(2Z)-1-ethyl-1,4-dihydro-7-methyl-N'-(2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enylidene)-4-oxo-1,8-naphthyridine-3-carbohydrazide | 1421832-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (2Z)-1-ethyl-1,4-dihydro-7-methyl-N'-(2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enylidene)-4-oxo-1,8-naphthyridine-3-carbohydrazide
• 英文别名: 1-ethyl-7-methyl-N-[(Z)-(2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ylidene)amino]-4-oxo-1,8-naphthyridine-3-carboxamide
• CAS: 1421832-25-8
• 化学式: C₂₂H₂₆N₄O₂
• 分子量: 378.474
• InChiKey: FQGNQHXQLCUGSZ-CLCOLTQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  香芹酮 、 nalidixic acid hydrazide 以 乙醇 为溶剂， 以70%的产率得到(2Z)-1-ethyl-1,4-dihydro-7-methyl-N'-(2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enylidene)-4-oxo-1,8-naphthyridine-3-carbohydrazide
  参考文献：
  名称：

  Synthesis, characterization, and in vitro anti-Mycobacterium tuberculosis activity of terpene Schiff bases

  摘要：

  A novel series of Schiff bases (3-13) were synthesized by the reaction of isoniazid (INH), nalidixic acid hydrazide, and fenamic acid hydrazides with monoterpenes (citral, camphor, and carvone) to obtain anti-mycobacterial agents in good yield and purity. The structures of the compounds were confirmed on the basis of their elemental analysis and spectral data. The structural modification of INH, nalidixic acid hydrazide, and fenamic acid hydrazides provided lipophilic adaptation of the respective hydrazides. The anti-mycobacterial activity of the synthesized compounds was investigated against four Mycobacterium strains: M. intercellulari (ATCC 35743), M. xenopi (ATCC 14470), M. cheleneo (ATCC 35751), and M. smegmatis (ATCC 35797). Compound 5, N'-[(1E)-2-methyl-5-(prop-1-en-2-yl) cyclohex-2-en-1-ylidene] pyridine-4-carbohydrazide with minimum inhibitory concentration (MIC 12 +/- A 0.03 mu g/mL) was found to be more potent than INH under the in vitro investigation conditions. It was found that there is no evident relation between the anti-tubercular activity of the tested compounds and their lipophilicity. However, lipophilicity has an influence on the activity, but it does not solely determine the anti-tubercular activity of these compounds. All compounds presented lipophilicity higher than that of respective parent hydrazide.

  DOI：

  10.1007/s00044-012-0458-3

文献信息

• Synthesis, characterization, and in vitro anti-Mycobacterium tuberculosis activity of terpene Schiff bases
  作者：Mashooq A. Bhat、Mohamed A. Al-Omar

  DOI：10.1007/s00044-012-0458-3

  日期：2013.9

  A novel series of Schiff bases (3-13) were synthesized by the reaction of isoniazid (INH), nalidixic acid hydrazide, and fenamic acid hydrazides with monoterpenes (citral, camphor, and carvone) to obtain anti-mycobacterial agents in good yield and purity. The structures of the compounds were confirmed on the basis of their elemental analysis and spectral data. The structural modification of INH, nalidixic acid hydrazide, and fenamic acid hydrazides provided lipophilic adaptation of the respective hydrazides. The anti-mycobacterial activity of the synthesized compounds was investigated against four Mycobacterium strains: M. intercellulari (ATCC 35743), M. xenopi (ATCC 14470), M. cheleneo (ATCC 35751), and M. smegmatis (ATCC 35797). Compound 5, N'-[(1E)-2-methyl-5-(prop-1-en-2-yl) cyclohex-2-en-1-ylidene] pyridine-4-carbohydrazide with minimum inhibitory concentration (MIC 12 +/- A 0.03 mu g/mL) was found to be more potent than INH under the in vitro investigation conditions. It was found that there is no evident relation between the anti-tubercular activity of the tested compounds and their lipophilicity. However, lipophilicity has an influence on the activity, but it does not solely determine the anti-tubercular activity of these compounds. All compounds presented lipophilicity higher than that of respective parent hydrazide.