(±)-3-(1-(dimethylamino)ethyl)-5-methoxyphenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (±)-3-(1-(dimethylamino)ethyl)-5-methoxyphenol
• 英文别名: 3-[1-(Dimethylamino)ethyl]-5-methoxyphenol；3-[1-(dimethylamino)ethyl]-5-methoxyphenol
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: IRWWKQIKDXBZDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-3-(1-(dimethylamino)ethyl)-5-methoxyphenol 在 bis-triphenylphosphine-palladium(II) chloride 、 水 、 氢溴酸 、 sodium acetate 作用下， 反应 42.25h， 生成 (±)-3-(1-(dimethylamino)ethyl)-1-hydroxy-6H-benzo[c]chromen-6-one hydrochloride
  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：

  3,5-二羟基苯乙酮 在 magnesium sulfate 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 19.0h， 生成 (±)-3-(1-(dimethylamino)ethyl)-5-methoxyphenol
  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] 1 -(DIMETHYLAMINO)ETHYL-SUBSTITUTED 6H-BENZO[C]CHROMEN-6-ONES AGAINST SENILE DEMENTIA<br/>[FR] 6H-BENZO[C]CHROMEN-6-ONES SUBSTITUTÉES PAR 1 -(DIMÉTHYLAMINO)ÉTHYLE CONTRE LA DÉMENCE SÉNILE
  申请人：FARGEM FARMASÖTİK ARAŞTIRMA GELİŞTİRME MERKEZİ SANAYİİ V

  公开号：WO2014129990A1

  公开（公告）日：2014-08-28

  This invention relates to novel (±)1-(Dimethylamino)ethyl substituted 6H-benzo[c]chromen-6-one compounds which are useful as pharmaceutical compositions.

  这项发明涉及一种新型的(±)1-(二甲氨基)乙基取代的6H-苯并[c]色满-6-酮化合物，其可用作药物组合物。
• 1 -(DIMETHYLAMINO)ETHYL-SUBSTITUTED 6H-BENZO[C]CHROMEN-6-ONES AGAINST SENILE DEMENTIA
  申请人：UNLU Serdar

  公开号：US20160002194A1

  公开（公告）日：2016-01-07

  This invention relates to novel (±)1-(Dimethylamino)ethyl substituted 6H-benzo[c]chromen-6-one compounds which are useful as pharmaceutical compositions.

  本发明涉及一种新型的(±)1-(二甲氨基)乙基取代的6H-苯并[c]色烯-6-酮化合物，其可用作制备药物组合物。
• 1-(DIMETHYLAMINO)ETHYL-SUBSTITUTED 6H-BENZO[C]CHROMEN-6-ONES AGAINST SENILE DEMENTIA
  申请人：Nobel Ilaç Sanayii Ve Ticaret A.S.

  公开号：EP2922834B1

  公开（公告）日：2016-08-24
• US9586925B2
  申请人：——

  公开号：US9586925B2

  公开（公告）日：2017-03-07
• 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.