(2S,5'R,2'R)-1-methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine | 623938-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,5'R,2'R)-1-methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine
• 英文别名: (2S,2'R,5'R)-1-methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine；(2S)-1-methyl-2-[(2R,5R)-2-methyl-1,3-oxathiolan-5-yl]pyrrolidine
• CAS: 623938-60-3
• 化学式: C₉H₁₇NOS
• 分子量: 187.306
• InChiKey: DFFDHBHFVHJKBU-VGMNWLOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,5'R,2'R)-1-methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine 在 双氧水 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 0.83h， 生成 (S)-1,1-Dimethyl-2-((2R,3S,5R)-2-methyl-3-oxo-3λ⁴-[1,3]oxathiolan-5-yl)-pyrrolidinium; iodide
  参考文献：
  名称：

  高度手性毒蕈碱配体：（2S，2'R，3'S，5'R）-1-甲基-2-（2-甲基-1,3-氧硫杂环戊基-5-基）吡咯烷3-亚砜甲基碘的发现，一种有效的，功能选择性的M2部分激动剂。

  摘要：

  通过先前研究的高度手性毒蕈碱激动剂的进一步空间复杂性，我们获得了对映异构和非对映异构的1-甲基-2-（2-甲基-1,3-氧硫杂环戊基-5-基）吡咯烷3-亚砜的小型手性文库。对在CHO细胞中表达的克隆的人类毒蕈碱受体的结合研究表明，引入第四个立体生成中心对hm1，hm3，hm4和hm5亚型具有不可检测的亲和力，而仅对hm2亚型具有相当适度的亲和力。但是，对模型M1-M4毒蕈碱组织的功能研究表明，[[-）-5，（-）-7，（+）-8]系列中的三种化合物具有功能活性并具有M2选择性部分激动剂的作用。 。其中，化合物（2S，2'R，3'S，5'R）-1-甲基-2-（2-甲基-1，

  DOI：

  10.1021/jm0510878
• 作为产物：
  描述：

  (1-carbobenzyloxy-2(S)-pyrrolidynyl)oxirane 在 盐酸 、 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 异丙醇 为溶剂， 反应 24.0h， 生成 (2S,5'R,2'R)-1-methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine
  参考文献：
  名称：

  Synthesis and cholinergic affinity of diastereomeric and enantiomeric isomers of 1-methyl-2-(2-methyl-1,3-dioxolan-4-yl)- pyrrolidine, 1-methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine and of Their iodomethylates

  摘要：

  Four out of the eight possible stereoisomers of 1-methyl-2-(2-methyl-1,3-dioxolan-4-yl)pyrrolidine, 1-methyl-2-(2methyl-1.3-oxathiolan-5-,I)pyrrolidine and the corresponding iodomethylates have been synthesised. They were formally derived from hybridisation of potent though unselective agonists studied before, such as 1,3-dioxolane 1 and 1,3-oxathiolane 2, with the structure of nicotine. It was expected that, by exalting the molecular complexity of the parent compounds, in particular through stereochemical complication in the proximity of the critical cationic head of the molecule, the chance to find agonists able to discriminate among cholinergic receptors subtypes would increase. The relative and absolute configuration of the compounds obtained has been established by means of NMR spectroscopy and X-ray crystallography. In preliminary studies, their binding affinity has been evaluated on rat brain nicotinic and muscarinic receptors. While none of the compounds showed any nicotinic affinity up to the dose of 10 muM, most of the iodomethylates were endowed with promising affinity for the muscarinic receptors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00236-0