3α-acetoxycholan-24-oyl chloride | 57365-35-2

• 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-acetoxycholan-24-oyl chloride
• 英文别名: (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-acetoxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl cloride；[(3R,5R,8R,9S,10S,13R,14S,17R)-17-[(2R)-5-chloro-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 57365-35-2
• 化学式: C₂₆H₄₁ClO₃
• 分子量: 437.063
• InChiKey: HKMJAADOZCUTCP-HCTDMSSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3α-acetoxycholan-24-oyl chloride 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 9-[2-[[4-(3α,7β-bis(acetyloxy)-5β-cholan-24-oyl)-1-piperazinyl]carbonyl]phenyl]-3,6-bis(diethylamino)xanthylium chloride
  参考文献：
  名称：

  Converting bile acids into mitocans

  摘要：

  DOI：

  10.1016/j.steroids.2022.109148
• 作为产物：
  描述：

  石胆酸 在 4-二甲氨基吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 3α-acetoxycholan-24-oyl chloride
  参考文献：
  名称：

  三氟甲基苯甲酸酯 (TFBz)：多功能三氟甲氧基化试剂

  摘要：

  苯甲酸三氟甲酯 (TFBz) 被开发为一种新的货架稳定的三氟甲氧基化试剂，它可以很容易地从廉价的原料中制备，使用 KF 作为唯一的氟源。芳烃的三氟甲氧基化-卤化、烷基（伪）卤化物的亲核取代、与芳基锡烷的交叉偶联和烯烃的不对称双官能化证明了 TFBz 的合成效力。在冠醚络合的钾阳离子的帮助下，芳炔的前所未有的三氟甲氧基化-卤化在室温下顺利进行，这显着稳定了衍生自 TFBz 的三氟甲氧基阴离子。

  DOI：

  10.1021/jacs.8b04000

文献信息

• Synthesis and Anticancer Activity of Hybrid Molecules Based on Lithocholic and (5Z,9Z)-Tetradeca-5,9-dienedioic Acids Linked via Mono(di,tri,tetra)ethylene Glycol and α,ω-Diaminoalkane Units
  作者：Vladimir A. D’yakonov、Regina A. Tuktarova、Lilya U. Dzhemileva、Svetlana R. Ishmukhametova、Usein M. Dzhemilev

  DOI：10.3390/ph14020084

  日期：——

  For the first time, hybrid molecules were synthesized on the basis of lithocholic and (5Z,9Z)-1,14-tetradeca-5,9-dienedicarboxylic acids, obtained in two stages using the homo-cyclomagnesiation reaction of 2-(hepta-5,6-diene-1-yloxy)tetrahydro-2H-pyran at the key stage. The resulting hybrid molecules containing 5Z,9Z-dienoic acids are of interest as novel synthetic biologically active precursors to create modern drugs for the treatment of human oncological diseases. The synthesized hybrid molecules were found to exhibit extremely high in vitro inhibitory activity against human topoisomerase I, which is 2–4 times higher than that of camptothecin, a known topoisomerase I inhibitor. Using flow cytometry and fluorescence microscopy, it was first shown that these new molecules are efficient apoptosis inducers in HeLa, U937, Jurkat, K562, and Hek293 cell cultures. In addition, the results of investigations into the effect of the synthesized acids on mitochondria and studies of possible DNA damage in Jurkat tumor cells are also presented.

  首次，基于麻黄酸和(5Z,9Z)-1,14-十四碳-5,9-二烯二羧酸，在两个阶段使用2-(庚-5,6-二烯-1-氧基)四氢-2H-吡喃的同环合镁反应合成了杂化分子。含有5Z,9Z-二烯酸的这些杂化分子作为新型合成生物活性前体，对于开发治疗人类肿瘤疾病的现代药物具有重要意义。合成的杂化分子显示出极高的体外抑制人类拓扑异构酶I活性，比已知的拓扑异构酶I抑制剂喜树碱高2-4倍。首次利用流式细胞术和荧光显微镜观察到这些新分子在HeLa、U937、Jurkat、K562和Hek293细胞培养中是有效的凋亡诱导剂。此外，还介绍了对合成酸对线粒体的影响以及对Jurkat肿瘤细胞可能的DNA损伤研究的结果。
• Synthesis of 24-(Piperidin-1-yl, Morpholin-4-yl and 4-Methylpiperazin-1-yl)-5β-cholan-3α-ols and Four Hydroxylated 23-(4,5-Dihydroimidazol-2-yl)-24-nor-5β-cholanes
  作者：Thi Thu Huong Nguyen、Jiří Protiva、Eva Klinotová、Jiří Urban、Miroslav Protiva

