Synthesis of 3-O-propargylated betulinic acid and its 1,2,3-triazoles as potential apoptotic agents

European Journal of Medicinal Chemistry

Volumn 63, Issue , 2013, Pages 782-792

  Majeed, Rabiya ^a   Sangwan, Payare L ^a   Chinthakindi, Praveen K ^a   Khan, Imran ^a   Dangroo, Nisar A ^a   Thota, Niranjan ^a   Hamid, Abid ^a   Sharma, Parduman R ^a   Saxena, Ajit K ^a   Koul, Surrinder ^a  

^a CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

Author keywords

Apoptosis; Betulinic acid 1,2,3 trizole derivatives; Click chemistry; Cytotoxicity; DNA fragmentation

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 3 [1N(2 CYANOPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(2 HYDROXYMETHYL PHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(2,3,4,6 TETRAACETYLGALACTOSO 1YL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(2,3,4,6 TETRAACETYLGLUCOSO 1YL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(3 HYDROXYMETHYLPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(3 IODOPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(3 METHOXYPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(3 METHYL 5 HYDROXYPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(3,4 METHYLENEDIOXYPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(3,4,5 TRIMETHOXYPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(4 BENZOYLPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(4 CHLOROPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(4 CYANOMETHYLPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(4 CYANOPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(4 METHOXYPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(4 NITROPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(5 HYDROXY NAPHTH 1YL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; 3 [1N(5 IODO 2 METHYLPHENYL) 1H 1,2,3 TRIAZOL 4YL]METHYLOXY BETULINIC ACID; BETULIC ACID; TERPENOID DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CELL MIGRATION; CLICK CHEMISTRY; COLONY FORMATION; CONTROLLED STUDY; CYTOTOXICITY; DNA FRAGMENTATION; DRUG ISOLATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; MEMBRANE DAMAGE; MITOCHONDRIAL MEMBRANE;

APOPTOSIS; CELL LINE, TUMOR; CELL MOVEMENT; CELL SURVIVAL; DNA FRAGMENTATION; DOSE-RESPONSE RELATIONSHIP, DRUG; ELECTROPHORESIS, AGAR GEL; HL-60 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; MCF-7 CELLS; MEMBRANE POTENTIAL, MITOCHONDRIAL; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES; TRITERPENES;

EID: 84875976313     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.03.028     Document Type: Article

References (26)

1. F.E. Koehn, and G.T. Carter Nat. Rev. Drug Discov. 4 2005 206 220
2. R.C. Santos, J.A.R. Salvador, S. Marin, M. Cascante, J.N. Moreira, and T.C.P. Dinis Bioorg. Med. Chem. 18 2010 4385 4396
3. R. Csuk, A. Barthel, R. Sczepek, B. Siewert, and S. Schwarz Arch. Pharm. Chem. Life Sci. 344 2011 37 49
4. A. Petronelli, G. Pannitteri, and U. Testa Anti-Cancer Drugs 20 2009 880 892
5. P. Dzubak, M. Hajduch, D. Vydra, A. Hustova, M. Kvasnica, D. Biedermann, L. Markova, M. Urban, and J. Sarek Nat. Prod. Rep. 23 2006 394 411
6. R.C. Santos, J.A.R. Salvador, S. Marin, and M. Cascante Bioorg. Med. Chem. 17 2009 6241 6250
7. K.M. Debatin Toxicol. Lett. 112 2000 41 48
8. R.H. Cichewicz, and S.A. Kouzi Med. Res. Rev. 24 2004 90 114
9. H. Yang, and P.Q. Dou Curr. Drug Targets 11 2010 733 744
10. S. Fulda Int. J. Mol. Sci. 9 2008 1096 1107
11. http://clinicaltrials.gov/show/NCT00346502.
12. M.V. Reddy, N. Thota, P.L. Sangwan, P. Malhotra, F. Ali, I.A. Khan, S.S. Chimni, and S. Koul Eur. J. Med. Chem. 45 2010 3125 3134
13. R. Majeed, M.V. Reddy, P.K. Chinthakindi, P.L. Sangwan, A. Hamid, G. Chashoo, A.K. Saxena, and S. Koul Eur. J. Med. Chem. 49 2012 55 67
14. R. Kharb, M.S. Yar, and P.C. Sharma Curr. Med. Chem. 18 2011 3265 3297
15. C.H. Zhou, and Y. Wang Curr. Med. Chem. 19 2012 239 280
16. S.G. Agalave, S.R. Maujan, and V.S. Pore Chem. Asian J. 6 2011 2696 2718
17. C. Denicourt, and S.F. Dowdy Science 305 2004 1411 1413
18. D.E. Fisher Cell 78 1994 539 542
19. J.S. Maria, H. Tewfik, M. Cedric, C. Carla, L. Celine, P. Anne, C.D. Jean, and L. Juan J. Cell. Physiol. 226 2011 3442 3451
20. 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 J. Med. Chem. 54 2011 5988 5999
21. S. Kaur, S. Kamboj, J. Singh, A.K. Saxena, and V.A. Dhuna Biotechnol. Lett. 27 2005 1815 1820
22. O.S. Frankfurt, and A. Krishnan Anti Cancer Drugs 14 2003 555 561
23. S. Davis, M.J. Weiss, J.R. Wong, T.J. Lampidis, and L.B. Chen J. Biol. Chem. 5 1985 13844 13850
24. A.P. Nicolas, M.R. Hans, S. Jan, H. Jap, and V.B. Chris Nat. Protoc. 5 2006 2315
25. A. Munshi, M. Hobbs, and R.E. Meyn Methods Mol. Med. 110 2005 21 28
26. W. Qian, D. Rajiv, and W. Alan Mol. Cancer 11 2012 10.1186/1476-4598-11-3