N'-benzoyl-N,N-dipropylthiourea | 58682-52-3

• 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: N'-benzoyl-N,N-dipropylthiourea
• 英文别名: N-(dipropylcarbamothioyl)benzamide；N,N-dipropyl-N'-benzoylthiourea；(n-propyl)2NC(S)NHC(O)C6H5
• CAS: 58682-52-3
• 化学式: C₁₄H₂₀N₂OS
• 分子量: 264.392
• InChiKey: NHHJDARLNRBGBP-UHFFFAOYSA-N

物化性质

• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N'-benzoyl-N,N-dipropylthiourea 、 nickel diacetate 以 乙醇 为溶剂， 生成 bis(N,N-dipropyl-N'-benzoylthiourea)nickel(II)
  参考文献：
  名称：

  Copper, nickel and cobalt complexes with N,N-disubstituted′-benzoyl thioureas

  摘要：

  The complexes of 8 N,N-disubstituted,N'-benzoyl thioureas with copper, nickel and cobalt have been studied. NMR spectra and magnetic measurements have shown square planar NiL2 and fac CoL3 compounds. The electrochemical parameters obtained from cyclic voltammetry for the irreversible process copper(II)/copper(I) redox systems are slightly influenced by the different substituents.

  DOI：

  10.1016/s0277-5387(00)81702-7
• 作为产物：
  描述：

  氯化苄 以 丙酮 为溶剂， 反应 1.0h， 生成 N'-benzoyl-N,N-dipropylthiourea
  参考文献：
  名称：

  新型双(2-(取代(甲基)氨基)-4-苯基噻唑-5-基)甲酮的合成与对接研究

  摘要：

  报道了双(2-(取代(甲基)氨基)-4-苯基噻唑-5-基)甲酮(PVS 1-9)的一系列新合成。羰基异硫氰酸酯 (3) 通过苯甲酰氯 (1) 与硫氰酸铵 (2) 的 C-Cl 键对位断裂合成。酰基异硫氰酸酯中羰基的存在增强了酰基异硫氰酸酯与取代仲胺 (4) 反应得到正烷基化加合物 (5) 的反应性，该加合物与二氯丙酮反应得到目标化合物 7。 作为肺抑制剂的取代衍生物基于对含有 EGFR L858R/T790M 双突变的 NSCLC H1975 的虚拟筛选细胞评估，乳腺癌和 EJFR 协助癌症表明，最活跃的化合物 PVS-7 可以在一个数字微摩尔级别抑制两种细胞系的增殖。酶学结果表明，化合物PVS-2、PVS-4和PVS-9是针对EGFR T790M及以上癌症活性最有效的抑制剂，约82%。所有化合物均通过光谱技术进行了充分表征，并通过 UV-HPLC 确认了其纯度。

  DOI：

  10.14233/ajchem.2022.24030

文献信息

• Acylthioureas as anion transporters: the effect of intramolecular hydrogen bonding
  作者：Cally J. E. Haynes、Nathalie Busschaert、Isabelle L. Kirby、Julie Herniman、Mark E. Light、Neil J. Wells、Igor Marques、Vítor Félix、Philip A. Gale

  DOI：10.1039/c3ob41522h

  日期：——

  Small molecule synthetic anion transporters may have potential application as therapeutic agents for the treatment of diseases including cystic fibrosis and cancer. Understanding the factors that can dictate the anion transport activity of such transporters is a crucial step towards their application in biological systems. In this study a series of acylthiourea anion transporters were synthesised and their anion binding and transport properties in POPC bilayers have been investigated. The transport activity of these receptors is dominated by their lipophilicity, which is in turn dependent on both substituent effects and the formation and strength of an intramolecular hydrogen bond as inferred from DFT calculations. This is in contrast to simpler thiourea systems, in which the lipophilicity depends predominantly on substituent effects alone.

