4-(4-乙氧基甲酰苯)-3-氨基硫脲 | 70619-50-0

• 物质功能分类: 化学试剂 - 有机试剂 - 硫脲
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(4-乙氧基甲酰苯)-3-氨基硫脲
• 中文别名: 4-(4-乙氧基羰基苯基)-3-氨基硫脲
• 英文名称: 4-hydrazinothiocarbonylamino-benzoic acid ethyl ester
• 英文别名: 4-<4-Ethoxycarbonyl-phenyl>-thiosemicarbazid；4-(4-Ethoxycarbonyl-phenyl)-thiosemicarbazid；4-(4-Ethoxycarbonylphenyl)-3-thiosemicarbazide；ethyl 4-(aminocarbamothioylamino)benzoate
• CAS: 70619-50-0
• 化学式: C₁₀H₁₃N₃O₂S
• mdl: MFCD00079754
• 分子量: 239.298
• InChiKey: AFWIXYFUAGZASP-UHFFFAOYSA-N

物化性质

• 熔点：
  135-137°C

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  4-(4-乙氧基甲酰苯)-3-氨基硫脲 在 盐酸 、 sodium nitrite 作用下， 生成 4-[1,2,3,4]thiatriazol-5-ylamino-benzoic acid ethyl ester
  参考文献：
  名称：

  Dubenko,R.G. et al., Journal of general chemistry of the USSR, 1963, vol. 33, p. 266 - 268

  摘要：

  DOI：
• 作为产物：
  描述：

  4-乙氧羰基苯基硫代异氰酸酯 在 肼 作用下， 生成 4-(4-乙氧基甲酰苯)-3-氨基硫脲
  参考文献：
  名称：

  2-乙酰基吡啶硫代半脲酮。1.一类潜在的抗疟药。

  摘要：

  基于对2-乙酰基吡啶4-苯基-3-硫代半乳糖苷（1）观察到的抗疟疾特性，制备了一系列相关的硫代半胱氨酸并在小鼠中对柏氏疟原虫进行了测试。筛选结果表明2-吡啶基亚乙基的存在是关键的，并且在硫半脲部分的N 4处的某些苯基，苄基，苯乙基或环烷基也有助于抗疟活性。

  DOI：

  10.1021/jm00193a020

文献信息

• Discovery of Novel Bromophenol–Thiosemicarbazone Hybrids as Potent Selective Inhibitors of Poly(ADP-ribose) Polymerase-1 (PARP-1) for Use in Cancer
  作者：Chuanlong Guo、Lijun Wang、Xiuxue Li、Shuaiyu Wang、Xuemin Yu、Kuo Xu、Yue Zhao、Jiao Luo、Xiangqian Li、Bo Jiang、Dayong Shi

  DOI：10.1021/acs.jmedchem.8b01946

  日期：2019.3.28

  Poly(ADP-ribose) polymerase-1 (PARP-1) is a new potential target for anticancer drug discovery. A series of bromophenol-thiosemicarbazone hybrids as PARP-1 inhibitors were designed, synthesized, and evaluated for their antitumor activities. Among them, the most promising compound, 11, showed excellent selective PARP-1 inhibitory activity (IC50 = 29.5 nM) over PARP-2 (IC50 > 1000 nM) and potent anticancer

  聚（ADP-核糖）聚合酶-1（PARP-1）是抗癌药物发现的新潜在目标。设计，合成并评估了一系列作为PARP-1抑制剂的溴酚-硫代半碳杂zone杂化物的抗肿瘤活性。其中，最有前途的化合物11对PARP-2（IC50> 1000 nM）表现出优异的选择性PARP-1抑制活性（IC50 = 29.5 nM），并对SK-OV-3，Bel-7402和在体内SK-OV-3细胞异种移植模型中，HepG2癌细胞系（IC50 = 2.39、5.45和4.60μM）以及肿瘤生长的抑制作用。进一步的研究表明，化合物11通过多种抗癌机制发挥了抗肿瘤作用，包括诱导凋亡和细胞周期停滞，DNA双链断裂的细胞蓄积，DNA修复改变，抑制H2O2触发的PARylation，通过产生细胞毒性活性氧而产生的抗增殖作用以及自噬。另外，化合物11显示出良好的药代动力学特性和良好的安全性。这些观察表明，化合物11可以用作发现新的抗癌药物的先导化合物。
• Application of Sulfinyl bis(2,4‐dihydroxythiobenzoyl) in the Synthesis of N‐Substituted 2‐Amino‐5‐(2,4‐dihydroxyphenyl)‐1,3,4‐thiadiazoles
  作者：Joanna Matysiak、Andrzej Niewiadomy

