3,5-Di-tert-butyl-4-methoxy-benzaldehyde oxime | 663604-13-5

• 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: 3,5-Di-tert-butyl-4-methoxy-benzaldehyde oxime
• 英文别名: N-[(3,5-Di-tert-butyl-4-methoxyphenyl)methylidene]hydroxylamine；N-[(3,5-ditert-butyl-4-methoxyphenyl)methylidene]hydroxylamine
• CAS: 663604-13-5
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: XXLMATAEGGLSON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 3,5-Di-tert-butyl-4-methoxy-benzaldehyde oxime 在 三乙胺盐酸盐 作用下， 以50%的产率得到(E)-(3,5-di-t-butyl)-4-methoxybenzaldehyde O-benzoyloxime
  参考文献：
  名称：

  Potent inhibitors of lipoprotein-associated phospholipase A2: Benzaldehyde O-heterocycle-4-carbonyloxime

  摘要：

  A series of multi-substituted oximes were prepared and their potencies for inhibiting-lipoprotein-associated phospholipase A(2) (Lp-PLA(2)) activity were evaluated in vitro. Among them, compounds 3a, 3b, and 3m were identified to display a micromolar potency for inhibiting Lp-PLA(2) in whole human plasma and isolated human LDL. Based on these results, structure-activity relationship was studied on modification of three parts of R-1, R-2, and R-3 to identify a potent pharmacophore for Lp-PLA(2). In an attempt to introduce various functional groups at R-2 and R-3, we discovered that replacement of less lipophilic groups led to an increase of inhibitory activity. Among the tested oxime derivatives, cyano- and morpholino-substituted analogue 4f at R-2 and R-3 had the highest potency with an IC50 value of 0.05 mu M in whole human plasma. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.031
• 作为产物：
  描述：

  3,5-di-tert-butyl-4-methoxybenzaldehyde 在 羟胺 、 sodium carbonate 作用下， 以95%的产率得到3,5-Di-tert-butyl-4-methoxy-benzaldehyde oxime
  参考文献：
  名称：

  Potent inhibitors of lipoprotein-associated phospholipase A2: Benzaldehyde O-heterocycle-4-carbonyloxime

  摘要：

  A series of multi-substituted oximes were prepared and their potencies for inhibiting-lipoprotein-associated phospholipase A(2) (Lp-PLA(2)) activity were evaluated in vitro. Among them, compounds 3a, 3b, and 3m were identified to display a micromolar potency for inhibiting Lp-PLA(2) in whole human plasma and isolated human LDL. Based on these results, structure-activity relationship was studied on modification of three parts of R-1, R-2, and R-3 to identify a potent pharmacophore for Lp-PLA(2). In an attempt to introduce various functional groups at R-2 and R-3, we discovered that replacement of less lipophilic groups led to an increase of inhibitory activity. Among the tested oxime derivatives, cyano- and morpholino-substituted analogue 4f at R-2 and R-3 had the highest potency with an IC50 value of 0.05 mu M in whole human plasma. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.031

文献信息

• (E)-Phenyl- and -heteroaryl-substituted O-benzoyl-(or acyl)oximes as lipoprotein-associated phospholipase A2 inhibitors
  作者：Tae-Sook Jeong、Mi Jeong Kim、Hana Yu、Kyung Soon Kim、Joong-Kwon Choi、Sung-Soo Kim、Woo Song Lee

  DOI：10.1016/j.bmcl.2004.11.063

  日期：2005.3

  A series of (E)-phenyl- and -heteroaryl- substituted O-benzoyl-(or acyl)oximes 3a-n were synthesized for evaluating their human lipoprotein-associated phospholiphase A(2) (Lp-PLA(2)) inhibitory activities. The less lipophilic derivatives 3a-c showed the most potent in vitro inhibitory activity on human Lp-PLA2. (c) 2004 Elsevier Ltd. All rights reserved.
• Potent inhibitors of lipoprotein-associated phospholipase A2: Benzaldehyde O-heterocycle-4-carbonyloxime
  作者：Hyung Jae Jeong、Yong-Dae Park、Ho-Yong Park、Il Yun Jeong、Tae-Sook Jeong、Woo Song Lee

  DOI：10.1016/j.bmcl.2006.08.031

  日期：2006.11

  A series of multi-substituted oximes were prepared and their potencies for inhibiting-lipoprotein-associated phospholipase A(2) (Lp-PLA(2)) activity were evaluated in vitro. Among them, compounds 3a, 3b, and 3m were identified to display a micromolar potency for inhibiting Lp-PLA(2) in whole human plasma and isolated human LDL. Based on these results, structure-activity relationship was studied on modification of three parts of R-1, R-2, and R-3 to identify a potent pharmacophore for Lp-PLA(2). In an attempt to introduce various functional groups at R-2 and R-3, we discovered that replacement of less lipophilic groups led to an increase of inhibitory activity. Among the tested oxime derivatives, cyano- and morpholino-substituted analogue 4f at R-2 and R-3 had the highest potency with an IC50 value of 0.05 mu M in whole human plasma. (c) 2006 Elsevier Ltd. All rights reserved.