3-oxo-4-cholenic acid | 1452-29-5

• 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: 3-oxo-4-cholenic acid
• 英文别名: 3-oxo-chol-4-en-24-oic acid；3-oxochol-4-en-24-oic acid；4-dafachronic acid；3-Oxo-chol-4-en-24-saeure；3-Oxo-cholen-(4)-saeure-(24)；(4R)-4-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 1452-29-5
• 化学式: C₂₄H₃₆O₃
• 分子量: 372.548
• InChiKey: WCFIGQHNBJXROP-IHMUCKAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-oxo-4-cholenic acid 在 palladium on activated charcoal potassium permanganate 、 sodium periodate 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 氨 、 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 sodium cyanoborohydride 、 sodium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 乙二醇 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 5.0~180.0 ℃ 、4.14 MPa 条件下， 反应 390.67h， 生成 6-[(R)-4-((4aR,4bS,6aR,7R,9aS,9bS,11aR)-1,4a,6a-Trimethyl-hexadecahydro-indeno[5,4-f]quinolin-7-yl)-pentanoylamino]-hexanoic acid tert-butyl ester
  参考文献：
  名称：

  一类由4-氮杂-石胆酸衍生的半抗原，用于产生具有类固醇合酶功能的催化抗体。

  摘要：

  描述了衍生自相同的4-氮杂-甾族骨架的一类三个半抗原的合成。该序列以可商购的光学纯的卵石酸的环A的氧化裂解开始。在位置4处插入氮，然后在600 psi H2下将所得的富电子富烯烯内酰胺进行立体选择性氢化，产生的系统类似于睾丸激素5-α-还原酶抑制剂。在用氢化铝锂彻底还原该化合物后，在环A中建立N-氧化物键官能团之前，先连接了用于生物缀合的连接基。该官能团被认为是真正的过渡态模拟物，可引发电子反应。 2,3-环氧-角​​鲨烯衍生物的阳离子环化。此外，它也有望在诱饵和转换策略中引发酸性残留物。值得注意的是，从mCPBA氧化得到的两种N-氧化物差向异构体都可以通过柱色谱法以60 mg的规模进行分离，并以对映纯形式用于单独的免疫接种。通过与先前已表征和已发布的系统进行比较研究，进行了可靠的配置分配。通过用在β位带有氨氧化物氧的半抗原进行免疫而获得了催化抗体（HA8-25A10）。令人惊讶地，抑制研

  DOI：

  10.1016/s0968-0896(00)00036-5
• 作为产物：
  描述：

  石胆酸 在 jones reagent 、 溴 、 lithium carbonate 、 溶剂黄146 、 lithium bromide 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.67h， 生成 3-oxo-4-cholenic acid
  参考文献：
  名称：

  Synthesis of [3,4-¹³C₂]-Enriched Bile Salts as NMR Probes of Protein−Ligand Interactions

  摘要：

  Synthetic methodology that allows for incorporation of isotopic carbon at the C-3 and C-4 positions of bile salts is reported. Three [3,4-C-13(2)]-enriched bile salts were synthesized from either deoxycholic or lithocholic acid. The steroid 3alpha-OH group was oxidized and the A-ring was converted into the Delta(4)-3-ketone. The C-24 carboxylic acid was next converted into the carbonate group and selectively reduced to the alcohol in the presence of the A-ring enone. Following protection of the 24-OH group, the Delta(4)-3-ketone was converted into the A-ring enol lactone. Condensation of the enol lactone with [1,2-C-13(2)]-enriched acetyl chloride and subsequent Robinson annulation afforded a [3,4-C-13(2)]-enriched Delta(4)-3-ketone that was subsequently converted back into a 3alpha-hydroxy-5beta-reduced bile steroid. C-7 hydroxylation, when necessary, was achieved via conversion of the Delta(4)-3-ketone into the corresponding Delta(4,6)-dien-3-one, epoxidation of the Delta(6)- double bond, and hydrogenolysis/hydrogenation of the 5,6-epoxy enone system. The [3,4-C-13(2)]-enriched bile salts were subsequently complexed to human ileal bile acid binding protein (I-BABP), and H-1-C-13 HSQC spectra were recorded to show the utility of the compounds for investigating the interactions of bile acids with I-BABP.

