3-(4-methylphenyl)propenoyl isothiocyanate | 19495-09-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(4-methylphenyl)propenoyl isothiocyanate
• 英文别名: 3-(4-Methylphenyl)prop-2-enoyl isothiocyanate
• CAS: 19495-09-1
• 化学式: C₁₁H₉NOS
• 分子量: 203.265
• InChiKey: DROXWCKLMKAZAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-methylphenyl)propenoyl isothiocyanate 在 三氟化硼乙醚 作用下， 以 氯仿 、 苯 为溶剂， 反应 25.5h， 生成 S-trideuteriomethyl N-(3-(4-methylphenyl)propenoyl)thiocarbamate
  参考文献：
  名称：

  Dzurilla, Milan; Kutschy, Peter; Koscik, Dusan, Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 3, p. 710 - 717

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲基肉桂酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-(4-methylphenyl)propenoyl isothiocyanate
  参考文献：
  名称：

  A novel serine racemase inhibitor suppresses neuronal over-activation in vivo

  摘要：

  Serine racemase (SRR) is an enzyme that produces o-serine from L-serine. D-Serine acts as an endogenous coagonist of NMDA-type glutamate receptors (NMDARs), which regulate many physiological functions. Over-activation of NMDARs induces excitotoxicity, which is observed in many neurodegenerative disorders and epilepsy states. In our previous works on the generation of SRR gene knockout (Srr-KO) mice and its protective effects against NMDA- and A beta peptide-induced neurodegeneration, we hypothesized that the regulation of NMDARs' over-activation by inhibition of SRR activity is one such therapeutic strategy to combat these disease states. In the previous study, we performed in silico screening to identify four compounds with inhibitory activities against recombinant SRR. Here, we synthesized 21 derivatives of candidate 1, one of four hit compounds, and performed screening by in vitro evaluations. The derivative 13J showed a significantly lower IC50 value in vitro, and suppressed neuronal over-activation in vivo. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.05.011

文献信息

• Dzurilla,M.; Kristian,P., Collection of Czechoslovak Chemical Communications, 1976, vol. 41, p. 1388 - 1395
  作者：Dzurilla,M.、Kristian,P.

  DOI：——

  日期：——
• Imrich, Jan; Kristian, Pavol; Podhradsky, Dusan, Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 8, p. 2334 - 2342
  作者：Imrich, Jan、Kristian, Pavol、Podhradsky, Dusan、Dzurilla, Milan

  DOI：——

  日期：——
• Dzurilla, Milan; Kristian, Pavol; Kutschy, Peter, Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 11, p. 2958 - 2964
  作者：Dzurilla, Milan、Kristian, Pavol、Kutschy, Peter

  DOI：——

  日期：——