1-picolinoyl-4-phenyl-3-thiosemicarbazide | 60838-16-6

• 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: 1-picolinoyl-4-phenyl-3-thiosemicarbazide
• 英文别名: N-Phenyl-2-(pyridine-2-carbonyl)hydrazine-1-carbothioamide；1-phenyl-3-(pyridine-2-carbonylamino)thiourea
• CAS: 60838-16-6
• 化学式: C₁₃H₁₂N₄OS
• 分子量: 272.33
• InChiKey: JJHSYWHPMJELRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 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：

  1-picolinoyl-4-phenyl-3-thiosemicarbazide 在 硫酸 作用下， 反应 2.0h， 生成 N-phenyl-5-(pyridin-2-yl)-1,3,4-thiadiazole-2-amine
  参考文献：
  名称：

  NNS 三齿氨基硫脲和一些过渡金属离子的 1,3,4-噻二唑-2-胺配合物：合成、结构和荧光特性

  摘要：

  摘要 Zn(II)、Mn(II) 和 Ni(II) 醋酸盐与 1-吡啶甲酰基-4-苯基-3-氨基硫脲 (Hppts) 反应生成 [Zn(ppts)2]·CHCl3 (3), [ Mn(ppts)2]·THF(4)和[Ni(ppts)2]·THF(5)，但HgCl2得到环化产物N-苯基-5-(吡啶-2-基)-1， 3,4-恶二唑-2-基-胺(2)。用浓度治疗 Hppts。H2SO4 形成 N-苯基-5-(吡啶-2-基)-1,3,4-噻二唑-2-基-胺 (1)。Hppts 是一种非荧光材料，但 3, 4 和环化产物 1,3,4-恶二唑/1,3,4-噻二唑是荧光材料。环化配体 N-苯基-5-(吡啶-2-基)-1,3,4-噻二唑-2-胺 (1) 形成 [Zn(2-Hppt)2(OAc)2] (6) 和 [ Cd2(2-Hppt)2(OAc)2(μ-OAc)2] (7) 其中 Cd(II) 具有双核醋酸桥连的七坐标五边形双锥几何。

  DOI：

  10.1080/00958972.2016.1160074
• 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 1-picolinoyl-4-phenyl-3-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

• A KHSO4 mediated facile synthesis of 2-amino-1,3,4-oxadiazole derivatives
  作者：Binyu Long、Binghua Tian、Qiang Tang、Xiangnan Hu、Lei Han、Zifan Wang、Chenyu Wang、Yue Wu、Yu Yu、Zongjie Gan

  DOI：10.1016/j.tet.2021.132382

  日期：2021.9

  A novel, efficient and mild KHSO4 mediated synthesis for 2-amino-1,3,4-oxadiazoles has been established via the cyclodesulfurization of benzoylhydrazine and isothiocyanate derivatives in one pot. The reactions proceeded smoothly at room temperature and produced corresponding products in moderate to good yields. This protocol also showed good functional group tolerance.

  通过苯甲酰肼和异硫氰酸酯衍生物的环化脱硫，建立了一种新型、高效且温和的 KHSO 4介导的 2-氨基-1,3,4-恶二唑合成方法。反应在室温下顺利进行，并以中等至良好的收率产生相应的产物。该协议还显示出良好的官能团耐受性。
• Design, Synthesis and Antibacterial Evaluation of 1-[(1<i>R</i>,2<i>S</i>)-2-Fluorocyclopropyl]ciprofloxacin-1,2,4-triazole-5(4<i>H</i>)-thione Hybrids
  作者：Yang Gao、Lu-Xin Na、Zhi Xu、Shu Zhang、A-Peng Wang、Kai Lü、Hui-Yuan Guo、Ming-Liang Liu

  DOI：10.1002/cbdv.201800261

  日期：2018.10

  4‐triazole‐5(4H)‐thione hybrids 6a – 6o was designed, synthesized and evaluated for their in vitro antibacterial activities against a panel of clinically important drug‐sensitive and drug‐resistant Gram‐positive and Gram‐negative pathogens. Our results revealed that all hybrids 6a – 6o had great potency against the tested strains, especially Gram‐negative pathogens. The synthesized hybrids were more potent

