3α,6α-diacetoxy-5β-cholan-24-oic acid | 7766-07-6

• 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,6α-diacetoxy-5β-cholan-24-oic acid
• 英文别名: (4R)-4-[(3R,5R,6S,8S,9S,10R,13R,14S,17R)-3,6-diacetyloxy-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: 7766-07-6
• 化学式: C₂₈H₄₄O₆
• 分子量: 476.654
• InChiKey: XSDQBBRWWRPKEO-FXFOLUKLSA-N

物化性质

• 熔点：
  120-125 °C
• 沸点：
  563.1±25.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3α,6α-diacetoxy-5β-cholan-24-oic acid 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 碘苯二乙酸 、 copper(II) acetate monohydrate 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 反应 104.0h， 生成 3α-hydroxy-24-nor-5α-chol-22-en-6-one
  参考文献：
  名称：

  C-3 与苯甲酸酯基团缀合的新型油菜素类固醇 24-去甲胆烷型类似物的合成

  摘要：

  油菜素类固醇的代谢导致环骨架或侧烷基链的结构改变。 C-3 处的酯化和糖基化是最常见的代谢途径，有人认为共轭油菜素类固醇活性较低或无活性。通过这种方式，植物调节活性油菜素类固醇的含量。在这项工作中，描述了在C-3处与苯甲酸酯基团缀合、在芳环上带有电子供体和电子吸引剂取代基的油菜素类固醇24-正胆烷型类似物的合成。此外，使用水稻叶片倾斜测试（RLIT）评估它们的生长促进活性，并与油菜素内酯（用作阳性对照）和非缀合类似物所表现出的活性进行比较。结果表明，在最低测试浓度（10 -8 –10 -7 M）下，所有C-3处缀合的类似物均表现出与油菜素内酯相似或更高的活性，并且C-22处具有S构型的非对映异构体活性更高。与芸苔素内酯相比，增加浓度（10 -6 M）会降低类似物的生物活性。

  DOI：

  10.3390/molecules26041173
• 作为产物：
  描述：

  猪去氧胆酸 在 吡啶 、 乙酸酐 作用下， 生成 3α,6α-diacetoxy-5β-cholan-24-oic acid
  参考文献：
  名称：

  Windaus, Justus Liebigs Annalen der Chemie, 1926, vol. 447, p. 233,253

  摘要：

  DOI：

文献信息

• Biological Activity of Brassinosteroids - Direct Comparison of Known and New Analogs<i>in planta</i>
  作者：Sebastian Wendeborn、Mathilde Lachia、Pierre M. J. Jung、Jörg Leipner、David Brocklehurst、Alain De Mesmaeker、Katharina Gaus、Régis Mondière

  DOI：10.1002/hlca.201600305

  日期：2017.2

  presented. We describe in detail their synthetic preparation, which includes significant improvements of previously reported protocols as well as access to new analogs with functional modifications of the steroid skeleton and of the C(17)‐attached side chain. We report the biological potency of the prepared brassinosteroid analogs as plant hormones, which were carefully established in the French bean

  提出了对油菜素类固醇结构修饰的系统研究。我们详细描述了它们的合成制备方法，其中包括对先前报道的方案的重大改进，以及获得对类固醇骨架和C（17）连接的侧链进行功能性修饰的新类似物的途径。我们报告了制备的油菜素类固醇类似物作为植物激素的生物效价，它们是在菜豆第二节间伸长测定中仔细建立的，并根据最近报道的结构数据详细讨论了我们的观察结果，该数据详述了三聚体复合物中油菜素内酯与三聚体之间的分子相互作用。蛋白受体激酶BRASSINOSTEROID INSENSITIVE 1（BRI1）和体细胞胚发生受体激酶1（SERK1）。2 24-picastastasterone的O溶形式，我们讨论它们的物理性质，水解稳定性和生物活性。
• Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives
  作者：Santiago N. Chanquia、Erika Ripani、Alicia Baldessari、Guadalupe García Liñares

  DOI：10.1016/j.steroids.2018.09.004

  日期：2018.12

  HIGHLIGHTSHyodeoxycholic acid derivatives were prepared by an enzymatic approach in a regioselective way.The influence of several parameters was considered.The lipase catalysis was a very efficient procedure, especially considering the low amount used. ABSTRACT In this work we present an efficient, environmentally friendly approach to the synthesis of a series of hyodeoxycholic acid derivatives applying Biocatalysis

