Lin, You-YuYou-YuLinChan, She-HungShe-HungChanYU-PU JUANGHsiao, Hsin-MinHsin-MinHsiaoJIH-HWA GUHPI-HUI LIANG2021-06-022021-06-022018-01-012235234https://www.scopus.com/inward/record.uri?eid=2-s2.0-85033481235&doi=10.1016%2fj.ejmech.2017.11.004&partnerID=40&md5=18a005a1c648a788cc8a7855cf2647c3https://scholars.lib.ntu.edu.tw/handle/123456789/564765A 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. ? 2017 Elsevier Masson SASCytotoxicity; Glycoside; Glycosylation; Oleanolic acid[SDGs]SDG33 o (2' n heptoxycarbonyl 2 deoxy beta d glucopyranosyl) oleanolic acid; alkyl group; amide; antineoplastic agent; carbamic acid; glucosamine; heptane; oleanolic acid derivative; saponin derivative; unclassified drug; urea derivative; antineoplastic agent; glucosamine; oleanolic acid; saponin; alkylation; Article; conjugation; controlled study; cytotoxicity; drug design; drug synthesis; HL-60 cell line; HT-29 cell line; human; human cell; structure activity relation; cell proliferation; chemical structure; chemistry; dose response; drug effects; drug screening; synthesis; tumor cell culture; Antineoplastic Agents; Cell Proliferation; Dose-Response Relationship, Drug; Drug Design; Drug Screening Assays, Antitumor; Glucosamine; Humans; Molecular Structure; Oleanolic Acid; Saponins; Structure-Activity Relationship; Tumor Cells, Culturedjournal article10.1016/j.ejmech.2017.11.004291330612-s2.0-85033481235