2-methylthio-1-phenylaminoimidazole-5-carboxaldehyde | 676566-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methylthio-1-phenylaminoimidazole-5-carboxaldehyde
• 英文别名: 1-phenylamino-2-methylthio-imidazole-5-carboxaldehyde；1-phenylamino-2-methylthio-1H-imidazole-5-carbaldehyde；2-Methylthio-1-phenylamino-1h-imidazole-5-carbaldehyde；3-anilino-2-methylsulfanylimidazole-4-carbaldehyde
• CAS: 676566-31-7
• 化学式: C₁₁H₁₁N₃OS
• 分子量: 233.294
• InChiKey: AUOAUUHRYRCWCP-UHFFFAOYSA-N

物化性质

• 沸点：
  438.1±37.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酰基乙酰对氯苯胺 、 2-methylthio-1-phenylaminoimidazole-5-carboxaldehyde 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以73%的产率得到4-(2-(methylthio)-1-(phenylamino)-1H-imidazol-5-yl)-2,6-dimethyl-N3,N5-di(4'-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxamide
  参考文献：
  名称：

  Synthesis and antitubercular activity of novel 4-substituted imidazolyl-2,6-dimethyl-N3,N5-bisaryl-1,4-dihydropyridine-3,5-dicarboxamides

  摘要：

  A series of 4-substituted imidazolyl-2,6-dimethyl-N-3,N-5-bisaryl-1,4-dihydropyridine-3,5-dicarboxamides were prepared. They were screened as antitubercular agents against Mycobacterium tuberculosis H(37)Rv. Minimum inhibitory concentrations (MICs) were determined using agar proportion method. Compound 3i with 1-benzyl-2-methylthio-1H-imidazole-5-yl substituent at C-4 position and 4'-chloromophenyl group at C-3 and C-5 positions of the 1,4-dihydropyridine ring was the most potent one among the tested compounds. It was as potent as rifampicin against M. tuberculosis H37RV. Compound 31 also was an active antitubercular agent with the same substituent as compound 3i at the C-4 position and 31-pyridyl group at C-3 and C-5 positions of the 1,4-dihydropyridine ring. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.027
• 作为产物：
  描述：

  5-hydroxymethyl-2-mercapto-1-phenylaminoimidazole 在 manganese(IV) oxide 、 氢氧化钾 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 11.0h， 生成 2-methylthio-1-phenylaminoimidazole-5-carboxaldehyde
  参考文献：
  名称：

  Synthesis and calcium antagonist activity of 1,4-dihydropyridines containing phenylaminoimidazolyl substituents

  摘要：

  Alkyl ester analogues of nifedipine, in which the ortho-nitrophenyl group at position 4 is replaced by 2-methylthio-1-phenylamino-5-imidazolyl substituent, were synthesized and evaluated as calcium-channel antagonists using the high K(+) contraction of guinea-pig ileal longitudinal smooth muscle. The results for the symmetrical esters showed that in the series of alkyl esters increasing the length of methylene chain in C-3 and C-5 ester substituents for more than two methylene units decreases activity. In the phenylalkyl ester series increasing the length of methylene chain also decreases activity. The results demonstrate that most of the compounds had similar activity to the reference drug nifedipine. In addition, two compounds, 5b and 5f were more active than the nifedipine.

  DOI：

  10.1016/s0014-827x(03)00159-9

文献信息

• Synthesis, calcium-channel blocking activity, and conformational analysis of some novel 1,4-dihydropyridines: application of PM3 and DFT computational methods
  作者：Afshin Fassihi、Karim Mahnam、Behzad Moeinifard、Maryam Bahmanziari、Hojjat Sadeghi Aliabadi、Afshin Zarghi、Razieh Sabet、Mona Salimi、Mahboubeh Mansourian

  DOI：10.1007/s00044-011-9807-x

  日期：2012.10

  calcium-channel blocking evaluation and conformational analysis using semi-empirical (PM3) and density functional theory (DFT) as computational methods. All molecules had a boat-like 1,4-dihydropyridine ring in both the methods. In PM3 method almost 54% of the molecules were deviated from planarity, but in DFT method all the molecules had perfect flattened-boat conformation. Using both the methods, the C-4

  合成了新型的1,4-二氢吡啶，并使用半经验（PM3）和密度泛函理论（DFT）作为计算方法，进行了钙通道阻断评估和构象分析。在两种方法中，所有分子均具有船形的1，4-二氢吡啶环。在PM3方法中，几乎54％的分子偏离了平面度，但在DFT方法中，所有分子均具有完美的扁平船形构象。使用这两种方法，C-4取代基均为假轴，其苯氨基取代基在82.14％的分子中呈sp取向。反式-反式与顺式-顺式构象分别曾在分子最大，比例最低。反式–在咪唑环上具有取代基的sp构象的反式构象异构体是活性钙通道阻滞剂。