5α-cholestan-3β-yl aminoethanoate | 16789-71-2

• 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: 5α-cholestan-3β-yl aminoethanoate
• 英文别名: Cholestanolglycinester
• CAS: 16789-71-2
• 化学式: C₂₉H₅₁NO₂
• 分子量: 445.729
• InChiKey: JHBVNVRTTWMKCV-DVNBGNEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  52.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5α-cholestan-3β-yl aminoethanoate 在 甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 4-(2-carboxyethyl)-4-[3-(5α-cholestan-3β-yloxycarbonylmethyl)ureido]heptanedioic acid
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of water-soluble, dendritic derivatives of epimeric 5α-cholestan-3-amines and 5α-cholestan-3-yl aminoethanoates

  摘要：

  To examine the effect of negatively charged steroidal amphiphiles on antimicrobial activity, two pairs of epimeric, dendritic tricarboxylato amphiphiles -4-(2-carboxyethyl)-4-[3-(5 alpha-cholestan-3-yl)ureido]heptanedioic acid (1) and 4-(2-carboxyethyl)-4-[3-(5 alpha-cholestan-3-yloxycarbonylmethyl)ureido]heptanedioic acid (2) - were synthesized. Abroad antimicrobial screen of 11 microbes revealed that these amphiphiles only showed good activity against a methicillin -resistant isolate of Staphylococcus aureus (MRSA) and modest activity against an unrelated strain of S aureus The best activity a minimal inhibitory concentration (MIC) of 27 mu M, was found for the 3 beta epimer of 1 against MRSA. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.04.001
• 作为产物：
  描述：

  3β-胆甾烷醇 在 4-二甲氨基吡啶 、 sodium azide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 36.0h， 生成 5α-cholestan-3β-yl aminoethanoate
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of water-soluble, dendritic derivatives of epimeric 5α-cholestan-3-amines and 5α-cholestan-3-yl aminoethanoates

  摘要：

  To examine the effect of negatively charged steroidal amphiphiles on antimicrobial activity, two pairs of epimeric, dendritic tricarboxylato amphiphiles -4-(2-carboxyethyl)-4-[3-(5 alpha-cholestan-3-yl)ureido]heptanedioic acid (1) and 4-(2-carboxyethyl)-4-[3-(5 alpha-cholestan-3-yloxycarbonylmethyl)ureido]heptanedioic acid (2) - were synthesized. Abroad antimicrobial screen of 11 microbes revealed that these amphiphiles only showed good activity against a methicillin -resistant isolate of Staphylococcus aureus (MRSA) and modest activity against an unrelated strain of S aureus The best activity a minimal inhibitory concentration (MIC) of 27 mu M, was found for the 3 beta epimer of 1 against MRSA. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.04.001

文献信息

• Cholestanol Esters of Amino Acids
  作者：Yoshio Matsumoto、Michiko Shirai、Michio Minagawa

  DOI：10.1246/bcsj.40.1650

  日期：1967.7

  The cholestanol (5α-cholestan-3β-ol) esters of amino acids were synthesized with an interest for their possible biochemical activities. The cholestanol esters of glycine, l-alanine, β-alanine, l-leucine and l-aspartic acid were synthesized by a direct fusion of the two components under the passing of hydrogen chloride through the reactants. That of glutamic acid was prepared by using quinoline hydrochloride as a solvent. From the condensation product of aspartic acid and cholestanol, mono- and di-ester were isolated. The monocholestanol ester of aspartic acid was also synthesized by the Gabriel process.

  为了研究氨基酸的生化活性，我们合成了氨基酸的胆甾醇（5α-胆甾烷-3β-醇）酯。甘氨酸、l-丙氨酸、β-丙氨酸、l-亮氨酸和 l-天门冬氨酸的胆甾醇酯是在氯化氢通过反应物的情况下，通过两种成分的直接融合合成的。谷氨酸是以盐酸喹啉为溶剂制备的。从天冬氨酸和胆甾醇的缩合产物中分离出了单酯和双酯。天门冬氨酸的单胆甾醇酯也是通过加布里埃尔工艺合成的。