  设计、合成和评估了一类新的 1-[(1R,2S)-2-氟环丙基]环丙沙星 (CPFX)-1,2,4-三唑-5(4H)-硫酮杂化物 6a-6o对一组临床上重要的药物敏感和耐药革兰氏阳性和革兰氏阴性病原体的抗菌活性。我们的结果表明，所有杂种 6a - 6o 对受试菌株，尤其是革兰氏阴性病原体具有很强的效力。合成的杂合体比亲本 1-[(1R,2S)-2-氟环丙基]CPFX (1) 更有效，并且与 CPFX 和左氧氟沙星对大多数测试病原体的作用相当，值得进一步研究。
• Syntheses, Structures, and Biological Activities of Pd(II) and Pt(II) Complexes with some 1-picolinoyl-4-substituted Thiosemicarbazides
  作者：Hung Huy Nguyen、Quang Trung Pham、Quan Manh Phung、Canh Dinh Le、Thu Thuy Pham、Thi Ngoc Oanh Pham、Chien Thang Pham

  DOI：10.1016/j.molstruc.2022.133871

  日期：2022.12

  thiosemicarbazides H2L, namely H2LEt, H2LCy, and H2LPh, with equimolar amounts of common Pd(II) or Pt(II) complexes [M(PPh3)2Cl2] (M = Pd, Pt) bring about the formation of stable heteroleptic complexes with the compositions [M(L)(PPh3)] (M = Pd, Pt). Their molecular structures show mononuclear square planar complexes in which the acyl thiosemicarbazides are doubly deprotonated and serve as tridentate ligands

  三种 1-picolinoyl-4-取代氨基硫脲H 2 L，即H 2 L Et、H 2 L Cy和H 2 L Ph与等摩尔量的常见 Pd(II) 或 Pt(II) 配合物 [M( PPh 3 ) 2 Cl 2 ] (M = Pd, Pt) 与组成 [M( L )(PPh 3 )形成稳定的杂配络合物)] (M = Pd, Pt)。它们的分子结构显示出单核方形平面配合物，其中酰基氨基硫脲被双重去质子化，并作为三齿配体通过 ( N吡啶, N 1 , S ) 供体组与金属离子中心键合。有机配体H 2 L Et和H 2 L Ph以及它们的所有金属配合物对所检测的微生物菌株仅表现出微弱的抑制作用，而H 2 L Cy的金属配合物对枯草芽孢杆菌和发酵乳杆菌表现出良好的抑制作用MIC值低于氨苄青霉素。此外，针对癌细胞系 MCF7 和 HepG2 测试了H 2 L和复合物的体外细胞毒性。对于两种细胞系，有机配体表现出适度的抗增殖作用，活性H
• Synthesis of 1,2,4,5-Tetrakis(1,2,4-Triazolyl) Benzene and 1,2,4,5-Tetrakis(1,3,4-Oxadiazolyl) Benzene Derivatives
  作者：Abbas Nikoo、Karim Akbari Dilmaghani

  DOI：10.1080/10426507.2011.597801

  日期：2012.2.1

  A series of 1,2,4,5-tetrakis(1,2,4-triazolyl)benzenes and 1,2,4,5-tetrakis(1,3,4-oxadiazolyl)benzenes was synthesized by nucleophilic addition of sodium salts of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 1,3,4-oxadiazole-2(3H)-thiones to 1,2,4,5-tetrakis(bromomethyl) benzene. The structure of the newly synthesized compounds was confirmed by elemental analysis, IR and H-1 and C-13 NMR spectra.
• Prabhu, Girish; Madhu, Chilakapathi; Sureshbabu, Vommina V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 7, p. 865 - 870
  作者：Prabhu, Girish、Madhu, Chilakapathi、Sureshbabu, Vommina V.

  DOI：——

  日期：——