去甲胆酸 | 60696-62-0

• 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
• 中文名称: 去甲胆酸
• 英文名称: 24-norcholic acid
• 英文别名: norcholic acid；3α,7α,12α-trihydroxy-24-nor-5β-cholanoic acid-(23)；3α,7α,12α-Trihydroxy-24-nor-5β-cholansaeure-(23)；23-nor-5β-cholanic acid-3α,7α,12α-triol；(3R)-3-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]butanoic acid
• CAS: 60696-62-0
• 化学式: C₂₃H₃₈O₅
• 分子量: 394.552
• InChiKey: SHUYNJFEXPRUGR-RTCCEZQESA-N

物化性质

• 熔点：
  183.5 °C
• 沸点：
  574.5±50.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO：微溶，甲醇：微溶

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  去甲胆酸 在 盐酸 作用下， 生成 23,24-dinorcholic acid
  参考文献：
  名称：

  Abbau derCholsäurezu 3,7,12-Trioxy-pregnan-20-on

  摘要：

  Der Abbau liefert aus 100克Cholsäuresowohlüberdie Dimethyl-wieüberdie二苯基-卡宾诺等 40克Nor-cholsäure，约克。10克Bis-nor-cholsäure和aus dieer ca. 1,5克三乙酰氧基-孕烷。（不干胶标签上的碱就好了，从0.5到0.8克的达芬·利弗恩就可以了。）（作者：déftesich noch etwas verbessern lassen und 0,5-0,8 g davon liefern。）

  DOI：

  10.1002/hlca.19370200102
• 作为产物：
  描述：

  胆酸甲酯 生成 去甲胆酸
  参考文献：
  名称：

  Bile acids. LII. The synthesis of 24-nor-5α-cholic acid and its 3β-isomer

  摘要：

  To aid in the identification of trihydroxy acidic metabolite(s) derived from beta-sitosterol, 3alpha,7alpha,12alpha-trihydroxy-24-nor-5beta-cholan-23-oic acid was prepared and its methyl ester was treated with Raney nickel in boiling p-cymene to provide methyl 3-oxo-7alpha,12alpha-dihydroxy-24-nor-5alpha-cholanate, 3-oxo-7alpha,12alpha-dihydroxy-24-nor-5beta-cholante and 3-oxo-7alpha,12alpha-dihydroxy-24-norchol-4-enoate. The latter compound was synthesized from the 3-oxo-5beta-derivative with SeO2 to provide a product with identical properties. Catalytic reduction of either saturated 3-oxo-derivative provided the appropriate 3,7,12-triols isomeric at C-3. Results from gas liquid and partition chromatography, mass spectrometry, and otherr physical properties of the acids, their methyl esters and other derivatives are compatible with the assigned structures.

  DOI：

  10.1016/0039-128x(76)90007-6

文献信息

• A New Generation of “Cholaphanes”:  Steroid-Derived Macrocyclic Hosts with Enhanced Solubility and Controlled Flexibility
  作者：Khadga M. Bhattarai、Anthony P. Davis、Justin J. Perry、Christopher J. Walter、Stephan Menzer、David J. Williams

  DOI：10.1021/jo971272w

  日期：1997.11.1

  such as carbohydrates in nonpolar media. New features are the externally directed alkyl chains, promoting solubility in organic solvents, and (in the case of 3b/c) reduced conformational freedom resulting from truncation of the steroidal side-chain. In particular, modeling shows that the smallest macrocycle 3c possesses very little flexibility, preferring an open conformation which is also revealed in

  大环“胆甾烷” 3a-c由廉价的类固醇胆酸合成。像早期的亲戚一样，它们的特征是带有向内羟基的大量空腔，适用于在非极性介质中结合极性分子，例如碳水化合物。新功能是外部定向的烷基链，提高了在有机溶剂中的溶解度，并且（在3b / c的情况下）由于类固醇侧链的截断而降低了构象自由度。特别地，建模显示最小的大环3c具有非常小的柔性，优选开放构象，其也在其五水合物的X射线晶体结构中揭示。NMR研究表明，所有三个胆cho与CDCl（3）中的辛基β-D-葡萄糖苷形成1：1配合物，K（a）= 600-1560 M（-）（1）。胆甾烷3b / c被证明能够从水溶液中提取甲基β-D-葡萄糖苷到CHCl（3）中。对于3c，也证明了甲基β-D-葡萄糖苷通过氯仿屏障的转运。
• A new chiral synthesis of bullfrog bile sterol 5β-ranol
  作者：Don W. Harney、Theodore A. Macrides

  DOI：10.1039/a607850h

  日期：——

  (24R)-27-Nor-5β-cholestane-3α,7α ,12α,24,26-pentol (5β-ranol) has been synthesised by the Wittig olefinic coupling of a steroidal module and a side-chain module followed by reduction and deprotection. The steroidal module is derived from cholic acid by a one-carbon degradation of the side chain to produce norcholic acid followed by the loss of a second carbon in an iododecarboxylation and then synthesis of the triphenylphosphonium iodide. The side-chain module is derived from (S)-(-)-butane-1,2,4-triol by benzylidene protection of the 2,4-diol followed by Swern oxidation to the aldehyde. This general synthetic scheme could be used to produce a range of bile sterols with the (24R)-hydroxy moiety which may have significant hepatoprotective activity against liver damage induced by free radicals or reactive metabolites.

