ethyl (2E)-3-(2',4'-dichlorophenyl)but-2-enoate | 648425-43-8

• 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
• 英文名称: ethyl (2E)-3-(2',4'-dichlorophenyl)but-2-enoate
• 英文别名: ethyl (E)-3-(2,4-dichlorophenyl)but-2-enoate
• CAS: 648425-43-8
• 化学式: C₁₂H₁₂Cl₂O₂
• 分子量: 259.132
• InChiKey: QXFNFRHRWFPXHJ-SOFGYWHQSA-N

物化性质

• 沸点：
  343.1±27.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (2E)-3-(2',4'-dichlorophenyl)but-2-enoate 在 二异丁基氢化铝 、 potassium carbonate 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 25.0h， 生成 9-propionyl-10-[3'-methyl-3'-(o,p-dichlorophenyl)prop-2'-en-1'-yl]-9,10-diazatricyclo[4.2.1.1^2,5]decane
  参考文献：
  名称：

  Synthesis of novel diazatricyclodecanes (DTDs). Effects of structural variation at the C3′ allyl end and at the phenyl ring of the cinnamyl chain on μ-receptor affinity and opioid antinociception

  摘要：

  Two series of analogues of 9-propionyl-10-cinnamyl-9,10-diazatricyclo[4.2.1.1(2,5)]decane (1a) and 2-propionyl-7-cinnamyl-2,7-diazatricyclo[4.4.0.0(3,8)]decane (2a), in which the cinnamyl moiety was replaced by various aralkenyl chains, 1b-1 and 2b-1, respectively, have been synthesized and evaluated for their ability to bind to the opioid mu-, delta- and kappa-receptors. The binding data indicated that compounds 1b,d,e,h and 2b,d,e,f,h,i showed a mu-affinity in the low nanomolar range with moderate or negligible affinity towards delta- and kappa-receptors. Selected DTDs, the pairs 1,2b,1,2e and 1,2h, were also evaluated for analgesic effect. In the hot plate test, only 1b given ip was found to have similar opioid antinociception and chronic tolerance as morphine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00373-0
• 作为产物：
  描述：

  2,4-二氯苯乙酮 在 碘 、 对甲苯磺酸 、 锌 作用下， 以 苯 为溶剂， 生成 ethyl (2E)-3-(2',4'-dichlorophenyl)but-2-enoate
  参考文献：
  名称：

  新型卤化芳基乙烯基-1,2,4 三恶烷作为有效的抗疟原虫和抗癌剂：合成、生物评价、构效关系和计算机内研究

  摘要：

  在此，我们合成了一系列亲脂性、卤化-芳基乙烯基-1,2,4-三恶烷8a - g（28 种化合物），并使用针对氯喹的 SYBRgreen-I 荧光测定法评估了它们在恶性疟原虫培养物中的体外抗疟原虫活性抗性Pf的INDO和耐青蒿素Pf的凸轮3.1 R539T（MRA-1240）菌株。此外，8a - g的细胞毒性潜力也已在体外针对 HEK293 细胞系进行了测定。在二十八种卤化芳基乙烯基-1,2,4-三恶烷中；十个类似物 ( 8a 2 , 8a4 , 8b 2 , 8b 4 , 8d 4 , 8e 1 , 8e 2 , 8e 4 , 8f 2和8g 4 ) 已显示出有效的体外抗疟原虫活性，IC 50  < 27 nM (IC 50范围 = 4.588-2)6 . 此外，发现这十种类似物的选择性指数 (SI) 在 72.00-3972.50 的范围内，这表明它们对疟原虫细胞的选择性潜力。两种最有效的化合物8a的细胞周期阶段特异性结果4

  DOI：

  10.1016/j.ejmech.2021.113685

文献信息

• Cycloalkyl Lactam Derivatives as Inhibitors of 11-Beta-Hydroxysteroid Dehydrogenase 1
  申请人：Aicher Thomas Daniel

  公开号：US20080275043A1

  公开（公告）日：2008-11-06

  The present invention discloses compounds of Formula I: (I) having 11beta-HSD type 1 antagonist activity, as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising compounds of Formula I, as well as the use of the Fomula I and compositions as medicaments to treat diabetes, hyperglycemia, obesity, hypertension, hyperlipidemia, Syndrome X, and other conditions associated with hyperglycemia.

