4-Dimethylamino-benzoylisothiocyanat | 63193-70-4

• 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: 4-Dimethylamino-benzoylisothiocyanat
• 英文别名: 4-dimethylamino-benzoyl isothiocyanate；4-(Dimethylamino)benzoyl isothiocyanate
• CAS: 63193-70-4
• 化学式: C₁₀H₁₀N₂OS
• 分子量: 206.268
• InChiKey: CLOUWRFZOHCLMU-UHFFFAOYSA-N

物化性质

• 熔点：
  58-65 °C
• 沸点：
  337.2±25.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基丁醇 、 4-Dimethylamino-benzoylisothiocyanat 以 二氯甲烷 为溶剂， 反应 18.0h， 以0.40 g的产率得到(R)-4-(dimethylamino)-N-(1-hydroxybutan-2-ylcarbamothioyl)benzamide
  参考文献：
  名称：

  Efficient synthesis of new (R)-2-amino-1-butanol derived ureas, thioureas and acylthioureas and in vitro evaluation of their antimycobacterial activity

  摘要：

  The synthesis of 22 structurally diverse urea, thiourea and acylthiourea derivatives containing the (R)-2-amino-1-butanol motif has been performed. The evaluation of their in vitro activity against Mycobacterium tuberculosis (H(37)Rv and strain 43) showed promising results in the case of the acylthiourea derivatives (MIC range 0.36-7.46 mu M for H(37)Rv strain). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.034
• 作为产物：
  描述：

  4-二甲氨基苯甲酰氯 、 lead(II) thiocyanate 在 苯 作用下， 生成 4-Dimethylamino-benzoylisothiocyanat
  参考文献：
  名称：

  Muraw'ewa; Sytschewa, Zhurnal Obshchei Khimii, 1956, vol. 26, p. 898,900; engl. Ausg. S. 1021, 1023

  摘要：

  DOI：

文献信息

• Intramolecular Hydrogen Bonding and Anion Binding of <i>N</i>-Benzamido-<i>N</i>‘-benzoylthioureas
  作者：Wen-Xia Liu、Yun-Bao Jiang

  DOI：10.1021/jo702159r

  日期：2008.2.1

  N-acylthiourea is known to be unable to bind anions due to a strong intramolecular hydrogen bond (IHB). We show here that by inserting an amido group in the N‘-phenyl side the newly designed N-benzamido-N‘-benzoylthioureas, despite this IHB too, bind strongly to anions with binding constants on the order of 106−107 mol-1 L. Results suggest that potential anion receptors or organocatalysts could be developed

  ñ - （p二甲基氨基）苯甲酰基Ñ “-phenylthiourea作为ñ -acylthiourea已知是不能结合的阴离子由于强的分子内氢键（IHB）。我们在这里表明，通过在N'-苯基侧插入一个酰胺基，尽管有这种IHB，新设计的N-苯甲酰胺基-N'-苯甲酰硫脲也能以10 6 -10 7 mol的结合常数牢固地与阴离子结合- 1个L.结果表明，潜在的阴离子受体或有机催化剂可能具有广泛的结构多样性这一框架的基础上进行开发。
• Rational design and optimization of acylthioureas as novel potent influenza virus non-nucleoside polymerase inhibitors
  作者：Xinjin Liu、Zhichao Xu、Jinsen Liang、Ting Xu、Wenting Zou、Lijun Zhu、Yihe Wu、Chune Dong、Ke Lan、Shuwen Wu、Hai-Bing Zhou

  DOI：10.1016/j.ejmech.2023.115678

  日期：2023.11

  exhibited satisfactory antiviral activity in a lethal influenza virus mouse model. Moreover, mechanistic studies indicated that these acylthiourea derivatives inhibited influenza virus proliferation by targeting influenza virus RNA-dependent RNA polymerase. Thus, 10m is a potential lead compound for the further exploration of treatment options for influenza.

