3α-acetoxy-5β-cholan-24-oic acid ethyl ester | 6080-93-9

• 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: 3α-acetoxy-5β-cholan-24-oic acid ethyl ester
• 英文别名: ethyl lithocholate 3-acetate；ethyl 3α-acetoxy-5β-cholan-24-oate；3α-Acetoxy-5β-cholan-24-saeure-aethylester；3α-Acetoxy-5β-cholansaeure-(24)-aethylester；ethyl (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-acetyloxy-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
• CAS: 6080-93-9
• 化学式: C₂₈H₄₆O₄
• 分子量: 446.671
• InChiKey: NYONHSUZVUBOFW-GZNVBANASA-N

物化性质

• 熔点：
  94-96 °C
• 沸点：
  500.0±18.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  石胆酸 在 Candida antarctica lipase B 、 Lipozyme RM IM 作用下， 以 正己烷 为溶剂， 反应 120.0h， 生成 3α-acetoxy-5β-cholan-24-oic acid ethyl ester
  参考文献：
  名称：

  胆汁酸衍生物的酶促合成及其对克鲁氏锥虫的生物学评价。

  摘要：

  应用酶催化合成三种胆汁酸的衍生物，并评价其生物学活性作为原生动物克氏锥虫的生长抑制剂。通过脂肪酶催化的乙酰化，酯化和醇解反应，可以很好地获得优异的收率和高度的区域选择性，得到了十二种脱氧胆酸，鹅去氧胆酸和石胆酸的单，二乙酰基和酯衍生物，其中七个是新化合物。在其中，获得了乙酰化的酯产物，其中脂肪酶在一锅中催化了两个反应。研究了酶反应中各种反应参数的影响，如酶的来源，酰化剂/底物的比例，酶/底物的比例，溶剂和温度等。某些被评估的化合物显示出作为克氏锥虫生长抑制剂的显着活性，用鹅去氧胆酸乙酯3-乙酸盐和鹅去氧胆酸3,7-二乙酸盐获得最佳结果，显示出IC50：分别为8.6和22.8μM。此外，为了阐明胆汁酸在酶促反应中的行为，对一些衍生物进行了分子建模。酶促方法所显示的优点，例如温和的反应条件和较低的环境影响，使生物催化成为合成这些胆汁酸衍生物的方便方法，并可用作潜在的抗寄生虫剂。

  DOI：

  10.1016/j.bmc.2015.05.035

文献信息

• Farm-related Factors Influencing the Adoption of Short-rotation Willow Coppice Production Among Swedish Farmers
  作者：Anders Roos、Håkan Rosenqvist、Erik Ling、Bo Hektor

  DOI：10.1080/090647100750014385

  日期：2000.1

  The area of short-rotation willow coppice energy plantations on Swedish farmland increased quickly in the early 1990s because of subsidies for energy crop production, an increased CO2 tax on fossil fuel and an already existing biofuel market in the country. In this study farm-related determinants for the adoption of short-rotation willow coppice production among Swedish farmers are identified and estimated. A Tobit model is applied to cross-sectional data on Swedish farmers in 1995. The results show that the decision to plant willow and the areas planted depend positively on arable land area, forest land area, the area of other land types, leasing out of arable land and tractor ownership. Negative factors an pasture areal tenancy and animal production. Differences in willow growing between ownership types, age groups and geographical regions are also important. The policy implications of the results are discussed.
• Lithocholic acid and derivatives: Antibacterial activity
  作者：Patrícia G.G. do Nascimento、Telma L.G. Lemos、Macia C.S. Almeida、Juliana M.O. de Souza、Ayla M.C. Bizerra、Gilvandete M.P. Santiago、José G.M. da Costa、Henrique D.M. Coutinho

  DOI：10.1016/j.steroids.2015.07.007

  日期：2015.12

  In order to develop bioactive lithocholic acid derivatives, we prepared fifteen semi-synthetic compounds through modification at C-3 and/or C-24. The reactions showed yields ranging from 37% to 100%. The structures of all compounds obtained were identified on the basis of their spectral data (IR, MS, 1D- and 2D-NMR). The activity of lithocholic acid and derivatives was evaluated against the growth of Escherichia coli, Staphylococcus aureus, Bacillus cereus and Pseudomonas aeruginosa. The derivative 3 alpha-formyloxy-5 beta-cholan-24-oic acid (LA-06) showed the best activity, with MIC values of 0.0790 mM against E. coli (Ec 27) and B. cereus in both cases, and 0.0395 mM against S. aureus (ATCC 12692). Lithocholic acid and the derivatives with MIC <= 1.2 mM were evaluated on the susceptibility of some bacterial pathogens to the aminoglycoside antibiotics neomycin, amikacin and gentamicin was evaluated. There are no previously reported studies about these compounds as modifiers of the action of antibiotics or any other drugs. (C) 2015 Published by Elsevier Inc.
• Nahar, Lutfun; Turner, Alan B., Journal of Chemical Research, 2004, # 5, p. 329 - 332
  作者：Nahar, Lutfun、Turner, Alan B.

  DOI：——

  日期：——
• Enzymatic synthesis of bile acid derivatives and biological evaluation against Trypanosoma cruzi
  作者：Guadalupe García Liñares、M. Antonela Zígolo、Leandro Simonetti、Silvia A. Longhi、Alicia Baldessari

  DOI：10.1016/j.bmc.2015.05.035

  日期：2015.8

  22.8 μM, respectively. In addition, in order to shed light to bile acids behavior in enzymatic reactions, molecular modeling was applied to some derivatives. The advantages showed by the enzymatic methodology, such as mild reaction conditions and low environmental impact, make the biocatalysis a convenient way to synthesize these bile acid derivatives with application as potential antiparasitic agents

  应用酶催化合成三种胆汁酸的衍生物，并评价其生物学活性作为原生动物克氏锥虫的生长抑制剂。通过脂肪酶催化的乙酰化，酯化和醇解反应，可以很好地获得优异的收率和高度的区域选择性，得到了十二种脱氧胆酸，鹅去氧胆酸和石胆酸的单，二乙酰基和酯衍生物，其中七个是新化合物。在其中，获得了乙酰化的酯产物，其中脂肪酶在一锅中催化了两个反应。研究了酶反应中各种反应参数的影响，如酶的来源，酰化剂/底物的比例，酶/底物的比例，溶剂和温度等。某些被评估的化合物显示出作为克氏锥虫生长抑制剂的显着活性，用鹅去氧胆酸乙酯3-乙酸盐和鹅去氧胆酸3,7-二乙酸盐获得最佳结果，显示出IC50：分别为8.6和22.8μM。此外，为了阐明胆汁酸在酶促反应中的行为，对一些衍生物进行了分子建模。酶促方法所显示的优点，例如温和的反应条件和较低的环境影响，使生物催化成为合成这些胆汁酸衍生物的方便方法，并可用作潜在的抗寄生虫剂。