Potent DNA-directed alkylating agents: Synthesis and biological activity of phenyl N-mustard-quinoline conjugates having a urea or hydrazinecarboxamide linker

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 6, 2010, Pages 2285-2299

  Kakadiya, Rajesh ^a,d   Dong, Huajin ^b   Kumar, Amit ^a   Narsinh, Dodia ^a   Zhang, Xiuguo ^b   Chou, Ting Chao ^b   Lee, Te Chang ^a   Shah, Anamik ^d   Su, Tsann Long ^a,c  

^a INSTITUTE OF BIOMEDICAL SCIENCES   (Taiwan)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^c CHINA MEDICAL UNIVERSITY   (Taiwan)

^d SAURASHTRA UNIVERSITY   (India)

Author keywords

Anticancer agents; DNA interstrand cross linking agents; DNA directed alkylating agents; Phenyl nitrogen mustards; Quinolines

Indexed keywords

BO 1037; CISPLATIN; CYCLOPHOSPHAMIDE; GEMCITABINE; HYDRAZINE DERIVATIVE; N [4 [BIS(2 CHLOROETHYL)AMINO]PHENYL] 2 (6 METHYL[1,3]DIOXOLO[4,5 G]QUINOLIN 8 YL)HYDRAZINECARBOXAMIDE; N [4 [BIS(2 CHLOROETHYL)AMINO]PHENYL] 2 [6 (DIMETHYLAMINO) 2 METHYL 4 QUINOLINYL]HYDRAZINECARBOXAMIDE; N [4 [BIS(2 CHLOROETHYL)AMINO]PHENYL] N' (2 METHYL 4 QUINOLINYL)UREA; N [4 [BIS(2 CHLOROETHYL)AMINO]PHENYL] N' [6 METHOXY 2 (3 METHOXYPHENYL) 4 QUINOLINYL]UREA; PACLITAXEL; PHENYL N MUSTARD QUINOLINE CONJUGATE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE; VINBLASTINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CARCINOMA; CANCER CELL CULTURE; CANCER INHIBITION; CONTROLLED STUDY; DNA CROSS LINKING; DRUG BLOOD LEVEL; DRUG HALF LIFE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; MALE; MOUSE; NONHUMAN; NUDE MOUSE; RAT; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS, ALKYLATING; CELL PROLIFERATION; DNA; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; HYDRAZINES; MALE; MICE; MICE, NUDE; MOLECULAR STRUCTURE; NEOPLASM TRANSPLANTATION; NEOPLASMS, EXPERIMENTAL; QUINOLINES; RATS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED; UREA;

ANIMALIA; BRASSICACEAE; MUS MUSCULUS; RATTUS;

EID: 77649231934     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.01.061     Document Type: Article

References (44)