  亮点猪去氧胆酸衍生物是通过酶促方法以区域选择性的方式制备的。考虑了几个参数的影响。脂肪酶催化是一种非常有效的方法，特别是考虑到使用量低。摘要 在这项工作中，我们提出了一种高效、环保的方法来合成一系列应用生物催化的猪去氧胆酸衍生物。通过酶促策略以完全区域选择性的方式获得了 15 种乙酰基和酯衍生物，其中 12 种是新的，并且收率非常好。为了找到最佳反应条件，考虑了酶源、醇或酰化剂：底物比、酶：底物比、温度和反应溶剂等几个参数的影响。获得的优异结果使该程序非常有效，特别是考虑到所需的酶量很少。此外，该方法使用温和的反应条件并减少了对环境的影响，使生物催化成为获得这些胆汁酸衍生物的合适方法。
• Sterol synthesis. Synthesis of 3β-hydroxy-25,26,26,26,27,27,27-heptafluorocholest-5-en-7-one and its effects on HMG-CoA reductase activity in Chinese hamster ovary cells, on ACAT activity in rat jejunal microsomes, and serum cholesterol levels in rats
  作者：Jeffery N Carroll、Frederick D Pinkerton、Xiangdong Su、Nicolas Gerst、William K Wilson、George J Schroepfer

  DOI：10.1016/s0009-3084(98)00058-9

  日期：1998.8

  prepared a side-chain fluorinated analog, 3 beta-hydroxy-25,26,26,26,27,27,27-heptafluorocholest-5-en-7-one (VI), with the anticipation that the F7 substitution would block major metabolism of the 7-ketosterol, and thereby enhance its potential in vivo effects on serum cholesterol levels and other parameters. Chromium trioxide/dimethyl pyrazole oxidation of the acetate derivative of the previously described

  3β-Hydroxycholestest-5-en-7-one（I; 7-ketocholesterol）是在生物学和医学领域持续受到关注的羟甾醇。在本研究中，我们已经制备了侧链氟化类似物3 beta-hydroxy-25,26,26,26,27,27,27-heptafluorocholest-5-en-7-one（VI）， F7取代会阻断7-酮固醇​​的主要代谢，从而增强其对血清胆固醇水平和其他参数的潜在体内作用。先前描述的25,26,26,26,27,27,27,27-七氟胆甾基5-en-3β-醇的乙酸衍生物的三氧化铬/二甲基吡唑氧化（Swaminathan等，1993. J. Lipid Res参见，J.Med.Chem.34，1805-1823），然后温和的碱水解得到VI。VI对中国仓鼠卵巢（CHO-K1）细胞中3-羟基-3-甲基戊二酰辅酶A（HMG-CoA）还原酶活性的影响，空
• Photochemische Reaktionen. 92. Mitteilung [1]. Photochemistry of Imidazolides II. C2-C3 Cleavage of Carboxylic Acid Chains. A Convenient New Method for the Side-Chain Degradation of Bile Acids and of Lanosterol
  作者：Shigeo Iwasaki

  DOI：10.1002/hlca.19760590814

  日期：1976.12.15

  AbstractIrradiation of N‐stearoylimidazole (1) gave hexadec‐1‐ene (4) in 45% yield, whereas irradiation of N‐(4‐methylstearoyl)imidazole (13) possessing a tertiary hydrogen atom γ to the carbonyl group led to 2‐methylhexadec‐1‐ene (14) in 62% yield. These results are explained by a two‐stage process: acyl migration, followed by Norrish Type II eliminatior. The reaction has been utilized for the side chain degradation of bile acids and of lanosterol, in which the second stage of the reaction was shown to proceed in up to 70% yield.
• Structure-activity relationship of hybrids of Cinchona alkaloids and bile acids with in vitro antiplasmodial and antitrypanosomal activities
  作者：Aurélie Leverrier、Joanne Bero、Julián Cabrera、Michel Frédérich、Joëlle Quetin-Leclercq、Jorge A. Palermo

  DOI：10.1016/j.ejmech.2015.05.044

  日期：2015.7

  In this work, a series of hybrid compounds were tested as antiparasitic substances. These hybrids were prepared from bile acids and a series of antiparasitic Cinchona alkaloids by the formation of a covalent C-C bond via a decarboxylative Barton-Zard reaction between the two entities. The bile acids showed only weak antiparasitic properties, but all the hybrids exhibited high in vitro activities (IC50: 0.48-5.39 mu M) against Trypanosoma brucei. These hybrids were more active than their respective parent alkaloids (up to a 135 fold increase in activity), and displayed good selectivity indices. Aditionally, all these compounds inhibited the in vitro growth of a chloroquine-sensitive strain of Plasmodium falciparum (3D7: IC50: 36.1 nM to 8.72 mu M), and the most active hybrids had IC(50)s comparable to that of artemisinin (IC50: 36 nM). Some structure-activity relationships among the group of 48 hybrids are discussed. The increase in antiparasitic activity may be explained by an improvement in bioavailability, since the more lipophilic derivatives showed the lowest IC(50)s. (C) 2015 Elsevier Masson SAS. All rights reserved.