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A novel and practical synthesis of CAT3: a phenanthroindolizidine alkaloid with potential in treating glioblastoma.
Wang, Ru-Bing; Lv, Hai-Ning; Zhu, Shan-Shan; Ren, Xiao-Dong; Xu, Song; Ma, Shuang-Gang; Liu, Yun-Bao; Qu, Jing; Yu, Shi-Shan.
Afiliação
  • Wang RB; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College Beijing 100050 China yushishan@imm.ac.cn qujing@imm.ac.cn +86-10-63017757.
  • Lv HN; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College Beijing 100050 China yushishan@imm.ac.cn qujing@imm.ac.cn +86-10-63017757.
  • Zhu SS; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College Beijing 100050 China yushishan@imm.ac.cn qujing@imm.ac.cn +86-10-63017757.
  • Ren XD; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College Beijing 100050 China yushishan@imm.ac.cn qujing@imm.ac.cn +86-10-63017757.
  • Xu S; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College Beijing 100050 China yushishan@imm.ac.cn qujing@imm.ac.cn +86-10-63017757.
  • Ma SG; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College Beijing 100050 China yushishan@imm.ac.cn qujing@imm.ac.cn +86-10-63017757.
  • Liu YB; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College Beijing 100050 China yushishan@imm.ac.cn qujing@imm.ac.cn +86-10-63017757.
  • Qu J; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College Beijing 100050 China yushishan@imm.ac.cn qujing@imm.ac.cn +86-10-63017757.
  • Yu SS; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College Beijing 100050 China yushishan@imm.ac.cn qujing@imm.ac.cn +86-10-63017757.
RSC Adv ; 8(51): 29301-29308, 2018 Aug 14.
Article em En | MEDLINE | ID: mdl-35547992
ABSTRACT
CAT3, one of the (+)-deoxytylophorinine-based phenanthroindolizidine alkaloids, is a promising therapeutic agent for the treatment of hedgehog (Hh)-driven glioblastoma and is currently being evaluated in preclinical studies. In this paper, a novel and practical synthetic route for CAT3 was firstly demonstrated with 10% overall yield in 11 steps and has been successfully validated for pilot-plant scale preparation. Investigation of the substitution at the 3-position of phenanthrene revealed that the electron-donating functionality can well preserve the S configuration. In particular, the excellent enantiomeric excess of CAT3 (≥99% ee) was achieved by introducing the strongly electron-donating tert-butyldimethylsilyl (TBS) group.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2018 Tipo de documento: Article
Texto completo
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2018 Tipo de documento: Article