2-Morpholin-4-yl-2-thioxo-N-o-tolyl-acetamide

• 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: 2-Morpholin-4-yl-2-thioxo-N-o-tolyl-acetamide
• 英文别名: N-(2-methylphenyl)-2-morpholin-4-yl-2-sulfanylideneacetamide
• 化学式: C₁₃H₁₆N₂O₂S
• 分子量: 264.348
• InChiKey: DVBXNUOFPHLGAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  2-Morpholin-4-yl-2-thioxo-N-o-tolyl-acetamide 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 N(1)-(2-methylphenyl)-2-hydrazino-2-thiooxacetamide
  参考文献：
  名称：

  5-硝基呋喃-2-基噻唑烷作为双重抗菌剂的合成和体外评价

  摘要：

  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。

  DOI：

  10.2174/1570180816666190221162055
• 作为产物：
  描述：

  邻甲苯胺 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 2-Morpholin-4-yl-2-thioxo-N-o-tolyl-acetamide
  参考文献：
  名称：

  Synthesis of (2-chloroquinolin-3-yl)-1,3,4-thiadiazole-2-carboxamides

  摘要：

  (2-氯喹啉-3-基)-1,3,4-噻二唑-2-甲酰胺是由 3-甲酰基-2-氯喹啉与草氨酸硫酰肼反应得到的酰肼合成的。

  DOI：

  10.1007/s11172-021-3194-3

文献信息

• 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.
• 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.
• Synthesis of carbamoylamidoximes
  作者：V. N. Yarovenko、S. A. Kosarev、I. V. Zavarzin、M. M. Krayushkin

  DOI：10.1007/bf02494503

  日期：1998.10

  A convenient procedure was developed for the synthesis of carbamoylamidoximes by the reaction of N(S)-substituted monothiooxamides with hydroxylamine hydrochloride in pyridine.
• Synthesis of (2-chloroquinolin-3-yl)-1,3,4-thiadiazole-2-carboxamides
  作者：A. N. Aksenov、M. M. Krayushkin、V. N. Yarovenko

  DOI：10.1007/s11172-021-3194-3

  日期：2021.6

  (2-Chloroquinolin-3-yl)-1,3,4-thiadiazole-2-carboxamides were synthesized from hydrazones obtained via the reaction of 3-formyl-2-chloroquinoline with oxamic acid thiohydrazides.

  (2-氯喹啉-3-基)-1,3,4-噻二唑-2-甲酰胺是由 3-甲酰基-2-氯喹啉与草氨酸硫酰肼反应得到的酰肼合成的。