6-(3-chloropropoxy)benzofuran-3-one | 113500-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 6-(3-chloropropoxy)benzofuran-3-one
• 英文别名: 6-(3-Chloropropoxy)-3-(2H)-benzofuranone；6-(3-chloropropyloxy)coumaran-3-one；Benzofuran-3(2H)-one, 6-(3-chloropropoxy)-；6-(3-chloropropoxy)-1-benzofuran-3-one
• CAS: 113500-08-6
• 化学式: C₁₁H₁₁ClO₃
• mdl: MFCD02089546
• 分子量: 226.66
• InChiKey: HUQBKGMQOOKCMY-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °C(Solv: toluene (108-88-3))
• 沸点：
  395.6±42.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(3-chloropropoxy)benzofuran-3-one 在 sodium hydroxide 、 sodium iodide 作用下， 以 乙醇 、 甲苯 、 丁酮 为溶剂， 反应 23.0h， 生成 (Z)-6-{3-[(3-hydroxybenzyl)methylamino]propoxy}-2-naphthalen-1-ylmethylenebenzofuran-3-one
  参考文献：
  名称：

  Cholinesterase Inhibitors:  Xanthostigmine Derivatives Blocking the Acetylcholinesterase-Induced β-Amyloid Aggregation

  摘要：

  In continuing research that led us to identify a now class of carbamate derivatives acting as potent (Rampa et al. J. Med. Chem. 1998, 41, 3976) and long-lasting (Rampa et al. J. Med. Chem. 2001, 44, 3810) acetylcholinesterase (AChE) inhibitors, we obtained sonic analogues able to simultaneously block both the catalytic and the beta-amyloid (A beta) proaggregatory activities of AChE. The key feature of these derivatives is a 2-arylidenebenzocycloalkanone moiety that provides the ability to bind at the AChE peripheral site responsible for promoting the A beta aggregation. The new carbamates were tested in vitro for the inhibition of both cholinesterases and also for the ability to prevent the AChE-induced All aggregation. All of the compounds had AChE IC50 values in the nanomolar range and showed the ability to block the AChE-induced A beta aggregation, thus supporting the feasibility of this new strategy in the search of compounds for the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm049515h
• 作为产物：
  描述：

  6-羟基-2H-苯并呋喃-3-酮 、 1-溴-3-氯丙烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以95%的产率得到6-(3-chloropropoxy)benzofuran-3-one
  参考文献：
  名称：

  Cholinesterase Inhibitors:  Xanthostigmine Derivatives Blocking the Acetylcholinesterase-Induced β-Amyloid Aggregation

  摘要：

  In continuing research that led us to identify a now class of carbamate derivatives acting as potent (Rampa et al. J. Med. Chem. 1998, 41, 3976) and long-lasting (Rampa et al. J. Med. Chem. 2001, 44, 3810) acetylcholinesterase (AChE) inhibitors, we obtained sonic analogues able to simultaneously block both the catalytic and the beta-amyloid (A beta) proaggregatory activities of AChE. The key feature of these derivatives is a 2-arylidenebenzocycloalkanone moiety that provides the ability to bind at the AChE peripheral site responsible for promoting the A beta aggregation. The new carbamates were tested in vitro for the inhibition of both cholinesterases and also for the ability to prevent the AChE-induced All aggregation. All of the compounds had AChE IC50 values in the nanomolar range and showed the ability to block the AChE-induced A beta aggregation, thus supporting the feasibility of this new strategy in the search of compounds for the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm049515h

文献信息

• NOVEL AMINES AND THEIR USE
  申请人：MITSUI PETROCHEMICAL INDUSTRIES, LTD.

  公开号：EP0424525A1

  公开（公告）日：1991-05-02

  Amines represented by general formula (1) and acid addition salts and quaternary ammonium salts thereof are disclosed. The amines represented by formula (1) or pharmaceutically acceptable acid addition salts and quaternary ammonium salts thereof are useful for treatment and prophylaxis of heart diseases of animals, particularly arrhythmia, myocardial infarction, angina pectoris, cardiac failure, etc.

  本发明公开了通式（1）代表的胺及其酸加成盐和季铵盐。由式（1）代表的胺或其药学上可接受的酸加成盐和季铵盐可用于治疗和预防动物的心脏疾病，特别是心律失常、心肌梗塞、心绞痛、心力衰竭等。
• Phenyl and heterocyclic tetrahydropyridyl and piperazinyl alkoxy-benzheterocyclic compounds as antipsychotic agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0237781B1

  公开（公告）日：1991-04-24
• US4704390A
  申请人：——

  公开号：US4704390A

  公开（公告）日：1987-11-03
• US4803203A
  申请人：——

  公开号：US4803203A

  公开（公告）日：1989-02-07
• US5192799A
  申请人：——

  公开号：US5192799A

  公开（公告）日：1993-03-09