  DOI：

  10.1021/jo0259109

文献信息

• Regio- and stereo-selective oxidation of steroids using 2,6-dichloropyridine N-oxide catalysed by ruthenium porphyrins
  作者：Tomoteru Shingaki、Keiko Miura、Tsunehiko Higuchi、Masaaki Hirobe、Tetsuo Nagano

  DOI：10.1039/a700096k

  日期：——

  Ruthenium porphyrins catalyse oxygen transfer from 2,6-dichloropyridine N-oxide to steroids with retention of configuration at the asymmetric centre, giving novel steroids.

  钌卟啉催化2,6-二氯吡啶 N-氧化物向甾体转移氧气，同时在不对称中心保持构型，生成新型甾体化合物。
• Synthesis of esters of bile acids and avermectin B1
  作者：E. I. Chernoburova、E. S. Polyukhova、M. A. Shchetinina、A. V. Kolobov、M. Kh. Dzhafarov、F. I. Vasilevich、I. V. Zavarzin

  DOI：10.1007/s11172-016-1685-4

  日期：2016.12

  Esters of bile acids and avermectin B1 were obtained for the first time by the reaction of avermectin B1 with bile acid anhydrides.

  阿维菌素B1与胆汁酸酐反应，首次得到胆汁酸与阿维菌素B1的酯。
• METHODS OF MAKING CHOLIC ACID DERIVATIVES AND STARTING MATERIALS THEREFOR
  申请人：Sandhill One, LLC

  公开号：US20220056070A1

  公开（公告）日：2022-02-24

  Methods of making cholic acid derivatives, particularly ursodeoxycholic acid, tauroursodeoxycholic acid, 7-ketolithocholic acid, obeticholic acid, their carboxylate salts and carboxylate esters, and starting materials and intermediates therefor.

  制备胆酸衍生物的方法，特别是优瑟酸、牛磺基优瑟酸、7-酮石胆酸、奥贝替酸，它们的羧酸盐和羧酸酯，以及相应的起始物和中间体。
• A process for the microbiological preparation of steroids; genetically modified microorganisms suitable therefor
  申请人：Rijksuniversiteit Groningen

  公开号：EP0375075A1

  公开（公告）日：1990-06-27

  The invention relates to a process for preparing steroids, in particular C-17 ketosteroids, by means of steroid side chain oxidation using genetically modified microorganisms, and to genetically modified microorganisms which are suitable therefor. According to the invention, said microorganisms are the result of a transfer of genetic material between two bacterial species, preferably from Actinomycetales to Pseudomonads.

  本发明涉及一种利用转基因微生物通过类固醇侧链氧化制备类固醇，特别是 C-17 酮类固醇的工艺，以及适用于该工艺的转基因微生物。根据本发明，所述微生物是两种细菌之间遗传物质转移的结果，最好是从放线菌到假单胞菌。
• Compound and method for the treatment and diagnosis of neurodegenerative conditions
  申请人：SWANSEA UNIVERSITY

  公开号：US10226475B2

  公开（公告）日：2019-03-12

  A reagent selected from cholestenoic acid or an inhibitor of an enzyme in the cholestenoic acid biosynthetic or metabolic pathway for use in the treatment of neurodegenerative conditions. In particular, the reagent is a cholestenoic acid of a particular form, such as 3β,7α-dihydroxycholest-5-en-26-oic (3β,7α-diHCA), not previously associated with neural tissue or CSF. Pharmaceutical compositions, methods of treatment or prevention of neurodegenerative conditions as well as diagnostic methods and novel biomarkers form further aspects of the invention.

  一种选自胆烯酸或胆烯酸生物合成或代谢途径中酶的抑制剂的试剂，用于治疗神经退行性疾病。特别是，该试剂是一种特殊形式的胆甾烯酸，如 3β,7α-二羟基胆甾烯-5-烯-26-酸（3β,7α-diHCA），以前与神经组织或 CSF 无关。本发明还包括药物组合物、治疗或预防神经退行性疾病的方法以及诊断方法和新型生物标记物。