[5-Chloro-2-(2,4-dichlorophenoxy)phenyl] 4-oxopentanoate | 1038342-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [5-Chloro-2-(2,4-dichlorophenoxy)phenyl] 4-oxopentanoate
• CAS: 1038342-56-1
• 化学式: C₁₇H₁₃Cl₃O₄
• 分子量: 387.647
• InChiKey: GTQOECMNBZPJRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羰基戊酰氯 、 三氯生 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以0.730 g的产率得到[5-Chloro-2-(2,4-dichlorophenoxy)phenyl] 4-oxopentanoate
  参考文献：
  名称：

  Design, synthesis, and application of novel triclosan prodrugs as potential antimalarial and antibacterial agents

  摘要：

  A number of new triclosan-conjugated analogs bearing biodegradable ester linkage have been synthesized, characterized and evaluated for their antimalarial and antibacterial activities. Many of these compounds exhibit good inhibition against Plasmodium falciparum and Escherichia coli. Among them tertiary amine containing triclosan-conjugated prodrug (5) inhibited both P. falciparum (IC50; 0.62 mu M) and E. coli (IC50; 0.26 mu M) at lower concentrations as compared to triclosan. Owing to the presence of a cleavable ester moiety, these new prodrugs are hydrolyzed under physiological conditions and parent molecule, triclosan, is released. Further, introduction of tertiary/quatemary functionality increases their cellular uptake. These properties impart them with higher potency to their antimalarial as well as antibacterial activities. The best compound among them 5 shows close to four-fold enhanced activities against P. falciparum and E. coli cultures as compared to triclosan. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.006

文献信息

• Design, synthesis, and application of novel triclosan prodrugs as potential antimalarial and antibacterial agents
  作者：Satyendra Mishra、Krishanpal Karmodiya、Prasanna Parasuraman、Avadhesha Surolia、Namita Surolia

  DOI：10.1016/j.bmc.2008.04.006

  日期：2008.5

  A number of new triclosan-conjugated analogs bearing biodegradable ester linkage have been synthesized, characterized and evaluated for their antimalarial and antibacterial activities. Many of these compounds exhibit good inhibition against Plasmodium falciparum and Escherichia coli. Among them tertiary amine containing triclosan-conjugated prodrug (5) inhibited both P. falciparum (IC50; 0.62 mu M) and E. coli (IC50; 0.26 mu M) at lower concentrations as compared to triclosan. Owing to the presence of a cleavable ester moiety, these new prodrugs are hydrolyzed under physiological conditions and parent molecule, triclosan, is released. Further, introduction of tertiary/quatemary functionality increases their cellular uptake. These properties impart them with higher potency to their antimalarial as well as antibacterial activities. The best compound among them 5 shows close to four-fold enhanced activities against P. falciparum and E. coli cultures as compared to triclosan. (C) 2008 Elsevier Ltd. All rights reserved.