7-benzyloxy-3-(4-methoxyphenyl)chroman-4-one | 10499-15-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-benzyloxy-3-(4-methoxyphenyl)chroman-4-one
• 英文别名: 7-benzyloxy-3-(4-methoxyphenyl)-3H-benzopyran-4-one；7-Benzyloxy-3-(4'-methoxyphenyl)-isoflavanon；7-Benzyloxy-4'-methoxy-isoflavanon；7-Benzyloxy-3-(4-methoxy-phenyl)-chroman-4-one；3-(4-methoxyphenyl)-7-phenylmethoxy-2,3-dihydrochromen-4-one
• CAS: 10499-15-7
• 化学式: C₂₃H₂₀O₄
• 分子量: 360.409
• InChiKey: AKJCDBZRKJRMKO-UHFFFAOYSA-N

物化性质

• 熔点：
  122-124 °C
• 沸点：
  558.0±50.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-3-(4-methoxyphenyl)chroman-4-one 在 5%-palladium/activated carbon 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到二氢芒柄花黄素
  参考文献：
  名称：

  Induction of targeted osteogenesis with 3-aryl- 2H -benzopyrans and 3-aryl- 3H -benzopyrans: Novel osteogenic agents

  摘要：

  Development of target oriented chemotherapeutics for treatment of chronic diseases have been considered as an important approach in drug development. Following this approach, in our efforts for exploration of new osteogenic leads, substituted 3-aryl-2H-benzopyran and 3-aryl-3H-benzopyran derivatives (19, 20a-e, 21, 22a-e, 26, 27, 28a-e, 29, 31a-b, 32 and 33) have been characterized as estrogen receptor-(3 selective osteogenic (bone forming) agents. The synthesized compounds were evaluated for osteogenic activity using mouse calvarial osteoblast cells. Four compounds viz 20b, 22a, 27and 32 showed significant osteogenic activity at EC50 values 1.35, 34.5, 407 and 29.5 pM respectively. Out of these, 20b and 32 were analyzed for their bone mineralization efficacy and osteogenic gene expression by qPCR. The results showed that 20b and 32 significantly increased mineral nodule formation and the transcript levels of BMP-2, RUNX-2 and osteocalcin at 100 pM concentrations respectively. Further mechanistic studies of 20b and 32 using transiently knocked down expression of ER-alpha and beta in mouse osteoblast (MOBs) showed that 20b and 32 exerts osteogenic efficacy via activation of estrogen receptor-beta preferentially. Additionally, compounds showed significant anticancer activity in a panel of cancer cell lines within the range of (IC50) 6.54-27.79 mu M. The most active molecule, 22b inhibited proliferation of cells by inducing apoptosis and arresting cell cycle at sub-G(0) phase with concomitant decrease in cells at S phase. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jsbmb.2016.01.010
• 作为产物：
  描述：

  1-(2,4-二羟基苯基)-2-(4-甲氧基苯基)乙酮 在 potassium carbonate 、 potassium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 生成 7-benzyloxy-3-(4-methoxyphenyl)chroman-4-one
  参考文献：
  名称：

  Induction of targeted osteogenesis with 3-aryl- 2H -benzopyrans and 3-aryl- 3H -benzopyrans: Novel osteogenic agents

  摘要：

  Development of target oriented chemotherapeutics for treatment of chronic diseases have been considered as an important approach in drug development. Following this approach, in our efforts for exploration of new osteogenic leads, substituted 3-aryl-2H-benzopyran and 3-aryl-3H-benzopyran derivatives (19, 20a-e, 21, 22a-e, 26, 27, 28a-e, 29, 31a-b, 32 and 33) have been characterized as estrogen receptor-(3 selective osteogenic (bone forming) agents. The synthesized compounds were evaluated for osteogenic activity using mouse calvarial osteoblast cells. Four compounds viz 20b, 22a, 27and 32 showed significant osteogenic activity at EC50 values 1.35, 34.5, 407 and 29.5 pM respectively. Out of these, 20b and 32 were analyzed for their bone mineralization efficacy and osteogenic gene expression by qPCR. The results showed that 20b and 32 significantly increased mineral nodule formation and the transcript levels of BMP-2, RUNX-2 and osteocalcin at 100 pM concentrations respectively. Further mechanistic studies of 20b and 32 using transiently knocked down expression of ER-alpha and beta in mouse osteoblast (MOBs) showed that 20b and 32 exerts osteogenic efficacy via activation of estrogen receptor-beta preferentially. Additionally, compounds showed significant anticancer activity in a panel of cancer cell lines within the range of (IC50) 6.54-27.79 mu M. The most active molecule, 22b inhibited proliferation of cells by inducing apoptosis and arresting cell cycle at sub-G(0) phase with concomitant decrease in cells at S phase. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jsbmb.2016.01.010