1. Wendtner C.M., Eichhorst B.F., and Hallek M.J. Semin. Hematol. 41 (2004) 224
2. Gajski S.R., and William R.M. Chem. Rev. 98 (1998) 2723
3. Denny W.A. Curr. Med. Chem. 8 (2001) 533
4. Grando S.A. Life Sci. 72 (2003) 2135
5. Suzukake K., Vistica B.P., and Vistica D.T. Biochem. Pharmacol. 32 (1983) 165
6. Rodney M., Carney J.P., Kelley M.R., Glassner B.J., Williams D.A., and Samson L. Proc. Natl. Acad. Sci. USA 93 (1996) 206
7. Gourdie T.A., Valu K.K., Gravatt G.L., Boritzki T.J., Baguley B.C., Wakelin L.P.G., Wilson W.R., Woodgate P.D., and Denny W.A. J. Med. Chem. 33 (1990) 1177
8. Prakash A.S., Denny W.A., Gourdie T.A., Value K.K., Woodgate P.D., and Wakelin L.P.G. Biochemistry 29 (1990) 9799
9. Gravatt G.L., Baguley B.C., Wilson W.R., and Denny W.A. J. Med. Chem. 37 (1994) 4338
10. Köhler B., Su T.-L., Chou T.-C., Jiang X.-J., and Watanabe K.A. J. Org. Chem. 58 (1993) 1680
11. Pezzoni G., Grandi M., Biasoli G., Capolongo L., Ballinari D., Giuliani F.C., Barbieri B., Pastori B., Pesenti E., Mongelli N., and Spreafico F. Br. J. Cancer 75 (1991) 1047
12. Springer C.J., Dowell R., Burke P.J., Hadley E., Davies D., Blakey D.C., Melton R.G., and Niculescu-Duyaz I. J. Med. Chem. 38 (1995) 5051
13. Jordan A.M., Khan T.H., Malkin H., Helen M.I., and Osborn H.M.I. Bioorg. Med. Chem. 10 (2002) 2625
14. Knaggs S., Malkin H., Osborn H.M.I., Williams N.A.O., and Yaqoob P. Org. Biomol. Chem. 3 (2005) 4002
15. Jordan A.M., Khan T.H., Osborn H.M.I., Photiou A., and Riley P.A. Bioorg. Med. Chem. 7 (1999) 1775
16. Springer C.J., Antoniw P., Bagshawe K.D., Searle F., Bisset G.M.F., and Jarman M. J. Med. Chem. 33 (1990) 677
17. Springer C.J. Drugs Future 18 (1993) 212
18. Friedlos F., Davies L., Scanlon I., Ogilvie L.M., Martin J., Stribbling S.M., Spooner R.A., Niculescu-Duvaz I., Marais R., and Springer C.J. Cancer Res. 62 (2002) 1724
19. Denny W.A., and Wilson W.R. J. Pharm. Pharmacol. 50 (1998) 387
20. Roth J.A., and Cristiano R.G. J. Natl. Cancer Inst. 89 (1997) 21
21. Bacherikov V.A., Chou T.-C., Dong H.-J., Chen C.-H., Lin Y.-W., Tsai T.-J., and Su T.-L. Bioorg. Med. Chem. Lett. 14 (2004) 4719
22. Bacherikov V.A., Chou T.-C., Dong H.-J., Zhang X., Chen C.-H., Lin Y.-W., Tsai T.-J., Lee R.-Z., Liu L.F., and Su T.-L. Bioorg. Med. Chem. 13 (2005) 3993
23. Su T.-L., Lin Y.-W., Chou T.-C., Zhang X., Bacherikov V.A., Chen C.-H., Liu L.F., and Tsai T.-J. J. Med. Chem. 49 (2006) 3710
24. Chen C.-H., Lin Y.-W., Zhang X., Chou T.-C., Tsai T.-J., Kapuriya N., Kakadiya R., and Su T.-L. Eur. J. Med. Chem. 44 (2009) 3056
25. Kapuriya N., Kapuriya K., Zhang X., Chou T.-C., Kakadiya R., Wu Y.-T., Tsai T.-H., Chen Y.-T., Lee T.-C., Shah A., Naliapara Y., and Su T.-L. Bioorg. Med. Chem. 16 (2008) 5413
26. Kapuriya N., Kapuriya K., Dong H., Zhang X., Chou T.-C., Chen Y.-T., Lee T.-C., Lee W.-C., Tsai T.-H., Naliapara Y., and Su T.-L. Bioorg. Med. Chem. 17 (2009) 1264
27. Atwell G.J., Fan J.-Y., Tan K., and Denny W.A. J. Med. Chem. 41 (1998) 4744
28. Kuo S.-C., Lee H.Z., Juang J.P., Lin Y.T., Wu T.S., Cheng J.J., Lednicer D., Paull K.D., Lin C.M., Hamel E., and Lee K.-H. J. Med. Chem. 36 (1993) 1146
29. Li L., Wuang H.K., Kuo S.-C., Lednicer D., Lin C.M., Hamel E., and Lee K.-H. J. Med. Chem. 37 (1994) 1126
30. Li L., Wang H.K., Kuo S.-C., Wu T.S., Mauger A., Lin C.M., Hamel E., and Lee K.-H. J. Med. Chem. 37 (1994) 3400
31. Xiao Z.P., Lv P.C., Xu S.P., Zhu T.T., and Zhu H.L. Chem. Med. Chem. 3 (2008) 1516
32. Andersen K.E., Lundt B.F., Jorgensen A.S., and Braestrup C. Eur. J. Med. Chem. 31 (1996) 417
33. Savini L., Chiasserini L., Gaeta A., and Pellerano C. Bioorg. Med. Chem. 10 (2002) 2193
34. Dowell R.I., Springer C.J., Davies D.H., Hadley E.M., Burke P.J., Boyle F.T., Melton R.G., and Connors T.A. J. Med. Chem. 39 (1996) 1100
35. Singh N.P., McCoy M.T., Tice R.R., Schneider E.L., and Schneider E.L. Exp. Cell Res. 175 (1988) 184
36. Friedmann B.J., Caplin M., Savic B., Shah T., Lord C.J., Ashworth A., Hartley J.A., and Hochhauser D. Mol. Cancer Ther. 5 (2006) 209
37. Moinet-Hedin V., Tabka T., Poulain L., Godard T., Lechevrel M., Saturnino C., Lancelot J.C., Le Talaer J.Y., and Gauduchon P. Anti-Cancer Drug Des. 15 (2000) 109
38. Scudiero D.A., Shoemaker R.H., Paull K.D., Monks A., Tierney S., Nofziger T.H., Currens M.J., Seniff D., and Boyd M.R. Cancer Res. 48 (1988) 4827
39. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenny S., and Boyd M.R. J. Natl. Cancer Inst. 82 (1990) 1107
40. Chou T.-C., O'Connor O.A., Tong W.P., Guan Y., Zhang Z.-G., Stachel S.J., Lee C., and Danishefsky S.J. Proc. Natl. Acad. Sci. USA 98 (2001) 8113
41. Al-Nasiry S., Hanssens M., Luyten C., and Pijnenborn R. Hum. Reprod. 22 (2007) 1304
42. Chou, T.-C.; Martin, N. ComboSyn, Inc., Paramus, NJ, 2005.
43. Chou T.-C., and Talalay P. Adv. Enzyme Regul. 22 (1984) 27
44. Chou T.-C. Pharmacol. Rev. 58 (2006) 621