64439-81-2Relevant articles and documents
Multi-gram scale synthesis of a bleomycin (BLM) carbohydrate moiety: exploring the antitumor beneficial effect of BLM disaccharide attached to 10-hydroxycamptothecine (10-HCPT)
Li, MaoLin,Huang, Weiping,Jiang, Zhilin,Shi, Yonghui,Yuan, Sisi,Fu, Kaishuo,Chen, YongJun,Zhou, Li,Zhou, Wen
, p. 6010 - 6020 (2019/04/17)
The “tumor-seeking” role of bleomycin (BLM) disaccharide has been demonstrated to serve as a promising tool for cancer diagnosis and a potential ligand for targeted therapy. However, these practical applications are often hampered by the lack of BLM disaccharide. Herein, an efficient multi-gram synthesis of peracetylated BLM disaccharide 20 is achieved by a TMSOTF-mediated glycosidation coupling manner in 43.6% overall yield in terms of benzyl galactoside. The critical innovation of the synthetic strategy is that inexpensive benzyl galactoside was first adopted to prepare an l-gulose subunit 3 as a glycosyl acceptor, with a much shorter route in 73.0% yield, and a 3-O-carbamoyl-mannose donor 4 was achieved in 47.2% yield by lowering the amount of dibutyltin oxide, and merging aminolysis and selective deacetylation into a one-pot reaction. Next, the incorporation of BLM disaccharide into 10-hydroxycamptothecin (10-HCPT), a non-specific model compound, to form conjugate 1 could significantly improve the antitumor activity and display obvious selectivity toward cancerous and normal cells in comparison with 10-HCPT. Moreover, BLM disaccharide itself was non-cytotoxic, clearly indicating the importance and potential of BLM disaccharide in solving the targeted antitumor therapy of cytotoxic drugs.
Short protecting group-free syntheses of camptothecin and 10-hydroxycamptothecin using cascade methodologies
Xu, Peng,Chen, Dong-Sheng,Xi, Jie,Yao, Zhu-Jun
supporting information, p. 976 - 981 (2015/04/14)
A convergent protecting group-free total synthesis route of camptothecin and 10-hydroxycamptothecin has been developed in this work. Cascade oxidation of 3-(hydroxymethyl)furan-2(5 H)-one and in situ intermolecular oxa Diels-Alder reaction with vinyl ether was developed and applied to construct the E-ring, and TMSCl-promoted cascade closure of the D-ring delivered the whole skeleton of the alkaloids in the total synthesis. The new short syntheses were advantageous with regard to step economy, low cost, easily available starting materials and reagents, and convenient operations.
Synthesis of 10-hydroxycamptothecin: Evaluation of new moderators for the chemoselective reduction of camptothecin
Sekhar,Anjaneyulu, Yerramilli,Acharyulu, V.R.Palle
experimental part, p. 2828 - 2834 (2011/08/22)
10-Hydroxycamptothecin is prepared by chemoselective catalytic hydrogenation of the B-ring of camptothecin over PtO2 with sulfur moderators followed by oxidation using iodobenzenediacetate. New moderators (viz. thioanisole, dimethyl sulfide, diphenyl sulfide, 2-mercapto ethanol), which moderate the hydrogenation of the B- ring of camptothecin, are being explored. Dr. Reddy's Laboratories Ltd.
