N-(3α-acetoxy-34-nor-5βH-cholane-23-carboxyl)-2-pyridinethione | 173776-80-2

• 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: N-(3α-acetoxy-34-nor-5βH-cholane-23-carboxyl)-2-pyridinethione
• 英文别名: (2-sulfanylidenepyridin-1-yl) (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-acetyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 173776-80-2
• 化学式: C₃₁H₄₅NO₄S
• 分子量: 527.769
• InChiKey: SRPWBVLPYUHGMV-HGONFWIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  87.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3α-acetoxy-34-nor-5βH-cholane-23-carboxyl)-2-pyridinethione 在 titanium(III) chloride 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 20.25h， 生成 5β-cholestane-3α,25-diol
  参考文献：
  名称：

  Barton, Derek H. R.; Boivin, Jean; Lelandais, Patrick, Journal of the Chemical Society. Perkin transactions I, 1989, p. 463 - 468

  摘要：

  DOI：
• 作为产物：
  描述：

  石胆酸 在 吡啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(3α-acetoxy-34-nor-5βH-cholane-23-carboxyl)-2-pyridinethione
  参考文献：
  名称：

  通过巴顿自由基脱羧和苯醌加成从胆汁酸合成甾体醌和氢醌。研究它们的细胞毒性和抗真菌活性

  摘要：

  通过巴顿脱羧反应制备了 12 种新的氢醌和醌（4a-c 至 7a-c）（4a-c 至 7a-c），这些化合物来自游离或过乙酰化胆汁酸，随后被苯醌捕获。所有新化合物均通过 2D NMR 技术完全表征，并筛选了抗真菌和细胞毒活性。其中一种新的氢醌 (7b) 对人胰腺导管癌细胞系 PANC1 显示出有希望的结果，具有与商业化疗药物阿霉素相似的细胞毒活性。

  DOI：

  10.1016/j.steroids.2011.09.012

文献信息

• The reaction of thionitrites with barton esters: a convenient free radical chain reaction for decarboxylative nitrosation
  作者：Pierre Girard、Nadine Guillot、William B. Motherwell、Robyn S. Hay-Motherwell、Pierre Potier

  DOI：10.1016/s0040-4020(98)01164-8

  日期：1999.3

  Tertiary thionitrite esters react with primary and secondary O-acyl derivatives of N-hydroxy-2-thiopyridone to give trans nitroso dimers as the principal products of a free radical chain reaction.

  叔硫亚硝酸酯与N-羟基-2-硫代吡啶酮的伯和仲O-酰基衍生物反应，生成反式亚硝基二聚体，作为自由基链反应的主要产物。
• Antiparasitic hybrids of Cinchona alkaloids and bile acids
  作者：Aurélie Leverrier、Joanne Bero、Michel Frédérich、Joëlle Quetin-Leclercq、Jorge Palermo

  DOI：10.1016/j.ejmech.2013.06.004

  日期：2013.8

  A series of 16 hybrids of Cinchona alkaloids and bile acids (4a-h, 5a-h) was prepared by means of a Barton-Zard decarboxylation reaction. Quinine, quinidine, cinchonine and cinchonidine were functionalized at position C-2 of the quinoline nucleus by radical attack of a norcholane substituent. The newly synthesized hybrids were evaluated in vitro for their antitrypanosomal, antileishmanial and antiplasmodial activities, along with their cytotoxicity against WI38, a normal human fibroblast cell line. Seven compounds (4d, 4f, 4h, 5b, 5d, 5f, 5h) showed promising trypanocidal activity with IC50 values in the same range as the commercial drug suramine. Moreover all the 16 hybrids showed antiplasmodial activity (IC50 <= 6 mu g/ml), particularly those containing a nor-chenodeoxycholane moiety (4b, 4d, 4f, 4h, 5b, 5d, 5f, 5h) with IC50 values comparable to those of the natural alkaloids, and selectivity indices in the range of 5.6-15.7. (C) 2013 Elsevier Masson SAS. All rights reserved.
• ——
  作者：Carl H. Schiesser、Melissa A. Skidmore、Jonathan M. White

  DOI：10.1071/ch01045

  日期：——

  7 alpha-(Dimethylstannyl)-24-nor-5 beta -cholane (12) and 3 beta-(dimethylstannyl)-24-nor-5 beta -cholane (11) have been prepared from cholic and lithocholic acid, respectively, as free-radical reducing agents. Limited enantioselectivity-testing data indicate that these compounds show promise as enantioselective free-radical reducing agents. For example, reaction of ethyl (rac)-2-bromo-2-cyclopentyl-2-phenylacetate with one equivalent of either (11) or (12) in the presence of one equivalent of (S,S)-(-)-N,N'-bis(3,5-di-tert-butylsalycidene)-1,2-cyclohexanediaminomanganese(III) chloride (7) in toluene at -78 degreesC provides ethyl (S)-2-cyclopentyl-2-phenylacetate, obtained with 62 and 90% ee, respectively.