S-(2-phthalimido-ethyl)-isothiourea

• 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: S-(2-phthalimido-ethyl)-isothiourea
• 英文别名: S-(2-Phthalimido-aethyl)-isothioharnstoff；2-(1,3-Dioxoisoindolin-2-YL)ethyl carbamimidothioate；2-(1,3-dioxoisoindol-2-yl)ethyl carbamimidothioate
• 化学式: C₁₁H₁₁N₃O₂S
• mdl: MFCD00680228
• 分子量: 249.293
• InChiKey: XXNPWNLDWANULI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-(2-phthalimido-ethyl)-isothiourea 在 盐酸 、 氯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以460 g的产率得到2-苯二(甲)酰亚氨基乙烷磺酰氯
  参考文献：
  名称：

  一种2-苯二（甲）酰亚氨基乙烷磺酰氯的合成方法

  摘要：

  本发明公开了一种2‑苯二（甲）酰亚氨基乙烷磺酰氯的合成方法，具体的反应步骤如下：(1)以邻苯二甲酸酐和乙醇胺为原料，在适当的温度和溶剂中，制备得到N‑(2‑羟基乙基)邻苯二甲酰亚胺；(2)将步骤(1)中合成的N‑(2‑羟基乙基)邻苯二甲酰亚胺，在适当的温度和溶剂条件下，和硫脲反应得到异硫脲化合物；(3)将步骤(1)中合成的异硫脲化合物，在适当的氯化试剂、温度和溶剂条件下，反应得到2‑苯二(甲)酰亚氨基乙烷磺酰氯。本发明采用一条新颖的合成路线来制备2‑苯二(甲)酰亚氨基乙烷磺酰氯，使用本工艺所获得目标产物的纯度高，反应条件温和，收率高，操作简便方便，生产成本低，适合放大生产。

  公开号：

  CN109456251A
• 作为产物：
  描述：

  N-羟乙基酞酰亚胺 在 氯化亚砜 、 乙醇 、 硫脲 作用下， 生成 S-(2-phthalimido-ethyl)-isothiourea
  参考文献：
  名称：

  Pichat; Herbert, Bulletin de la Societe Chimique de France, 1958, p. 820

  摘要：

  DOI：

文献信息

• The Preparation of Some Amino Sulfonamides
  作者：Ellis Miller、James M. Sprague、L. W. Kissinger、Lane F. McBurney

  DOI：10.1021/ja01865a053

  日期：1940.8
• The Synthesis of Some Sulfur-Containing Amines
  作者：R. O. Clinton、C. M. Suter、S. C. Laskowski、Mary Jackman、W. Huber

  DOI：10.1021/ja01220a028

  日期：1945.4
• Low Molecular Weight Amidoximes that Act as Potent Inhibitors of Lysine-Specific Demethylase 1
  作者：Stuart Hazeldine、Boobalan Pachaiyappan、Nora Steinbergs、Shannon Nowotarski、Allison S. Hanson、Robert A. Casero、Patrick M. Woster

  DOI：10.1021/jm3002845

  日期：2012.9.13

  The recently discovered enzyme lysine-specific demethylase 1 (LSD1) plays an important role in the epigenetic control of gene expression, and aberrant gene silencing secondary to LSD1 dysregulation is thought to contribute to the development of cancer. We reported that (bis)guanidines, (bis)biguanides, and their urea- and thiourea isosteres are potent inhibitors of LSD1 and induce the re-expression of aberrantly silenced tumor suppressor genes in tumor cells in vitro. We now report a series of small molecule amidoximes that are moderate inhibitors of recombinant LSD1 but that produce dramatic changes in methylation at the histone 3 lysine 4 (H3K4) chromatin mark, a specific target of LSD1, in Calu-6 lung carcinoma cells. In addition, these analogues increase cellular levels of secreted frizzle-related protein (SFRP) 2, H-cadherin (HCAD), and the transcription factor GATA4. These compounds represent leads for an important new series of drug-like epigenetic modulators with the potential for use as antitumor agents.
• 498. Coenzyme A. Part II. Evidence for its formulation as a derivative of pantothenic acid-4? phosphate
  作者：J. Baddiley、E. M. Thain

  DOI：10.1039/jr9510002253

  日期：——
• B-CYCLODEXTRIN DERIVATIVES AND THEIR USE AGAINST ANTHRAX LETHAL TOXIN
  申请人：Hecht Sidney

  公开号：US20090005343A1

  公开（公告）日：2009-01-01

  The invention provides low molecular weight compounds that block the pore formed by protective antigen and inhibit anthrax toxin action. Structures of the compounds are derivatives of β-cyclodextrin. Per-substituted alkylamino derivatives displayed inhibitory activity, and they were protective against anthrax lethal toxin action at low micromolar concentrations. Also, the addition of one of the alkylamino derivatives to the bilayer lipid membrane with multiple PA channels caused a significant decrease in membrane conductance. Thus, the invention also provides methods for protection against anthrax toxicity.