  DOI：10.1135/cccc19970471

  日期：——

  Lithocholic (1a), chenodeoxycholic (1b), deoxycholic (1c) and cholic acid (1d) were used for the synthesis of the title compouds. Reactions of O-acetyllithocholic acid chloride with piperidine, morpholine and 1-methylpiperazine gave the corresponding amides 2a-2c which were reduced with lithium aluminium hydride to 24-(piperidin-1-yl)-5β-cholan-3α-ol (3a) and analogues 3b and 3c. Heating of the acids 1a-1d with ethylenediamine monotosylate afforded 23-(4,5-dihydroimidazol-2-yl)-24-nor-5β-cholan-3α-ol (4a) and analogues 4b-4d. Compound 4a was similarly obtained from 3α-acetoxy-24-nor-5β-cholane-23-carbonitrile. Identity of the products was corroborated by spectral characterization. Some of the products (in the form of salts) were tested for cancerostatic and antimicrobial activities in vitro with partially promising results.

  石胆酸（1a），陈胆酸（1b），去氧胆酸（1c）和胆酸（1d）被用于合成标题化合物。将O-乙酰石胆酸氯化物与哌啶，吗啉和1-甲基哌嗪反应，得到相应的酰胺2a-2c，然后用氢化铝锂还原为24-(哌啶-1-基)-5β-胆烷-3α-醇（3a）及类似物3b和3c。将酸1a-1d与乙二胺单对甲苯磺酸酯加热，得到23-(4,5-二氢咪唑-2-基)-24-去-5β-胆烷-3α-醇（4a）及类似物4b-4d。化合物4a也可以从3α-乙酰氧基-24-去-5β-胆烷-23-碳腈中类似地获得。通过光谱表征证实了产物的身份。其中一些产物（以盐的形式）经过体外测试，显示出部分有希望的抗癌和抗微生物活性。
• Synthesis of Several Hydroxylated 23-(Benzimidazol-2-yl-, Benzoxazol-2-yl and Benzothiazol-2-yl)norcholanes and Some Related Compounds
  作者：Thi Thu Huong Nguyen、Jiří Urban、Eva Klinotová、Jan Sejbal、Jiří Protiva、Pavel Drašar、Miroslav Protiva

  DOI：10.1135/cccc19950257

  日期：——

  The bile acids Ia - Id (lithocholic, chenodeoxycholic, deoxycholic, cholic) and their derivatives (O-acetylated acids and O-acetylated acid chlorides) reacted under various conditions with 1,2-diaminobenzene, 2-aminophenol and 2-aminothiophenol and afforded the title benzimidazoles II and VII, benzoxazoles V and benzothiazoles VI. Alkylation of the benzimidazole derivative IIa with 2-dimethylaminoethyl chloride resulted in 3α-hydroxy-23-[1-(2-dimethylaminoethyl)ben zimidazol-2-yl]- norcholane (IVa). The use of 1,2-diamino-4-methylbenzene enabled the preparation of 3α-acetoxy-23-[5(6)-methylbenzimidazol-2-y l]norcholane (VIII). Reactions of the 3α-hydroxy compounds IVa, Va and VIa with succinic anhydride resulted in the hemisuccinates IVi - VIi. The boric acid mediated condensation of O-acetyllithocholic acid (Ie) with 3,4-diaminopyridine gave compound X which was transformed to 3α-acetoxy-23-[1H-imidazo(4,5- c)pyridin-2-yl]norcholane (IX). The structure of the products was corroborated by the mass, IR, ¹H NMR and ¹³C NMR spectra. Some of the compounds were tested for antileukemic and for the anti-HIV activity in vitro.