文献信息

• A Simple One-Pot Synthesis of Isoflavanones
  作者：Piero Valenti、Federica Belluti、Angela Rampa、Alessandra Bisi

  DOI：10.1080/00397919908085910

  日期：1999.11

  Abstract A new simple one-pot synthesis of isoflavanones 2 by reaction of benzyl 2-hydroxyphenylketones 1 with bis(dimethylamino)methane in boiling ethanol is described.

  摘要 描述了通过苄基 2-羟基苯基酮 1 与双（二甲氨基）甲烷在沸腾乙醇中反应的一种新的简单一锅法合成异黄酮 2。
• Synthesis of 1-Amino-5,6-diaryl-3-cyano-1<i>H</i>-pyridin-2-ones and 6,7-Diaryl-4-cyano-3-hydroxy-1<i>H</i>-[1,2]diazepines from Isoflavones
  作者：Mu-Lin Zhu、Zun-Ting Zhang、Dong Xue、Hui-Liang Hua、Yong Liang、Stanislaw F. Wnuk

  DOI：10.1002/hlca.201300246

  日期：2014.4

  The one‐step cyclocondensation of substituted isoflavones (=3‐phenyl‐4H‐1‐benzopyran‐4‐ones) with cyanoacetohydrazide in the presence of KOH afforded a mixture of 1‐amino‐5,6‐diaryl‐3‐cyano‐1H‐2‐pyridin‐2‐ones and 6,7‐diaryl‐4‐cyano‐3‐hydroxy‐1H‐[1,2]diazepines.

  在KOH存在的情况下，将取代的异黄酮（= 3-苯基-4 H -1-苯并吡喃-4-酮）与氰基乙酰肼进行一步式环缩合反应可得到1-氨基-5,6-二芳基-3-氰基的混合物1 H -2-吡啶-2-酮和6,7-二芳基-4-氰基-3-羟基-1 H -1，[1,2]二氮杂s。
• Efficient and Simple Synthesis of Substituted 3‐Phenyl‐7‐methoxybenzopyrans as Pseudo‐Vitamin‐D₃ Analogs
  作者：Atul Gupta、Suprabhat Ray

  DOI：10.1080/00397910701545056

  日期：2007.9.1

  An efficient and simple synthesis of substituted 3-phenyl-7-methoxybenzo-pyrans as pseudo-vitamin-D-3 analogs in good yields under mild reaction conditions is described.
• In vivo evaluation of substituted 3-phenyl,7-methoxy-benzopyrans as modified estrogens
  作者：Atul Gupta、Govind Keshri、M. M. Singh、Suprabhat Ray

  DOI：10.1007/s00044-009-9169-9

  日期：2010.2

  Substituted 3-phenyl,7-methoxy-benzopyran derivatives and vitamin D-3 (cholecalciferol, 1) were evaluated for their estrogen agonistic and antagonistic activities in immature female Sprague-Dawley rat model. The benzopyran derivatives 17 and 18, which were made as hybrids of estrogen and vitamin D-3 (pseudo vitamin D-3 analogs), showed significant estrogen agonistic activity (up to 48%) and weak estrogen antagonistic activity (up to 6%) at 10 mg/kg, whereas vitamin D-3 showed significant estrogen agonistic (82%) and antagonistic activities (39%) at 10 mg/kg.Substituted 3-phenyl, 7-methoxy-benzopyran derivavtives and vitamin-D3 (Cholecalciferol, 1) were evaluated for their estrogen agonistic and antagonistic activities in mature female Sprague-Dawley rat model. The benzopyran derivatives, which were made as hybrids of estrogen and vitamin-D3 (pseudo vitamin-D3 analogs), showed significant estrogen agonistic activity (upto 48%) and weak estrogen antagonistic activity (upto 6%) at 10 mg kg(-1). Whereas, vitamin-D3 showed significant estrogen agonistic (82%) and antagonistic activities (39%) at 10 mg kg(-1).