBAMATE; TERT BUTYL [4 (BENZYLOXY) 5 [[(1 HEXADECYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 YL] CARBAMATE; TERT BUTYL [4 (BENZYLOXY) 5 [[(1 NONYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 YL] CARBAMATE; TERT BUTYL [4 (BENZYLOXY) 5 [[(1 OCTADECYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 YL] CARBAMATE; TERT BUTYL [4 (BENZYLOXY) 5 [[(1 OCTYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 YL] CARBAMATE; TERT BUTYL [4 (BENZYLOXY) 5 [[(1 TETRADECYL 1H 1,2,3 TRIAZOL 4 YL)METHOXY]METHYL]TETRAHYDROFURAN 3 YL] CARBAMATE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; PACHASTRISSAMINE; SPHINGOSINE; TRIAZOLE DERIVATIVE;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; APOPTOSIS ASSAY; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CLICK CHEMISTRY; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MCF 7 CELL LINE; ANALOGS AND DERIVATIVES; CELL CYCLE; CELL PROLIFERATION; CHEMICAL PHENOMENA; CHEMISTRY; DRUG EFFECTS; IC50; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; CHEMISTRY TECHNIQUES, SYNTHETIC; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INHIBITORY CONCENTRATION 50; SPHINGOSINE; TRIAZOLES;

EID: 84901295826     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.03.022     Document Type: Article

References (43)

1. I. Kuroda, M. Musman, I.I. Ohtani, T. Ichiba, J. Tanaka, D.G. Gravalos, and T. Higa Pachastrissamine, a cytotoxic anhydrophytosphingosine from a marine sponge, Pachastrissa species Journal of Natural Products 65 2002 1505 1506 (Pubitemid 35239644)
2. V. Ledroit, C. Debitus, C. Lavaud, and G. Massiot Jaspines A and B: two new cytotoxic sphingosine derivatives from the marine sponge Jaspis sp. Tetrahedron Letters 44 2003 225 228 (Pubitemid 35449550)
3. V. Dhand, S. Chang, and R. Britton Total synthesis of the cytotoxic anhydrophytosphingosine Pachastrissamine (Jaspine B) Journal of Organic Chemistry 78 2013 8208 8213
4. Y. Salma, E. Lafont, N. Therville, S. Carpentier, M.J. Bonnafe, T. Levade, Y. Genisson, and N. Andrieu-Abadie The natural marine anhydrophytosphingosine, Jaspine B, induces apoptosis in melanoma cells by interfering with ceramide metabolism Biochemical Pharmacology 78 2009 477 485
5. M. Martinkova, K. Pomikalova, J. Gonda, and M. Vilkova A common approach to the total synthesis of L-arabino-, L-ribo-C18-phytosphingosines, ent-2-epi-jaspine B and 3-epi-jaspine B from D-mannose Tetrahedron 69 2013 8228 8244
6. Y. Yoshimitsu, S. Oishi, J. Miyagaki, S. Inuki, H. Ohno, and N. Fujii Pachastrissamine (Jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C Bioorganic and Medicinal Chemistry 19 2011 5402 5408
7. N. Sudhakar, A.R. Kumar, A. Prabhakar, B. Jagadeesh, and B.V. Rao The first synthesis of the anhydrophytosphingosine Pachastrissamine (Jaspine B) from Garner's aldehyde Tetrahedron Letters 46 2005 325 327 (Pubitemid 39602628)
8. Y. Salma, S. Ballereau, C. Maaliki, N. Andrieu-Abadie, and Y. Genisson Flexible and enantioselective access to Jaspine B and biologically active chain-modified analogues thereof Organic and Biomolecular Chemistry 8 2010 3227 3243
9. A. Rives, S. Ladeira, T. Levade, N. Andrieu-Abadie, and Y. Genisson Synthesis of cytotoxic aza analogues of Jaspine B Journal of Organic Chemistry 75 2010 7920 7923
10. G. Reddipalli, M. Venkataiah, M.K. Mishra, and N.W. Fadnavis Stereoselective synthesis of 2-epi-Jaspine B via base-catalyzed intramolecular oxy-Michael conjugate addition approach Tetrahedron Asymmetry 20 2009 1802 1805
11. Y. Yoshimitsu, S. Inuki, S. Oishi, N. Fujii, and H. Ohno Stereoselective divergent synthesis of four diastereomers of Pachastrissamine (Jaspine B) Journal of Organic Chemistry 75 2010 3843 3846
12. S. Cruz-Gregorio, C. Espinoza-Rojas, L. Quintero, and F. Sartillo-Piscil Ave-step formal synthesis of (-)-Jaspine B Tetrahedron Letters 52 2011 6370 6371
13. J. Llaveria, Yolanda Díaz, M.I. Matheu, and S. Castillón Enantioselective synthesis of Jaspine B (Pachastrissamine) and its C-2 and/or C-3 epimers European Journal of Organic Chemistry 8 2011 1514 1519
