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Volume 29 Issue 1
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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.
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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.
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