N-(4-Fluorophenyl)-2-morpholin-4-yl-2-thioxoacetamide | 635292-93-2

• 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-Fluorophenyl)-2-morpholin-4-yl-2-thioxoacetamide
• 英文别名: N-(4-fluorophenyl)-2-(morpholin-4-yl)-2-thioxoacetamide；N-(4-fluorophenyl)-2-morpholin-4-yl-2-sulfanylideneacetamide
• CAS: 635292-93-2
• 化学式: C₁₂H₁₃FN₂O₂S
• 分子量: 268.312
• InChiKey: FWIWSWFCYYHMSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-Fluorophenyl)-2-morpholin-4-yl-2-thioxoacetamide 在 一水合肼 作用下， 生成 N(1)-(4-fluorophenyl)-2-hydrazino-2-thiooxacetamide
  参考文献：
  名称：

  新型铜（II），钴（II）和镍（II）与5-（4-氧代-4H-铬-3-基）-4,5-二氢-1,3,4-噻二唑-2-羧酰胺的配合物：合成，结构，光谱学研究

  摘要：

  摘要一系列新颖的有机配体5-（4-oxo-4H-chromen-3-yl）-4,5-dihydro-1,3,4-thiadiazole-2-carboxamide，是2-的互变异构形式。由3-甲酰基色酮和草酰胺合成了氧代-2-（芳基氨基）-（2E）-2-[（4-羟基-2-氧代-2H-1苯并吡喃-3-基）-亚甲基]乙硫酸酰肼酸硫酰肼。铜（II），钴（II）和镍（II）与2-oxo-2-（芳基氨基）-（2E）-2-[（4-羟基-2-oxo-2H-1-苯并吡喃-3-）的配合物通过相应的有机配体与MCl2（M = Cu，Co，Ni）的相互作用合成了yl）甲基亚烯基]乙硫基乙酰肼。与5-（4-氧代-4H-铬-3-基）-N-苯基-4,5-二氢-1,3,4-噻二唑-2-羧酰胺的铜（II）配合物的晶体结构为通过单晶X射线衍射法解决。复杂分子中的铜（II）离子由变形的三角双锥体几何结构中的醛亚胺氮原子，硫醇

  DOI：

  10.1016/j.poly.2017.10.027
• 作为产物：
  描述：

  4-氟苯胺 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-Fluorophenyl)-2-morpholin-4-yl-2-thioxoacetamide
  参考文献：
  名称：

  源自 thiooxamohydrazides 和 3-formyl-4-hydroxycoumarin 的腙：合成、结构和断裂

  摘要：

  从 thiooxamohydrazides 和 3-3-formyl-4-hydroxycoumarin 中获得了新型腙。根据核磁共振谱和X射线衍射数据，所得化合物中的香豆素片段以4-羟基香豆素或色烷-2,4-二酮形式存在。当溶解在二甲亚砜中时，这些腙会分裂成 1,3,4-噻二唑和 4-羟基香豆素的衍生物。

  DOI：

  10.1007/s11172-012-0325-x

文献信息

• Novel copper(II), cobalt(II) and nickel(II) complexes with 5-(4-oxo-4H-chromen-3-yl)-4,5-dihydro-1,3,4-thiadiazole-2-carboxamide: Synthesis, structure, spectroscopic studies
  作者：Ksenia A. Myannik、Vladimir N. Yarovenko、Elena K. Beloglazkina、Anna A. Moiseeva、Mikhail M. Krayushkin

  DOI：10.1016/j.poly.2017.10.027

  日期：2018.1

  Abstract A series of novel organic ligands, 5-(4-oxo-4H-chromen-3-yl)-4,5-dihydro-1,3,4-thiadiazole-2-carboxamide, which are the tautomeric forms of 2-oxo-2-(arylamino)-(2E)-2- [(4-hydroxy-2-oxo-2H-1-benzopyran-3-yl)-methyledene]ethanethioic acid hydrazides, have been synthesized from 3-formylchromone and oxamic acid thiohydrazides. Copper(II), cobalt(II) and nickel(II) complexes with 2-oxo-2-(ary

  摘要一系列新颖的有机配体5-（4-oxo-4H-chromen-3-yl）-4,5-dihydro-1,3,4-thiadiazole-2-carboxamide，是2-的互变异构形式。由3-甲酰基色酮和草酰胺合成了氧代-2-（芳基氨基）-（2E）-2-[（4-羟基-2-氧代-2H-1苯并吡喃-3-基）-亚甲基]乙硫酸酰肼酸硫酰肼。铜（II），钴（II）和镍（II）与2-oxo-2-（芳基氨基）-（2E）-2-[（4-羟基-2-oxo-2H-1-苯并吡喃-3-）的配合物通过相应的有机配体与MCl2（M = Cu，Co，Ni）的相互作用合成了yl）甲基亚烯基]乙硫基乙酰肼。与5-（4-氧代-4H-铬-3-基）-N-苯基-4,5-二氢-1,3,4-噻二唑-2-羧酰胺的铜（II）配合物的晶体结构为通过单晶X射线衍射法解决。复杂分子中的铜（II）离子由变形的三角双锥体几何结构中的醛亚胺氮原子，硫醇
• 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.
• Novel agonists of free fatty acid receptor 1 (GPR40) based on 3-(1,3,4-thiadiazol-2-yl)propanoic acid scaffold
  作者：Mikhail Krasavin、Alexey Lukin、Nikolay Zhurilo、Alexey Kovalenko、Ihor Zahanich、Sergey Zozulya

  DOI：10.3109/14756366.2016.1142984

  日期：2016.11.1

  1,3,4-Thiadiazole was explored as a more polar, heterocyclic replacement for the phenyl ring in the 3-arylpropionic acid pharmacophore present in the majority of GPR40 agonists. Out of 13 compounds synthesized using a flexible, three-step protocol (involving no chromatographic purification), four compounds were confirmed to activate the target in micromolar concentration range. While the potency of the series should be subject of further optimization, the remarkable aqueous solubility and microsomal stability observed for the lead compound (8g) apparently attests to this new scaffold's high promise in the GPR40 agonist field.
• 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.
• Synthesis of Carbamoyl-Containing N,S-Heterocyclic Compounds
  作者：V. N. Yarovenko、A. A. Es'kov、I. V. Zavarzin、E. I. Chernoburova、A. Yu. Martynkin、M. M. Krayuskin

  DOI：10.1080/10426500307911

  日期：2003.6

  Monothioxamides unsubstituted at the thioamidic nitrogen atom were obtained by the reaction of NS-morpholino-NO-R-thioxamides with ammonia. Carbampyl-containing 5-phenylcarbamoyl-1,2,4-dithiazoles, 6-phenylcarbamoyl-5,6-dihydro-[1,2,4,5]-dithiadiazin-3-one, and 5-phenylcarbainoyl-2-oxy-1,3,4-thiadiazole were synthesized by the reaction of monothioxamides or thiohydrazides of oxamic acids with chlorocarbonylsulfenyl chloride.