N-(4-Chloro-phenyl)-2-morpholin-4-yl-2-thioxo-acetamide | 220897-82-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(4-Chloro-phenyl)-2-morpholin-4-yl-2-thioxo-acetamide
• 英文别名: N-(4-chlorophenyl)-2-(morpholin-4-yl)-2-thioxoacetamide；N-(4-chlorophenyl)-2-morpholin-4-yl-2-sulfanylideneacetamide
• CAS: 220897-82-5
• 化学式: C₁₂H₁₃ClN₂O₂S
• 分子量: 284.766
• InChiKey: OQRKEJYXIFGNSL-UHFFFAOYSA-N

物化性质

• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-Chloro-phenyl)-2-morpholin-4-yl-2-thioxo-acetamide 在 potassium carbonate 、 一水合肼 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 17-(N-(4′-chlorophenyl)-6′H-1′,3′,4′-thiadiazine-2′-carboxamide)-3β-acetoxy-androst-5,17-diene
  参考文献：
  名称：

  新型甾体1,3,4-噻二嗪：雄激素受体阳性前列腺癌22Rv1细胞的合成和生物学评估。

  摘要：

  公开了一种对甾体的以前未知的螺合的和连接的1,3,4-噻二嗪衍生物具有选择性控制杂环化模式的灵活方法。（N-芳基氨基甲酰基）螺雄甾烯17,6'[1,3,4]噻二嗪和（N-芳基氨基甲酰基）17- [1'，3'，4']噻二嗪取代的雄烯酮是由新型杂类固醇制备的16 β，17 β -epoxypregnenolone和21 bromopregna -5,16-二烯-20-酮在良好至高产率通过用草氨酸硫代酰肼的治疗。筛选合成的化合物对人雄激素受体阳性前列腺癌细胞系22Rv1的抗增殖活性。大部分（N-芳基氨基甲酰基）17- [1'，3'，4']噻二嗪取代的雄烯酮显示出 比抗雄激素比卡鲁胺更好的抗增殖能力（IC 50 = 2.1–6.6 µM）。 在研究的系列中，IC 50 = 3.0μM的化合物7d和IC 50  = 2.1μM的化合物7j被证明是活性最高的。铅合成的化合物7j下调22Rv1细胞中AR

  DOI：

  10.1016/j.bioorg.2019.103142
• 作为产物：
  描述：

  对氯苯胺 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-Chloro-phenyl)-2-morpholin-4-yl-2-thioxo-acetamide
  参考文献：
  名称：

  棉酚与草肟酸硫代酰肼的反应

  摘要：

  棉酚与草酸硫代酰肼反应生成相应的以亚胺-亚胺形式存在的腙。

  DOI：

  10.1007/s11172-024-4150-9

文献信息

• 5-Nitrofuran-2-yl Thiohydrazones as Double Antibacterial Agents Synthesis and In Vitro Evaluation
  作者：Alexey Yurjevich Lukin、Tatiana Sergeevna Vedekhina、Mikhail Vassiljevich Chudinov

  DOI：10.2174/1570180816666190221162055

  日期：2020.3.27

  5-nitrofuran derivatives has been proposed. Methods: A small library of 5-Nitrofuran-2-yl Thiohydrazones was developed, and initial screening demonstrated good activity against bacteria and fungi of ESKAPE panel. Results and Conclusion: The synthesis of the desired thiohydrazones was carried out via condensation of 5-nitrofuran-2-carbaldehyde with thiohydrazides of substituted oxamic acids.

  背景：已经提出将“双重药物”策略应用于5-硝基呋喃衍生物。 方法：建立了一个小的5-硝基呋喃-2-基噻唑烷文库，初步筛选证明它对ESKAPE板的细菌和真菌具有良好的活性。 结果与结论：通过5-硝基呋喃-2-甲醛与取代的乙酰胺酸的硫代肼的缩合反应，可合成所需的硫代azo。
• Synthesis of Oxamic Acids Thiohydrazides and Carbamoyl-1,3,4-thiadiazoles
  作者：V. N. Yarovenko、A. V. Shirokov、O. N. Krupinova、I. V. Zavarzin、M. M. Krayushkin

  DOI：10.1023/b:rujo.0000010181.01921.77

  日期：2003.8

  A convenient preparation method was developed for oxamic acids thiohydrazides by reaction of alpha-chloroacetamides with a preliminary prepared solution of elemental sulfur and hydrazines. A series of carbamoyl-1,3,4-thiadiazole derivatives was obtained.
• A Straightforward Approach toward Multifunctionalized Pyridazines via Imination/Electrocyclization
  作者：Alexander V. Komkov、Anna S. Komendantova、Leonid G. Menchikov、Elena I. Chernoburova、Yulia A. Volkova、Igor V. Zavarzin

  DOI：10.1021/acs.orglett.5b01718

  日期：2015.8.7

  A facile synthesis of functionalized 3-carbamide pyridazines starting from readily available chlorovinyl aldehydes and oxamic acid thiohydrazides via cascade imination/electrocyclization is reported. In the presence of p-toluenesulfuric acid, various ketones have been efficiently incorporated into the pyridazine derivatives through a two-step sequence involving a VilsmeierHaack reaction and imination. The synthetic value of this method has been demonstrated by efficient synthesis of steroidal pyridazines.
• Novel free fatty acid receptor 1 (GPR40) agonists based on 1,3,4-thiadiazole-2-carboxamide scaffold
  作者：Mikhail Krasavin、Alexey Lukin、Nikolay Zhurilo、Alexey Kovalenko、Ihor Zahanich、Sergey Zozulya、Daniel Moore、Irina G. Tikhonova

  DOI：10.1016/j.bmc.2016.04.065

  日期：2016.7

  Free fatty acid receptor 1 (FFA1), previously known as GPR40 is a G protein-coupled receptor and a new target for treatment of type 2 diabetes. Two series of FFA1 agonists utilizing a 1,3,4-thiadiazole-2-caboxamide scaffold were synthetized. Both series offered significant improvement of the potency compared to the previously described 1,3,4-thiadiazole-based FFA1 agonists and high selectivity for FFA1. Molecular docking predicts new aromatic interactions with the receptor that improve agonist potency. The most potent compounds from both series were profiled for in vitro ADME properties (plasma and metabolic stability, Log D, plasma protein binding, hERG binding and CYP inhibition). One series suffered very rapid degradation in plasma and in presence of mouse liver microsomes. However, the other series delivered a lead compound that displayed a reasonable ADME profile together with the improved FFA1 potency. (C) 2016 Elsevier Ltd. All rights reserved.
• Reactions of monothiooxamides with N-nucleophiles. Synthesis of 4,5-dihydroimidazole-2-carboxanilides
  作者：V. N. Yarovenko、S. A. Kosarev、I. V. Zavarzin、M. M. Krayushkin

  DOI：10.1007/bf02496262

  日期：1999.4

  A convenient procedure was developed for the preparation of 4,5-dihydroimidazole-2-carboxanilides by the reaction of monothiooxamides with ethylenediamine.