1-bromo-3-(4-octylphenoxy)propan-2-one | 1214281-87-4

• 英文名称: 1-bromo-3-(4-octylphenoxy)propan-2-one
• CAS: 1214281-87-4
• 化学式: C₁₇H₂₅BrO₂
• 分子量: 341.288
• InChiKey: IQNAAXGXCZQAHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  20.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  咪唑 、 1-bromo-3-(4-octylphenoxy)propan-2-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以35%的产率得到1-imidazol-1-yl-3-(4-octylphenoxy)propan-2-one
  参考文献：
  名称：

  1-Indol-1-yl-propan-2-ones and related heterocyclic compounds as dual inhibitors of cytosolic phospholipase A2α and fatty acid amide hydrolase

  摘要：

  Cytosolic phospholipase A(2)alpha (cPLA(2)alpha) and fatty acid amide hydrolase (FAAH) are enzymes, which have emerged as attractive targets for the development of analgetic and anti-inflammatory drugs. We recently reported that 1-[3-(4-octylphenoxy)-2-oxopropyl]indole-5-carboxylic acid (10) and related compounds are inhibitors of cPLA(2)alpha. Since cPLA(2)alpha and FAAH possess several common structural features, we now screened this substance series together with some new derivatives for FAAH inhibition. Some of the assayed compounds proved to be selective cPLA(2)alpha inhibitors, while others showed high FAAH and moderate cPLA(2)alpha inhibitory potency. Furthermore, several derivatives were favorably active against both enzymes and, therefore, could represent agents, which have improved analgetic and anti-inflammatory qualities in comparison with selective cPLA(2)alpha and FAAH inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.028
• 作为产物：
  描述：

  1-bromo-3-(4-octylphenoxy)propan-2-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以82%的产率得到1-bromo-3-(4-octylphenoxy)propan-2-one
  参考文献：
  名称：

  1-Indol-1-yl-propan-2-ones and related heterocyclic compounds as dual inhibitors of cytosolic phospholipase A2α and fatty acid amide hydrolase

  摘要：

  Cytosolic phospholipase A(2)alpha (cPLA(2)alpha) and fatty acid amide hydrolase (FAAH) are enzymes, which have emerged as attractive targets for the development of analgetic and anti-inflammatory drugs. We recently reported that 1-[3-(4-octylphenoxy)-2-oxopropyl]indole-5-carboxylic acid (10) and related compounds are inhibitors of cPLA(2)alpha. Since cPLA(2)alpha and FAAH possess several common structural features, we now screened this substance series together with some new derivatives for FAAH inhibition. Some of the assayed compounds proved to be selective cPLA(2)alpha inhibitors, while others showed high FAAH and moderate cPLA(2)alpha inhibitory potency. Furthermore, several derivatives were favorably active against both enzymes and, therefore, could represent agents, which have improved analgetic and anti-inflammatory qualities in comparison with selective cPLA(2)alpha and FAAH inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.028

文献信息

• 1-Heteroarylpropan-2-ones as inhibitors of fatty acid amide hydrolase: Studies on structure-activity relationships and metabolic stability
  作者：Stefan Zahov、David Garzinsky、Walburga Hanekamp、Matthias Lehr

  DOI：10.1016/j.bmc.2016.11.025

  日期：2017.2

  The serine hydrolase fatty acid amide hydrolase (FAAH) catalyzes the degradation of the endocannabinoid anandamide, which possesses analgesic and anti-inflammatory effects. A new series of 1-heteroarylpropan-2-ones was synthesized and evaluated for FAAH inhibition. Structure-activity relationship studies revealed that 1H-benzotriazol-1-yl, 1H-7-azabenzotriazol-1-yl, 1H-tetrazol-1-yl and 2H-tetrazol-2-yl

  丝氨酸水解酶脂肪酸酰胺水解酶（FAAH）催化内源性大麻素anandamide的降解，具有镇痛和抗炎作用。合成了一系列新的1-杂芳基丙烷-2-酮，并评估了其对FAAH的抑制作用。结构-活性关系研究表明，1 H-苯并三唑-1-基，1 H -7-氮杂苯并三唑-1-基，1 H-四唑-1-基和2 H-四唑-2-基对取代的影响最大。抑制力。此外，尝试通过在该丝氨酸反应性基团附近引入屏蔽的烷基取代基来增加这些化合物的酮官能团的有限的代谢稳定性，以降低代谢。