  有证据表明，快速进化的病毒亚变体有可能使当前的疫苗和抗流感药物失效。因此，探索抗流感药物的新支架或新靶点刻不容缓。在此，我们报告了通过支架跳跃策略产生的一系列酰基硫脲衍生物的发现，作为针对甲型和乙型流感亚型的有效抗病毒剂。最有效的化合物10m对 H1N1 增殖表现出亚纳摩尔活性 (EC 50  = 0.8 nM)，并对其他流感病毒株表现出抑制活性，包括乙型流感病毒和 H1N1 变种（H1N1、H274Y）。此外，成药性评估​​表明，10m表现出良好的药代动力学特性，并且在来自三个不同物种的肝微粒体制剂以及人血浆中代谢稳定。体外和体内毒性研究证实10m具有很高的安全性。此外，10m在致死性流感病毒小鼠模型中表现出令人满意的抗病毒活性。此外，机理研究表明，这些酰基硫脲衍生物通过靶向流感病毒RNA依赖性RNA聚合酶来抑制流感病毒增殖。因此， 10m是进一步探索流感治疗方案的潜在先导化合物。
• Discovery and structure–activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: Potential impact in diabetes
  作者：Xu Deng、Yu Shen、Jing Yang、Juan He、Yu Zhao、Li-Yan Peng、Ying Leng、Qin-Shi Zhao

  DOI：10.1016/j.ejmech.2013.05.010

  日期：2013.7

  The biological screening of a collection of nature occurring diterpenoids against 11 beta-HSD1 resulted in the discovery of the lead compound 1b, which pointed to the therapeutic potential for type 2 diabetes. Subsequently, an optimization project was initiated. Starting from compound 1b and its counterpart 2, the hemi-synthesis was performed on kaurenic acid scaffolds yielding 36 derivatives. Further evaluations on both human and mouse 11 beta-HSD revealed that seven urea derivatives exhibited significant improved potency and selectivity. Especially, the urea 19a has an IC50 (human 11 beta-HSD1) = 9.4 nM and selectivity index (human 11 beta-HSD) > 10,649. The 2D and 3D binding models of the complex 19a/11 beta-HSD1 were generated using docking simulations. Based on the results, the structural activity relationships (SARs) of compounds 1b and 2 were also discussed. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Design and synthesis of indole, 2,3-dihydro-indole, and 3,4-dihydro-2H-quinoline-1-carbothioic acid amide derivatives as novel HCV inhibitors
  作者：Iou-Jiun Kang、Li-Wen Wang、Sheng-Ju Hsu、Chung-Chi Lee、Yen-Chun Lee、Yen-Shian Wu、Tsu-An Hsu、Andrew Yueh、Yu-Sheng Chao、Jyh-Haur Chern

  DOI：10.1016/j.bmcl.2009.06.009

  日期：2009.8

  An efficient synthetic methodology to provide indole, 2,3-dihydro-indole, and 3,4-dihydro-2H-quinoline-1-carbothioic acid amide derivatives is described. These conformationally restricted heterobicyclic scaffolds were evaluated as a novel class of HCV inhibitors. Introduction of an acyl group at the NH2 of the thiourea moiety has been found to enhance inhibitory activity. The chain length and the position of the alkyl group on the indoline aromatic ring markedly influenced anti-HCV activity. The indoline scaffold was more potent than the corresponding indole and tetrahydroquinoline scaffolds and analogue 31 displayed excellent activity (EC50 = 510 nM) against HCV without significant cytotoxicity (CC50 > 50 mu M). (C) 2009 Elsevier Ltd. All rights reserved.
• Efficient synthesis of new (R)-2-amino-1-butanol derived ureas, thioureas and acylthioureas and in vitro evaluation of their antimycobacterial activity
  作者：Georgi M. Dobrikov、Violeta Valcheva、Yana Nikolova、Iva Ugrinova、Evdokia Pasheva、Vladimir Dimitrov

  DOI：10.1016/j.ejmech.2013.02.034

  日期：2013.5

  The synthesis of 22 structurally diverse urea, thiourea and acylthiourea derivatives containing the (R)-2-amino-1-butanol motif has been performed. The evaluation of their in vitro activity against Mycobacterium tuberculosis (H(37)Rv and strain 43) showed promising results in the case of the acylthiourea derivatives (MIC range 0.36-7.46 mu M for H(37)Rv strain). (C) 2013 Elsevier Masson SAS. All rights reserved.