N,N'-(1,2-dimethylene)bisbenzoylthiourea | 7710-08-9

• 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: N,N'-(1,2-dimethylene)bisbenzoylthiourea
• 英文别名: 3-benzoyl-1-(2-{[(phenylformamido)methanethioyl]amino}ethyl)thiourea；N',N'''-dibenzoyl-N,N''-ethanediyl-bis-thiourea；N',N'''-Dibenzoyl-N,N''-aethandiyl-bis-thioharnstoff；1,2-bis(N'-benzoylthioureido)ethane；N-[2-(benzoylcarbamothioylamino)ethylcarbamothioyl]benzamide
• CAS: 7710-08-9
• 化学式: C₁₈H₁₈N₄O₂S₂
• 分子量: 386.499
• InChiKey: ZYNTZYCVPWXECP-UHFFFAOYSA-N

物化性质

• 熔点：
  212 °C
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-(1,2-dimethylene)bisbenzoylthiourea 在 sodium hydroxide 作用下， 以 水 为溶剂， 以93 %的产率得到N,N''-乙烷-1,2-二基二(硫代脲)
  参考文献：
  名称：

  Zn(II) 自组装体对体外和卵内癌细胞具有选择性细胞毒活性的临床前评估

  摘要：

  双齿配体L 1和L 2与Zn 2+和Cu 2+形成双核双螺旋，这些自组装体可以结合磷酸根和4-硝基苯基磷酸根阴离子。该复合物显示出选择性细胞毒性和抗肿瘤活性，但这高度依赖于所使用的配体、金属离子和阴离子。先导化合物[( L 2 ) 2 Zn 2 ] 2+在卵内显示出功效，肿瘤重量减少67%，胚胎存活率100%。

  DOI：

  10.1002/chem.202302803
• 作为产物：
  描述：

  苯甲酰氯 在 polyethylene glycol-400 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 N,N'-(1,2-dimethylene)bisbenzoylthiourea
  参考文献：
  名称：

  Antibacterial and Antifungal Activities of Bisbenzoylthiourea Compounds from Benzoyl Isothiocyanate and Diamines

  摘要：

  在固液相转移催化条件下，以苯甲酰异硫氰酸酯和不同的二胺为原料，在 CH2Cl2 介质中合成了五种双苯甲酰硫脲化合物。通过元素分析以及红外光谱和 1H NMR 光谱对这些化合物的结构进行了表征。对这些化合物进行了抗菌和抗真菌活性测试。结果表明，大多数化合物都具有良好的抗菌活性，尤其是在防治农业真菌病方面。

  DOI：

  10.14233/ajchem.2013.15157a

文献信息

• Dihydrogen phosphate-containing dinuclear double assemblies that demonstrate phosphate reactivity to the tetrafluoroborate anion
  作者：Robert A. Faulkner、Nathan J. Patmore、Craig R. Rice、Christopher Slater

  DOI：10.1039/c8cc04900a

  日期：——

  Ligands L1 and L2 both form dinuclear assemblies with Cu(ii) and these react with dihydrogen phosphate to give [Cu₂L₂(H₂PO₄)]³⁺. However, in the presence of tetrafluoroborate anions the phosphate undergoes reaction with the anion forming [Cu₃(L1)₃(O₃POBF₃)]³⁺ and [Cu₂(L²)₂(O₂P(OBF₃)₂)]⁺.

  配体L1和L2均与Cu(II)形成双核组合物，并且与二氢磷酸盐反应生成[Cu2L2(H2PO4)]3+。然而，在四氟硼酸盐阴离子存在的情况下，磷酸盐与阴离子发生反应，形成[Cu3(L1)3(O3POBF3)]3+和[Cu2(L2)2(O2P(OBF3)2)]+。
• Synthesis and Antibacterial Activity of Copper(I) Complexes with Bisbenzoylthiourea
  作者：Meng-Meng Zhao、Xiu-Yan Dong、Gang Li、Xiao-Qin Yang

  DOI：10.14233/ajchem.2014.15897

  日期：——

  Two copper(I) complexes, [Cu(L)]ClO4 (1) and [Cu(L)Cl]·C2H5OH (2), have been synthesized by the reaction of copper(II) perchlorate hexahydrate and copper(II) chloride dihydrate with N,N-(1,2-dimethylene)bisbenzoylthiourea (L), respectively and characterized by elemental analyses as well as IR spectra and TG-DTA analyses. Antibacterial activity assays exhibit MIC50 values of the two copper(I) complexes comparable to standard drugs for both Gram-positive and Gram-negative bacteria, both of them show stronger antibacterial activity.

  通过高氯酸铜(II)六水合物与氯化铜(II)反应合成了两种铜(I)配合物[Cu(L)]ClO4 (1)和[Cu(L)Cl]·C2H5OH (2)分别与 N,N-(1,2-二亚甲基)双苯甲酰硫脲 (L) 形成二水合物，并通过元素分析以及红外光谱和 TG-DTA 分析进行表征。抗菌活性测定显示两种铜(I)配合物对革兰氏阳性菌和革兰氏阴性菌的MIC50值与标准药物相当，两者均表现出更强的抗菌活性。
• MACROCYCLES AND MACROCYCLE STABILIZED PEPTIDES
  申请人：Saulnier Mark G.

