title: Efficient total synthesis and biological activities of 6-deoxyisojacareubin.
abstract: 6-Deoxyisojacareubin was directly synthesized in a six-step route with an overall yield of about 20%. In this route, the excellent site selectivity of this Claisen rearrangement-cyclization reaction cascade was achieved by inserting a bulky p-tosyl group into the free 1-OH, and in the last step, some efficient demethylation methods were explored. Furthermore, all synthesized intermediates including 6-deoxyisojacareubin were evaluated for their inhibitory activity against the QGY-7703 cell line. Of these, compound 1 and 6-deoxyisojacareubin showed moderate activities with IC50 values of 39.61 and 9.65 µM, respectively, when compared to the positive control 5-fluorouracil with an IC50 value of 11.24 µM. Further investigation using non-radioactive detection of protein kinase C (PKC) suggested that these two compounds possessed potency in the inhibition of PKC.
authors.affiliation: Department of Phytochemistry, School of Pharmacy, Second Military Medical University, Shanghai, PR China.
authors.forename: Ming
authors.initials: M
authors.lastname: Dai
authors.forename: Xing
authors.initials: X
authors.lastname: Yuan
authors.forename: Zhi-Jun
authors.initials: ZJ
authors.lastname: Zhu
authors.forename: Lei
authors.initials: L
authors.lastname: Shan
authors.forename: Run-Hui
authors.initials: RH
authors.lastname: Liu
authors.forename: Qing-Yan
authors.initials: QY
authors.lastname: Sun
authors.forename: Wei-Dong
authors.initials: WD
authors.lastname: Zhang
mesh_terms: D000970:Antineoplastic Agents / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology*; D006528:Carcinoma, Hepatocellular / Q000188:drug therapy* / Q000473:pathology; D002460:Cell Line; D045744:Cell Line, Tumor; D005472:Fluorouracil / Q000008:administration & dosage / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D008113:Liver Neoplasms / Q000188:drug therapy* / Q000473:pathology; D011493:Protein Kinase C / Q000037:antagonists & inhibitors; D011714:Pyrans / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology*; D014966:Xanthenes / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology*
chemical_list: C584498:6-deoxyisojacareubin; D000970:Antineoplastic Agents; D011714:Pyrans; D014966:Xanthenes; D011493:Protein Kinase C; D005472:Fluorouracil