  胆汁酸Ia - Id（石胆酸、烯二氧胆酸、去氧胆酸、胆酸）及其衍生物（O-乙酰化酸和O-乙酰化酸氯化物）在不同条件下与1,2-二氨基苯、2-氨基苯酚和2-氨基噻吩反应，得到了标题苯并咪唑II和VII，苯并噁唑V和苯并噻唑VI。苯并咪唑衍生物IIa与2-二甲基氨基乙基氯化物烷基化，得到3α-羟基-23-[1-(2-二甲基氨基乙基)苯并咪唑-2-基]-诺胆烷（IVa）。使用1,2-二氨基-4-甲基苯使得制备3α-乙酰氧基-23-[5(6)-甲基苯并咪唑-2-基]诺胆烷（VIII）。3α-羟基化合物IVa，Va和VIa与琥珀酸酐反应，得到半琥珀酸酯IVi - VIi。硼酸介导的O-乙酰化石胆酸（Ie）与3,4-二氨基吡啶的缩合反应产生化合物X，转化为3α-乙酰氧基-23-[1H-咪唑(4,5-c)吡啶-2-基]诺胆烷（IX）。通过质谱、红外光谱、1H核磁共振和13C核磁共振谱证实了产物的结构。部分化合物在体外进行了抗白血病和抗HIV活性测试。
• Amphiphilic Porphinatoirons Having Steroid Groups and Their Oxygen-Adduct Formation in an Aqueous Medium
  作者：Eishun Tsuchida、Teruyuki Komatsu、Takeshi Babe、Taisaku Nakata、Hiroyuki Nishide、Hidenari Inoue

  DOI：10.1246/bcsj.63.2323

  日期：1990.8

  Amphiphilic heme derivatives having four steroid groups (steroid-heme), 5,10,15,20-tetrakis[α,α,α,α-o-[2,2-dimethyl-8-(3α-hydroxycholan-24-oyloxy)octanamido]phenyl]porphinatoiron (1b) and 5,10,15,20-tetrakis[α,α,α,α-o-(3-acetoxycholan-24-oylamino)phenyl]porphinatoiron (2b), were synthesized as a model of an oxygen carrier. They were efficiently embedded in the bilayer of a phospholipid liposome based on their high compatibility with the lipid. The oxygen-binding ability of 1b was compared with those of hemoglobin (Hb) and myoglobin (Mb). The dioxygen adduct of 1b was also characterized by Mössbauer and infrared spectroscopy.

  具有四个类固醇基团的两亲血红素衍生物（类固醇血红素），5,10,15,20-四[α,α,α,α-o-[2,2-二甲基-8-(3α-羟基胆烷-24-酰氧基)辛酰氨基]苯基]卟吩藤铁（1b）和 5、10、15、20-四[α,α,α,α-o-(3-乙酰氧基胆烷-24-酰氨基)苯基]卟吩他铁(2b)，作为氧载体的模型。由于它们与脂质高度相容，因此能有效地嵌入磷脂脂质体的双分子层中。将 1b 的氧结合能力与血红蛋白（Hb）和肌红蛋白（Mb）进行了比较。1b 的二氧加合物也通过莫斯鲍尔和红外光谱进行了表征。
• Photoinduced Desaturation of Amides by Palladium Catalysis
  作者：Sen Yang、Huike Fan、Licheng Xie、Guangbin Dong、Ming Chen

  DOI：10.1021/acs.orglett.2c02594

  日期：2022.9.9

  their α,β-unsaturated counterparts is reported. The reaction does not require strong base/acid or sulfur/selenium and oxidant reagents and can be carried out at room temperature through a simple one-step operation. The protocol exhibits great scalability and functional group tolerance. The reaction mechanism has been investigated through deuterium labeling experiments, radical clock, radical capture

  报道了一种适用于将线性酰胺转化为其 α,β-不饱和对应物的光诱导钯催化去饱和方法。该反应不需要强碱/酸或硫/硒和氧化剂试剂，可通过简单的一步操作在室温下进行。该协议表现出极大的可扩展性和功能组耐受性。反应机理已通过氘标记实验、自由基时钟、自由基捕获和动力学研究进行了研究。机理研究表明涉及芳基/烷基钯自由基中间体的自由基途径。