butyryloxymethyl p-nitrophenyl carbonate | 194995-45-4

• 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: butyryloxymethyl p-nitrophenyl carbonate
• 英文别名: (((4-Nitrophenoxy)carbonyl)oxy)methyl butyrate；(4-nitrophenoxy)carbonyloxymethyl butanoate
• CAS: 194995-45-4
• 化学式: C₁₂H₁₃NO₇
• 分子量: 283.238
• InChiKey: CYRVOHXQOCOPTO-UHFFFAOYSA-N

物化性质

• 沸点：
  413.5±45.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  butyryloxymethyl p-nitrophenyl carbonate 在 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Mono and bis double ester prodrugs of novel aminomethyl-THF 1β-methylcarbapenems

  摘要：

  Mono and bis double ester prodrugs of aminomethyl THF 1 beta-methylcarbapenems 1 were Mono double ester derivatives (2, 4 and 7) did not demonstrate significantly improved oral activity due to the presence of the charged species. However, bis double ester derivatives (3 and 5) demonstrated enhanced oral activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00305-3
• 作为产物：
  描述：

  mercury(II) butyrate 、 氯甲基(4-硝基苯基)碳酸酯 在 溶剂黄146 作用下， 以85%的产率得到butyryloxymethyl p-nitrophenyl carbonate
  参考文献：
  名称：

  Mono and bis double ester prodrugs of novel aminomethyl-THF 1β-methylcarbapenems

  摘要：

  Mono and bis double ester prodrugs of aminomethyl THF 1 beta-methylcarbapenems 1 were Mono double ester derivatives (2, 4 and 7) did not demonstrate significantly improved oral activity due to the presence of the charged species. However, bis double ester derivatives (3 and 5) demonstrated enhanced oral activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00305-3

文献信息

• Novel prodrugs of meropenem with two lipophilic promoieties: synthesis and pharmacokinetics
  作者：Shunkichi Tanaka、Hiroshi Matsui、Masayasu Kasai、Kazuyoshi Kunishiro、Nobuharu Kakeya、Hiroaki Shirahase

  DOI：10.1038/ja.2010.164

  日期：2011.3

  To improve the oral absorption of meropenem (MEPM), we synthesized and evaluated a series of its double-promoiety prodrugs, in which lipophilic promoieties were introduced into carboxyl and pyrrolidinyl groups. Among these prodrugs, pivaloyloxymethyl (1R,5S,6S)-2-[(3S,5S)-5-(N,N-dimethylcarbamoyl)-1-(isobutyryloxymethyloxycarbonyl)pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (4) and 1-ethylpropyloxycarbonyloxymethyl (1R,5S,6S)-2-[(3S,5S)-5-(N,N-dimethylcarbamoyl)-1-(isobutyryloxymethyloxycarbonyl)pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (8) were chosen for further evaluation. Compounds 4 and 8 were well absorbed after oral administration to rats and beagles (bioavailability 18.2–38.4%), and expected to show potent therapeutic efficacy in patients infected with various pathogens, such as penicillin-resistant S. pneumoniae and β-lactamase-negative ampicillin-resistant H. influenzae.

  为了改善美罗培南（MEPM）的口服吸收，我们合成并评估了一系列双促渗前药，在这些前药中，疏水性促渗基团被引入到羧基和吡咯烷基团中。在这些前药中，匹伐酸氧甲基（1R，5S，6S）-2-[(3S，5S)-5-(N，N-二甲基氨基甲酰基)-1-(异丁酰氧甲基氧羰基)吡咯烷-3-基硫]-6-[(1R)-1-羟基乙基]-1-甲基碳青霉烯-2-烯-3-羧酸酯（4）和1-乙基丙氧基羰氧甲基（1R，5S，6S）-2-[(3S，5S)-5-(N，N-二甲基氨基甲酰基)-1-(异丁酰氧甲基氧羰基)吡咯烷-3-基硫]-6-[(1R)-1-羟基乙基]-1-甲基碳青霉烯-2-烯-3-羧酸酯（8）被选为进一步评估的对象。化合物4和8在大鼠和比格犬中口服后被良好吸收（生物利用度为18.2-38.4%），并预期在感染各种病原体的患者中显示出强大的疗效，例如耐青霉素的肺炎链球菌和耐β内酰胺酶阴性的氨苄西林流感嗜血杆菌。
• CARBAPENEM COMPOUND
  申请人：Kyoto Pharmaceutical Industries, Ltd.

  公开号：EP1398314A1

  公开（公告）日：2004-03-17

  A carbapenem compound represented by the formula (I'): wherein each symbol is as defined in the specification, and an antibacterial agent containing this compound as an active ingredient are provided. The carbapenem compound of the present invention is superior in absorbability from the gastrointestinal tract by oral administration and extremely useful for the prophylaxis or treatment of infectious diseases (particularly, bacterial infectious diseases).

  提供了由式（I'）代表的碳青霉烯类化合物： 式（I'）代表的碳青霉烯类化合物，其中各符号如说明书中所定义，本发明还提供了以该化合物为活性成分的抗菌剂。 本发明的碳青霉烯类化合物口服后可从胃肠道吸收，对预防或治疗传染病（特别是细菌性传染病）极为有用。
• Carbapenem compound
  申请人：——

  公开号：US20040176350A1

  公开（公告）日：2004-09-09

  A carbapenem compound represented by the formula (I′): 1 wherein each symbol is as defined in the specification, and an antibacterial agent containing this compound as an active ingredient are provided. The carbapenem compound of the present invention is superior in absorbability from the gastrointestinal tract by oral administration and extremely useful for the prophylaxis or treatment of infectious diseases (particularly, bacterial infectious diseases).

  本发明提供了一种由式（I′）：1 所代表的碳青霉烯类化合物，其中各符号如说明书中所定义，还提供了一种以该化合物为有效成分的抗菌剂。 本发明的碳青霉烯类化合物口服后可从胃肠道吸收，对预防或治疗传染病（特别是细菌性传染病）极为有用。
• EP1398314
  申请人：——

  公开号：——

  公开（公告）日：——