5-氟-2-甲氧基肉桂酸 | 157518-45-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 5-氟-2-甲氧基肉桂酸
• 英文名称: trans-3-(5-fluoro-2-methoxyphenyl)propenoic acid
• 英文别名: (E)-3-(5-fluoro-2-methoxyphenyl)propenoic acid；5-Fluoro-2-methoxycinnamic acid；(E)-3-(5-fluoro-2-methoxyphenyl)prop-2-enoic acid
• CAS: 157518-45-1
• 化学式: C₁₀H₉FO₃
• 分子量: 196.178
• InChiKey: WWZPWGXNJORULY-GORDUTHDSA-N

物化性质

• 沸点：
  334.3±27.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 海关编码：
  2918990090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-氟-2-甲氧基肉桂酸 在 palladium diacetate 、 sodium hydroxide 、 硫酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 (1S,2S)-2-(5-fluoro-2-methoxyphenyl)cyclopropane-1-carboxylic acid
  参考文献：
  名称：

  trans-2-Aryl-N,N-dipropylcyclopropylamines:  Synthesis and Interactions with 5-HT_1A Receptors

  摘要：

  Twelve N,N-dipropyl-substituted derivatives of trans-2-arylcyclopropylamine have been prepared and assayed for their ability to displace [H-3]-8-OH-DPAT from rat brain 5-HT1A receptors. The new derivatives include phenyl (7a), bromo- (7b) and fluorophenyl (7c-e), 2-methoxy-5-fluorophenyl (7h), and 2-hydroxy-5-fluorophenyl (7I) as well as trifluoromethylphenyl (7f) and 2,3-dichlorophenyl (7g) analogues. In the present series of compounds, electron-withdrawing substituents in the phenyl ring appear to decrease the affinity for 5-HT1A receptors. In contrast, electron-rich aryl groups, such as 2- or 3-thienyl (7j and 7k, respectively), provide compounds with high affinity. The additional bulk produced by the aromatic moiety in the 2-benzothienyl derivative 7i appears to be detrimental to 5-HT1A receptor affinity. The racemic mixtures of the interesting 7j and 7I were resolved into the enantiomers; 7j and 7I exhibited a high enantiomeric 5-HT1A receptor affinity ratio (75-fold and 100-fold, respectively). The enantiomers of 7j and 7I were evaluated in vivo by use of biochemical and behavioral tests in rats. Compound (LR,2R)-7j behaved as a partial agonist whereas (1R,2S)-7I appeared as an efficacious 5-HT1A receptor agonist, stimulating both autoreceptors and postsynaptic receptors.

  DOI：

  10.1021/jm9507136
• 作为产物：
  描述：

  对氟苯甲醚 在 哌啶 、 盐酸 、 乌洛托品 、 硫酸 、 溶剂黄146 作用下， 以 吡啶 为溶剂， 反应 28.0h， 生成 5-氟-2-甲氧基肉桂酸
  参考文献：
  名称：

  Vallaerda, Jerk; Appelberg, Ulf; Csoeregh, Ingeborg, Journal of the Chemical Society. Perkin transactions I, 1994, # 4, p. 461 - 470

  摘要：

  DOI：

文献信息

• 2-Phenylcyclopropylmethylamine Derivatives as Dopamine D₂ Receptor Partial Agonists: Design, Synthesis, and Biological Evaluation
  作者：Wenzhong Yan、Luyu Fan、Jing Yu、Ruiquan Liu、Huan Wang、Liang Tan、Sheng Wang、Jianjun Cheng

  DOI：10.1021/acs.jmedchem.1c01327

  日期：2021.12.9

  Partial agonist activity at the dopamine D2 receptor (D2R) is the primary pharmacological feature of the third-generation antipsychotics─aripiprazole, brexpiprazole, and cariprazine. However, all these drugs share a common phenyl-piperazine moiety as the primary pharmacophore. In this study, we designed and synthesized a series of novel compounds based on the 2-phenylcyclopropylmethylamine (PCPMA)

  对多巴胺 D 2受体 (D 2 R) 的部分激动剂活性是第三代抗精神病药——阿立哌唑、brexpiprazole 和卡利拉嗪的主要药理学特征。然而，所有这些药物都有一个共同的苯基哌嗪部分作为主要药效团。在这项研究中，我们设计并合成了一系列基于 2-苯基环丙基甲胺 (PCPMA) 支架的新型化合物，并研究了它们在 D 2 R 的药理活性。一些有效的 D 2通过结合亲和力筛选和 G 蛋白和 β-抑制蛋白测定中的功能活性分析鉴定 R 部分激动剂。结构-功能活性关系结果表明，间隔基团对于微调这些化合物的内在活性至关重要。化合物(+)- 14j和(+)- 14l显示出良好的药代动力学特性和对5-羟色胺2A (5-HT 2A ) 受体的出乎意料的选择性。小鼠超运动模型中的初步抑制作用证明这些 PCPMA 衍生的 D 2 R 部分激动剂作为潜在的新型抗精神病药是有效的。
• THIENOPYRIMIDINE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：LES LABORATOIRES SERVIER

  公开号：US20150175623A1

  公开（公告）日：2015-06-25

  Compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 12 , X, A and n are as defined in the description. Medicinal products containing the same which are useful in treating pathologies involving a deficit in apoptosis, such as cancer, auto-immune diseases, and diseases of the immune system.

  式(I)的化合物，其中R1、R2、R3、R4、R5、R6、R7、R12、X、A和n的定义如说明中所述。含有该化合物的药物可用于治疗涉及凋亡缺陷的病理学，如癌症、自身免疫性疾病和免疫系统疾病。
• Thienopyrimidine derivatives, a process for their preparation and pharmaceutical compositions containing them
  申请人：LES LABORATOIRES SERVIER

  公开号：US10278972B2

  公开（公告）日：2019-05-07

  Compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, R12, X, A and n are as defined in the description. Medicinal products containing the same which are useful in treating pathologies involving a deficit in apoptosis, such as cancer, auto-immune diseases, and diseases of the immune system.

  式(I)化合物： 其中 R1、R2、R3、R4、R5、R6、R7、R12、X、A 和 n 如说明中所定义。 含有相同成分的药物产品，可用于治疗涉及细胞凋亡缺陷的病症，如癌症、自身免疫性疾病和免疫系统疾病。
• New thienopyrimidine derivatives, a process for their preparation and pharmaceutical compositions containing them
  申请人：Les Laboratoires Servier

  公开号：EP2886545B1

  公开（公告）日：2016-06-29
• US9670227B2
  申请人：——

  公开号：US9670227B2

  公开（公告）日：2017-06-06