2-(2,4-dimethoxyphenyl)-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one | 1592683-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2,4-dimethoxyphenyl)-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 2-(2,4-Dimethoxyphenyl)-6,7-dimethoxy-tetralin-1-one；2-(2,4-dimethoxyphenyl)-6,7-dimethoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 1592683-89-0
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: HJYMNQBTQOZCOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2,4-dimethoxyphenyl)-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 5,6-dihydronaphtho[1,2-b]benzofuran-2,3,9-triol
  参考文献：
  名称：

  5-Carba-pterocarpens: A new scaffold with anti-HCV activity

  摘要：

  The synthesis of a series of 5-carba-pterocarpens derivatives involving the cyclization of alpha-aryl-alpha-tetralones is described. Several compounds demonstrated potent activity and selectivity in vitro against HCV replicon reporter cells. The best profile in Huh7/Rep-Feolb replicon reporter cells was observed with 2h (EC50 = 5.5 mu M/SI = 20), while 2e was the most active in Huh7.5-FGR-JC1-Rluc2A replicon reporter cells (EC50 = 1.5 mu M/SI = 70). Hydroxy groups at A- and D-rings are essential for anti-HCV activity, and substitutions in the A-ring at positions 3 and 4 resulted in enhanced activity of the compounds. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2016.02.010
• 作为产物：
  描述：

  2,4-二甲氧基溴苯 、 6,7-二甲氧基-3,4-二氢-2H-1-萘酮 在 potassium hydroxide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.67h， 以77%的产率得到2-(2,4-dimethoxyphenyl)-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  5-Carbapterocarpens 合成 5-Carbapterocarpens 通过四氢酮的 α-芳基化，然后用 BBr3 进行一锅脱甲基/环化

  摘要：

  来自巴西机构 Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior（CAPES-DGU 项目编号 200/09）、Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq)、Fundacao de Amparo a Pesquisa do Estado do Rio de Janeiro (FAPERJ) 的财政支持感激地承认。西班牙国家科学与创新部长 (MICINN)（项目编号 PHB2008-0037-PC、CTQ2007-62771/BQU、CTQ2010-20387、Consolider INGENIO 2010 授权编号 CSD2007-00006），（项目编号 CSD2007-00006），(PROMETENEO/Generalita2

  DOI：

  10.1002/ejoc.201301505

文献信息

• Synthesis and biological evaluation of α-aryl-α-tetralone derivatives as hepatitis C virus inhibitors
  作者：Dinesh Manvar、Talita de A. Fernandes、Jorge L.O. Domingos、Erdenechimeg Baljinnyam、Amartya Basu、Eurides F.T. Junior、Paulo R.R. Costa、Neerja Kaushik-Basu

  DOI：10.1016/j.ejmech.2015.01.057

  日期：2015.3

  The synthesis of a novel series of 1-carba-isoflavanones through the α-arylation of α-tetralones is described. Several of these compounds demonstrated potent activity and selectivity in-vitro against HCV replicon reporter cells. Compound 10 (LQB-314) exhibited the best profile being active and selective in both replicon reporter cells (IC50 1.8 μM, SI > 111 and IC50 4.3 μM, SI > 46 in Huh7/Rep-Feo1b

  描述了通过α-四氢萘酮的α-芳基化合成一系列新的1-carba-异黄烷酮。这些化合物中的几种表现出对HCV复制子报道细胞的有效活性和体外选择性。化合物10（LQB- 314）在两个复制子报告子细胞中均表现出最佳的活性和选择性（IC 50 1.8μM，SI> 111和IC 50 4.3μM，SI> 46在Huh7 / Rep-Feo1b和Huh7.5-FGR中-JC1-Rluc2A）。化合物3（LQB-307）对Huh7.5-FGR-JC1-Rluc2A复制子报告基因细胞更具效力和选择性（IC 50 1.5μM ，SI> 101.4）。
• Synthesis of 5-Carbapterocarpens by α-Arylation of Tetralones Followed by One-Pot Demethylation/Cyclization with BBr₃
  作者：Talita de A. Fernandes、Jorge L. O. Domingos、Luiza I. A. da Rocha、Sabrina de Medeiros、Carmen Nájera、Paulo R. R. Costa

  DOI：10.1002/ejoc.201301505

  日期：2014.2

  Financial support from the Brazilian agencies Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES-DGU Project number 200/09), Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq), Fundacao de Amparo a Pesquisa do Estado do Rio de Janeiro (FAPERJ) is gratefully acknowledged. The Spanish Ministerio de Ciencia e Innovacion (MICINN) (project numbers PHB2008-0037-PC, CTQ2007-62771/BQU

  来自巴西机构 Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior（CAPES-DGU 项目编号 200/09）、Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq)、Fundacao de Amparo a Pesquisa do Estado do Rio de Janeiro (FAPERJ) 的财政支持感激地承认。西班牙国家科学与创新部长 (MICINN)（项目编号 PHB2008-0037-PC、CTQ2007-62771/BQU、CTQ2010-20387、Consolider INGENIO 2010 授权编号 CSD2007-00006），（项目编号 CSD2007-00006），(PROMETENEO/Generalita2
• 5-Carba-pterocarpens: A new scaffold with anti-HCV activity
  作者：Talita de A. Fernandes、Dinesh Manvar、Jorge L.O. Domingos、Amartya Basu、Daniel Brian Nichols、Neerja Kaushik-Basu、Paulo R.R. Costa

  DOI：10.1016/j.ejmech.2016.02.010

  日期：2016.4

  The synthesis of a series of 5-carba-pterocarpens derivatives involving the cyclization of alpha-aryl-alpha-tetralones is described. Several compounds demonstrated potent activity and selectivity in vitro against HCV replicon reporter cells. The best profile in Huh7/Rep-Feolb replicon reporter cells was observed with 2h (EC50 = 5.5 mu M/SI = 20), while 2e was the most active in Huh7.5-FGR-JC1-Rluc2A replicon reporter cells (EC50 = 1.5 mu M/SI = 70). Hydroxy groups at A- and D-rings are essential for anti-HCV activity, and substitutions in the A-ring at positions 3 and 4 resulted in enhanced activity of the compounds. Published by Elsevier Masson SAS.