  DOI：10.1080/00397910600591896

  日期：2006.6.1

  Abstract One‐stage synthesis of N‐substituted 2‐amino‐5‐(2,4‐dihydroxyphenyl)‐1,3,4‐thiadiazoles is described. The compounds were prepared by the reaction of the sulfinyl bis(2,4‐dihydroxythiobenzoyl) (STB) with 4‐substituted 3‐thiosemicarbazides. STB was obtained from 2,4‐dihydroxybenzenecarbodithioic acid and thionyl dichloride. The structure of compounds was confirmed by IR, 1H NMR, 13C NMR, and

  摘要描述了 N 取代的 2-氨基-5-(2,4-二羟基苯基)-1,3,4-噻二唑的一步合成。这些化合物是通过亚磺酰基双（2,4-二羟基硫代苯甲酰基）（STB）与 4-取代的 3-氨基硫脲反应制备的。STB 由 2,4-二羟基苯碳二硫代酸和亚硫酰二氯得到。化合物的结构经IR、1H NMR、13C NMR和EI-MS数据确证。
• Synthesis and anticonvulsant and neurotoxicity evaluation of N4-phthalimido phenyl (thio) semicarbazides
  作者：P Yogeeswari、D Sriram、V Saraswat、J.Vaigunda Ragavendran、M.Mohan Kumar、S Murugesan、R Thirumurugan、J.P Stables

  DOI：10.1016/j.ejps.2003.08.002

  日期：2003.11

  The phenyl (thio) semicarbazide derivatives of phthalimido pharmacophore were synthesized and evaluated for their anticonvulsant and neurotoxic properties. Initial anticonvulsant screening was performed using intraperitoneal (i.p.), maximal electroshock-induced seizure (MES), subcutaneous pentylenetetrazole (scPTZ) and subcutaneous strychnine (sc STY)-induced seizure threshold tests in mice. Compound

  合成了邻苯二甲酰亚胺药效基团的苯基（硫代）氨基脲衍生物，并对其抗惊厥和神经毒性特性进行了评估。在小鼠中使用腹膜内（ip），最大电击诱发的癫痫发作（MES），皮下戊烯四唑（scPTZ）和皮下士的宁（sc STY）诱发的癫痫发作阈值测试进行了初始抗惊厥筛选。化合物2c在所有三个屏幕中均提供了保护。除1d，2a和2d外的化合物在300 mg / kg以下均无神经毒性。发现化合物1a，1b，2c，2d，2g和2i具有口服MES活性。该化合物表现出中枢神经系统抑制和行为绝望的副作用，比常规的抗癫痫药要小。
• Efficient one-pot synthesis of substituted 2-amino-1,3,4-oxadiazoles
  作者：Eugene L. Piatnitski Chekler、Hassan M. Elokdah、John Butera

  DOI：10.1016/j.tetlet.2008.09.057

  日期：2008.11

  A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles has been developed. The method is a significant improvement over previously reported syntheses. Reaction of carboxylic acids with thiosemicarbazides afforded the corresponding oxadiazoles in moderate to good yields. In general, the products precipitated from the reaction mixture, and were collected by filtration. In most of the cases, no chromatographic separations were required. To explore the scope and limitations of this reaction, various aliphatic, aromatic, and heteroaromatic carboxylic acids were reacted with different substituted thiosemicarbazides. The influence of R-1 and R-2 substituents on the reaction yield and additional results demonstrating the versatility of this method are presented. (c) 2008 Elsevier Ltd. All rights reserved.
• Oxindole derivatives as inhibitors of TAK1 kinase
  作者：Jeffrey W. Lockman、Matthew D. Reeder、Rosann Robinson、Patricia A. Ormonde、Daniel M. Cimbora、Brandi L. Williams、J. Adam Willardsen

  DOI：10.1016/j.bmcl.2011.01.077

  日期：2011.3

  Several series of oxindole analogues were synthesized and screened for inhibitory activity against transforming growth factor-beta-activating kinase 1 (TAK1). Modifications around several regions of the lead molecules were made, with a distal hydroxyl group in the D region being critical for activity. The most potent compound 10 shows an IC50 of 8.9 nM against TAK1 in a biochemical enzyme assay, with compounds 3 and 6 showing low micromolar cellular inhibition. (C) 2011 Elsevier Ltd. All rights reserved.