14. S. Ballereau, M. Baltas, and Y. Génisson Sphingolipids cyclic derivatives: occurrence, biological relevance and synthetic Current Organic Chemistry 15 2011 953 986
15. R.J. van den Berg, T.J. Boltje, C.P. Verhagen, R.E. Litjens, G.A. van der Marel, and H.S. Overkleeft An efficient synthesis of the natural tetrahydrofuran pachastrissamine starting from D-ribo-phytosphingosine Journal of Organic Chemistry 71 2006 836 839 (Pubitemid 43100786)
16. M.L. Zhao, E. Zhang, J. Gao, Z. Zhang, Y.T. Zhao, W. Qu, and H.M. Liu An efcient and convenient formal synthesis of Jaspine B from D-xylose Carbohydrate Research 351 2012 126 129
17. A. Kumar Jana, and G. Panda Stereoselective synthesis of Jaspine B and its C2 epimer from Garner aldehyde RSC Advances 3 2013 16795 16801
18. C. Santos, I. Fabing, N. Saffon, S. Ballereau, and Y. Genisson Rapid access to jaspine B and its enantiomer Tetrahedron 69 2013 7227 7233
19. D.R. Buckle, D.J. Outred, C.J.M. Rockell, H. Smith, and B.A. Spicer Studies on v-triazoles. 7. Antiallergic 9-oxo-1H, 9H-benzopyrano [2,3-d]-v-triazoles Journal of Medicinal Chemistry 26 1983 251 254 (Pubitemid 13187355)
20. M.J. Gifn, H. Heaslet, A. Brik, Y.C. Lin, G. Cauvi, C.H. Wong, D.E. McRee, J.H. Elder, C.D. Stout, and B.E. Torbett A copper(I)-catalyzed 1, 2, 3-triazole azidealkyne click compound is a potent inhibitor of a multidrug-resistant HIV-1 protease variant Journal of Medicinal Chemistry 51 2008 6263 6270
21. S.R. Patpi, L. Pulipati, P. Yogeeswari, D. Sriram, N. Jain, B. Sridhar, R. Murthy, D.T. Anjana, S.V. Kalivendi, and S. Kantevar Design, synthesis, and structure-activity correlations of novel dibenzo [b,d] furan, dibenzo [b,d] thiophene, and N-methylcarbazole clubbed 1,2,3-triazoles as potent inhibitors of mycobacterium tuberculosis Journal of Medicinal Chemistry 55 2012 3911 3922
22. J.A. Demaray, J.E. Thuener, M.N. Dawson, and S.J. Sucheck Synthesis of triazole oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity Bioorganic & Medicinal Chemistry Letters 18 2008 4868 4871
23. P. Singh, R. Raj, V. Kumar, M.P. Mahajan, P.M.S. Bedi, T. Kaur, and A.K. Saxena 1, 2, 3-Triazole tethered β-lactam-chalcone bifunctional hybrids: synthesis and anticancer evaluation European Journal of Medicinal Chemistry 47 2012 594 600
24. A. Kamal, N. Shankaraiah, V. Devaiah, K.L. Reddy, A. Juvekar, S. Sen, N. Kurianb, and S. Zingde Synthesis of 1, 2, 3-triazole-linked pyrrolobenzodiazepine conjugates employing 'click' chemistry: DNA-binding affinity and anticancer activity Bioorganic & Medicinal Chemistry Letters 18 2008 1468 1473 (Pubitemid 351226525)
25. H. Elamari, R. Slimi, G.G. Chabot, L. Quentin, D. Scherman, and C. Girard Synthesis and in vitro evaluation of potential anticancer activity of mono- and bis-1,2,3-triazole derivatives of bis-alkynes European Journal of Medicinal Chemistry 60 2013 360 364
26. J.A. Stefely, R. Palchaudhuri, P.A. Miller, R.J. Peterson, G.C. Moraski, P.J. Hergenrother, and M.J. Miller N-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl) arylamide as a new scaffold that provides rapid access to antimicrotubule agents: synthesis and evaluation of antiproliferative activity against select cancer cell lines Journal of Medicinal Chemistry 53 2010 3389 3395
27. M.J. Soltis, H.J. Yeh, K.A. Cole, N. Whittaker, R.P. Wersto, and E.C. Kohn Identication and characterization of human metabolites of CAI [5-amino-1-1(4'-chlorobenzoyl-3, 5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide) Drug Metabolism and Disposition 24 1996 799 806 (Pubitemid 26244224)
28. H.C. Kolb, M.G. Finn, and K.B. Sharpless Click Chemistry: diverse chemical function from a few good reactions Angewantde Chemie International Edition 40 2001 2004 2021
29. H.C. Kolb, and K.B. Sharpless The growing impact of click chemistry on drug discovery Drug Discovery Today 8 2003 1128 1137 (Pubitemid 37547919)