  小分子合成阴离子转运体可能在治疗包括囊性纤维化和癌症等疾病方面具有潜在应用。理解可以决定这些转运体阴离子转运活性的因素是其在生物系统中应用的重要一步。在本研究中，合成了一系列酰基硫脲阴离子转运体，并研究了它们在POPC脂质双层中的阴离子结合和转运性质。这些受体的转运活性主要由它们的亲脂性主导，而亲脂性又依赖于取代基效应及分子内氢键的形成和强度，这一点通过DFT计算可以推断。这与简单的硫脲系统形成对比，后者的亲脂性主要依赖于取代基效应。
• Experimental and Theoretical DFT Study of Cu(I)/<i>N</i>,<i>N</i>-Disubstituted-<i>N</i>′-acylthioureato Anticancer Complexes: Actin Cytoskeleton and Induction of Death by Apoptosis in Triple-Negative Breast Tumor Cells
  作者：Celisnolia M. Leite、João Honorato、Ana Carolina B. M. Martin、Rafael G. Silveira、Felippe M. Colombari、Jéssica C. Amaral、Analu R. Costa、Márcia R. Cominetti、Ana M. Plutín、Debora de Aguiar、Boniek G. Vaz、Alzir A. Batista

  DOI：10.1021/acs.inorgchem.1c03389

  日期：2022.1.10

  TNBC), MCF-7 (breast cancer), and A549 (lung cancer)]. In the MDA-MB-231 cell line, complex 1 significantly altered the cytoskeleton of the cells, reducing the density and promoting the condensation of F-actin filaments. In addition, the compound caused an increase in the percentage of cells in the fragmented DNA region (sub-G0) and induced cell death via the apoptotic pathway starting at the IC50 concentration

  合成了六种具有通式[Cu(酰基硫脲)(PPh 3 ) 2 ]的配合物，并使用光谱技术（红外、紫外/可见光、一维和二维核磁共振）、质谱、元素分析和X射线衍射进行表征。 Cu(I) 配合物的体外细胞毒性数据的解释考虑了它们在细胞培养基中的稳定性。 DFT 计算表明，NMR 特性（例如碳原子的屏蔽）会受到相对论效应的影响，这一点在理论计算中得到了 ZORA 哈密顿量的支持。此外，前沿分子轨道能量的计算预测酰基硫脲配体的结构变化不会引起反应性描述符的显着变化。所有复合物对所评估的肿瘤细胞系[MDA-MB-231（三阴性乳腺癌，TNBC）、MCF-7（乳腺癌）和A549（肺癌）]均具有细胞毒性。在 MDA-MB-231 细胞系中，复合物1显着改变了细胞的细胞骨架，降低了密度并促进了 F-肌动蛋白丝的凝结。此外，该化合物导致DNA片段化区域（sub-G0）的细胞百分比增加，并通过从IC 50浓度开始的
• Kukushkin, Yu. N.; Sibirskaya, V. V.; Vorob'ev-Desyatovskii, N. V., Journal of general chemistry of the USSR, 1981, vol. 51, p. 146 - 152
  作者：Kukushkin, Yu. N.、Sibirskaya, V. V.、Vorob'ev-Desyatovskii, N. V.、Hoyer, E.、Beyer, L.、et al.

  DOI：——

  日期：——
• Thermal behaviours of Co(II), Ni(II), Cu(II)), and Pb(II) complexes of N,N-dipropyl-N′-benzoylthiourea
  作者：N. Ozpozan、T. Ozpozan、H. Arslan、F. Karipçin、N. Külcü

  DOI：10.1016/s0040-6031(99)00208-7

  日期：1999.9

  The Co(II), Ni(II), Cu(II)), and Pb(II) complexes of N,N-dipropyl-N'-benzoylthiourea (DPBT) are synthesised. The order, the activation energies, the entropies, and the pre-exponential factors of the thermal decomposition reactions are calculated with the thermogravimetric curves. The kinetic analysis of the thermogravimetric data was performed by using the Coats-Redfern and Horowitz-Metzger methods. (C) 1999 Published by Elsevier Science B.V. All rights reserved.
• Copper, nickel and cobalt complexes with N,N-disubstituted′-benzoyl thioureas
  作者：Aminou Mohamadou、Isabelle Déchamps-Olivier、Jean-Pierre Barbier

  DOI：10.1016/s0277-5387(00)81702-7

  日期：1994.5

  The complexes of 8 N,N-disubstituted,N'-benzoyl thioureas with copper, nickel and cobalt have been studied. NMR spectra and magnetic measurements have shown square planar NiL2 and fac CoL3 compounds. The electrochemical parameters obtained from cyclic voltammetry for the irreversible process copper(II)/copper(I) redox systems are slightly influenced by the different substituents.