N'-(5,5-dimethyl-3-oxo-1-cyclohexen-1-yl)isonicotinohydrazide | 202601-82-9

• 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'-(5,5-dimethyl-3-oxo-1-cyclohexen-1-yl)isonicotinohydrazide
• 英文别名: N'-(5,5-dimethyl-3-oxocyclohexen-1-yl)pyridine-4-carbohydrazide
• CAS: 202601-82-9
• 化学式: C₁₄H₁₇N₃O₂
• 分子量: 259.308
• InChiKey: ZFTSKUDOGVQQTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  、 N'-(5,5-dimethyl-3-oxo-1-cyclohexen-1-yl)isonicotinohydrazide 、 氰乙酸甲酯 在 哌啶 作用下， 以85%的产率得到methyl 1-allyl-2'-amino-6-chloro-1'-(isonicotinamido)-7',7'-dimethyl-2,5'-dioxo-1,1',2,4',5',6',7',8'-octahydro-3,4'-biquinoline-3'-carboxylate
  参考文献：
  名称：

  Design and synthesis of biquinolone–isoniazid hybrids as a new class of antitubercular and antimicrobial agents

  摘要：

  Twenty four biquinolone-isoniazid hybrids were designed based on molecular hybridization technique and synthesized via multicomponent cyclocondensation (MCC) approach. All the newly synthesized compounds were screened for their antimicrobial and antitubercular activities. The brine shrimp bioassay was carried out to study the cytotoxicity of the synthesized compounds. Hybrids 7f (MIC = 25 mu g/mL); 7a, 7e and 7m (MIC = 50 mu g/mL); 7g, 7h and 7k (MIC = 62.5 mu g/mL) exhibited excellent antimicrobial activity as compared with standard drugs. Hybrids 71 and 7j displayed 99% inhibition against Mycobacterium tuberculosis bacteria with better LC50 values 35.39 and 34.59 mu g/mL, respectively. These results indicate that the synthesized compounds can act as leads for the development of newer antimicrobial and antitubercular compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.003
• 作为产物：
  描述：

  异烟肼 、 5,5-二甲基-1,3-环己二酮 以 neat (no solvent) 为溶剂， 反应 0.5h， 生成 N'-(5,5-dimethyl-3-oxo-1-cyclohexen-1-yl)isonicotinohydrazide
  参考文献：
  名称：

  新型3,4'-联碳青霉素衍生物作为有效的抗微生物剂，抗结核药和抗疟药的文库设计，合成和生物学探索

  摘要：

  摘要文库包含通过分子杂交技术设计并通过多组分反应合成的多样化取代的新型3,4'-联碳青霉素衍生物。化合物G22（MIC = 12.5 µg / mL）和G38（MIC = 25 µg / mL）对结核分枝杆菌表现出99％的抑制作用，而化合物G40（IC 50  = 0.019 µg / mL）和G20（IC 50  = 0.028 µg / mL） ）被发现对恶性疟原虫具有优异的活性。化合物G37（MIC = 25 µg / mL）和G8，G18和G38（MIC = 50 µg / mL）与标准药物相比具有出色的抗菌活性。生物学结果表明，标题化合物的效力很大程度上取决于在N -1处各种间隔基的长度和柔韧性，R 1上的取代基的电子影响以及Bicarbostyril系统在R 2上的CH 3基团的亲脂性。 图形概要

  DOI：

  10.1007/s00044-017-1797-x

文献信息

• Design and synthesis of biquinolone–isoniazid hybrids as a new class of antitubercular and antimicrobial agents
  作者：Hardik H. Jardosh、Manish P. Patel

  DOI：10.1016/j.ejmech.2013.05.003

  日期：2013.7

  Twenty four biquinolone-isoniazid hybrids were designed based on molecular hybridization technique and synthesized via multicomponent cyclocondensation (MCC) approach. All the newly synthesized compounds were screened for their antimicrobial and antitubercular activities. The brine shrimp bioassay was carried out to study the cytotoxicity of the synthesized compounds. Hybrids 7f (MIC = 25 mu g/mL); 7a, 7e and 7m (MIC = 50 mu g/mL); 7g, 7h and 7k (MIC = 62.5 mu g/mL) exhibited excellent antimicrobial activity as compared with standard drugs. Hybrids 71 and 7j displayed 99% inhibition against Mycobacterium tuberculosis bacteria with better LC50 values 35.39 and 34.59 mu g/mL, respectively. These results indicate that the synthesized compounds can act as leads for the development of newer antimicrobial and antitubercular compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Library design, synthesis and biological exploration of novel 3,4′-bicarbostyril derivatives as potent antimicrobial, antitubercular and antimalarial agents
  作者：Hardik H. Jardosh、Nileshkumar D. Vala、Manish P. Patel

  DOI：10.1007/s00044-017-1797-x

  日期：2017.5

  AbstractA library comprises diversely substituted novel 3,4′-bicarbostyril derivatives have been designed by molecular hybridization technique and synthesized via multi-component reaction . Compounds G22 (MIC = 12.5 µg/mL) and G38 (MIC = 25 µg/mL) exhibited 99% inhibition against Mycobacterium tuberculosis, while compounds G40 (IC50 = 0.019 µg/mL) and G20 (IC50 = 0.028 µg/mL) found to have excellent

  摘要文库包含通过分子杂交技术设计并通过多组分反应合成的多样化取代的新型3,4'-联碳青霉素衍生物。化合物G22（MIC = 12.5 µg / mL）和G38（MIC = 25 µg / mL）对结核分枝杆菌表现出99％的抑制作用，而化合物G40（IC 50  = 0.019 µg / mL）和G20（IC 50  = 0.028 µg / mL） ）被发现对恶性疟原虫具有优异的活性。化合物G37（MIC = 25 µg / mL）和G8，G18和G38（MIC = 50 µg / mL）与标准药物相比具有出色的抗菌活性。生物学结果表明，标题化合物的效力很大程度上取决于在N -1处各种间隔基的长度和柔韧性，R 1上的取代基的电子影响以及Bicarbostyril系统在R 2上的CH 3基团的亲脂性。 图形概要