tropic acid-(2-diethylamino-ethyl ester) | 39755-33-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: tropic acid-(2-diethylamino-ethyl ester)
• 英文别名: Tropasaeure-(2-diaethylamino-aethylester)；dl-Tropasaeure-(β-diaethylamino-aethylester)；2-(Diethylamino)ethyl 3-hydroxy-2-phenylpropanoate
• CAS: 39755-33-4
• 化学式: C₁₅H₂₃NO₃
• 分子量: 265.353
• InChiKey: ZYTWFXHYHNPICI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴甲烷 、 tropic acid-(2-diethylamino-ethyl ester) 在 乙醇 作用下， 生成 diethyl-methyl-(2-tropoyloxy-ethyl)-ammonium; bromide
  参考文献：
  名称：

  Synthetic Mydriatics. III

  摘要：

  DOI：

  10.1021/ja01250a045
• 作为产物：
  描述：

  DL-托品酸 在 盐酸 、 氯化亚砜 作用下， 反应 30.5h， 生成 tropic acid-(2-diethylamino-ethyl ester)
  参考文献：
  名称：

  Differential analgesic activity of the enantiomers of atropine derivatives does not correlate with their muscarinic subtype selectivity

  摘要：

  The enantiomers of several tropic and p-substituted tropic acid esters related to atropine obtained by esterification under non-racemizing conditions after resolution of the corresponding racemic acids [(+)- and (-)-18, (+)- and (-)-19] are reported. They were tested in vitro on muscarinic subtype receptors and in vivo for their analgesic activity on mice. As in the case of the lead compound, R-(+)-hyoscyamine, these substances show enantioselectivity in analgesic tests, the eutomers being the R-(+) or R-(+)-p-substituted tropic acid derivatives. However, this property, which is a consequence of increased central release of ACh, seems unrelated to muscarinic subtype selectivity insofar as the compounds are unable to discriminate muscarinic subtype receptors. A possible explanation of these results which does not involve subtype selectivity is proposed, based on the recently developed concept of inverse agonism.

  DOI：

  10.1016/s0223-5234(97)83285-0

文献信息

• Molecular modification of anticholinergics as probes for muscarinic receptors. 1. Amino esters of .alpha.-substituted phenylacetic acid and related analogs
  作者：Matthias C. Lu、Walley E. Wung、Lisa B. Shih、Soledad Callejas、James E. Gearien、Emmanuel B. Thompson

  DOI：10.1021/jm00385a008

  日期：1987.2

  Two series of compounds having the general structure of C6H5CRR'COOCH2CH2NEt2 were synthesized and examined for their antispasmodic activities. These compounds were selected as structural probes for exploring the nature of muscarinic cholinergic receptor binding sites that interact with atropine-like anticholinergics. These studies indicate a rather strict size limitation for the hydrophobic region

  合成了具有C6H5CRR'COOCH2CH2NEt2的一般结构的两个系列的化合物，并研究了它们的解痉活性。选择这些化合物作为结构探针，以探索与阿托品样抗胆碱能药物相互作用的毒蕈碱胆碱能受体结合位点的性质。这些研究表明，对于受体的疏水区域存在相当严格的尺寸限制，并建议分子内氢键作为解释观察到的立体选择性的可能手段。
• Antispasmodics. I. Basic Esters of Some Arylacetic Acids¹
  作者：Robert R. Burtner、John W. Cusic

  DOI：10.1021/ja01242a036

  日期：1943.2