methyl (4R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-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]pentanoate | 1092107-33-9

• 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: methyl (4R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-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]pentanoate
• CAS: 1092107-33-9
• 化学式: C₄₂H₇₁N₅O₁₀
• 分子量: 806.053
• InChiKey: HVDNBYQPTTUVJD-SIUIXZIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  57
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  222
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (4R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-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]pentanoate 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以94%的产率得到methyl (4R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[3-[3-[3-(3-aminopropanoylamino)propanoylamino]propanoylamino]propanoylamino]-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
  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
• 作为产物：
  描述：

  (3β,5β,7α,12α)-3-amino-7,12-dihydroxycholan-24-oic acid methyl ester 、 Boc-β-Ala4-OH 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到methyl (4R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-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]pentanoate
  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

文献信息

• Synthesis of chimeric tetrapeptide-linked cholic acid derivatives: Impending synergistic agents
  作者：Sudhir N. Bavikar、Deepak B. Salunke、Braja G. Hazra、Vandana S. Pore、Robert H. Dodd、Josiane Thierry、Fazal Shirazi、Mukund V. Deshpande、Sreenath Kadreppa、Samit Chattopadhyay

  DOI：10.1016/j.bmcl.2008.09.013

  日期：2008.10

  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.