3-(2-chloroethoxy)-6H-benzo[c]chromen-6-one | 1622846-52-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(2-chloroethoxy)-6H-benzo[c]chromen-6-one
• 英文别名: 3-(2-Chloroethoxy)benzo[c]chromen-6-one；3-(2-chloroethoxy)benzo[c]chromen-6-one
• CAS: 1622846-52-9
• 化学式: C₁₅H₁₁ClO₃
• 分子量: 274.704
• InChiKey: UWCMUUWRHQPSJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  1-苄基哌嗪 、 3-(2-chloroethoxy)-6H-benzo[c]chromen-6-one 在 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 0.61h， 生成 3-(2-(4-benzylpiperazin-1-yl)ethoxy)-6H-benzo[c]chromen-6-one dihydrochloride
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 6H-benzo[c]chromen-6-one, and 7,8,9,10-tetrahydro-benzo[c]chromen-6-one derivatives as potential cholinesterase inhibitors

  摘要：

  Hydroxylated 6H-benzo[c]chromen-6-one derivatives (i.e., urolithins) are the main bioavailable metabolites, and biomarkers of ellagitannins present in various nutrition. Although these dietaries, the sources of urolithins, are employed in folk medicine as cognitive enhancer in the treatment of Alzheimer's Disease, urolithins have negligible potential to inhibit acetylcholinesterase and butyrylcholinesterase enzymes, the validated targets of Alzheimer's Disease. Therefore, within this research, a series of 6H-benzo[c]chromen-6-one, and 7,8,9,10-tetrahydro-benzo[c]chromen-6-one derivatives has been designed, synthesized, and their biological activities were evaluated as potential acetylcholinesterase and butyrylcholinesterase inhibitors. The compounds synthesized exerted comparable activity in comparison to rivastigmine, galantamine, and donepezil both in in vitro and in vivo studies.

  DOI：

  10.1016/j.bmc.2014.08.016
• 作为产物：
  描述：

  2-碘苯甲酸 在 sodium ethanolate 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 7.5h， 生成 3-(2-chloroethoxy)-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 6H-benzo[c]chromen-6-one, and 7,8,9,10-tetrahydro-benzo[c]chromen-6-one derivatives as potential cholinesterase inhibitors

  摘要：

  Hydroxylated 6H-benzo[c]chromen-6-one derivatives (i.e., urolithins) are the main bioavailable metabolites, and biomarkers of ellagitannins present in various nutrition. Although these dietaries, the sources of urolithins, are employed in folk medicine as cognitive enhancer in the treatment of Alzheimer's Disease, urolithins have negligible potential to inhibit acetylcholinesterase and butyrylcholinesterase enzymes, the validated targets of Alzheimer's Disease. Therefore, within this research, a series of 6H-benzo[c]chromen-6-one, and 7,8,9,10-tetrahydro-benzo[c]chromen-6-one derivatives has been designed, synthesized, and their biological activities were evaluated as potential acetylcholinesterase and butyrylcholinesterase inhibitors. The compounds synthesized exerted comparable activity in comparison to rivastigmine, galantamine, and donepezil both in in vitro and in vivo studies.

  DOI：

  10.1016/j.bmc.2014.08.016

文献信息

• [EN] 3-SUBSTITUTED-6H-BENZO[C]CHROMEN-6-ONES AND 3-SUBSTITUTED-7,8,9,10-TETRAHYDRO-6H-BENZO[C]CHROMEN-6-ONES AGAINST SENILE DEMENTIA<br/>[FR] 6H-BENZO[C]CHROMÉN-6-ONES 3 SUBSTITUÉES ET 7,8,9,10-TÉTRAHYDRO-6H-BENZO[C]CHROMÉN-6-ONES 3 SUBSTITUÉES CONTRE LA DÉMENCE SÉNILE
  申请人：FARGEM FARMASÖTİK ARAŞTIRMA GELİŞTİRME MERKEZİ SANAYİ VE T&Id

  公开号：WO2014129989A1

  公开（公告）日：2014-08-28

  This invention is related with the conversion of xenobiotics to potent ACHE and BCHE inhibitors that have activity comparable to the current ACHE and BCHE inhibitor drugs (i.e., donepezil, rivastigmine, and galantamine).

  这项发明涉及将异物转化为具有与当前阿托品酯酶（ACHE）和丁酰胆碱酯酶（BCHE）抑制剂药物（如多奈哌齐、利伏韦明和加兰他明）相当活性的化合物。
• 3-SUBSTITUTED-6H-BENZO[C]CHROMEN-6-ONES AND 3-SUBSTITUTED-7,8,9,10-TETRAHYDRO-6H-BENZO[C]CHROMEN-6-ONES AGAINST SENILE DEMENTIA
  申请人：Nobel Ilaç Sanayii Ve Ticaret A.S.

  公开号：EP2958906A1

  公开（公告）日：2015-12-30
• Design, synthesis and biological evaluation of novel 6H-benzo[c]chromen-6-one, and 7,8,9,10-tetrahydro-benzo[c]chromen-6-one derivatives as potential cholinesterase inhibitors
  作者：Hayrettin Ozan Gulcan、Serdar Unlu、İlker Esiringu、Tugba Ercetin、Yasemin Sahin、Demet Oz、Mustafa Fethi Sahin

  DOI：10.1016/j.bmc.2014.08.016

  日期：2014.10

  Hydroxylated 6H-benzo[c]chromen-6-one derivatives (i.e., urolithins) are the main bioavailable metabolites, and biomarkers of ellagitannins present in various nutrition. Although these dietaries, the sources of urolithins, are employed in folk medicine as cognitive enhancer in the treatment of Alzheimer's Disease, urolithins have negligible potential to inhibit acetylcholinesterase and butyrylcholinesterase enzymes, the validated targets of Alzheimer's Disease. Therefore, within this research, a series of 6H-benzo[c]chromen-6-one, and 7,8,9,10-tetrahydro-benzo[c]chromen-6-one derivatives has been designed, synthesized, and their biological activities were evaluated as potential acetylcholinesterase and butyrylcholinesterase inhibitors. The compounds synthesized exerted comparable activity in comparison to rivastigmine, galantamine, and donepezil both in in vitro and in vivo studies.