3-(4-fluorobenzyl)isoquinolin-1(2H)-one | 474779-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3-(4-fluorobenzyl)isoquinolin-1(2H)-one
• 英文别名: 3-(4-Fluorobenzyl)-1-isoquinolinone；3-[(4-fluorophenyl)methyl]-2H-isoquinolin-1-one
• CAS: 474779-48-1
• 化学式: C₁₆H₁₂FNO
• 分子量: 253.276
• InChiKey: QVGBRVBPCQOXOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(4-Fluorobenzyl)isocoumarin 在 ammonium hydroxide 作用下， 以 乙二醇乙醚 为溶剂， 以61%的产率得到3-(4-fluorobenzyl)isoquinolin-1(2H)-one
  参考文献：
  名称：

  取代基的合成及其对3-（卤代苄基）异卡西丁腈抗炎活性的影响

  摘要：

  摘要设计并合成了一系列新的基于天然产物骨架的3-（卤代苄基）异羰基苯乙烯（2a – 2i），以研究不同卤化物取代基的位置对抗炎活性的影响。结构与活性的关系表明卤化物取代基的位置对体外抗炎活性具有重要影响。3-（邻卤代苄基）异咔唑（2a，2d和2g）表现出最低的活性，这很可能是由于卤化物与酰胺N–H之间的分子内氢键封闭了药效团的位置。相反，3-（对-卤代苄基）异咔唑2c，2f和2i表现出中等至非常好的炎症活性。发现化合物2c（IC 50  =  251.002±2.910）具有与标准药物（吲哚美辛，IC 50  =  271.210±2.127）相当的活性。为了进一步理解卤化物取代基的位置对3-（卤代苄基）异咔唑的影响，进行了计算POM。具有建设性命题的研究可能有助于设计更有效的类似物。 图形概要

  DOI：

  10.1007/s00044-014-1027-8

文献信息

• Isoquinolinone derivatives
  申请人：KuDOS Pharmaceuticals Limited

  公开号：US20030008896A1

  公开（公告）日：2003-01-09

  Derivatives of isoquinolinone and dihydrolisoquinolinone, and related compounds, and their use as pharmaceuticals in the treatment of a disease by inhibition of the enzyme poly(ADP-ribose)polymerase (“PARP”) are disclosed.

  本发明公开了异喹啉酮和二氢异喹啉酮及其衍生物的衍生物，以及它们在通过抑制酶聚(ADP-核糖)聚合酶（“PARP”）治疗疾病中作为药物的应用。
• ISOQUINOLINONE DERIVATIVES AS PARP INHIBITORS
  申请人：Kudos Pharmaceuticals Limited

  公开号：EP1397350A1

  公开（公告）日：2004-03-17
• US6664269B2
  申请人：——

  公开号：US6664269B2

  公开（公告）日：2003-12-16
• [EN] ISOQUINOLINONE DERIVATIVES AS PARP INHIBITORS<br/>[FR] DERIVES D'ISOQUINOLINONE COMME INHIBITEURS DE PARP
  申请人：KUDOS PHARM LTD

  公开号：WO2002090334A1

  公开（公告）日：2002-11-14

  The use of a compound of the formula (I) and isomers, salts, solvates, chemically protected forms, and prodrugs thereof, in the preparation of a medicament for inhibiting the activity of PARP, wherein A and B together represent an optionally substituted, fused aromatic ring, the dotted line between the 3 and 4 positions indicates the optional presence of a double bond, at least one of RC1 and RC2 is independently represented by -L-RL, and if one of RC1 and RC2 is not represented by -L-RL, then that group is H, where L is of formula: -(CH2)¿n1¿-Q¿n2?-(CH2)n3-wherein n1, n2 and n3 are each selected from 0, 1, 2 and 3, the sum of n1, n2 and n3 is 1, 2 or 3 and each Q (if n2 is greater than 1) is selected from O, S, NR3, C(=O), or -CR1R2-, where R1 and R2 are independently selected from hydrogen, halogen or optionally substituted C1-7 alkyl, or may together with the carbon atom to which they are attached form a C3-7 cyclic alkyl group, which may be saturated (a C3-7 cycloalkyl group) or unsaturated (a C3-7 cycloalkenyl group), or one of R1 and R2 may be attached to an atom in RL to form an unsaturated C3-7 cycloalkenyl group which comprises the carbon atoms to which R1 and R2 are attached in Q, -(CH2)n3- (if present) and part of RL, and where R3 is selected from H or C1-7 alkyl, and RL is selected from optionally substituted C3-20 heterocyclyl, C5-20 aryl and carbonyl, and RN is selected from hydrogen, optionally substituted C1-7 alkyl, C3-20 heterocyclyl, C5-20 aryl, hydroxy, ether, nitro, amino, thioether, sulfoxide and sulfone.
• Synthesis and effect of substituent position on anti-inflammatory activity of 3-(halobenzyl)isocarbostyrils
  作者：Tariq Mahmood Babar、Muhammad Moazzam Naseer、Farukh Iftakhar Ali、Nasim Hasan Rama、Taibi Ben Hadda

  DOI：10.1007/s00044-014-1027-8

  日期：2014.10

  skeleton based 3-(halobenzyl)isocarbostyrils (2a–2i), were designed and synthesized to examine the effect of position of different halide substituents on anti-inflammatory activity. The structure–activity relationship shows a significant influence of position of halide substituents on in vitro anti-inflammatory activity. 3-(o-halobenzyl)isocarbostyrils (2a, 2d, and 2g) showed the lowest activity most probably

  摘要设计并合成了一系列新的基于天然产物骨架的3-（卤代苄基）异羰基苯乙烯（2a – 2i），以研究不同卤化物取代基的位置对抗炎活性的影响。结构与活性的关系表明卤化物取代基的位置对体外抗炎活性具有重要影响。3-（邻卤代苄基）异咔唑（2a，2d和2g）表现出最低的活性，这很可能是由于卤化物与酰胺N–H之间的分子内氢键封闭了药效团的位置。相反，3-（对-卤代苄基）异咔唑2c，2f和2i表现出中等至非常好的炎症活性。发现化合物2c（IC 50  =  251.002±2.910）具有与标准药物（吲哚美辛，IC 50  =  271.210±2.127）相当的活性。为了进一步理解卤化物取代基的位置对3-（卤代苄基）异咔唑的影响，进行了计算POM。具有建设性命题的研究可能有助于设计更有效的类似物。 图形概要