2-(4-Bromo-2-methylphenyl)-4-(3-methoxyphenyl)-1,3-thiazole | 1415718-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-Bromo-2-methylphenyl)-4-(3-methoxyphenyl)-1,3-thiazole
• 英文别名: 2-(4-bromo-2-methylphenyl)-4-(3-methoxyphenyl)-1,3-thiazole
• CAS: 1415718-90-9
• 化学式: C₁₇H₁₄BrNOS
• 分子量: 360.274
• InChiKey: HASARKNBHJJUMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-3‘-甲氧基苯乙酮 、 4-溴-2-甲基硫代苯甲酰胺 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以49%的产率得到2-(4-Bromo-2-methylphenyl)-4-(3-methoxyphenyl)-1,3-thiazole
  参考文献：
  名称：

  Optimization of thiazole analogues of resveratrol for induction of NAD(P)H:quinone reductase 1 (QR1)

  摘要：

  NAD(P)H:quinone reductase 1 (QR1) belongs to a class of enzymes called cytoprotective enzymes. It exhibits its cancer protective activity mainly by inhibiting the formation of intracellular semiquinone radicals, and by generating alpha-tocopherolhydroquinone, which acts as a free radical scavenger. It is therefore believed that QR1 inducers can act as cancer chemopreventive agents. Resveratrol (1) is a naturally occurring stilbene derivative that requires a concentration of 21 mu M to double QR1 activity (CD = 21 mu M). The stilbene double bond of resveratrol was replaced with a thiadiazole ring and the phenols were eliminated to provide a more potent and selective derivative 2 (CD = 2.1 mu M). Optimizing the substitution pattern of the two phenyl rings and the central heterocyclic linker led to a highly potent and selective QR1 inducer 9o with a CD value of 0.087 mu M. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.006

文献信息

• Optimization of thiazole analogues of resveratrol for induction of NAD(P)H:quinone reductase 1 (QR1)
  作者：Abdelrahman S. Mayhoub、Laura Marler、Tamara P. Kondratyuk、Eun-Jung Park、John M. Pezzuto、Mark Cushman

  DOI：10.1016/j.bmc.2012.10.006

  日期：2012.12

  NAD(P)H:quinone reductase 1 (QR1) belongs to a class of enzymes called cytoprotective enzymes. It exhibits its cancer protective activity mainly by inhibiting the formation of intracellular semiquinone radicals, and by generating alpha-tocopherolhydroquinone, which acts as a free radical scavenger. It is therefore believed that QR1 inducers can act as cancer chemopreventive agents. Resveratrol (1) is a naturally occurring stilbene derivative that requires a concentration of 21 mu M to double QR1 activity (CD = 21 mu M). The stilbene double bond of resveratrol was replaced with a thiadiazole ring and the phenols were eliminated to provide a more potent and selective derivative 2 (CD = 2.1 mu M). Optimizing the substitution pattern of the two phenyl rings and the central heterocyclic linker led to a highly potent and selective QR1 inducer 9o with a CD value of 0.087 mu M. (C) 2012 Elsevier Ltd. All rights reserved.