(2S,4R,5R)-4-fluoro-2-iodomethyl-5-<<(4-methylphenyl)sulfenyl>methyl>tetrahydrofuran | 132113-39-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2S,4R,5R)-4-fluoro-2-iodomethyl-5-<<(4-methylphenyl)sulfenyl>methyl>tetrahydrofuran
• 英文别名: (2R,3R,5S)-3-fluoro-5-iodomethyl-2-<(4-methylphenyl)sulphenyl>methyltetrahydrofuran；(2R,3R,5S)-3-fluoro-5-(iodomethyl)-2-[(4-methylphenyl)sulfanylmethyl]oxolane
• CAS: 132113-39-4
• 化学式: C₁₃H₁₆FIOS
• 分子量: 366.238
• InChiKey: XADPNTSWSCTIAV-UHTWSYAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4R,5R)-4-fluoro-2-iodomethyl-5-<<(4-methylphenyl)sulfenyl>methyl>tetrahydrofuran 在 Rraney-Ni 作用下， 以 乙醇 为溶剂， 反应 3.08h， 生成 (1S)-1,4-脱水-2,3,5-三脱氧-5-(二甲基氨基)-2-氟-1-甲基-D-赤式-戊糖醇
  参考文献：
  名称：

  Bravo, Pierfrancesco; Frigerio, Massimo; Resnati, Giuseppe, Gazzetta Chimica Italiana, 1990, vol. 120, # 4, p. 275 - 276

  摘要：

  DOI：
• 作为产物：
  描述：

  (4R,5R)-4-fluoro-5-hydroxy-6-<(4-methylphenyl)sulfenyl>hex-1-ene 在 碘 、 碳酸氢钠 作用下， 以 四氯化碳 为溶剂， 反应 72.0h， 生成 (2S,4R,5R)-4-fluoro-2-iodomethyl-5-<<(4-methylphenyl)sulfenyl>methyl>tetrahydrofuran 、 (2R,4R,5R)-4-fluoro-2-iodomethyl-5-<<(4-methylphenyl)sulfenyl>methyl>tetrahydrofuran
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of enantiomerically pure 4-deoxy-4-fluoromuscarines

  摘要：

  Four isomers of [(4-fluoro-5-methyl-tetrahydrofuran-2-yl)methyl]trimethylammonium iodide (4-deoxy-4-fluoro-muscarines) were prepared in enantiomerically and diastereomerically pure form from (S)-(-)-methyl 4-methylphenyl sulfoxide, ethyl fluoroacetate, and allyl bromide. Their absolute configurations were assigned by H-1 NMR analyses. The four optically pure compounds were tested in vitro on guinea pig and their muscarinic potency was evaluated at M3 (ileum and bladder) and M2 (heart) muscarinic receptor subtypes. Compound 1a, the most potent isomer of the series, was also tested in vivo on pithed rat and its muscarinic activity at the M1 receptor subtype was compared with that of muscarine. Moreover, affinity and relative efficacy were calculated in vitro for this compound at M2 (heart force and rate) and M3 (ileum and bladder) receptors in order to investigate muscarinic receptor heterogeneity. The 4-deoxy-4-fluoromuscarines display a similar trend of potency as the corresponding muscarines and compound 1a shows differences in the affinity constants among the studied tissues. Replacement of a hydroxyl group for a fluorine atom in the 4 position of muscarine produces 1 order of magnitude increase in affinity for cardiac M2 muscarinic receptors controlling rate, while the affinity at cardiac M2 muscarinic receptors controlling force is unchanged, opening the possibility of a further classification of cardiac muscarinic receptors.

  DOI：

  10.1021/jm00095a003

文献信息

• BRAVO, PIERFRANCESCO;FRIGERIO, MASSIMO;RESNATI, GIUSEPPE;VIANI, FIORENZA;+, GAZZ. CHIM. ITAL., 120,(1990) N, C. 275-276
  作者：BRAVO, PIERFRANCESCO、FRIGERIO, MASSIMO、RESNATI, GIUSEPPE、VIANI, FIORENZA、+

  DOI：——

  日期：——