methyl 2-chloro-5-ethenylbenzoate | 272130-85-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-chloro-5-ethenylbenzoate
• 英文别名: Methyl 2-chloro-5-vinylbenzoate
• CAS: 272130-85-5
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: LNEHUMFLJTYIRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2-chloro-5-ethenylbenzoate 在 sodium tetrahydroborate 、 9-borabicyclo[3.3.1]nonane dimer 、 sodium hydride 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 methyl 2-chloro-5-[2-(8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl)ethyl]benzoate
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 3. SAR of 3-(Carboxyarylalkyl)coformycin Aglycon Analogues

  摘要：

  N3-Substituted coformycin aglycon analogues with improved AMP deaminase (AMPDA) inhibitory potency are described. Replacement of the 5-carboxypentyl substituent in the lead AMPDA inhibitor 3-(5-carboxypentyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (2) described in the previous article with various carboxyarylalkyl groups resulted in compounds with 10-100-fold improved AMPDA inhibitory potencies. The optimal N3 substituent had m-carboxyphenyl with a two-carbon alkyl tether. For example, 3-[2-(3-carboxy-5-ethylphenyl)-ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d] [1,3]diazepin-8-ol (43g) inhibited human AMPDA with a K-i = 0.06 mu M. The compounds within the series also exhibited >1000-fold specificity for AMPDA relative to adenosine deaminase.

  DOI：

  10.1021/jm990448e
• 作为产物：
  描述：

  5-溴-2-氯苯甲酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 硫酸 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 19.5h， 生成 methyl 2-chloro-5-ethenylbenzoate
  参考文献：
  名称：

  [EN] SUBSTITUTED CYCLOPROPYL-2,2'-BIPYRIMIDINYL COMPOUNDS, ANALOGUES THEREOF, AND METHODS USING SAME
  [FR] COMPOSÉS DE CYCLOPROPYL-2,2'-BIPYRIMIDINYL SUBSTITUÉS, ANALOGUES DE CEUX-CI, ET PROCÉDÉS LES UTILISANT

  摘要：

  本公开涵盖了新型的取代环丙基-2,2'-双嘧啶基化合物，以及包含这些化合物的组合物，可用于治疗或预防患者体内的乙型肝炎病毒（HBV）感染和/或丙型肝炎病毒（HDV）感染。

  公开号：

  WO2021025976A1

文献信息

• Identification and optimisation of 7-azaindole PAK1 inhibitors with improved potency and kinase selectivity
  作者：William McCoull、Edward J. Hennessy、Kevin Blades、Matthew R. Box、Claudio Chuaqui、James E. Dowling、Christopher D. Davies、Andrew D. Ferguson、Frederick W. Goldberg、Nicholas J. Howe、Paul D. Kemmitt、Gillian M. Lamont、Katrina Madden、Claire McWhirter、Jeffrey G. Varnes、Richard A. Ward、Jason D. Williams、Bin Yang

  DOI：10.1039/c4md00280f

  日期：——

  A novel series of PAK1 inhibitors was discovered from a kinase directed screen. SAR exploration in the selectivity pocket and solvent tail regions was conducted to understand and optimise PAK1 potency and selectivity against targeted kinases. A liganded PAK1 crystal structure was utilised to guide compound design. Permeability and kinase selectivity impacted the translation of enzyme to cellular PAK1 potency. Compound 36 (AZ-PAK-36) demonstrated improved Gini coefficient, good PAK1 cellular potency and has utility as a tool compound for target validation studies.

  通过激酶定向筛选发现了一系列新型 PAK1 抑制剂。对选择性口袋和溶剂尾部区域进行了 SAR 探索，以了解和优化 PAK1 对目标激酶的效力和选择性。配体 PAK1 晶体结构用于指导化合物设计。渗透性和激酶选择性影响了从酶到细胞的 PAK1 效用转化。化合物 36（AZ-PAK-36）显示出更高的基尼系数和良好的 PAK1 细胞效力，可用作靶点验证研究的工具化合物。
• [EN] SUBSTITUTED CYCLOPROPYL-2,2'-BIPYRIMIDINYL COMPOUNDS, ANALOGUES THEREOF, AND METHODS USING SAME<br/>[FR] COMPOSÉS DE CYCLOPROPYL-2,2'-BIPYRIMIDINYL SUBSTITUÉS, ANALOGUES DE CEUX-CI, ET PROCÉDÉS LES UTILISANT
  申请人：ARBUTUS BIOPHARMA INC

  公开号：WO2021025976A1

  公开（公告）日：2021-02-11

  The present disclosure includes novel substituted cyclopropyl-2,2'-bipyrimidinyl compounds, and compositions comprising the same, that can be used to treat or prevent hepatitis B virus (HBV) infection and/or hepatitis D virus (HDV) infection in a patient.

  本公开涵盖了新型的取代环丙基-2,2'-双嘧啶基化合物，以及包含这些化合物的组合物，可用于治疗或预防患者体内的乙型肝炎病毒（HBV）感染和/或丙型肝炎病毒（HDV）感染。
• AMP Deaminase Inhibitors. 3. SAR of 3-(Carboxyarylalkyl)coformycin Aglycon Analogues
  作者：Srinivas Rao Kasibhatla、Brett C. Bookser、Gary Probst、James R. Appleman、Mark D. Erion

  DOI：10.1021/jm990448e

  日期：2000.4.1

  N3-Substituted coformycin aglycon analogues with improved AMP deaminase (AMPDA) inhibitory potency are described. Replacement of the 5-carboxypentyl substituent in the lead AMPDA inhibitor 3-(5-carboxypentyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (2) described in the previous article with various carboxyarylalkyl groups resulted in compounds with 10-100-fold improved AMPDA inhibitory potencies. The optimal N3 substituent had m-carboxyphenyl with a two-carbon alkyl tether. For example, 3-[2-(3-carboxy-5-ethylphenyl)-ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d] [1,3]diazepin-8-ol (43g) inhibited human AMPDA with a K-i = 0.06 mu M. The compounds within the series also exhibited >1000-fold specificity for AMPDA relative to adenosine deaminase.