European Journal of Medicinal Chemistry p. 1942 - 1958 (2018)
Update date:2022-08-15
Topics:
Lin, You-Yu
Chan, She-Hung
Juang, Yu-Pu
Hsiao, Hsin-Min
Guh, Jih-Hwa
Liang, Pi-Hui
A series of N-acyl, N-alkoxycarbonyl, and N-alkylcarbamoyl derivatives of 2′-deoxy-glucosyl bearing oleanolic saponins were synthesized and evaluated against HL-60, PC-3, and HT29 tumor cancer cells. The SAR studies revealed that the activity increased in order of conjugation of 2′ -amino group with carbamate > amide > urea derivatives. Lengthening the alkyl chain increased the cytotoxicity, the peak activity was found to around heptyl to nonyl substitutions. 2′-N-heptoxycarbonyl derivative 56 was found to be the most cytotoxic (IC50 = 0.76 μM) against HL-60 cells. Due to the interesting SARs of alkyl substitutions, we hypothesized that their location in the cell was different, and pursued a location study using 2′-(4″-pentynoylamino) 2′-deoxy-glucosyl OA, which suggested that these compounds distributed mainly in the cytosol.
View MoreShijiazhuang Sdyano Fine Chemical Co., Ltd
Contact:+86-311-89830448
Address:NO.48 Ta Nan Road,Yuhua District,Shijiazhuang,Hebei,China
Jinan Hongfangde Pharmatech Co.,Ltd
Contact:86-531-88870908
Address:F Bldg. West Unit North Area of Univ. Tech. Garden Xinyu Rd. Jinan New & High Tech Industry Development Zone Shandong, China
Jiangxi Hessence Chemicals Co., Ltd.
Contact:+86 796 3511924
Address:Chengxi Industrial Park, Jishui County, Jiangxi Province 331600 China.
SHANGHAI ARCADIA BIOTECHNOLOGY LTD.
Contact:+86-21-61353236
Address:SUITE 901, BUILDING WENSLI, 1378 LU JIA BANG RD, SHANGAHI 200011, P.R.CHINA
Hangzhou Mole's Science & Technology Co.,Ltd.(expird)
Contact:+86-571-56880228
Address:15F Guodu development Building, NO.182 Zhaohui Road
Doi:10.1039/c4ob00957f
(2014)Doi:10.1016/j.ejmech.2014.05.082
(2014)Doi:10.1039/c39950000259
(1995)Doi:10.1021/ja504458j
(2014)Doi:10.1002/anie.201608444
(2017)Doi:10.1039/c4ob01088d
(2014)