N-[(3S,6S,9S,11R,15S,18S,25S,27R)-3-(3-aminopropyl)-11,27-dihydroxy-15-[(1R)-1-hydroxyethyl]-6-[2-(4-hydroxyphenyl)ethyl]-2,5,8,14,17,24-hexaoxo-1,4,7,13,16,23-hexazatricyclo[23.3.0.09,13]octacosan-18-yl]-4-[4-(4-pentoxyphenyl)phenyl]benzamide | 1345195-58-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(3S,6S,9S,11R,15S,18S,25S,27R)-3-(3-aminopropyl)-11,27-dihydroxy-15-[(1R)-1-hydroxyethyl]-6-[2-(4-hydroxyphenyl)ethyl]-2,5,8,14,17,24-hexaoxo-1,4,7,13,16,23-hexazatricyclo[23.3.0.09,13]octacosan-18-yl]-4-[4-(4-pentoxyphenyl)phenyl]benzamide
• CAS: 1345195-58-5
• 化学式: C₅₉H₇₆N₈O₁₂
• 分子量: 1089.3
• InChiKey: VYVUXUPRFSVHFC-SFHMAFBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  79
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  302
• 氢给体数：
  10
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  在 三异丙基硅烷 、 水 、 三氟乙酸 作用下， 反应 1.0h， 以20.4 mg的产率得到N-[(3S,6S,9S,11R,15S,18S,25S,27R)-3-(3-aminopropyl)-11,27-dihydroxy-15-[(1R)-1-hydroxyethyl]-6-[2-(4-hydroxyphenyl)ethyl]-2,5,8,14,17,24-hexaoxo-1,4,7,13,16,23-hexazatricyclo[23.3.0.09,13]octacosan-18-yl]-4-[4-(4-pentoxyphenyl)phenyl]benzamide
  参考文献：
  名称：

  Synthesis and evaluation of novel macrocyclic antifungal peptides

  摘要：

  Echinocandins are a novel class of macrocyclic antifungal peptides that act by inhibiting the beta-(1,3)-D-glucan synthase complex, which is not present in mammalian cells. Due to the large number of hydroxyl groups present in these complex macrocyclic lipopeptides, most structure-activity relationship studies have relied upon semisynthetic derivatives. In order to probe the influence of the cyclic peptide backbone on the antifungal activity we developed a successful strategy for the synthesis of novel echinocandins analogues by on-resin ring closing metathesis or disulfide formation. The specific minimum inhibitory activity of each mimic was determined against Candida albicans. Our results indicate that ring size is an important factor for antifungal activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.034