(Z)-2-fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (Z)-2-fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzoic acid
• 英文别名: 2-fluoro-5-[(Z)-(3-oxo-2-benzofuran-1-ylidene)methyl]benzoic acid
• 化学式: C₁₆H₉FO₄
• 分子量: 284.243
• InChiKey: FAZXGENUOIVDTH-ZSOIEALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-2-fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzoic acid 在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 生成 5-[(3,4-二氢-4-氧代-1-酞嗪基)甲基]-2-氟苯甲酸
  参考文献：
  名称：

  Phthalazinones 2: Optimisation and synthesis of novel potent inhibitors of poly(ADP-ribose)polymerase

  摘要：

  We have previously described the discovery of poly(ADP-ribose)polymerase-1 (PARP-1) inhibitors based on a phthalazinone scaffold. Subsequent optimisation of inhibitory activity, metabolic stability and pharmacokinetic parameters has led to a novel series of meta-substituted 4-benzyl-2H-phthalazin-1-one PARP-1 inhibitors which retain low nM cellular activity and show good stability in vivo and efficacy in cell based models. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.081
• 作为产物：
  描述：

  2-氟-5-甲酰基苯腈 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-2-fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzoic acid
  参考文献：
  名称：

  Phthalazinones 2: Optimisation and synthesis of novel potent inhibitors of poly(ADP-ribose)polymerase

  摘要：

  We have previously described the discovery of poly(ADP-ribose)polymerase-1 (PARP-1) inhibitors based on a phthalazinone scaffold. Subsequent optimisation of inhibitory activity, metabolic stability and pharmacokinetic parameters has led to a novel series of meta-substituted 4-benzyl-2H-phthalazin-1-one PARP-1 inhibitors which retain low nM cellular activity and show good stability in vivo and efficacy in cell based models. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.081

文献信息

• Effective Palladium-Catalyzed Hydroxycarbonylation of Aryl Halides with Substoichiometric Carbon Monoxide
  作者：Signe Korsager、Rolf H. Taaning、Troels Skrydstrup

  DOI：10.1021/ja3114032

  日期：2013.2.27

  A protocol for the Pd-catalyzed hydroxycarbonylation of aryl iodides, bromides, and chlorides has been developed using only 1-5 mol % of CO, corresponding to a p(CO) as low as 0.1 bar. Potassium formate is the only stoichiometric reagent, acting as a mildly basic nucleophile and a reservoir of CO. The substoichiometric CO could be delivered to the reaction from an acyl-Pd(II) precatalyst, which provides

  已开发出一种用于芳基碘化物、溴化物和氯化物的 Pd 催化羟基羰基化的方案，仅使用 1-5 mol% 的 CO，对应于低至 0.1 bar 的 ap(CO)。甲酸钾是唯一的化学计量试剂，作为温和的碱性亲核试剂和 CO 的储库。亚化学计量的 CO 可以从酰基-Pd(II) 预催化剂输送到反应中，提供 CO 和活性催化剂，和从而避免了处理有毒气体的需要。
• Phthalazinones 2: Optimisation and synthesis of novel potent inhibitors of poly(ADP-ribose)polymerase
  作者：Xiao-ling Cockcroft、Krystyna J. Dillon、Lesley Dixon、Jan Drzewiecki、Frank Kerrigan、Vincent M. Loh、Niall M.B. Martin、Keith A. Menear、Graeme C.M. Smith

  DOI：10.1016/j.bmcl.2005.10.081

  日期：2006.2

  We have previously described the discovery of poly(ADP-ribose)polymerase-1 (PARP-1) inhibitors based on a phthalazinone scaffold. Subsequent optimisation of inhibitory activity, metabolic stability and pharmacokinetic parameters has led to a novel series of meta-substituted 4-benzyl-2H-phthalazin-1-one PARP-1 inhibitors which retain low nM cellular activity and show good stability in vivo and efficacy in cell based models. (c) 2005 Elsevier Ltd. All rights reserved.