Synthesis and evaluation of in vitro anticancer activity of novel solasodine derivatives

Chinese Chemical Letters

Volumn 21, Issue 9, 2010, Pages 1087-1090

  Zha, Xiao Ming ^a   Zhang, Fei Ran ^b   Shan, Jia Qi ^a   Zhang, Yi Hua ^a   Liu, Jun O ^b   Sun, Hong Bin ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Derivatives; In vitro anticancer; Solasodine

Indexed keywords

EID: 77955050584     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2010.04.020     Document Type: Article

References (21)

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17. Crystallographic data (excluding structure factors) has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 689358 (compound 3). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ. UK (fax: +44 (0)1223 336033 or E-mail: deposit@ccdc.cam.ac.uk or ). http://www.ccdc.cam.ac.uk/.
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19. Analytical data for compound 18: Mp 264-265°C. IR (KBr): 3417, 2933, 1460, 1046cm-1. 1H NMR (300MHz, CDCl3): δ 5.36 (brd, 1H), 4.42 (m, 1H), 3.53 (m, 1H), 3.00 (brd, 1H), 2.57 (brd, 1H), 1.06 (d, 3H, J=7.1Hz), 1.02 (s, 3H), 0.93 (s, 3H), 0.83 (d, 3H, J=6.6Hz). 13C NMR (300MHz, CDCl3): δ 140.8; 121.6; 71.8; 71.2; 62.8; 59.8; 54.5; 54.4; 50.3; 42.8; 42.4; 40.2; 37.3; 36.6; 35.9; 35.9; 33.7; 31.9; 31.7; 31.6; 31.5; 31.5; 27.5; 20.9; 19.4; 19.0; 13.5. TOF-MS (m/z): 416.3 ([M+H]+). (The analytical data of 18 were identical with the data reported: see Ref. [16]).
20. Analytical data for compound 19: Mp. >300°C. IR (KBr): 3433, 2948, 1719, 1276, 756cm-1. 1H NMR (300MHz, CDCl3): δ 7.63 (m, 1H); 7.55 (m, 1H), 7.31 (m, 1H), 7.09 (m,1H), 5.42 (brd, 1H), 4.84 (m, 1H), 4.48 (m, 1H), 3.85 (s, 3H), 3.20 (brd, 1H), 2.85 (brd, 1H), 2.46 (brd, 2H), 1.13 (d, 3H, J=7.2Hz), 1.07 (s, 3H), 0.93 (s, 3H), 0.88 (d, 3H, J=6.4Hz). 13C NMR (300MHz, CDCl3): δ 165.8; 159.6; 139.7; 132.3; 129.3; 122.6; 122.0; 119.2; 114.2; 77.2; 74.7; 62.3; 58.6; 55.5; 54.3; 53.3; 50.1; 42.8; 40.0; 38.2; 37.1; 36.7; 34.9; 33.0; 31.8; 31.6; 30.2; 27.9; 27.0; 20.8; 19.4; 19.1; 18.2; 13.4. TOF-HRMS (m/z): calcd for C35H52NO4 ([M+H]+) 550.3896, found 550.3878.
21. PC-3 cells were obtained from ATCC and were cultured in RPMI medium, supplemented with 10% FBS and 50units/mL penicillin plus 50mg/mL streptomycin. Cells were grown in a humidified incubator at 37°C in an atmosphere of 5% CO2. In cell proliferation analysis, cultured PC-3 cells were seeded into 96-well plates before treatment with drug for 28h. 0.5μCi [3H]-thymidine was added for the last 6h before cells were trypsinized and harvested by Cell Harvester (Tomtech, CT). The scintillation counts from the isotope incorporated in the newly synthesized DNA was counted by Beta-Counter (PerkinElmer). Data were collected and analyzed by GraphPad Prism (La Jolla, CA) 4.0 software.