N-(4-methoxy-phenyl)-α-thiopicolinamide | 13225-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-methoxy-phenyl)-α-thiopicolinamide
• 英文别名: pyridine-2-carbothioic acid p-anisidide；Pyridin-2-thiocarbonsaeure-p-anisidid；2-(4-Methoxy-phenylthiocarbamoyl)-pyridin；2-Thiopyridincarboxy-p-anisidid；Thiopicolin-p-methoxyanilid；N-(4-methoxyphenyl)pyridine-2-carbothioamide
• CAS: 13225-85-9
• 化学式: C₁₃H₁₂N₂OS
• 分子量: 244.317
• InChiKey: NXGCPYBRGINPQF-UHFFFAOYSA-N

物化性质

• 熔点：
  97.5-98 °C
• 沸点：
  390.7±48.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-methoxy-phenyl)-α-thiopicolinamide 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 生成 6-methoxy-2-(pyridin-2-yl)benzo[d]thiazole
  参考文献：
  名称：

  Saikachi et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 1318,1321

  摘要：

  DOI：
• 作为产物：
  描述：

  碳酸甲丙酯 、 甲氧苯胺 在 sulfur 作用下， 反应 12.0h， 以54%的产率得到N-(4-methoxy-phenyl)-α-thiopicolinamide
  参考文献：
  名称：

  Synthesis and pharmacological activities of some mononuclear Ru(II) complexes

  摘要：

  A series of mononuclear Ru(II) complexes of the type [Ru(M)(2) (U)](2+), where M = 2,2'-bipyridine/1,10-phenanthroline and U = tpl (Rul), 4-Cl-tpl (Ru2), 4-CH3-tPl (Ru3), 4-CH3O-tPl (Ru4), and 4-NO2-tpl (Ru5), -pai (Ru6), where tpl = thiopicolinanilide and pai = 2-phenyl-azo-imidazole, have been prepared and characterized by IR, UV-Vis, H-l NMR, C-13-NMR, FAB-Mass spectrophotometer, and elemental analysis. The complexes display metal-ligand charge transfer (MLCT) transitions in the visible region. The title complexes were subjected to in vivo anticancer activity tests against a transplantable murine tumor cell line, Ehrlich's ascitic carcinoma (EAC and in vitro antibacterial activity against Gram positive and Gram negative microorganisms. Rul-Ru6 were found to increase the life span of the tumor hosts by 19-52%, and decreased tumor volume and viable ascitic cell count. The results of the present study clearly demonstrated the tumor inhibitory activity of the ruthenium chelates against transplantable murine tumor cell line. The treatment with ruthenium complexes could be secondary to tumor regression or due to the action of the compounds itself. The significant antibacterial activity was observed for Rul-Ru4 against microorganisms like Vibrio cholera 865, Staphylococcus aureus 657 1, and Shigella flexneri as compared to that of standard drug chloramphenical. Ru5 showed moderate activity against S. aureus 8530. However, all the complexes fail to show significant antibacterial activity against V cholera 14033 and Shigella sonnai. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.047

文献信息

• Complex formation of copper(II) and nickel(II) with N-arylthiopicolinamides
  作者：A. P. Ranskii、B. A. Bovykin、V. G. Kartsev、Z. G. Aliev

  DOI：10.1007/bf00699177

  日期：1993.9

  The reactions of N-arylthiopicolinamides (HL) with copper(II) and nickel(II) ions in organic and aqueous-organic solutions were studied. On addition of HCl, the transformation of ML2 complexes into M(HL)Cl2 occurs, while the reverse reaction takes place under the action of amphoteric protic solvents. The structures of the isolated complexes were established by IR and UV spectroscopy.

  研究了 N-芳基硫代吡啶酰胺 (HL) 与铜 (II) 和镍 (II) 离子在有机和水-有机溶液中的反应。加入 HCl 后，ML2 络合物转化为 M(HL)Cl2，而在两性质子溶剂的作用下发生逆反应。通过红外和紫外光谱确定了分离的配合物的结构。
• Bidentate Chelate Compounds. I
  作者：Francis Lions、Kenneth V. Martin

  DOI：10.1021/ja01540a020

  日期：1958.4
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Ni: MVol.C2, 8.15, page 998 - 1009
  作者：

  DOI：——

  日期：——
• Bag, S. P.; Bhattacharya, Journal of the Indian Chemical Society, 1984, vol. 61, # 4, p. 356 - 359
  作者：Bag, S. P.、Bhattacharya

  DOI：——

  日期：——
• The cycloauration of pyridine-2-thiocarboxamide ligands
  作者：Kelly J. Kilpin、William Henderson、Brian K. Nicholson

  DOI：10.1016/j.ica.2009.10.003

  日期：2010.1

  Reactions of H[AuCl4] with N-substituted 2-pyridine thiocarboxamide ligands 2-(C5H4N)C(S)NHR (R = p-C6H4Me, CH2Ph, Me, p-C6H4OMe) gave cycloaurated derivatives (C5H4N)C(S)NR}AuCl2, with the ligand bonded as the thiol tautomer through the deprotonated SH group and the pyridine N atom to give a five-membered metallacyclic ring. The X-ray structure determination of the R = CH2Ph derivative shows a square-planar gold(III) complex that dimerises in the solid state by weak Au center dot center dot center dot S intermolecular interactions. In contrast, in the reaction of H[AuCl4] with 2-(C5H4N)C(S)NHR where R = 2-pyridyl, the ligand was oxidised to give a 1,2,4-thiadiazolo[2,3-a] pyridinium heterocyclic ring that was crystallographically characterised. (C) 2009 Elsevier B.V. All rights reserved.