ethyl (4-mercaptophenyl)carbamate | 73443-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (4-mercaptophenyl)carbamate
• 英文别名: ethyl N-(4-sulfanylphenyl)carbamate
• CAS: 73443-73-9
• 化学式: C₉H₁₁NO₂S
• mdl: MFCD18762126
• 分子量: 197.258
• InChiKey: BYGNGADJTTVVOD-UHFFFAOYSA-N

物化性质

• 沸点：
  265.9±23.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-<2-(1,1'-biphenyl-4-yl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl>methyl methanesulfonate 、 ethyl (4-mercaptophenyl)carbamate 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以96%的产率得到(+/-)-cis-[4-[[2-(1,1'-biphenyl-4-yl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methylthio]phenyl]carbamic acid ethyl ester
  参考文献：
  名称：

  New Structural Analogues of Tubulozole Induce Apoptosis, [Ca2+]i Modifications and Cytoskeletal Disorganization in Glial (GL15) and Neuronal-like (PC12) Cell Lines

  摘要：

  The synthesis and the biological activity of (+/-)-cis- and (+/-)-trans-[4-[[2-(1,1'-biphenyl-4-yl)-2-(1H-imidazol-1-ylmethyl)-1, 3-dioxolan-4-yl]methylthio]phenyl]carbamic acid ethyl esters (2a and 2b) are discussed. They were designed as structural analogues of Tubulozole, a synthetic tubulin polymerisation inhibitor with antimitotic properties. Biological tests were carried out on PC12, a neuronal-like cell line derived from rat pheochromocytoma, and on GL15, a cell line derived from human glioblastoma. The exposure (from 5 to 20 h) of GL15 and PC12 cells to different concentrations (0.1-1000 microM; IC50 approximately 1 microM) of 2a or 2b resulted in a drastic decrease in the number of viable cells without an apparent effect on the cell distribution in the various phases of the cell cycle. Compound 2a or 2b (10 microM) induced cell death by activating apoptosis. This was correlated with the activation of an oscillating Ca(2+)-dependent mechanism which increased the intracellular calcium concentration ([Ca2+]i) via Ca(2+)-release from internal stores. Moreover, 2a (10 microM) also induced severe damage of cytoskeletal F-actin filaments after a 5 h incubation in GL15 cells. This was also observed but to a smaller extent, for 2b. Under the same experimental conditions, PC12 cells showed similar actin deregulation.

  DOI：

  10.1002/1521-4184(200011)333:11<373::aid-ardp373>3.0.co;2-6
• 作为产物：
  描述：

  氯甲酸乙酯 、 4-氨基苯硫酚 在 碳酸氢钠 作用下， 以 petroleumether 、 二氯甲烷 、 异丙醚 为溶剂， 生成 ethyl (4-mercaptophenyl)carbamate
  参考文献：
  名称：

  (2-Aryl-4-phenylthioalkyl-1,3-dioxolan-2-ylmethyl)azole derivatives

  摘要：

  这项发明涉及一系列(2-芳基-4-苯基硫代烷基-1,3-二氧杂环戊烷-2-基甲基)唑类衍生物，可用作抗真菌和抗肿瘤药物。

  公开号：

  US04490540A1

文献信息

• Synthesis of Acetaminophen Analogues Containing α-Amino Acids and Fatty Acids for Inhibiting Hepatotoxicity
  作者：Seunghee Jung、Yuya Kawashima、Takuya Noguchi、Nobuyuki Imai

  DOI：10.1055/s-0037-1611893

  日期：2019.10

  reactive metabolite N-acetyl-p-benzoquinone imine (NAPQI). We have obtained acetaminophen analogues in 57–99% yields by using aniline derivatives with protected α-amino acids and fatty acids via the corresponding mixed carbonic carboxylic anhydrides in aqueous MeCN. We have also succeeded in synthesizing AM404 analogues in 76–97% yields, which are expected to be promising candidates for reducing hepatotoxicity

  献给EJ科里教授在他的90之际个生日。 抽象的 对乙酰氨基酚是一种流行的解热镇痛药，与非甾体类抗炎药（NSAIDs）相比，抗炎作用弱，副作用发生率低。然而，对乙酰氨基酚由于反应性代谢产物N-乙酰基-对苯醌亚胺（NAPQI）而引起肝毒性。通过在水性MeCN中通过相应的混合碳羧酸酐使用受保护的α-氨基酸和脂肪酸的苯胺衍生物，我们以57-99％的产率获得了对乙酰氨基酚类似物。我们还成功地以76–97％的产率合成了AM404类似物，有望降低肝毒性。 对乙酰氨基酚是一种流行的解热镇痛药，与非甾体类抗炎药（NSAIDs）相比，抗炎作用弱，副作用发生率低。然而，对乙酰氨基酚由于反应性代谢产物N-乙酰基-对苯醌亚胺（NAPQI）而引起肝毒性。通过在水性MeCN中通过相应的混合碳羧酸酐使用受保护的α-氨基酸和脂肪酸的苯胺衍生物，我们以57-99％的产率获得了对乙酰氨基酚类似物。我们还成功地以76–97％的产
• Compounds, compositions and anti-neoplastic methods
  申请人：Janssen Pharmaceutica N.V.

  公开号：US05236944A1

  公开（公告）日：1993-08-17

  Method of treating neoplasms hosting in mammals by administering a C.sub.1-4 alkyl [4-[2-(4-C.sub.1-4 alkylphenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl-thio]pheny l]carbamate. Pharmaceutical compositions containing the same as active ingredient. Compounds used in said method and process for preparing said compounds.

  通过给哺乳动物投予一种C.sub.1-4烷基[4-[2-(4-C.sub.1-4烷基苯基)-2-(1H-咪唑-1-基甲基)-1,3-二氧杂环戊烷-4-基硫基]苯基]氨基甲酸酯来治疗寄生肿瘤的方法。包含该物质作为活性成分的药物组合物。在该方法中使用的化合物以及制备该化合物的过程。
• METHOD FOR SCREENING DRUG AND THERAPEUTIC TARGET USED FOR TREATING ALZHEIMER'S DISEASE
  申请人：Jiangsu Nuo-Beta Pharmaceutical Technology Co., Ltd.

  公开号：EP3290525A1

  公开（公告）日：2018-03-07

  The present invention discloses that down-regulation of PI4KIIIα protein, RBO/EFR3/EFR3A/EFR3B protein, TTC7 protein, and amount of membrane protein complexes thereof or activities of related enzymes using genetic means or related inhibitors can facilitate Aβ (particularly Aβ42) secretion of neuron cells and correspondingly reduce intraneuronal Aβ accumulation, so as to ameliorate neural deficits in Drosophila and mouse AD models.

  本发明公开了利用基因手段或相关抑制剂下调PI4KⅢα蛋白、RBO/EFR3/EFR3A/EFR3B蛋白、TTC7蛋白及其膜蛋白复合物的量或相关酶的活性，可以促进神经元细胞分泌Aβ（尤其是Aβ42），相应减少神经元内Aβ的积累，从而改善果蝇和小鼠AD模型的神经缺陷。