1-(2-chlorophenyl)-5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylic acid ethyl ester | 126839-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-chlorophenyl)-5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 1-(2-chlorophenyl)-5-(4-methoxyphenyl)pyrazole-3-carboxylate
• CAS: 126839-70-1
• 化学式: C₁₉H₁₇ClN₂O₃
• 分子量: 356.809
• InChiKey: ZAIBKIVIECNEPX-UHFFFAOYSA-N

物化性质

• 沸点：
  519.2±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-chlorophenyl)-5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylic acid ethyl ester 在 氢氧化钾 、 氯化亚砜 、 溴 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationship, and Evaluation of SR141716 Analogues:  Development of Central Cannabinoid Receptor Ligands with Lower Lipophilicity

  摘要：

  Exploration of the central CB1 cannabinoid receptors using positron emission tomography (PET) will allow for an understanding of the pharmacological and physiological role played by these receptors in the CNS. Current tracers are highly lipophilic compounds that exhibit very high nonspecific to specific binding ratios and as a result are inapt for use in humans. We have synthesized a series of less lipophilic analogues of SR141716 to serve as potential radioligands. Binding affinities of the series and a functional electrophysiological assay of three of our compounds have been presented.

  DOI：

  10.1021/jm020157x
• 作为产物：
  描述：

  2-氯苯肼盐酸盐 以 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 1-(2-chlorophenyl)-5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Murray, William V.; Wachter, Michael P., Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1389 - 1392

  摘要：

  DOI：

文献信息

• Synthesis ofN-(piperidin-1-yl)-5-(4-methoxyphenyl)-1-(2-chlorophenyl)-4-[18F]fluoro-1H-pyrazole-3-carboxamide by nucleophilic [18F] fluorination: a PET radiotracer for studying CB1 cannabinoid receptors
  作者：Reeti Katoch-Rouse、Andrew G. Horti

  DOI：10.1002/jlcr.647

  日期：2003.1

  The feasibility of nucleophilic displacement of bromide in the 4-bromopyrazole ring with [18F]fluoride has been demonstrated by the synthesis of two radiolabeled compounds: N-(piperidin-1-yl)-5-(4-methoxyphenyl)-1-(2-chlorophenyl)-4-[18F]fluoro-1H-pyrazole-3-carboxamide, ([18F] NIDA-42033) 1b and 1-(2-chlorophenyl)-4-[18F]fluoro-5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylic acid, ethyl ester 4. The radiochemical yields were in the range of 1–6%. [18F]NIDA-42033, a potential radiotracer for the study of CB1 cannabinoid receptors in the animal brain by positron emission tomography, has been synthesized in sufficient quantities with specific radioactivity greater than 2500 mCi/μmol and radiochemical purity >95%. Copyright © 2002 John Wiley & Sons, Ltd.

  通过合成两种放射性标记化合物，证明了用[18F]氟化物对 4-溴吡唑环中的溴化物进行亲核置换的可行性：N-(piperidin-1-yl)-5-(4-methoxyphenyl)-1-(2-chlorophenyl)-4-[18F]fluoro-1H-pyrazole-3-carboxamide, ([18F] NIDA-42033) 1b 和 1-(2-chlorophenyl)-4-[18F]fluoro-5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylic acid, ethyl ester 4。放射化学收率在 1-6% 之间。[18F]NIDA-42033是一种潜在的放射性示踪剂，可通过正电子发射断层扫描技术研究动物大脑中的CB1大麻素受体，目前已合成了足够数量的[18F]NIDA-42033，比放射性大于2500 mCi/μmol，放射化学纯度大于95%。Copyright © 2002 John Wiley & Sons, Ltd. All Rights Reserved.