tert-butyl N-[3-[[3-[[3-[[3-[[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-17-[(2R)-5-hydroxypentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino]-3-oxopropyl]amino]-3-oxopropyl]amino]-3-oxopropyl]amino]-3-oxopropyl]carbamate | 1092107-41-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: tert-butyl N-[3-[[3-[[3-[[3-[[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-17-[(2R)-5-hydroxypentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino]-3-oxopropyl]amino]-3-oxopropyl]amino]-3-oxopropyl]amino]-3-oxopropyl]carbamate
• CAS: 1092107-41-9
• 化学式: C₄₁H₇₁N₅O₉
• 分子量: 778.043
• InChiKey: BQJDKSYTZNBTJQ-YVOKFAGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  55
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  215
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  [(4R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7-acetyloxy-12-hydroxy-10,13-dimethyl-3-[3-[3-[3-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoylamino]propanoylamino]propanoylamino]propanoylamino]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentyl] acetate 在 lithium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以84%的产率得到tert-butyl N-[3-[[3-[[3-[[3-[[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-17-[(2R)-5-hydroxypentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino]-3-oxopropyl]amino]-3-oxopropyl]amino]-3-oxopropyl]amino]-3-oxopropyl]carbamate
  参考文献：
  名称：

  Synthesis of chimeric tetrapeptide-linked cholic acid derivatives: Impending synergistic agents

  摘要：

  Tetrapeptides derived from glycine and beta-alanine were hooked at the C-3 beta position of the modified cholic acid to realize novel linear tetrapeptide-linked cholic acid derivatives. All the synthesized compounds were tested against a wide variety of microorganisms (Gram-negative bacteria, Gram-positive bacteria and fungi) and their cytotoxicity was evaluated against human embryonic kidney (HEK293) and human mammary adenocarcinoma (MCF-7) cell lines. While relatively inactive by themselves, these compounds interact synergistically with antibiotics such as fluconazole and erythromycin to inhibit growth of fungi and bacteria, respectively, at 1-24 mu g/mL. The synergistic effect shown by our novel compounds is due to their inherent amphiphilicity. The fractional inhibitory concentrations reported are comparable to those reported for Polymyxin B derivatives. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.013