2-Fluoro-3-methoxybenzenecarbothioamide | 1415718-95-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Fluoro-3-methoxybenzenecarbothioamide
• 英文别名: 2-fluoro-3-methoxybenzenecarbothioamide
• CAS: 1415718-95-4
• 化学式: C₈H₈FNOS
• 分子量: 185.222
• InChiKey: NBTIJOGTPUGTDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Fluoro-3-methoxybenzenecarbothioamide 、 2-溴-3‘-甲氧基苯乙酮 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以32%的产率得到2-(2-Fluoro-3-methoxyphenyl)-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
• 作为产物：
  描述：

  2-fluoro-3-methoxybenzaldehyde oxime 在 劳森试剂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.03h， 生成 2-Fluoro-3-methoxybenzenecarbothioamide
  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.