N-cyclohexyl-2-(thiophene-2-carbonyl)hydrazinecarbothioamide | 331461-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: N-cyclohexyl-2-(thiophene-2-carbonyl)hydrazinecarbothioamide
• 英文别名: 4-cyclohexyl-1-(thiophen-2-yl)carbonylthiosemicarbazide；N-cyclohexyl-2-(2-thienylcarbonyl)-1-hydrazinecarbothioamide；1-cyclohexyl-3-(thiophene-2-carbonylamino)thiourea
• CAS: 331461-23-5
• 化学式: C₁₂H₁₇N₃OS₂
• 分子量: 283.418
• InChiKey: UGMCLDASMRDHHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-2-(thiophene-2-carbonyl)hydrazinecarbothioamide 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以89%的产率得到4-cyclohexyl-3-thiophen-2-yl-1H-1,2,4-triazole-5-thione
  参考文献：
  名称：

  Chemical and Pharmacological Properties of 3-(Thiophen-2-yl)-4-substituted-Δ²-1,2,4-triazoline-5-thiones

  摘要：

  Three 3-(thiophen-2-yl)-4-substituted-Delta(2)-1,2,4-triazoline-5-thiones were synthesized by intramolecular cyclization of 1-(thiophen-2-ylcarbonyl)-4-substituted thiosemicarbazides in alkaline medium. Their effects on the central nervous system (CNS) of mice in some behavioral tests were investigated. All investigated compounds displayed antinociceptive activity. The correlation between the structural features and bioactivity has been discussed.

  DOI：

  10.1080/10426500801968136
• 作为产物：
  描述：

  2-噻吩羧酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 N-cyclohexyl-2-(thiophene-2-carbonyl)hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis and anti-endoplasmic reticulum stress activity of N-substituted-2-arylcarbonylhydrazinecarbothioamides

  摘要：

  Misfolded or unfolded proteins are accumulated in lumen of endoplasmic reticulum (ER) in ER stress condition. It has been implicated in many pathological conditions such as Alzheimer's disease, diabetic retinopathy, atherosclerosis, beta-cell apoptosis and lung inflammation. We found a series of N-substituted-2-arylcarbonylhydrazinecarbothioamides to potently decrease ER stress signal, showing up to almost 300-fold better activity than 1-hydroxynaphthoic acid and tauro-ursodesoxycholic acid, positive controls, respectively. Structure-activity relationship (SAR) study showed that 2-arylcarbonyl moiety is critical for the activity of the hydrazinecarbothioamide analogues and side chains tethering on thioamide moiety were relatively insensitive to the activity. Some analogues were found to consistently exert the potency under more physiologically relevant condition where ER stress was induced by palmitic acid. ER stress markers such as CHOP and phosphorylated eIF2 alpha and PERK were accordingly decreased in western blotting upon treatment of compound 4h. Potential ER stress inhibitory activity and novel structures could provide a novel platform for new chemical chaperone and therapy for protein misfolding diseases.

  DOI：

  10.1007/s00044-019-02442-1

文献信息

• 1,4-Disubstituted Thiosemicarbazide Derivatives are Potent Inhibitors of Toxoplasma gondii Proliferation
  作者：Katarzyna Dzitko、Agata Paneth、Tomasz Plech、Jakub Pawełczyk、Paweł Stączek、Joanna Stefańska、Piotr Paneth

  DOI：10.3390/molecules19079926

  日期：——

  A series of 4-arylthiosemicarbazides substituted at the N1 position with a 5-membered heteroaryl ring was synthesized and evaluated in vitro for T. gondii inhibition proliferation and host cell cytotoxicity. At non-toxic concentrations for the host cells all studied compounds displayed excellent anti-parasitic effects when compared to sulfadiazine, indicating a high selectivity of their anti-T. gondii activity. The differences in bioactivity investigated by DFT calculations suggest that the inhibitory activity of 4-aryl-thiosemicarbazides towards T. gondii proliferation is connected with the electronic structure of the molecule. Further, these compounds were tested as potential antibacterial agents. No growth-inhibiting effect on any of the test microorganisms was observed for all the compounds, even at high concentrations.

