N-(2,5-dimethyl-1H-pyrrol-1-yl)isonicotinamide | 5588-11-4

• 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-(2,5-dimethyl-1H-pyrrol-1-yl)isonicotinamide
• 英文别名: 1-(4-pyridoyl)amino-2,5-dimethylpyrrole；isonicotinic acid-(2,5-dimethyl-pyrrol-1-ylamide)；Isonicotinsaeure-(2,5-dimethyl-pyrrol-1-ylamid)；N-(2,5-Dimethylpyrrol-1-yl)isonicotinamide；N-(2,5-dimethylpyrrol-1-yl)pyridine-4-carboxamide
• CAS: 5588-11-4
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: BZSIVBPSSDJJOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  zinc(II) chloride dihydrate 、 N-(2,5-dimethyl-1H-pyrrol-1-yl)isonicotinamide 以 乙醇 为溶剂， 反应 4.0h， 生成 Zn(N-(2,5-dimethyl-1H-pyrrol-1-yl)isonicotinamide)₂Cl₂
  参考文献：
  名称：

  Synthesis, crystal structure, characterization and biological activity of 2,5-hexanedione bis(isonicotinylhydrazone) and N-(2,5-dimethyl-1H-pyrrol-1-yl)isonicotinamide complexes

  摘要：

  The reaction between 2,5-hexanedione and isonicotinic acid hydrazide in Et0H gave two products. The ethanol insoluble product was identified as 2,5-hexanedione bis(isonicotinylhydrazone) [HINH] and the soluble ethanol product as N-(2,5-dimethyl-1H-pyrrol-1-yl)isonicotinamide [DINA]. A series of Cr3+, Fe3+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Hg2+ and Pd2+ complexes of HINH and Co2+, Cu2+, Zn2+ and Hg2+ complexes of DINA have been synthesized and structurally characterized. Based on the elemental analysis, mass spectra and molar conductance, the complexes have assigned the proposed imperical formulae. The crystal structures of N-(2,5-dimethyl-1H-pyrrol-1-yl)isonicotinamide and its Zn2+ and Hg2+ complexes have been solved by X-ray diffraction having [Zn(DINA)(2)Cl-2] and [Hg(DINA)(2)Cl-2] in a tetrahedral structure. In the DINH complexes, the ligand coordinates as a monodentate through the pyridine nitrogen. On the other hand, HINH behaves as a tetradentate (neutral or binegative) manner with the two metal ions. The magnetic moments and electronic spectra of all complexes provide tetrahedral, square-planar, trigonal biyramid and/or octahedral structure. The thermal decomposition of the complexes revealed the outer and inner solvents as well as the end product. The steady part of [Zn(DINA)(2)Cl-2] and [Hg(DINA)(2)Cl-2] thermograms till 303 and 286 degrees C indicates the absence of any outside solvents. All compounds have activity against bacteria more than fungi. [Cd-4(HINH)Cl-8]center dot 3H(2)O has the highest values. 0 2015 Elsevier B.V, All rights reserved.

  DOI：

  10.1016/j.saa.2015.05.071
• 作为产物：
  描述：

  异烟肼 在 乙醇 、 乙二醇 作用下， 生成 N-(2,5-dimethyl-1H-pyrrol-1-yl)isonicotinamide
  参考文献：
  名称：

  结核的化学疗法。第六部分 异烟酸的一些衍生物

  摘要：

  DOI：

  10.1039/jr9550004315

文献信息

• Preparation and properties<i>in vitro</i>and<i>in vivo</i>of antitubercular pyrroles
  作者：Michael J. Hearn、Michaeline F. Chen、Marianne S. Terrot、Eleanor R. Webster、Michael H. Cynamon

  DOI：10.1002/jhet.352

  日期：——

  1‐Acylamino‐2,5‐dimethylpyrroles were prepared in the exploration of heterocyclic structures useful for their antitubercular activity. The pyrroles were conveniently formed from the reaction of aromatic acid hydrazides with hexane‐2,5‐dione in water or ethanol, without resorting to acid catalysis. In each case, the procedure provided a single pyrrole in pure form, and the product was identified without

  1-酰基氨基-2,5-二甲基吡咯是在探索可用于其抗结核活性的杂环结构中制备的。吡咯是由芳族酰肼与己烷-2,5-二酮在水或乙醇中的反应方便地形成的，而无需借助酸催化。在每种情况下，该程序都提供了一个纯净的吡咯，并且根据高度特征的光谱特征轻松鉴定了产物。该类别的某些成员在体外具有抗药性结核的显着活性，并在该疾病的严格小鼠模型中提供了重要的保护。J.杂环化​​学。（2010）。
• Chemotherapy of Experimental Tuberculosis. VIII. The Synthesis of Acid Hydrazides, their Derivatives and Related Compounds^1,2
  作者：Harry L. Yale、Kathryn Losee、Joseph Martins、Mary Holsing、Frances M. Perry、Jack Bernstein

  DOI：10.1021/ja01104a046

  日期：1953.4
• FURTHER STUDIES ON THE KNORR-PAAL SYNTHESIS OF 2,5-DIALKYLPYRROLES
  作者：NG. PH. BUU-HOÏ、NG. D. XUONG

  DOI：10.1021/jo01125a008

  日期：1955.7
• Synthetic Tuberculostats. XI. Trialkyl and Other Derivatives of Isonicotinylhydrazine
  作者：H. HERBERT FOX、J. T. GIBAS

  DOI：10.1021/jo01109a024

  日期：1956.3
• The chemotherapy of tuberculosis. Part VI. Some derivatives of isonicotinic acid
  作者：J. Cymerman-Craig、D. Willis

  DOI：10.1039/jr9550004315

  日期：——