Synthesis of analogues of linckoside B, a new neuritogenic steroid glycoside

被引：8
|
作者：
Liu, Qingchao [1 ]
Yu, Yue [2 ]
Wang, Peng [2 ]
Li, Yingxia [3 ]
机构：
[1] NW Univ Xian, Dept Pharmaceut Engn, Xian 710069, Peoples R China
[2] Ocean Univ China, Sch Med & Pharm, Qingdao 266003, Peoples R China
[3] Fudan Univ, Sch Pharm, Shanghai 201203, Peoples R China
来源：
NEW JOURNAL OF CHEMISTRY | 2013年 / 37卷 / 11期
基金：
中国国家自然科学基金; 中国博士后科学基金;
关键词：
NERVE GROWTH-FACTOR; NEURODEGENERATION; GLYCOSYLATION; STRATEGIES; SAPONINS;
D O I：
10.1039/c3nj00514c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A facile synthetic approach toward six designed analogues (2-7) of linckoside B, a new neuritogenic steroid glycoside isolated from the Okinawan starfish Linckia laevigata, has been developed. The key steroid aglycon was achieved by a dimethylaluminum chloride-mediated 'ene' reaction. A versatile strategy was employed for the construction of glycosidic bonds through Schmidt's procedure using a glycosyl trichloroacetimidate donor.
引用
收藏
页码：3647 / 3661
页数：15
相关论文
共 50 条
  • [1] Design and Synthesis of Dimeric Securinine Analogues with Neuritogenic Activities
    Tang, Genyun
    Liu, Xin
    Ma, Nan
    Huang, Xiaojie
    Wu, Zhen-Long
    Zhang, Wen
    Wang, Ying
    Zhao, Bing-Xin
    Wang, Zhen-Ya
    Ip, Fanny C. F.
    Ip, Nancy Y.
    Ye, Wen-Cai
    Shi, Lei
    Chen, Wei-Min
    ACS CHEMICAL NEUROSCIENCE, 2016, 7 (10): : 1442 - 1451
  • [2] Linckosides A and B, two new neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata
    Qi, JH
    Ojika, M
    Sakagami, Y
    BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (06) : 1961 - 1966
  • [3] A new Co(0) complex mediated synthesis of C-glycoside analogues
    Orsini, F
    Di Teodoro, E
    TETRAHEDRON-ASYMMETRY, 2003, 14 (17) : 2521 - 2528
  • [4] New neuritogenic steroid glycosides from the Vietnamese starfish Linckia laevigata
    Kicha, Alla A.
    Ivanchina, Natalia V.
    Kalinovsky, Anatoly I.
    Dmitrenok, Pavel S.
    Palyanova, Natalia V.
    Pankova, Tatyana M.
    Starostina, Marina V.
    Gavagnin, Margherita
    Stonik, Valentin A.
    NATURAL PRODUCT COMMUNICATIONS, 2007, 2 (01) : 41 - 46
  • [5] Chemoenzymatic Synthesis of GAA-7 Glycan Analogues and Evaluation of Their Neuritogenic Activities
    Tseng, Hsin-Kai
    Su, Yung-Yu
    Lai, Po-Jen
    Lo, Shao-Lun
    Liu, Hsien-Chein
    Reddy, Sabbasani Rajasekhara
    Chen, Linyi
    Lin, Chun-Cheng
    ACS CHEMICAL NEUROSCIENCE, 2024, 15 (03): : 656 - 670
  • [6] Synthesis of novel spin labeled analogues of podophyllotoxin glycoside
    Lu, KK
    Wang, YG
    Chen, YZ
    SYNTHETIC COMMUNICATIONS, 1997, 27 (11) : 1963 - 1968
  • [7] Short synthesis of phenylpropanoid glycoside grayanoside-A and analogues
    Khong, Duc Thinh
    Judeh, Zaher M. A.
    CARBOHYDRATE RESEARCH, 2016, 436 : 50 - 53
  • [8] ANALOGUES OF STEROID COMPOUNDS WITHOUT CYCLE B .7. NEW ROUTE TO SYNTHESIS OF DOISYNOLIC ACID DERIVATIVES WITHOUT CYCLE - B
    AKHREM, AA
    KULIKOVA, LE
    LEVINA, IS
    TITOV, YA
    IZVESTIYA AKADEMII NAUK SSSR-SERIYA KHIMICHESKAYA, 1971, (03): : 588 - +
  • [9] New class of alkynyl glycoside analogues as tyrosinase inhibitors
    Saehlim, Natthiya
    Athipornchai, Anan
    Sirion, Uthaiwan
    Saeeng, Rungnapha
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2020, 30 (15)
  • [10] Chemoenzymatic Total Synthesis of the Neuritogenic Echinoderm Ganglioside LLG-5 and Related Analogues
    Cho, Yuan-Ting
    Adak, Avijit K.
    Su, Yung-Yu
    Chang, Ting-Wei
    Lin, Chun-Cheng
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (20) : 3573 - 3588
12345