2-(4-Acetylphenoxy)-1-(4-methylphenyl)ethanone | 897790-98-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-Acetylphenoxy)-1-(4-methylphenyl)ethanone
• CAS: 897790-98-6
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: VOOXDDIGRMUGQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-Acetylphenoxy)-1-(4-methylphenyl)ethanone 、 2-氨基二苯甲酮 在 camphor-10-sulfonic acid 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 以80%的产率得到2-(4-methylphenyl)-4-phenyl-3-[4-(4-phenyl-2-quinolyl)phenoxy]quinoline
  参考文献：
  名称：

  Camphorsulfonic acid catalysed facile tandem double Friedlander annulation protocol for the synthesis of phenoxy linked bisquinoline derivatives and discovery of antitubercular agents

  摘要：

  A series of phenoxy linked bisquinoline derivatives were synthesised from the Friedlander annulation of 2-(4-acetylphenoxy)-1-aryl-1-ethanones with 2-aminobenzophenone in good yields using (+/-)-camphor-10- sulfonic acid (CSA) as the catalyst. These compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and among the 23 compounds screened, 2-(3-bromophenyl)-6-chloro-3-[4-(6-chloro-4-phenyl-2-quinolyl) phenoxy]-4-phenylquinoline (3q) and 2-(4-bromophenyl)-6-chloro-3-[4-(6-chloro-4-phenyl-2-quinolyl) phenoxy]-4-phenylquinoline (3o) were found to be the most active compounds with MIC of 1.1 and 2.2 mu M against MTB. The cytotoxic effects against mouse fibroblasts (NIH 3T3) in vitro were evaluated for 3o and 3q, which displayed no toxic effects against mouse fibroblast cell line NIH 3T3. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.119
• 作为产物：
  描述：

  对甲基苯乙酮 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 12.0h， 生成 2-(4-Acetylphenoxy)-1-(4-methylphenyl)ethanone
  参考文献：
  名称：

  氨基胍和3-氨基-1,2,4-三唑衍生物作为潜在的抗菌剂的合成及抗菌评价

  摘要：

  已合成了一系列带有1,3,4-恶二唑或哌嗪部分的氨基胍衍生物，并与一系列3-氨基-1,2,4-三唑衍生物一起进行了全面表征，并评估了所得化合物的抗-细菌活性。这些化合物大多数对革兰氏阳性和革兰氏阴性细菌均具有广谱抗菌活性，其最低抑菌浓度（MIC）和最低杀菌浓度（MBC）值在1–64μg/ mL范围内，包括耐多药临床分离株和真菌。值得注意的是，化合物19e和19f的抗甲氧西林金黄色葡萄球菌（3167和3506）和喹诺酮抗S的活性高于加替沙星和莫西沙星。金黄色葡萄球菌（3505和3519）的MIC和MBC值在1-2 µg / mL范围内。这两种化合物还显示出显着的抗真菌活性，对白色念珠菌7535的MIC值为1μg/ mL，相当于标准药物氟康唑的MIC值。因此，这些结果表明，不含哌嗪部分的氨基胍衍生物是开发新型抗菌剂的令人感兴趣的支架。

  DOI：

  10.2174/1570180813666160819151239

文献信息

• Synthesis and Antimicrobial Evaluation of Aminoguanidine and 3-amino- 1,2,4-triazole Derivatives as Potential Antibacterial Agents
  作者：Tian-Yi Zhang、Chao Li、Ya-Ru Li、Xiao-Zhen Li、Liang-Peng Sun、Chang-Ji Zheng、Hu-Ri Piao

  DOI：10.2174/1570180813666160819151239

  日期：2016.10.31

  A series of aminoguanidine derivatives bearing a 1,3,4-oxadiazole or piperazine moiety has been synthesized and fully characterized together with a series of 3-amino-1,2,4-triazole derivatives, and the resulting compounds were evaluated for their anti-bacterial activity. Most of these compounds showed broad-spectrum antibacterial activities against both Gram-positive and Gram-negative bacteria with

  已合成了一系列带有1,3,4-恶二唑或哌嗪部分的氨基胍衍生物，并与一系列3-氨基-1,2,4-三唑衍生物一起进行了全面表征，并评估了所得化合物的抗-细菌活性。这些化合物大多数对革兰氏阳性和革兰氏阴性细菌均具有广谱抗菌活性，其最低抑菌浓度（MIC）和最低杀菌浓度（MBC）值在1–64μg/ mL范围内，包括耐多药临床分离株和真菌。值得注意的是，化合物19e和19f的抗甲氧西林金黄色葡萄球菌（3167和3506）和喹诺酮抗S的活性高于加替沙星和莫西沙星。金黄色葡萄球菌（3505和3519）的MIC和MBC值在1-2 µg / mL范围内。这两种化合物还显示出显着的抗真菌活性，对白色念珠菌7535的MIC值为1μg/ mL，相当于标准药物氟康唑的MIC值。因此，这些结果表明，不含哌嗪部分的氨基胍衍生物是开发新型抗菌剂的令人感兴趣的支架。
• Camphorsulfonic acid catalysed facile tandem double Friedlander annulation protocol for the synthesis of phenoxy linked bisquinoline derivatives and discovery of antitubercular agents
  作者：Nidhin Paul、Muthuchamy Murugavel、Shanmugam Muthusubramanian、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2011.12.119

  日期：2012.2

  A series of phenoxy linked bisquinoline derivatives were synthesised from the Friedlander annulation of 2-(4-acetylphenoxy)-1-aryl-1-ethanones with 2-aminobenzophenone in good yields using (+/-)-camphor-10- sulfonic acid (CSA) as the catalyst. These compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and among the 23 compounds screened, 2-(3-bromophenyl)-6-chloro-3-[4-(6-chloro-4-phenyl-2-quinolyl) phenoxy]-4-phenylquinoline (3q) and 2-(4-bromophenyl)-6-chloro-3-[4-(6-chloro-4-phenyl-2-quinolyl) phenoxy]-4-phenylquinoline (3o) were found to be the most active compounds with MIC of 1.1 and 2.2 mu M against MTB. The cytotoxic effects against mouse fibroblasts (NIH 3T3) in vitro were evaluated for 3o and 3q, which displayed no toxic effects against mouse fibroblast cell line NIH 3T3. (C) 2011 Elsevier Ltd. All rights reserved.