N-(4-chlorophenyl)-2-nicotinoylhydrazinecarbothioamide | 127055-57-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(4-chlorophenyl)-2-nicotinoylhydrazinecarbothioamide
• 英文别名: N-(4-chlorophenyl)-2-nicotinoylhydrazine-1-carbothioamide；1-(4-chlorophenyl)-3-(pyridine-3-carbonylamino)thiourea
• CAS: 127055-57-6
• 化学式: C₁₃H₁₁ClN₄OS
• 分子量: 306.776
• InChiKey: NJGDQYRFQQVACL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenyl)-2-nicotinoylhydrazinecarbothioamide 在 三乙胺 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (E)-3-((4-(4-chlorophenyl)-5-(pyridin-3-yl)-4H-1,2,4-triazol-3-yl)thio)-4-hydroxypent-3-en-2-one
  参考文献：
  名称：

  1,2,4-三唑基-硫代戊烷-2,4-二酮体系的激发态动力学及其向生物活性新型三唑-S-吡唑杂化物的转化

  摘要：

  目前的研究重点是设计和合成通过硫原子相互连接的新型1,2,4-三唑附加吡唑。在此，我们报道了烟酰肼和异烟酰肼与芳基异硫氰酸酯衍生物的缩合，得到硫代硫酰胺，将其环化生成4-芳基-5-(吡啶基)-2,4-二氢-3 H -1,2,4-三唑-碱性条件下的3-硫酮衍生物。此外，硫酮与3-氯-戊烷-2,4-二酮缩合生成新型1,2,4-三唑基-硫代-戊烷-2,4-二酮体系，借助光谱研究了酮-烯醇互变异构现象数据（FT-IR、NMR 和质量）。三种不同互变异构体（螯合烯醇、酮、非螯合烯醇）之间的低能垒导致螯合烯醇的转化⇌非螯合烯醇⇌在紫外线照射下形成酮。研究了溶剂对二酮5a中激发态分子内质子转移 (ESIPT) 的影响，并通过 TD-DFT 研究记录了实验结果。生成的1,3-二酮用水合肼处理得到三唑基-S-吡唑杂化物6。根据光谱数据鉴定了合成化合物的结构。代表性化合物6a的单晶 X 射线衍射 (SC-XRD)

  DOI：

  10.1016/j.molstruc.2023.136015
• 作为产物：
  描述：

  烟酸乙酯 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 N-(4-chlorophenyl)-2-nicotinoylhydrazinecarbothioamide
  参考文献：
  名称：

  Patil, Priyanka A.; Khulbe, Preeti; Magdum, Chandrakant S., Indian Journal of Heterocyclic Chemistry, 2023, vol. 33, # 1, p. 76 - 78

  摘要：

  DOI：

文献信息

• The rapid preparation of 2-aminosulfonamide-1,3,4-oxadiazoles using polymer-supported reagents and microwave heating
  作者：Ian R. Baxendale、Steven V. Ley、Marisa Martinelli

  DOI：10.1016/j.tet.2005.03.062

  日期：2005.5

  Herein, we report on the preparation of a library of 5-substituted-2-amino-1,3,4-oxadiazoles and the corresponding thiadiazole analogues. Presented is a one-pot preparation of the 2-ammosulfonylated analogues through a three component coupling of an acylhydrazine, an isocyanate and sulfonyl chloride promoted by a polymer-supported phosphazine base under microwave dielectric heating. Also described is the optimization process and details pertaining to the elucidation of the reaction products. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.
• ZHANG, LIXUE;ZHANG, ZIYI;ZENG, FULI, GAODEHN SYUEHSYAO XUASYUEH SYUEHBAO, 11,(1990) N, S. 148-153
  作者：ZHANG, LIXUE、ZHANG, ZIYI、ZENG, FULI

  DOI：——

  日期：——