(3R,5R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-17-((R)-5-oxo-5-((2-thioxopyridin-1(2H)-yl)oxy)pentan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diyl diacetate | 89025-70-7

• 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: (3R,5R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-17-((R)-5-oxo-5-((2-thioxopyridin-1(2H)-yl)oxy)pentan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diyl diacetate
• CAS: 89025-70-7
• 化学式: C₃₃H₄₇NO₆S
• 分子量: 585.805
• InChiKey: OAVCDPIQNZVBBK-SNYZNSQJSA-N

物化性质

• 沸点：
  629.6±65.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  41.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  83.83
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3R,5R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-17-((R)-5-oxo-5-((2-thioxopyridin-1(2H)-yl)oxy)pentan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diyl diacetate 在 吡啶 、 氧气 、 叔丁基硫醇 、 对甲苯磺酰氯 作用下， 生成 3α,12α-diacetoxy-24-nor-5βH-cholan-23-al
  参考文献：
  名称：

  新的自由基链反应的发明。第八部分 硫代异羟肟酸酯的自由基化学；一种由羧酸生成碳自由基的新方法

  摘要：

  N-羟基吡啶-2-硫酮的脂族和脂环族酯很容易在自由基链反应中被三丁基锡烷还原以提供正烷烃。1在不存在锡烷的情况下，会发生平滑的脱羧latlive重排，从而生成2-取代的硫代吡啶。1该反应中存在的自由基与-丁基硫醇一起引发有效的自由基反应，形成正构烷烃和2-吡啶基-丁基二硫化物。1类似地，这些碳自由基可通过卤素原子转移而捕获，得到正烷基氯化物，溴化物和碘化物。2在叔丁基硫醇的存在下，用氧气在另一个自由基链反应中形成相应的正烷基氢过氧化物。3

  DOI：

  10.1016/s0040-4020(01)97173-x
• 作为产物：
  描述：

  去氧胆酸 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， 生成 (3R,5R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-17-((R)-5-oxo-5-((2-thioxopyridin-1(2H)-yl)oxy)pentan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diyl diacetate
  参考文献：
  名称：

  Structure-activity relationship of hybrids of Cinchona alkaloids and bile acids with in vitro antiplasmodial and antitrypanosomal activities

  摘要：

  In this work, a series of hybrid compounds were tested as antiparasitic substances. These hybrids were prepared from bile acids and a series of antiparasitic Cinchona alkaloids by the formation of a covalent C-C bond via a decarboxylative Barton-Zard reaction between the two entities. The bile acids showed only weak antiparasitic properties, but all the hybrids exhibited high in vitro activities (IC50: 0.48-5.39 mu M) against Trypanosoma brucei. These hybrids were more active than their respective parent alkaloids (up to a 135 fold increase in activity), and displayed good selectivity indices. Aditionally, all these compounds inhibited the in vitro growth of a chloroquine-sensitive strain of Plasmodium falciparum (3D7: IC50: 36.1 nM to 8.72 mu M), and the most active hybrids had IC(50)s comparable to that of artemisinin (IC50: 36 nM). Some structure-activity relationships among the group of 48 hybrids are discussed. The increase in antiparasitic activity may be explained by an improvement in bioavailability, since the more lipophilic derivatives showed the lowest IC(50)s. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.044

文献信息

• New and improved methods for the radical decarboxylation of acids
  作者：Derek H. R. Barton、David Crich、William B. Motherwell

  DOI：10.1039/c39830000939

  日期：——

  Carboxylic acid esters derived from N-hydroxypyridine-2-thione undergo efficient radical chain decarboxylation to the corresponding nor-alkane on treatment with either tri-n-butylstannane or t-butylmercaptan; in the absence of these hydrogen atom donors a smooth decarboxylative rearrangement giving noralkyl 2-pyridyl sulphides is observed.

  在用三正丁基锡烷或叔丁基硫醇处理时，衍生自N-羟基吡啶-2-硫酮的羧酸酯进行有效的自由基链脱羧成相应的正构烷烃。在没有这些氢原子供体的情况下，观察到平滑的脱羧重排，给出了正烷基2-吡啶基硫化物。
• Conversion of aliphatic and alicyclic carboxylic acids into nor-hydroperoxides, nor-alcohols, and nor-oxo derivatives using radical chemistry
  作者：Derek H. R. Barton、David Crich、William B. Motherwell

  DOI：10.1039/c39840000242

  日期：——

  Radicals generated from esters of N-hydroxypyridine-2-thione react smoothly with oxygen in the presence of t-butyl thiol to furnish nor-hydroperoxides, from which the corresponding alcohols and carbonyl derivatives can be readily obtained.

  由N-羟基吡啶-2-硫酮的酯产生的自由基在叔丁基硫醇的存在下与氧平稳反应，得到正氢过氧化物，由此可以容易地获得相应的醇和羰基衍生物。