30. L.T. Li, L.F. Zhou, Y.J. Li, J. Huang, R.H. Liu, B. Wang, and P. Wang Facile synthesis of 1, 2, 3-triazole analogs of SGLT2 inhibitors by 'click chemistry' Bioorganic & Medicinal Chemistry Letters 22 2012 642 644
31. M.A. Ibrahim, H.W.B. Johnson, J.W. Jeong, G.L. Lewis, X. Shi, R.T. Noguchi, M. Williams, J.W. Leahy, J.M. Nuss, J. Woolfrey, M. Banica, F. Bentzien, Y.C. Chou, A. Gibson, N. Heald, P. Lamb, L. Mattheakis, D. Matthews, A. Shipway, X. Wu, W.T. Zhang, S.H. Zhou, and G. Shankar Discovery of a novel class of potent and orally bioavailable sphingosine 1-phosphate receptor 1 antagonists Journal of Medicinal Chemistry 55 2012 1368 1381
32. N. Boechat, V.F. Ferreira, S.B. Ferreira, M.L.G. Ferreira, F.C. Silva, M.M. Bastos, M.S. Costa, M.C.S. Lourenco, A.C. Pinto, A.U. Krettli, A.C. Aguiar, B.M. Teixeira, N.V. Silva, P.R.C. Martins, F.A.F.M. Bezerra, A.L.S. Camilo, G.P. Silva, and C.C.P. Costa Novel 1, 2, 3-triazole derivatives for use against Mycobacterium tuberculosis H37Rv (ATCC 27294) Strain Journal of Medicinal Chemistry 54 2011 5988 5999
33. Y. Durust, H. Karakus, M. Kaiser, and D. Tasdemir Synthesis and anti-protozoal activity of novel dihydropyrrolo[3,4-d][1,2,3]triazoles European Journal of Medicinal Chemistry 48 2012 296 304
34. I.S. Bennet, G. Brooks, N.J.P. Broom, S.H. Calvert, K. Coleman, and I. Francois 6-(substituted methylene) penems, potent broad spectrum inhibitors of bacterial β-Lactamse. V. chiral 1, 2, 3-triazolyl derivatives Journal of Antibiotics 44 1991 969 978
35. N.S. Vatmurge, B.G. Hazra, V.S. Pore, F. Shirazi, P.S. Chavan, and M.V. Deshpande Synthesis and antimicrobial activity of β-lactam-bile acid conjugates linked via triazole Bioorganic & Medicinal Chemistry Letters 18 2008 2043 2047 (Pubitemid 351380871)
36. H. Chen, S. Zuo, X. Wang, X. Tang, M. Zhao, Y. Lu, L. Chen, J. Liu, Y. Liu, D. Liu, S. Zhang, and T. Li Synthesis of 4beta-triazole-podophyllotoxin derivatives by azide-alkyne cycloaddition and biological evaluation as potential antitumor agents European Journal of Medicinal Chemistry 46 2011 4709 4714
37. J. Doiron, A.H. Soultan, R. Richard, M.M. Toure, N. Picot, R. Richard, M. Cuperlovic-Culf, G.A. Robichaud, and M. Touaibia Synthesis and structure-activity relationship of 1- and 2-substituted-1,2,3-triazole letrozole-based analogues as aromatase inhibitors European Journal of Medicinal Chemistry 46 2011 4010 4024
38. A. Kamal, S. Prabhakar, M.J. Ramaiah, P.V. Reddy, C.H.R. Reddy, A. Mallareddy, N. Shankaraiah, T.L.N. Reddy, S.N.C.V.L. Pushpavalli, and M. Pal-Bhadra Synthesis and anticancer activity of chalcone-pyrrolobenzodiazepine conjugates linked via 1,2,3-triazole ring side-armed with alkane spacers European Journal of Medicinal Chemistry 46 2011 3820 3831
39. Y.C. Duan, Y.C. Ma, E. Zhang, X.J. Shi, M.M. Wang, X.W. Ye, and H.M. Liu Design and synthesis of novel 1,2,3-triazole-dithiocarbamate hybrids as potential anticancer agents European Journal of Medicinal Chemistry 62 2013 11 19
40. Y.C. Duan, Y.C. Zheng, X.C. Li, M.M. Wang, X.W. Ye, Y.Y. Guan, G.Z. Liu, J.X. Zheng, and H.M. Liu Design, synthesis and antiproliferative activity studies of novel 1,2,3-triazoleedithiocarbamateeurea hybrids European Journal of Medicinal Chemistry 64 2013 99 110
41. Y.C. Zheng, Y.C. Duan, J.L. Ma, R.M. Xu, X.L. Zi, W.L. Lv, M.M. Wang, X.W. Ye, S. Zhu, D. Mobley, Y.Y. Zhu, J.W. Wang, J.F. Li, Z.R. Wang, W. Zhao, and H.M. Liu Triazole-dithiocarbamate based selective lysine specific demethylase 1 (lsd1) inactivators inhibit gastric cancer cell growth, invasion, and migration Journal of Medicinal Chemistry 56 2013 8543 8560
42. Y. Yoshimitsu, J. Miyagaki, S. Oishi, N. Fujii, and H. Ohno Synthesis of Pachastrissamine (Jaspine B) and its derivatives by the late-stage introduction of the C-2 alkyl side-chains using olefin cross metathesis Tetrahedron 69 2013 4211 4220
43. M. Swetha, P. Venkata Ramana, and S.G. Shirodkar Simple and efficient method for the synthesis of azides in Water-THF solvent system Organic Preparations and Procedures International 43 2011 348 353