  本发明公开了具有11beta-HSD type 1拮抗活性的化合物的公式I：（I），以及制备这种化合物的方法。在另一实施例中，本发明公开了包含公式I化合物的制药组合物，以及将公式I和组合物用作药物治疗糖尿病，高血糖，肥胖症，高血压，高脂血症，综合征X和与高血糖有关的其他疾病的用途。
• CYCLOALKYL LACTAM DERIVATIVES AS INHIBITORS OF 11-BETA-HYDROXYSTEROID DEHYDROGENASE 1
  申请人：AICHER Thomas Daniel

  公开号：US20100184764A1

  公开（公告）日：2010-07-22

  The present invention discloses compounds of Formula I: (I) having 11beta-HSD type 1 antagonist activity, as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising compounds of Formula I, as well as the use of the Formula I and compositions as medicaments to treat diabetes, hyperglycemia, obesity, hypertension, hyperlipidemia, Syndrome X, and other conditions associated with hyperglycemia.

  本发明揭示了具有11beta-HSD type 1拮抗活性的I式化合物：（I），以及制备这种化合物的方法。在另一种实施方式中，本发明揭示了包括I式化合物的制药组合物，以及将I式和组合物用作药物治疗糖尿病，高血糖，肥胖症，高血压，高脂血症，X综合症和其他与高血糖有关的疾病的用途。
• US7713979B2
  申请人：——

  公开号：US7713979B2

  公开（公告）日：2010-05-11
• [EN] CYCLOALKYL LACTAM DERIVATIVES AS INHIBITORS OF 11-BETA-HYDROXYSTEROID DEHYDROGENASE 1<br/>[FR] INHIBITEURS DE LA 11-BÉTA-HYDROXYSTÉROÏDE DÉSHYDROGÉNASE 1 DÉRIVÉS DE CYCLOALKYLLACTAMES
  申请人：LILLY CO ELI

  公开号：WO2006049952A1

  公开（公告）日：2006-05-11

  [EN] The present invention discloses compounds of Formula I: (I) having 11beta -HSD type 1 antagonist activity, as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising compounds of Formula I, as well as the use of the Fomula I and compositions as medicaments to treat diabetes, hyperglycemia, obesity, hypertension, hyperlipidemia, Syndrome X, and other conditions associated with hyperglycemia.
  [FR] La présente invention décrit des composés de Formule I : (I) présentant une activité antagoniste de la 11-béta-HSD de type 1, ainsi que des méthodes de synthèse de tels composés. Dans un autre mode de l'invention, cette dernière décrit également des préparations pharmaceutiques comprenant des composés de Formule I, de même que l'emploi de la Formule I et desdites préparations comme médicaments dans le traitement du diabète, de l'hyperglycémie, de l'obésité, de l'hypertension, de l'hyperlipidémie, du Syndrome X, et d'autres afflictions associées à l'hyperglycémie.
• Synthesis of novel diazatricyclodecanes (DTDs). Effects of structural variation at the C3′ allyl end and at the phenyl ring of the cinnamyl chain on μ-receptor affinity and opioid antinociception
  作者：Gérard Aimè Pinna、Giorgio Cignarella、Stefania Ruiu、Giovanni Loriga、Gabriele Murineddu、Stefania Villa、Giuseppe Enrico Grella、Gregorio Cossu、Walter Fratta

  DOI：10.1016/s0968-0896(03)00373-0

  日期：2003.9

  Two series of analogues of 9-propionyl-10-cinnamyl-9,10-diazatricyclo[4.2.1.1(2,5)]decane (1a) and 2-propionyl-7-cinnamyl-2,7-diazatricyclo[4.4.0.0(3,8)]decane (2a), in which the cinnamyl moiety was replaced by various aralkenyl chains, 1b-1 and 2b-1, respectively, have been synthesized and evaluated for their ability to bind to the opioid mu-, delta- and kappa-receptors. The binding data indicated that compounds 1b,d,e,h and 2b,d,e,f,h,i showed a mu-affinity in the low nanomolar range with moderate or negligible affinity towards delta- and kappa-receptors. Selected DTDs, the pairs 1,2b,1,2e and 1,2h, were also evaluated for analgesic effect. In the hot plate test, only 1b given ip was found to have similar opioid antinociception and chronic tolerance as morphine. (C) 2003 Elsevier Ltd. All rights reserved.