2-[2-(4-庚基苯基)乙基]-6-羟基苯甲酸 | 1243583-85-8

• 物质功能分类: 生物化工 - 抑制剂 - 表观遗传学(Epigenetics)
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2-[2-(4-庚基苯基)乙基]-6-羟基苯甲酸
• 英文名称: MG149
• 英文别名: 2-(4-Heptylphenethyl)-6-hydroxybenzoic acid；2-[2-(4-heptylphenyl)ethyl]-6-hydroxybenzoic acid
• CAS: 1243583-85-8
• 化学式: C₂₂H₂₈O₃
• 分子量: 340.463
• InChiKey: WBHQYBZRTAEHRR-UHFFFAOYSA-N

物化性质

• 沸点：
  477.8±33.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO 中≥114 mg/mL；乙醇中≥30.5 mg/mL；不溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

制备方法与用途

生物活性

MG149 是一种强效的组蛋白乙酰转移酶（histone acetyltransferase）抑制剂，其对 Tip60 和 MOF 的半数抑制浓度（IC50）分别为 74 μM 和 47 μM。

体外研究

MG149 以乙酰辅酶 A 结合位点为靶点，能够抑制从小鼠不同大脑区域组织样本中提取的细胞核的乙酰转移酶活性。此外，MG149 还会抑制 p53 和 NF-κB 信号通路。

靶点

Target	Value
MOF (Cell-free assay)	47 μM
Tip60 (Cell-free assay)	74 μM

反应信息

• 作为产物：
  描述：

  5-(4-heptylphenethyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 在 水 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到2-[2-(4-庚基苯基)乙基]-6-羟基苯甲酸
  参考文献：
  名称：

  Improved inhibition of the histone acetyltransferase PCAF by an anacardic acid derivative

  摘要：

  Several lines of evidence indicate that histone acetyltransferases (HATs) are novel drug targets for treatment of diseases like, for example, cancer and inflammation. The natural product anacardic acid is a starting point for development of small molecule inhibitors of the histone acetyltransferase (HAT) p300/CBP associated factor (PCAF). In order to optimize the inhibitory potency, a binding model for PCAF inhibition by anacardic acid was proposed and new anacardic acid derivatives were designed. Ten new derivatives were synthesized using a novel synthetic route. One compound showed a twofold improved inhibitory potency for the PCAF HAT activity and a twofold improved inhibition of histone acetylation in HEP G2 cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.089

文献信息

• TARGETED EPIGENETIC THERAPY FOR INHERITED AORTIC ANEURYSM CONDITION
  申请人：The Johns Hopkins University

  公开号：EP3675880A1

  公开（公告）日：2020-07-08
• Compounds
  申请人：CTxT Pty Limited

  公开号：US20200039945A1

  公开（公告）日：2020-02-06

  A compound of formula (I), or a pharmaceutical salt thereof:
• Benzisoxazole Sulfonamide Derivatives
  申请人：Pfizer Inc.

  公开号：US20200399258A1

  公开（公告）日：2020-12-24

  The present invention relates to compounds of formula (1) or pharmaceutically acceptable salts thereof, wherein Ring A, R 1 -R 8 , and n are defined herein. The novel benzisoxazole sulfonamide derivatives are useful in the treatment of abnormal cell growth, such as cancer, in patients. Additional embodiments relate to pharmaceutical compositions containing the compounds and to methods of using the compounds and compositions in the treatment of abnormal cell growth in patients.
• Fused [1,2,4]Thiadiazine Derivatives Which Act as KAT Inhibitors of the MYST Family
  申请人：CTxT Pty Limited

  公开号：US20210380548A1

  公开（公告）日：2021-12-09

  A compound of formula (I): which inhibits the activity of one or more KATs of the MYST family, i.e., TIP60, KAT6B, MOZ, HBO1, and MOF.
• Cycloalkyl and Heterocycloalkyl Benzisoxazole Sulfonamide Derivatives
  申请人：Pfizer Inc.

  公开号：US20220251075A1

  公开（公告）日：2022-08-11

  The present invention relates to compounds of formula (I) or pharmaceutically acceptable salts thereof, wherein Ring A, Y, R 1 -R 8 , m, n and p are defined herein. The novel cycloalkyl and heterocycloalkyl benzisoxazole sulfonamide derivatives are useful in the treatment of abnormal cell growth, such as cancer, in patients. Additional embodiments relate to pharmaceutical compositions containing the compounds and to methods of using the compounds and compositions in the treatment of abnormal cell growth in patients.