  (24R)-27-去甲-5δ-胆甾烷-3δ±,7δ±,12δ±,24,26-戊醇（5δ²-ranol）是通过一个甾体模块和一个侧链模块的维蒂希烯烃偶联，然后进行还原和脱保护而合成的。甾体模块来自胆酸，通过侧链的一碳降解生成去甲胆酸，然后在碘羧化过程中失去第二个碳，最后合成碘化三苯基膦。侧链模块来自(S)-(-)-丁烷-1,2,4-三醇，通过对 2,4-二醇进行亚苄基保护，然后通过斯韦尔恩氧化反应生成醛。 这种通用合成方案可用于生产一系列具有 (24R)- 羟基分子的胆固醇，这些胆固醇可能对自由基或活性代谢物引起的肝损伤具有显著的保肝活性。
• A convenient synthesis of dinorbile acids:
  作者：Ashok K. Batta、Subhash C. Datta、G.Stephen Tint、David S. Alberts、David L. Earnest、Gerald Salen

  DOI：10.1016/s0039-128x(99)00064-1

  日期：1999.11

  dinorbile acids (23,24-dinor-5beta-cholan-22-oic acids, pregnane-20-carboxylic acids) in fair to good yields from norbile acid nitriles in one step by oxidative hydrolysis with oxygen in the presence of potassium-t-butoxide. The method results in stepwise overall removal of two carbon atoms in bile acid side chains in two steps. Dinorbile acids corresponding to several common bile acids have been prepared

  我们报告了一种简便的方法，可通过氧化水解与一步法从nor酸腈中以合理至良好的产率合成双壬酸（23,24-dinor-5beta-cholan-22-oic酸，pregnane-20-羧酸）叔丁醇钾存在下的氧气。该方法分两步逐步除去胆汁酸侧链中的两个碳原子。已经制备了对应于几种常见胆汁酸的双丁诺酸，并通过光谱法确认了它们的结构。这种简单的合成双降nor酸的方法可能有助于其代谢研究。
• Syntheses of 22- and 23-hydroxylated bile alcohols.
  作者：TAIJU KURAMOTO、NAOKO MATSUMOTO、TAKAHIKO HOSHITA

  DOI：10.1248/cpb.26.2788

  日期：——

  The syntheses of four new bile alcohols, 5β-cholestane-3α, 7α, 12α, 22α-tetrol, 5β-cholestane-3α, 7α, 12α, 22β-tetrol, 5β-cholestane-3α, 7α, 12α, 23α-tetrol, and 5β-cholestane-3α, 7α, 12α, 23β-tetrol, were described. The 22-hydroxy compounds were prepared from bisnorcholyl aldehyde by the Grignard reaction with 3-methylbutylmagnesium chloride. The 23-hydroxy compounds were prepared from norcholic acid by the condensation with diisobutylcadmium and the subsequent lithium aluminum hydride reduction of the resulting 3α, 7α, 12α-trihydroxy-5β-cholestan-23-one. One of the synthetic tetrols, 5β-cholestane-3α, 7α, 12α, 23β-tetrol was identical with a bile alcohol isolated from a patient with cerebrotendinous xanthomatosis.

  介绍了四种新胆汁醇的合成：5β-胆甾烷-3α、7α、12α、22α-四醇、5β-胆甾烷-3α、7α、12α、22β-四醇、5β-胆甾烷-3α、7α、12α、23α-四醇和 5β-胆甾烷-3α、7α、12α、23β-四醇。22- 羟基化合物是由双正胆醛与 3-甲基丁基氯化镁通过格氏反应制备的。23- 羟基化合物是以去甲胆酸为原料，通过与二异丁基镉缩合，然后用氢化铝锂还原生成 3α，7α，12α-三羟基-5β-胆甾烷-23-酮制备的。其中一种合成四醇，即 5β-胆甾烷-3α，7α，12α，23β-四醇，与一种从脑黄疽患者体内分离出的胆汁醇相同。
• [EN] COMPOUND HAVING ANTISPORULANT ACTIVITY AND PHARMACEUTICAL COMPOSITION THEREOF<br/>[FR] COMPOSÉ PRÉSENTANT UNE ACTIVITÉ D'ANTISPORULANT ET COMPOSITION PHARMACEUTIQUE DE CELUI-CI<br/>[ZH] 一种具有抗芽孢活性的化合物及其药用组合物
  申请人：CHENGDU BIOBEL COMPANY LTD

  公开号：WO2021147123A1

  公开（公告）日：2021-07-29

  本发明提供了一种具有抗芽孢活性的化合物及其药用组合物，具体提供了式（I）所示的化合物、或其盐、或其立体异构体。该化合物能够有效抑制艰难梭菌芽孢的萌发，具有显著的抑菌活性，在制备预防和/或治疗艰难梭菌感染性疾病、艰难梭菌感染性疾病的复发、或艰难梭菌感染性疾病并发症的药物中具有非常好的应用前景。