Message Board

Respected readers, authors and reviewers, you can add comments to this page on any questions about the contribution, review,        editing and publication of this journal. We will give you an answer as soon as possible. Thank you for your support!

Name
E-mail
Phone
Title
Content
Verification Code
x Close Forever Close
Volume 29 Issue 1
. 
Turn off MathJax
Article Contents
Article Navigation >  Journal of Pharmaceutical Practice and Service  > 2011  >  29(1): 17-20

ZHOU Ting, YAO Jian-Zhong, ZHANG Dong-Wei, LIU Hong-Ming, SHENG Chun-Quan, MIAO Zhen-Yuan, ZHANG Wan-Nian. Synthesis of 4'-alkoxy-1,1'-bisphenyl-4-carboxylic acid lipotripeptides[J]. Journal of Pharmaceutical Practice and Service, 2011, 29(1): 17-20.
Citation: ZHOU Ting, YAO Jian-Zhong, ZHANG Dong-Wei, LIU Hong-Ming, SHENG Chun-Quan, MIAO Zhen-Yuan, ZHANG Wan-Nian. Synthesis of 4'-alkoxy-1,1'-bisphenyl-4-carboxylic acid lipotripeptides[J]. Journal of Pharmaceutical Practice and Service, 2011, 29(1): 17-20.
shu

Synthesis of 4'-alkoxy-1,1'-bisphenyl-4-carboxylic acid lipotripeptides

  • School of Pharmacy, Second Military Medical University, Shanghai 200433, China

  • Received Date: 2010-06-06
  • Rev Recd Date: 2011-01-04
  • Objective To prepare 4'-alkoxy-1,1'-bisphenyl-4-carboxylic acid lipotripeptides , which is the key intermediates for total synthesis of novel caspofungin-like cyclohexalipopeptide antifungal agents. Methods Starting from Pro-O-t-Bu , the target compound 1 were prepared via 5 steps including condensation with N-Fmoc-L-Thr(O-t-Bu)-OH (a) or N-Fmoc-L-Ser(O-t-Bu)-OH (b), then removed of N-Fmoc group and coupling with Nα-Fmoc-Nδ-Cbz-L-Orn-OH followed by removal of Nα-Fmoc group and reaction with 4'-alkoxy-1,1-4-carboxylic acid N-hydroxybenzotriazole ester (Ie~If). Results 8 target compounds 1ae~1af and 1be~1bf had been synthesized in an overall yield ranged from 67.4% to 80.0%. The structures were confirmed by ESI-MS spectra and elemental analysis. Conclusion The process developed had several adventages of facile reaction conditions, convenient workup and high yield.
  • [1] Georgopapadakou NH. Update on antifungals targeted to the cell wall:focus on beta-1,3-glucan synthase inhibitors[J]. Expert Opin Invest Drugs, 2001, 10(2): 269.
    [2] 郑玉果,朱宝泉,陈代杰. 芬净类抗真菌抗生素的研究开发和临床应用[J]. 世界临床药物,2007, 28(2): 738.
    [3] Klein LL, Li L, Chen HJ, et al. Total synthesis and antifungal evaluation of cyclic aminohexapeptides[J]. Bioorg Med Chem, 2000, 8(7): 1677.
    [4] Journet M, Cai DW, DiMichele LM, et al. Semisynthesis of an antifungal lipopeptide echinocandin[J]. J Org Chem, 1999, 64(7): 2411.
  • 加载中
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Get Citation
PDF
XML

Article Metrics

Article views(2446) PDF downloads(108) Cited by()

Related
Proportional views

Synthesis of 4'-alkoxy-1,1'-bisphenyl-4-carboxylic acid lipotripeptides

  • School of Pharmacy, Second Military Medical University, Shanghai 200433, China
  • Received Date: 2010-06-06
  • Rev Recd Date: 2011-01-04

Abstract: Objective To prepare 4'-alkoxy-1,1'-bisphenyl-4-carboxylic acid lipotripeptides , which is the key intermediates for total synthesis of novel caspofungin-like cyclohexalipopeptide antifungal agents. Methods Starting from Pro-O-t-Bu , the target compound 1 were prepared via 5 steps including condensation with N-Fmoc-L-Thr(O-t-Bu)-OH (a) or N-Fmoc-L-Ser(O-t-Bu)-OH (b), then removed of N-Fmoc group and coupling with Nα-Fmoc-Nδ-Cbz-L-Orn-OH followed by removal of Nα-Fmoc group and reaction with 4'-alkoxy-1,1-4-carboxylic acid N-hydroxybenzotriazole ester (Ie~If). Results 8 target compounds 1ae~1af and 1be~1bf had been synthesized in an overall yield ranged from 67.4% to 80.0%. The structures were confirmed by ESI-MS spectra and elemental analysis. Conclusion The process developed had several adventages of facile reaction conditions, convenient workup and high yield.

ZHOU Ting, YAO Jian-Zhong, ZHANG Dong-Wei, LIU Hong-Ming, SHENG Chun-Quan, MIAO Zhen-Yuan, ZHANG Wan-Nian. Synthesis of 4'-alkoxy-1,1'-bisphenyl-4-carboxylic acid lipotripeptides[J]. Journal of Pharmaceutical Practice and Service, 2011, 29(1): 17-20.
Citation: ZHOU Ting, YAO Jian-Zhong, ZHANG Dong-Wei, LIU Hong-Ming, SHENG Chun-Quan, MIAO Zhen-Yuan, ZHANG Wan-Nian. Synthesis of 4'-alkoxy-1,1'-bisphenyl-4-carboxylic acid lipotripeptides[J]. Journal of Pharmaceutical Practice and Service, 2011, 29(1): 17-20.
shu

    HTML

Reference (4)

Catalog

    版权所有：《药学实践与服务》编辑委员会

    Supervisor & Sponsors: Address: No 325 Guohe Road, ShanghaiPost Code: 200433

    Tel: （021）81871324,81871397 E-mail: yxsjzzs@163.com

    网站备案号 沪ICP备05003363号-1

    Supported by: Beijing Renhe Information Technology Co., Ltd.  

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return