2-chloro-4,4'-dimethoxy-5-methylbiphenyl-3-carbaldehyde | 1310800-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-4,4'-dimethoxy-5-methylbiphenyl-3-carbaldehyde
• 英文别名: 2-Chloro-6-methoxy-3-(4-methoxyphenyl)-5-methylbenzaldehyde
• CAS: 1310800-62-4
• 化学式: C₁₆H₁₅ClO₃
• 分子量: 290.746
• InChiKey: XOOWWHVHGJZCSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  2-chloro-4,4'-dimethoxy-5-methylbiphenyl-3-carbaldehyde 在 盐酸羟胺 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.08h， 生成 (E)-2-chloro-4,4'-dihydroxy-5-methylbiphenyl-3-carbaldehyde oxime
  参考文献：
  名称：

  Selective and potent agonists for estrogen receptor beta derived from molecular refinements of salicylaldoximes

  摘要：

  In a continuing effort to improve the subtype selectivity and agonist potency of estrogen receptor beta (ER beta) ligands, we have designed and developed a thus far unexplored structural series obtained by molecular refinements of monoaryl-substituted salicylaldoximes (Salaldox B). The most interesting compounds in this series (2c, d) show remarkably high ER beta-binding affinities, with K(i) values reaching the sub-nanomolar range (K(i) = 0.38 nM for 2c and 0.57 nM for 2d), and have very high levels of ER beta-subtype selectivity. Both compounds show a potent full agonist character on ER beta (EC(50) = 0.23 nM for 2c and 1.3 nM for 2d). Furthermore, 2d shows a remarkable functional subtype selectivity, with a beta/alpha transcription potency ratio 50-fold higher than that of estradiol. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.030
• 作为产物：
  描述：

  5-氯-2-甲基苯酚 在 sodium periodate 、 四氧化锇 、 potassium tert-butylate 、 水 、 溴 、 palladium diacetate 、 sodium carbonate 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 二甲基亚砜 、 丙酮 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 72.0h， 生成 2-chloro-4,4'-dimethoxy-5-methylbiphenyl-3-carbaldehyde
  参考文献：
  名称：

  Selective and potent agonists for estrogen receptor beta derived from molecular refinements of salicylaldoximes

  摘要：

  In a continuing effort to improve the subtype selectivity and agonist potency of estrogen receptor beta (ER beta) ligands, we have designed and developed a thus far unexplored structural series obtained by molecular refinements of monoaryl-substituted salicylaldoximes (Salaldox B). The most interesting compounds in this series (2c, d) show remarkably high ER beta-binding affinities, with K(i) values reaching the sub-nanomolar range (K(i) = 0.38 nM for 2c and 0.57 nM for 2d), and have very high levels of ER beta-subtype selectivity. Both compounds show a potent full agonist character on ER beta (EC(50) = 0.23 nM for 2c and 1.3 nM for 2d). Furthermore, 2d shows a remarkable functional subtype selectivity, with a beta/alpha transcription potency ratio 50-fold higher than that of estradiol. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.030

文献信息

• Selective and potent agonists for estrogen receptor beta derived from molecular refinements of salicylaldoximes
  作者：Simone Bertini、Andrea De Cupertinis、Carlotta Granchi、Barbara Bargagli、Tiziano Tuccinardi、Adriano Martinelli、Marco Macchia、Jillian R. Gunther、Kathryn E. Carlson、John A. Katzenellenbogen、Filippo Minutolo

  DOI：10.1016/j.ejmech.2011.03.030

  日期：2011.6

  In a continuing effort to improve the subtype selectivity and agonist potency of estrogen receptor beta (ER beta) ligands, we have designed and developed a thus far unexplored structural series obtained by molecular refinements of monoaryl-substituted salicylaldoximes (Salaldox B). The most interesting compounds in this series (2c, d) show remarkably high ER beta-binding affinities, with K(i) values reaching the sub-nanomolar range (K(i) = 0.38 nM for 2c and 0.57 nM for 2d), and have very high levels of ER beta-subtype selectivity. Both compounds show a potent full agonist character on ER beta (EC(50) = 0.23 nM for 2c and 1.3 nM for 2d). Furthermore, 2d shows a remarkable functional subtype selectivity, with a beta/alpha transcription potency ratio 50-fold higher than that of estradiol. (C) 2011 Elsevier Masson SAS. All rights reserved.