  公开号：US20130281657A1

  公开（公告）日：2013-10-24

  The invention provides methods of preparing macrocycles including macrocycle stabilized peptides (MSPs). Macrocycles and MSPs are prepared according to nucleophilic capture of an iminoquinomethide type intermediate generated from a suitably substituted 2-amino-thiazol-5-yl carbinol. The preferred nucleophile may be selected from an electron rich aromatic moiety in the case of macrocycles and, in the case of MSPs, at least one amino acid comprises an electron rich aromatic moiety. In addition, the concept can be extended to other related 5-membered heterocyclic systems in place of the thiazole, such as imidazole or oxazole. The conditions for the generation of the corresponding iminoquinomethide type intermediates may be similar or different than the conditions used for the 2-amino-thiazol-5-yl carbinol.

  本发明提供了制备大环化合物的方法，包括稳定大环化肽（MSPs）。根据适当取代的2-氨基噻唑-5-基甲醇生成的亚胺喹啉甲烷型中间体的亲核捕获，制备大环和MSP。在大环的情况下，首选亲核试剂可以从富电子芳香基团中选择，在MSP的情况下，至少有一种氨基酸包含富电子芳香基团。此外，该概念可以扩展到取代噻唑的其他相关5-成员杂环系统，例如咪唑或噁唑。生成相应的亚胺喹啉甲烷型中间体的条件可能与用于2-氨基噻唑-5-基甲醇的条件相似或不同。
• Macrocycles and macrocycle stabilized peptides
  申请人：Saulnier Mark G.

  公开号：US09169295B2

  公开（公告）日：2015-10-27

  The invention provides methods of preparing macrocycles including macrocycle stabilized peptides (MSPs). Macrocycles and MSPs are prepared according to nucleophilic capture of an iminoquinomethide type intermediate generated from a suitably substituted 2-amino-thiazol-5-yl carbinol. The preferred nucleophile may be selected from an electron rich aromatic moiety in the case of macrocycles and, in the case of MSPs, at least one amino acid comprises an electron rich aromatic moiety. In addition, the concept can be extended to other related 5-membered heterocyclic systems in place of the thiazole, such as imidazole or oxazole. The conditions for the generation of the corresponding iminoquinomethide type intermediates may be similar or different than the conditions used for the 2-amino-thiazol-5-yl carbinol.

  该发明提供了制备大环化合物的方法，包括大环稳定的肽（MSPs）。通过从适当取代的2-氨基噻唑-5-基甲醇生成的亚胺喹啉甲亚型中间体的亲核捕获来制备大环和MSPs。在大环的情况下，优选的亲核试剂可以从富电子芳香基团中选择，在MSPs的情况下，至少一个氨基酸包含一个富电子芳香基团。此外，该概念可以扩展到取代噻唑的其他相关5-成员杂环系统，例如咪唑或噁唑。生成相应的亚胺喹啉甲亚型中间体的条件可以与用于2-氨基噻唑-5-基甲醇的条件相似或不同。
• Synthesis, Characterization and Biological Activity of Some Dithiourea Derivatives
  作者：Felix Odame、Eric Hosten、Jason Krause、Michelle Isaacs、Heinrich Hoppe、Setshaba D. Khanye、Yasien Sayed、Carminita Frost、Kevin Lobb、Zenixole Tshentu

  DOI：10.17344/acsi.2019.5689

  日期：——

  Novel dithiourea derivatives have been designed as HIV-1 protease inhibitors using Auto dock 4.2, synthesized and characterized by spectroscopic methods and microanalysis. 1-(3-Bromobenzoyl)-3- [2-([(3-bromophenyl)form amido] methanethioyllamino)phenyl] thiourea (10) and 3-benzoyl-1 [(phenylformamido)methanethioyl] amino}thiourea (12) gave a percentage viability of 17.9 +/- 5.6% and 11.2 +/- 0.9% against Trypanosoma brucei. Single crystal X-ray diffraction analysis of 1-benzoyl-3-(5-methyl-2-[(phenylformamido)methanethioyl]amino}phenyl)thiourea (1), 3-benzoyl-1- (2-[(phenylformamido)methanethioyl]amino}ethyl)thiourea (11), 3-benzoyl-1-[(phenylformamido)methanethioyl]amino}thiourea (12) and 3-benzoyl-1- (4- [(phenylformamido)methanethioyl] amino}butyl)thioure a (14) have been presented. 1-(3-Bromobenzoyl) 3 [2-([(3-bromophenyl)formamido]methanethioyl}amino)phenyl]thiourea (10) gave a percentage inhibition of 97.03 +/- 0.37% against HIV-1 protease enzyme at a concentration of 100 mu M.