ethyl 5-(4-(2,6-dichlorobenzyloxy)phenyl)-2-aminothiophene-3-carboxylate | 1334930-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: ethyl 5-(4-(2,6-dichlorobenzyloxy)phenyl)-2-aminothiophene-3-carboxylate
• 英文别名: Ethyl 2-amino-5-[4-[(2,6-dichlorophenyl)methoxy]phenyl]thiophene-3-carboxylate
• CAS: 1334930-94-7
• 化学式: C₂₀H₁₇Cl₂NO₃S
• 分子量: 422.332
• InChiKey: YXRKWBQUTYIHOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  89.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-(2,6-dichlorobenzyloxy)phenyl)-2-aminothiophene-3-carboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-(5-(4-(2,6-dichlorobenzyloxy)phenyl)-3-(ethoxycarbonyl)thiophen-2-ylamino)-2-oxoacetic acid
  参考文献：
  名称：

  Design, synthesis and anti-tubercular evaluation of new 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives. Part 1

  摘要：

  A series of 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives were synthesized and evaluated for anti-tubercular activity. Among these compounds, 10d, 15, 12h and 12k inhibited Mycobacterium tuberculosis (Mtb) growth with MIC values between 1.9 and 7.7 mu M and low toxicity against VERO cells. The four compounds were also tested against multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) clinical strains, which were found to show moderate activity. In addition, molecular docking simulation was performed to position compounds 10d, 15, 12h and 12k into mtFabH active site to predict the probable binding mode. These studies thus suggest that the designed 2-amino-5-phenylthiophene-3-carboxylic acid scaffold may serve as new promising template for further elaboration as anti-TB drugs. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.018
• 作为产物：
  描述：

  对羟基苯乙醇 在 2,2,6,6-四甲基哌啶氧化物 、 sodium bromite trihydrate 、 碳酸氢钠 、 potassium carbonate 、 sulfur 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 24.5h， 生成 ethyl 5-(4-(2,6-dichlorobenzyloxy)phenyl)-2-aminothiophene-3-carboxylate
  参考文献：
  名称：

  Design, synthesis and anti-tubercular evaluation of new 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives. Part 1

  摘要：

  A series of 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives were synthesized and evaluated for anti-tubercular activity. Among these compounds, 10d, 15, 12h and 12k inhibited Mycobacterium tuberculosis (Mtb) growth with MIC values between 1.9 and 7.7 mu M and low toxicity against VERO cells. The four compounds were also tested against multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) clinical strains, which were found to show moderate activity. In addition, molecular docking simulation was performed to position compounds 10d, 15, 12h and 12k into mtFabH active site to predict the probable binding mode. These studies thus suggest that the designed 2-amino-5-phenylthiophene-3-carboxylic acid scaffold may serve as new promising template for further elaboration as anti-TB drugs. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.018