3-bromo-5-chloro-6-hydroxy-2-methylbenzaldehyde | 1310800-55-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-bromo-5-chloro-6-hydroxy-2-methylbenzaldehyde
• 英文别名: 5-Bromo-3-chloro-2-hydroxy-6-methylbenzaldehyde
• CAS: 1310800-55-5
• 化学式: C₈H₆BrClO₂
• 分子量: 249.491
• InChiKey: DIFGNIXPGMZTOH-UHFFFAOYSA-N

物化性质

• 熔点：
  55-57 °C
• 沸点：
  275.2±35.0 °C(Predicted)
• 密度：
  1.733±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-5-chloro-6-hydroxy-2-methylbenzaldehyde 在 盐酸羟胺 、 palladium diacetate 、 三溴化硼 、 sodium carbonate 、 potassium carbonate 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 22.08h， 生成 (E)-5-chloro-3'-fluoro-4,4'-dihydroxy-2-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：

  3-氯-2-羟基-6-甲基苯甲醛 在 溴 、 溶剂黄146 作用下， 反应 48.0h， 以43%的产率得到3-bromo-5-chloro-6-hydroxy-2-methylbenzaldehyde
  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

• EZH1/2抑制剂及其制备和抗肿瘤治疗中的应用
  申请人：江苏天士力帝益药业有限公司

  公开号：CN116496263A

  公开（公告）日：2023-07-28

  本发明涉及EZH1/2抑制剂及其制备和抗肿瘤治疗中的应用，具体包括式I或式II所示的化合物、或其氘代化合物、或其立体异构体、或其药学上可接受的盐，本发明进一步包括所述化合物的药物组合物，及它们作为EZH1/2抑制剂在制备治疗相关疾病的药物中的用途。
• WO2022272060A1
  申请人：——

  公开号：WO2022272060A1

  公开（公告）日：2022-12-29
• 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.