N-(3-Methylphenyl)-2-morpholin-4-yl-2-thioxoacetamide | 635293-05-9

• 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-(3-Methylphenyl)-2-morpholin-4-yl-2-thioxoacetamide
• 英文别名: N-(3-methylphenyl)-2-morpholin-4-yl-2-sulfanylideneacetamide
• CAS: 635293-05-9
• 化学式: C₁₃H₁₆N₂O₂S
• 分子量: 264.348
• InChiKey: ZOXPCTPOPMZBOG-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：

  N-(3-Methylphenyl)-2-morpholin-4-yl-2-thioxoacetamide 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到2-hydrazinyl-N-(3-methylphenyl)-2-thioxoacetamide
  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：

  吗啉 、 2-氯-N-(3-甲基苯基)乙酰胺 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-(3-Methylphenyl)-2-morpholin-4-yl-2-thioxoacetamide
  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

文献信息

• 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 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.
• 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.
• Novel steroidal 1,3,4-thiadiazines: Synthesis and biological evaluation in androgen receptor-positive prostate cancer 22Rv1 cells
  作者：Anna S. Komendantova、Alexander M. Scherbakov、Alexander V. Komkov、Viktoriya V. Chertkova、Alexey O. Gudovanniy、Elena I. Chernoburova、Danila V. Sorokin、Yaraslau U. Dzichenka、Valerii Z. Shirinian、Yulia A. Volkova、Igor V. Zavarzin

  DOI：10.1016/j.bioorg.2019.103142

  日期：2019.10

  A flexible approach to previously unknown spirofused and linked 1,3,4-thiadiazine derivatives of steroids with selective control of heterocyclization patterns is disclosed. (N-Arylcarbamoyl)spiroandrostene-17,6′ [1,3,4]thiadiazines and (N-arylcarbamoyl)17-[1′,3′,4′]thiadiazine-substituted androstenes, novel types of heterosteroids, were prepared from 16β,17β-epoxypregnenolone and 21-bromopregna-5,16-dien-20-one

  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