1,5-pentanedioic acid mono[2-(dimethylamino)ethyl] ester | 10549-60-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,5-pentanedioic acid mono[2-(dimethylamino)ethyl] ester
• 英文别名: mono(2-dimethylaminoethyl) glutarate；Glutarsaeure-mono-(2-dimethylamino-ethylester)；5-[2-(Dimethylamino)ethoxy]-5-oxopentanoic acid；5-[2-(dimethylamino)ethoxy]-5-oxopentanoic acid
• CAS: 10549-60-7
• 化学式: C₉H₁₇NO₄
• 分子量: 203.238
• InChiKey: QDRFWBKIHHTEMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氯生 、 1,5-pentanedioic acid mono[2-(dimethylamino)ethyl] ester 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以54%的产率得到5-O-[5-chloro-2-(2,4-dichlorophenoxy)phenyl] 1-O-[2-(dimethylamino)ethyl] pentanedioate
  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
• 作为产物：
  描述：

  戊二酸酐 、 N,N-二甲基乙醇胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到1,5-pentanedioic acid mono[2-(dimethylamino)ethyl] ester
  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

• Short,J.H.; Biermacher,U., Chimica Therapeutica, 1966, vol. 1, p. 456 - 460
  作者：Short,J.H.、Biermacher,U.

  DOI：——

  日期：——
• 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.