  研究人员合成了一系列 N1 位被 5 元杂芳基环取代的 4-芳基硫代氨基甲酸盐，并在体外评估了它们对淋球菌增殖的抑制作用和对宿主细胞的细胞毒性。在对宿主细胞无毒的浓度下，与磺胺嘧啶相比，所有研究化合物都显示出了极佳的抗寄生虫效果，这表明它们的抗淋球菌活性具有很高的选择性。通过 DFT 计算研究的生物活性差异表明，4-芳基-硫代氨基甲酸盐对淋球菌增殖的抑制活性与分子的电子结构有关。此外，这些化合物还被测试为潜在的抗菌剂。即使在高浓度下，也没有观察到所有化合物对任何受试微生物有抑制生长的作用。
• Synthesis and anti-prion aggregation activity of acylthiosemicarbazide analogues
  作者：Dong Hwan Kim、Jaehyeon Kim、Hakmin Lee、Dongyun Lee、So Myoung Im、Ye Eun Kim、Miryeong Yoo、Yong-Pil Cheon、Jason C. Bartz、Young-Jin Son、Eun-Kyoung Choi、Yong-Sun Kim、Jae-Ho Jeon、Hyo Shin Kim、Sungeun Lee、Chongsuk Ryou、Tae-gyu Nam

  DOI：10.1080/14756366.2023.2191164

  日期：2023.12.31
• Synthesis, characterizations, crystal structure and anticancer activity of Mn(II), Co(II) and Ni(II) complexes of N′-cyclohexyl-2-thiophene-carbonyl hydrazine carbothioamide
  作者：Shubham Jaiswal、Lokesh Yadav、Shivendra Kumar Pandey、Suryansh Chandra、M.K. Bharty、L.B. Prasad、A. Acharya

  DOI：10.1016/j.poly.2023.116408

  日期：2023.7
• Synthesis and anti-endoplasmic reticulum stress activity of N-substituted-2-arylcarbonylhydrazinecarbothioamides
  作者：Hoon Choi、Wheesahng Yun、Jung-hun Lee、Seoul Jang、Sang Won Park、Dong Hwan Kim、Kyoung Pyo Seon、Jung-mi Hyun、Kwiwan Jeong、Jin-mo Ku、Tae-gyu Nam

  DOI：10.1007/s00044-019-02442-1

  日期：2019.12

  Misfolded or unfolded proteins are accumulated in lumen of endoplasmic reticulum (ER) in ER stress condition. It has been implicated in many pathological conditions such as Alzheimer's disease, diabetic retinopathy, atherosclerosis, beta-cell apoptosis and lung inflammation. We found a series of N-substituted-2-arylcarbonylhydrazinecarbothioamides to potently decrease ER stress signal, showing up to almost 300-fold better activity than 1-hydroxynaphthoic acid and tauro-ursodesoxycholic acid, positive controls, respectively. Structure-activity relationship (SAR) study showed that 2-arylcarbonyl moiety is critical for the activity of the hydrazinecarbothioamide analogues and side chains tethering on thioamide moiety were relatively insensitive to the activity. Some analogues were found to consistently exert the potency under more physiologically relevant condition where ER stress was induced by palmitic acid. ER stress markers such as CHOP and phosphorylated eIF2 alpha and PERK were accordingly decreased in western blotting upon treatment of compound 4h. Potential ER stress inhibitory activity and novel structures could provide a novel platform for new chemical chaperone and therapy for protein misfolding diseases.
• Chemical and Pharmacological Properties of 3-(Thiophen-2-yl)-4-substituted-Δ²-1,2,4-triazoline-5-thiones
  作者：Agata Siwek、Monika Wujec、Maria Dobosz、Ewa Jagiełło-Wójtowicz、Agnieszka Kleinrok、Anna Chodkowska、Piotr Paneth

  DOI：10.1080/10426500801968136

  日期：2008.10.7

  Three 3-(thiophen-2-yl)-4-substituted-Delta(2)-1,2,4-triazoline-5-thiones were synthesized by intramolecular cyclization of 1-(thiophen-2-ylcarbonyl)-4-substituted thiosemicarbazides in alkaline medium. Their effects on the central nervous system (CNS) of mice in some behavioral tests were investigated. All investigated compounds displayed antinociceptive activity. The correlation between the structural features and bioactivity has been discussed.