4-benzyl-1-(2-pyridoyl) thiosemicarbazide | 211572-58-6

• 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: 4-benzyl-1-(2-pyridoyl) thiosemicarbazide
• 英文别名: N-benzyl-2-picolinoylhydrazinecarbothioamide；1-Benzyl-3-(pyridine-2-carbonylamino)thiourea
• CAS: 211572-58-6
• 化学式: C₁₄H₁₄N₄OS
• 分子量: 286.357
• InChiKey: FVNWMYOGRZUTFY-UHFFFAOYSA-N

物化性质

• 熔点：
  178-181 °C(Solv: ethanol (64-17-5))
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  4-benzyl-1-(2-pyridoyl) thiosemicarbazide 在 sodium hydroxide 作用下， 反应 0.03h， 以85%的产率得到4-benzyl-3-(pyridin-2-yl)-1H-1,2,4-triazole-5(4H)-thione
  参考文献：
  名称：

  缩氨基硫脲的微波辅助脱水环化形成取代的1,2,4-三唑

  摘要：

  不同类型的 4,5-二取代 1,2,4-三唑-3-硫酮是通过微波辐射和经典方法制备的。描述了微波辐射对氨基硫脲在不同反应介质中脱水环化的有益影响。我们的结果表明，微波辐射对所研究反应的影响是反应时间的缩短（从 2-9 小时到 2-4 分钟）和产率的轻微下降（1-4%）。通过FTIR、MS和1H NMR光谱数据确定了新化合物的结构。

  DOI：

  10.1080/10426500500543859
• 作为产物：
  描述：

  2-吡啶甲酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 4-benzyl-1-(2-pyridoyl) thiosemicarbazide
  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

• The Microwave-Assisted Dehydrative Cyclization of Thiosemicarbazides Forming Substituted 1,2,4-Triazoles
  作者：Khosrow Zamani、Shirindokht Bagheri

  DOI：10.1080/10426500500543859

  日期：2006.8.1

  irradiation as well as by a classical method. The beneficial effect of microwave irradiation on the dehydrative cyclization of thiosemicarbazides in different reaction media is described. Our results show that the effect of microwave irradiation on the reaction studied was the shortening of reaction times (from 2–9 h to 2–4 min) and a minor decrease (1–4%) in yields. The structure of the new compounds was

  不同类型的 4,5-二取代 1,2,4-三唑-3-硫酮是通过微波辐射和经典方法制备的。描述了微波辐射对氨基硫脲在不同反应介质中脱水环化的有益影响。我们的结果表明，微波辐射对所研究反应的影响是反应时间的缩短（从 2-9 小时到 2-4 分钟）和产率的轻微下降（1-4%）。通过FTIR、MS和1H NMR光谱数据确定了新化合物的结构。
• Facile Synthesis of Naphtho[2,3-<i>d</i>]thiazoles, Naphtho[2,3-<i>e</i>][1,3,4]thiadiazines and Bis(naphtho[2,3-<i>d</i>]thiazolyl)copper(II) Derivatives from Heteroylthiosemicarbazides
  作者：Alaa A. Hassan、Nasr K. Mohamed、Lamiaa E. Abd El-Haleem、Stefan Bräse、Martin Nieger

  DOI：10.1002/cjoc.201600195

  日期：2016.8

  A one step synthesis protocol for the conversion of heteroylthiosemicarbazides and 2,3‐dichloro‐1,4‐naphthoquinone to naphtho[2,3‐d]thiazoles, naphtho[2,3‐e][1,3,4]thiadiazines as well as bis(naphtho[2,3‐d]thiazolyl)copper(II) derivatives is described. The products were conclusively confirmed by single crystal X‐ray analyses. A mechanism for the formation of the products is presented.

  一步合成方案，用于将杂芳基硫代氨基脲和2,3-二氯-1,4-萘醌转化为萘并[2,3- d ]噻唑，萘并[2,3- e ] [1,3,4]噻二嗪以及双（萘[2,3- d ]噻唑基）铜（II）衍生物的描述。产品通过单晶X射线分析最终确认。提出了形成产物的机制。
• Small molecule inhibitors of HIV RT Ribonuclease H
  作者：Martin Di Grandi、Matthew Olson、Amar S. Prashad、Geraldine Bebernitz、Amara Luckay、Stanley Mullen、Yongbo Hu、Girija Krishnamurthy、Keith Pitts、John O’Connell

  DOI：10.1016/j.bmcl.2009.10.043

  日期：2010.1

  Two classes of compounds, thiocarbamates 1 and triazoles 2, have been identified as HIV RT RNase H inhibitors using a novel FRET-based HTS assay. The potent analogs in each series exhibited selectivity and were active in cell-based assays. In addition, saturable, 1: 1 stoichiometric binding to target was established and time of addition studies were consistent with inhibition of RT-mediated HIV replication. (C) 2009 Elsevier Ltd. All rights reserved.
• Zamani, Khosrow; Faghihi, Khalil; Bagheri, Shirindokht, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 12, p. 2716 - 2718
  作者：Zamani, Khosrow、Faghihi, Khalil、Bagheri, Shirindokht、Kalhor, Mahdi

  DOI：——

  日期：——
• Iqbal, Rashid; Rama, Nasim H.; Ahmad, Nasir, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 5, p. 506 - 509
  作者：Iqbal, Rashid、Rama, Nasim H.、Ahmad, Nasir、Zamani, Khosrow、Ebrahim, Samia、Iqbal, Nasir

  DOI：——

  日期：——