N-cyclohexyl-2-(methylthio)nicotinamide | 141841-67-0

• 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-cyclohexyl-2-(methylthio)nicotinamide
• 英文别名: N-cyclohexyl-2-(methylsulfanyl)pyridine-3-carboxamide；N-cyclohexyl-2-methylsulfanylpyridine-3-carboxamide
• CAS: 141841-67-0
• 化学式: C₁₃H₁₈N₂OS
• 分子量: 250.365
• InChiKey: OBXHPQYBEAVYNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  441.6±30.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-巯基烟酸 在 potassium carbonate 作用下， 反应 24.0h， 生成 N-cyclohexyl-2-(methylthio)nicotinamide
  参考文献：
  名称：

  Three 2-(methysulfanyl)nicotinamides

  摘要：

  三种 N-烷基-2-(甲硫基)烟酰胺衍生物的分子构象，即 N-环己基-2-(甲硫基)烟酰胺，C13H18N2OS，(I)；N-异丙基-2-(甲硫基)烟酰胺，C10H14N2OS，(II)、以及 N-（2-羟乙基）-2-（甲硫基）烟酰胺二水合物 C9H12N2O2S-2H2O（III）与四种未取代的 N-烷基烟酰胺化合物进行了比较。与未取代的化合物相比，取代的化合物显示出吡啶环相对于酰胺基的扭转程度更高，前者的二面角在 40-60° 之间，后者的二面角在 20-35° 之间。在(I)和(II)中，超分子结构由酰胺-N 至羰基-O 链确定。在(III)中，烟酰胺分子通过氢键与两个水分子相连，形成两个相连的环链，构成三维网络。

  DOI：

  10.1107/s0108270113004344

文献信息

• Three 2-(methysulfanyl)nicotinamides
  作者：Ligia R. Gomes、John Nicolson Low、James L. Wardell、Alessandra C. Pinheiro、Thais C. N. de Mendonça、Marcus V. N. de Souza

  DOI：10.1107/s0108270113004344

  日期：2013.3.15

  The molecular conformations of threeN-alkyl-2-(methylsulfanyl)nicotinamide derivatives, namelyN-cyclohexyl-2-(methylsulfanyl)nicotinamide, C₁₃H₁₈N₂OS, (I),N-isopropyl-2-(methylsulfanyl)nicotinamide, C₁₀H₁₄N₂OS, (II), in which there are two molecules in the asymmetric unit which were chosen to form a hydrogen-bonded pair, andN-(2-hydroxyethyl)-2-(methylsulfanyl)nicotinamide dihydrate, C₉H₁₂N₂O₂S·2H₂O, (III), are compared with those of four unsubstitutedN-alkylnicotinamide compounds. The substituted compounds show a higher degree of torsion of the pyridine ring with respect to the amide group than do the unsubstituted compounds, with dihedral angles in the range 40–60° for the former and 20–35° for the latter. In (I) and (II), the supramolecular structure is defined by amide-N to carbonyl-O chains. In (III), the nicotinamide molecules are linked by hydrogen bonds to two water molecules resulting in two linked chains of rings which form the three-dimensional network.

  三种 N-烷基-2-(甲硫基)烟酰胺衍生物的分子构象，即 N-环己基-2-(甲硫基)烟酰胺，C13H18N2OS，(I)；N-异丙基-2-(甲硫基)烟酰胺，C10H14N2OS，(II)、以及 N-（2-羟乙基）-2-（甲硫基）烟酰胺二水合物 C9H12N2O2S-2H2O（III）与四种未取代的 N-烷基烟酰胺化合物进行了比较。与未取代的化合物相比，取代的化合物显示出吡啶环相对于酰胺基的扭转程度更高，前者的二面角在 40-60° 之间，后者的二面角在 20-35° 之间。在(I)和(II)中，超分子结构由酰胺-N 至羰基-O 链确定。在(III)中，烟酰胺分子通过氢键与两个水分子相连，形成两个相连的环链，构成三维网络。
• Synthesis and Antifungal Activity of Nicotinamide Derivatives as Succinate Dehydrogenase Inhibitors
  作者：Yong-Hao Ye、Liang Ma、Zhi-Cheng Dai、Yu Xiao、Ying-Ying Zhang、Dong-Dong Li、Jian-Xin Wang、Hai-Liang Zhu

  DOI：10.1021/jf405437k

  日期：2014.5.7

  Thirty-eight nicotinamide derivatives were designed and synthesized as potential succinate dehydrogenase inhibitors (SDHI) and precisely characterized by H-1 NMR, ESI-MS, and elemental analysis. The compounds were evaluated against two phytopathogenic fungi, Rhizoctonia solani and Sclerotinia sclerotiorum, by mycelia growth inhibition assay in vitro. Most of the compounds displayed moderate activity, in which, 3a-17 exhibited the most potent antifungal activity against R. solani and S. sclerotiorum with IC50 values of 15.8 and 20.3 mu M, respectively, comparable to those of the commonly used fungicides boscalid and carbendazim. The structure-activity relationship (SAR) of nicotinamide derivatives demonstrated that the meta-position of aniline was a key position contributing to the antifungal activity. Inhibition activities against two fungal SDHs were tested and achieved the same tendency with the data acquired from in vitro antifungal assay. Significantly, 3a-17 was demonstrated to successfully suppress disease development in S. sclerotiorum infected cole in vivo. In the molecular docking simulation, sulfur and chlorine of 3a-17 were bound with PHE291 and PRO150 of the SDH homology model, respectively, which could explain the probable mechanism of action between the inhibitory and target protein.