2-{2-[(naphthalen-2-yloxy)acetyl]hydrazinyl}-N-(1,3-thiazol-2-yl)acetamide | 1370228-72-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-{2-[(naphthalen-2-yloxy)acetyl]hydrazinyl}-N-(1,3-thiazol-2-yl)acetamide
• 英文别名: 2-[2-(2-naphthalen-2-yloxyacetyl)hydrazinyl]-N-(1,3-thiazol-2-yl)acetamide
• CAS: 1370228-72-0
• 化学式: C₁₇H₁₆N₄O₃S
• 分子量: 356.405
• InChiKey: NJTFPVWIQXBRIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(2-氯乙酰胺基)噻唑 、 2-(2-萘氧基)乙酰肼 以 乙醇 为溶剂， 反应 6.0h， 以73%的产率得到2-{2-[(naphthalen-2-yloxy)acetyl]hydrazinyl}-N-(1,3-thiazol-2-yl)acetamide
  参考文献：
  名称：

  Regioselective synthesis and antimicrobial activities of some novel aryloxyacetic acid derivatives

  摘要：

  Reaction of aryloxyacetic acid hydrazides 1a,b with alpha-haloketones such as hydrazonoyl chlorides 2a,b; phenacyl bromides 6a,b; and 2-chloro-N-(1,3-thiazol-2-yl)acetamide 10 led to the formation N-(4-halophenyl)-2-[2-(aryloxyacetyl)hydrazinylidene]propanehydrazonoyl chloride 3a-d; (ethene-1,2-diyl) bis-2-(naphthalen-2-yloxy)acetohydrazides 9a,b; and 2-[(2-aryloxyacetyl)hydrazinyl)]-N-(1,3-thiazol-2-yl)acetamides 11a,b; respectively. The nucleophilic substitution reaction of 3a-d with thiophenol and sodium benzenesulfinate furnished the corresponding hydrazinylidenepropanehydrazonothioates 4a-d and sulfones 5a-d, respectively. The antimicrobial activities of the synthesized compounds were evaluated. The obtained data indicated that the majority of the tested compounds exhibited antibacterial activity while all those compounds showed antifungal activity. Sulfone 5d showed greater effect with all tested organism than well known antibacterial and antifungal agents with minimal inhibitory concentration (MIC) ranged between 4.125 and 16.5 mu g/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.028

文献信息

• Regioselective synthesis and antimicrobial activities of some novel aryloxyacetic acid derivatives
  作者：Bakr F. Abdel-Wahab、Rizk E. Khidre、Ghada E.A. Awad

  DOI：10.1016/j.ejmech.2012.01.028

  日期：2012.4

  Reaction of aryloxyacetic acid hydrazides 1a,b with alpha-haloketones such as hydrazonoyl chlorides 2a,b; phenacyl bromides 6a,b; and 2-chloro-N-(1,3-thiazol-2-yl)acetamide 10 led to the formation N-(4-halophenyl)-2-[2-(aryloxyacetyl)hydrazinylidene]propanehydrazonoyl chloride 3a-d; (ethene-1,2-diyl) bis-2-(naphthalen-2-yloxy)acetohydrazides 9a,b; and 2-[(2-aryloxyacetyl)hydrazinyl)]-N-(1,3-thiazol-2-yl)acetamides 11a,b; respectively. The nucleophilic substitution reaction of 3a-d with thiophenol and sodium benzenesulfinate furnished the corresponding hydrazinylidenepropanehydrazonothioates 4a-d and sulfones 5a-d, respectively. The antimicrobial activities of the synthesized compounds were evaluated. The obtained data indicated that the majority of the tested compounds exhibited antibacterial activity while all those compounds showed antifungal activity. Sulfone 5d showed greater effect with all tested organism than well known antibacterial and antifungal agents with minimal inhibitory concentration (MIC) ranged between 4.125 and 16.5 mu g/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.