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Privileged Biorenewable Secologanin-Based Diversity-Oriented Synthesis for Pseudo-Natural Alkaloids: Uncovering Novel Neuroprotective and Antimalarial Frameworks.
Zhu, Huajian; Cai, Yunrui; Ma, Shijia; Futamura, Yushi; Li, Jinbiao; Zhong, Wen; Zhang, Xiangnan; Osada, Hiroyuki; Zou, Hongbin.
Afiliação
  • Zhu H; College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058, P. R. China.
  • Cai Y; College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058, P. R. China.
  • Ma S; College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058, P. R. China.
  • Futamura Y; Chemical Biology Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.
  • Li J; College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058, P. R. China.
  • Zhong W; College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058, P. R. China.
  • Zhang X; College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058, P. R. China.
  • Osada H; Chemical Biology Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.
  • Zou H; College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058, P. R. China.
ChemSusChem ; 14(23): 5320-5327, 2021 Dec 06.
Article em En | MEDLINE | ID: mdl-34636473
Bioprivileged molecules hold great promise for supplementing petrochemicals in sustainable organic synthesis of a diverse bioactive products library. Secologanin, a biorenewable monoterpenoid glucoside with unique structural elements, is the key precursor for thousands of natural monoterpenoid alkaloids. Inspired by its inherent highly congested functional groups, a secologanin-based diversity-oriented synthesis (DOS) strategy for novel pseudo-natural alkaloids was developed. All the reactive units of secologanin were involved in these operation simplicity protocols under mild reaction conditions, including the one-step enantioselective transformation of exocyclic C8, C8/C11, and C8/C9/C10 as well as the chemoenzymatic manipulation of endocyclic C2/C6 via the attack by various nucleophiles. A combinatory scenario of the aforementioned reactions further provided diverse polycyclic products with multiple chiral centers. Preliminary activity screening of these newly constructed molecules led to the discovery of antimalarial and highly potent neuroprotective skeletons. The application of green biorenewable secologanin in diversity-oriented pseudo-natural monoterpenoid alkaloid synthesis might encourage the pursuit of valuable bioactive frameworks.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Alcaloides de Triptamina e Secologanina / Alcaloides / Antimaláricos Idioma: En Revista: ChemSusChem Assunto da revista: QUIMICA / TOXICOLOGIA Ano de publicação: 2021 Tipo de documento: Article País de publicação: Alemanha

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Alcaloides de Triptamina e Secologanina / Alcaloides / Antimaláricos Idioma: En Revista: ChemSusChem Assunto da revista: QUIMICA / TOXICOLOGIA Ano de publicação: 2021 Tipo de documento: Article País de publicação: Alemanha