methyl 3α-acetyloxy-12-oxime-5β-cholan-24-oate | 403607-30-7

• 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: methyl 3α-acetyloxy-12-oxime-5β-cholan-24-oate
• 英文别名: methyl 3α-acetoxy-12-oximino-5β-cholan-24-oate
• CAS: 403607-30-7
• 化学式: C₂₇H₄₃NO₅
• 分子量: 461.642
• InChiKey: AKXQNJLGPOJSFB-KXKMLXBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  85.19
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3α-acetyloxy-12-oxime-5β-cholan-24-oate 在 platinum(IV) oxide 4-二甲氨基吡啶 、 lithium hydroxide 、 三正丁胺 、 偶氮二异丁腈 、 氢气 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 氯仿 、 溶剂黄146 为溶剂， 反应 203.17h， 生成 N-methyl-N'-[(3-trimethoxysilylpropylthio)propyl]-3α-(3,5-dichlorophenyl)carbamoyloxy-12α-N-(3,5-dimethylbenzoyl)amino-5β-cholan-24-amide
  参考文献：
  名称：

  Synthesis of deoxycholic-derived chiral stationary phases possessing both arylcarbamate and arylamide moieties: evaluation of their chiral discrimination properties in the HPLC resolution of racemic compounds

  摘要：

  Two families of chiral selectors derived from deoxycholic acid, possessing both an arylamide and an arylcarbamate group on the cholestanic backbone were synthesized and covalently bonded to silica gel to afford new chiral stationary phases (CSPs A1-D1 and A2-D2) for the HPLC resolution of racemic compounds. The chromatographic data concerning the resolution of selected racemic compounds on CSPs A1-D1 and A2-D2 were compared with those obtained using analogous CSPs possessing only arylcarbamate groups on the cholestanic system (CSPs A-D). This has allowed its to establish that the resolution capability of CSPs A1-D1 and A2-D2 depends not only on the position of the arylamide group on the cholestanic backbone, but also on the electronic characteristics of the aromatic substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00490-6
• 作为产物：
  描述：

  去氧胆酸 在 potassium dichromate 、 盐酸羟胺 、 sodium acetate 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 24.5h， 生成 methyl 3α-acetyloxy-12-oxime-5β-cholan-24-oate
  参考文献：
  名称：

  Synthesis of deoxycholic-derived chiral stationary phases possessing both arylcarbamate and arylamide moieties: evaluation of their chiral discrimination properties in the HPLC resolution of racemic compounds

  摘要：

  Two families of chiral selectors derived from deoxycholic acid, possessing both an arylamide and an arylcarbamate group on the cholestanic backbone were synthesized and covalently bonded to silica gel to afford new chiral stationary phases (CSPs A1-D1 and A2-D2) for the HPLC resolution of racemic compounds. The chromatographic data concerning the resolution of selected racemic compounds on CSPs A1-D1 and A2-D2 were compared with those obtained using analogous CSPs possessing only arylcarbamate groups on the cholestanic system (CSPs A-D). This has allowed its to establish that the resolution capability of CSPs A1-D1 and A2-D2 depends not only on the position of the arylamide group on the cholestanic backbone, but also on the electronic characteristics of the aromatic substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00490-6

文献信息

• Synthesis of B- and C-ring-modified lithocholic acid analogues as potential sialyltransferase inhibitors
  作者：Hajjaj H.M. Abdu-Allah、Tzu Ting Chang、Wen-Shan Li

  DOI：10.1016/j.steroids.2016.04.013

  日期：2016.8

  (ST) novel analogues with modifications of the skeleton (7-9, 16-18 and 20) were designed and synthesized. Methyl 3alpha-acetoxy-7-oxo-cholanate (1), methyl 3alpha-acetoxy-12-oxo-cholanate (2) and methyl 3alpha,7alpha-diacetoxy-12-oxo-cholanate (3) were subjected to Baeyer-Villiger oxidation to provide homolactones (7-9) or to the Beckmann rearrangement of the corresponding oximes to give homolactams

  为了鉴定对抑制唾液酸转移酶（ST）至关重要的石胆酸（LCA）的结构特征，设计并合成了具有骨架修饰的新型类似物（7-9、16-18和20）。对3α-乙酰氧基-7-羟基胆酸甲酯（1），3α-乙酰氧基-12-羟基胆酸甲酯（2）和3α，7α-二乙酰氧基-12-羟基胆酸甲酯（3）进行Baeyer-Villiger氧化提供高内酯（7-9）或相应的肟的贝克曼重排，得到高内酰胺（16-18）。两种反应均在区域和立体选择性上进行。有效地合成了石胆酸（20）的B环同系物。在这些化合物中，发现7、9和16具有显着活性，对α-2,6-（N）-ST的选择性IC50值为3μM，比Lith-O-Asp低5倍。
• Synthesis and antiproliferative activity of C-homo-lactam derivatives of 7-deoxycholic acid
  作者：Yanmin Huang、Jianguo Cui、Sijing Chen、Chunfang Gan、Qiucui Yao、Qifu Lin

  DOI：10.1016/j.bmcl.2012.08.064

  日期：2013.4

  Using deoxycholic acid as starting materials, a series of 12a-aza-C-homo-12-one 7-deoxycholic acid derivatives were synthesized The antiproliferative activity of the synthesized compounds against some carcinoma cell lines was investigated. The results showed that some 12-oxy-12a-aza-C-homo-7-deoxycholic acid derivatives displayed distinct cytotoxicity to HeLa (human cervical carcinoma) and Tu 686 (laryngocarcinoma) tumor cell lines. In particular, the IC50 values of the compounds 6 and 7 against Tu 686 cells are 16.7 and 19.8 mu M/L respectively. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs. (C) 2012 Elsevier Ltd. All rights reserved.