3α-hydroxy-12α-acetoxy-5β-cholan-24-oic acid | 76756-34-8

• 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-hydroxy-12α-acetoxy-5β-cholan-24-oic acid
• 英文别名: (4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-12-acetyloxy-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 76756-34-8
• 化学式: C₂₆H₄₂O₅
• 分子量: 434.616
• InChiKey: VLXRZJYCQLHQNC-UMHLJENVSA-N

物化性质

• 沸点：
  554.3±35.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3α-hydroxy-12α-acetoxy-5β-cholan-24-oic acid 在 吡啶 、 chromium(VI) oxide 、 氢氧化钾 、 氢溴酸 、 溴 、 溶剂黄146 作用下， 生成 12α-hydroxy-3-oxochol-4-en-24-oic acid
  参考文献：
  名称：

  Matsumoto, Journal of Biochemistry, 1944, vol. 36, p. 183,189

  摘要：

  DOI：
• 作为产物：
  描述：

  3α,12α-二乙酰氧基-5β-胆烷-24-酸甲酯 在 氢氧化钾 作用下， 生成 3α-hydroxy-12α-acetoxy-5β-cholan-24-oic acid
  参考文献：
  名称：

  Matsumoto, Journal of Biochemistry, 1944, vol. 36, p. 183,189

  摘要：

  DOI：

文献信息

• 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。
• Hard acid and soft nucleophile systems. 3. Dealkylation of esters with aluminum halide-thiol and aluminum halide-sulfide systems
  作者：Manabu Node、Kiyoharu Nishide、Midori Sai、Kaoru Fuji、Eiichi Fujita

  DOI：10.1021/jo00323a004

  日期：1981.5
• Experimental verifications on chemical carcinogenesis, a bifunctional alkylation between DNA interstrands
  作者：Qianhuan Dai、Qingrong Zhang、Lihui Wang、Shu Pei、Qing Wang、Bo Qu

  DOI：10.1007/bf02887177

  日期：2000.6

  It is evidenced by the filter elution method that two carcinogenic aromatic hydrocarbons, benzo[a]pyrene and dibenzo[a,h]anthracene, two carcinogenic metal salts, beryllium chloride and cadmium chloride, four carcinogenic aromatic amines, 2-aminofluorene, beta-naphthylamine, 4-aminobiphenyl and benzidine, can all induce DNA interstrand and DNA-protein cross-link in L-1210 culture. However, under the same condition, the corresponding non-carcinogenic compounds, including benzo[k]fluorancene, anthracene, magnesium chloride, zinc chloride, alpha-naphthylamine, 2-aminobiphenyl and m-toluidine, cannot produce any cross-link adducts. Atl these results are consistent with the di-region theory that carcinogens are bio-bifunctional alkylation agents. This method can also be used to discriminate carcinogens and non-carcinogens.
• Synthesis of Cyclocholates and Derivatives
  作者：Hongwu Gao、Jerry Ray Dias

  DOI：10.1080/00397919708004196

  日期：1997.3

  A synthesis of bile acid cyclooligomers by the Yamaguchi method is described. Cyclotrimerization is the principal reaction route for the cholic acid system, and cyclotetramerization is the principal reaction route for the 24-norcholic acid.
• Remarkable Structures of Cyclotri(deoxycholate) and Cyclotetra(24-norcholate) Acetate Esters
  作者：Jerry Ray Dias、Robert A. Pascal、Jason Morrill、Andrew J. Holder、Hongwu Gao、Charles Barnes

  DOI：10.1021/ja011797c

  日期：2002.5.1

  X-ray crystallographic determinations and AM1 calculations have defined the solid-state and gas-phase structures of cyclotri(deoxycholate) and cyclotetra(24-norcholate). The latter cyclotetramer is one of the largest open macrocycles ever subjected to crystallography.