4-(phenylthio)phthalimide | 343223-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-(phenylthio)phthalimide
• 英文别名: 5-(phenylthio)isoindoline-1,3-dione；4-(phenylsulfanyl)phthalimide；5-(Phenylsulfanyl)Phthalimide；5-phenylsulfanylisoindole-1,3-dione
• CAS: 343223-65-4
• 化学式: C₁₄H₉NO₂S
• 分子量: 255.297
• InChiKey: MTDTVBKMGPNHPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(phenylthio)phthalimide 、 cobalt(II) chloride 在 ammonium molybdate sodium sulfate 、 尿素 作用下， 以 neat (no solvent) 为溶剂， 以48%的产率得到cobalt tetra-(5-phenylsulfanyl)phthalocyanine
  参考文献：
  名称：

  Derkacheva, V. M.; Luk#yanets, E. A., Journal of general chemistry of the USSR, 1980, vol. 50, p. 1874 - 1878

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴邻苯二甲酸 在 copper(l) iodide 、 乙酸酐 、 potassium carbonate 、 尿素 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 4-(phenylthio)phthalimide
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship studies of morpholino-1H-phenalene derivatives that antagonize Mcl-1/Bcl-2

  摘要：

  We report herein characteristic studies of Mcl-1 and Bcl-2 dual inhibitors. It was found that a protruding carbonyl group forming hydrogen bond with R263 plays a predominant role compared with the hydrophobic group that occupies the p2 pocket. A series of dual inhibitors representing different parts of the morpholino-1H-phenalene were designed, synthesized and evaluated. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.047

文献信息

• Novel sulfanylphthalimide analogues as highly potent inhibitors of monoamine oxidase B
  作者：Mietha M. Van der Walt、Gisella Terre’Blanche、Anél Petzer、Jacobus P. Petzer

  DOI：10.1016/j.bmcl.2012.08.113

  日期：2012.11

  Monoamine oxidase (MAO) plays an essential role in the catabolism of neurotransmitter amines. The two isoforms of this enzyme, MAO-A and -B, are considered to be drug targets for the therapy of depression and neurodegenerative diseases, respectively. Based on a recent report that the phthalimide moiety may be a useful scaffold for the design of potent MAO-B inhibitors, the present study examines a series of 5-sulfanylphthalimide analogues as potential inhibitors of both human MAO isoforms. The results document that 5-sulfanylphthalimides are highly potent and selective MAO-B inhibitors with all of the examined compounds possessing IC50 values in the nanomolar range. The most potent inhibitor, 5-(benzylsulfanyl)phthalimide, exhibits an IC50 value of 0.0045 mu M for the inhibition of MAO-B with a 427-fold selectivity for MAO-B compared to MAO-A. We conclude that 5-sulfanylphthalimides represent an interesting class of MAO-B inhibitors and may serve as lead compounds for the design of antiparkinsonian therapy. (C) 2012 Elsevier Ltd. All rights reserved.
• Derkacheva, V. M.; Luk'yanets, E. A., Journal of general chemistry of the USSR, 1980, vol. 50, p. 1874 - 1878
  作者：Derkacheva, V. M.、Luk'yanets, E. A.

  DOI：——

  日期：——
• DERKACHEVA V. M.; LUKYANETS E. A., ZH. OBSHCH. XIMII, 1980, 50, HO 10, 2313-2318
  作者：DERKACHEVA V. M.、 LUKYANETS E. A.

  DOI：——

  日期：——
• Design, synthesis and structure–activity relationship studies of morpholino-1H-phenalene derivatives that antagonize Mcl-1/Bcl-2
  作者：Xiangqian Li、Xiaomeng Liang、Ting Song、Pengchen Su、Zhichao Zhang

  DOI：10.1016/j.bmc.2014.09.047

  日期：2014.11

  We report herein characteristic studies of Mcl-1 and Bcl-2 dual inhibitors. It was found that a protruding carbonyl group forming hydrogen bond with R263 plays a predominant role compared with the hydrophobic group that occupies the p2 pocket. A series of dual inhibitors representing different parts of the morpholino-1H-phenalene were designed, synthesized and evaluated. (C) 2014 Elsevier Ltd. All rights reserved.
• Derkacheva, V. M.; Luk#yanets, E. A., Journal of general chemistry of the USSR, 1980, vol. 50, p. 1874 - 1878
  作者：Derkacheva, V. M.、Luk#yanets, E. A.

  DOI：——

  日期：——