p-nitrobenzyl 2-(2-acetoxyaziridin-1-yl)-carbapen-2-em-3-carboxylate | 101989-50-8

• 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: p-nitrobenzyl 2-(2-acetoxyaziridin-1-yl)-carbapen-2-em-3-carboxylate
• 英文别名: (4-nitrophenyl)methyl 3-(2-acetyloxyaziridin-1-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 101989-50-8
• 化学式: C₁₈H₁₇N₃O₇
• 分子量: 387.349
• InChiKey: JVNWOYUSKFXDRI-UHFFFAOYSA-N

物化性质

• 沸点：
  596.3±50.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  119.06
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  p-nitrobenzyl 3-(p-toluenesulfonyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate 在 叠氮化钾 、 碳酸氢钠 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 生成 p-nitrobenzyl 2-(2-acetoxyaziridin-1-yl)-carbapen-2-em-3-carboxylate
  参考文献：
  名称：

  The preparation and reactions of 2-azidocarbapenems

  摘要：

  DOI：

  10.1016/s0040-4039(00)98220-0

文献信息

• 2-aza-substituted 1-carbadethiapen-2-em-3 carboxylic acids
  申请人：Merck & Co., Inc.

  公开号：US04782051A1

  公开（公告）日：1988-11-01

  Disclosed are 2-aza-substituted 1-carbadethiapen-2-em-3-carboxylic acids I, where the generic 2-aza group includes azido, acylamino, amino, alkylamino, dialkylamino, trizolyl, triazolinyl, aziridinyl, and their pharmaceutically acceptable salt, ester, anhydride and amide derivatives which are useful as antibiotics. Also disclosed are processes for the preparation of I from the known, appropriately substituted bicyclic keto ester II via the 2-azido central intermediate III: ##STR1## wherein R.sup.16 is H or CH.sub.3, preferably beta-methyl; R.sup.6, and R.sup.7 are independently hydrogen, linear, branched or cyclic C.sub.1 -C.sub.5 alkyl, which can be substituted with fluoro, hydroxy, protected hydroxy, sulfoxy, amino, protected amino, wherein R.sup.6 and R.sup.7 taken together can also be C.sub.2 -C.sub.4 alkylidene, similarly substituted; with the proviso that both R.sup.6 and R.sup.7 are not unsubstituted alkyl, R.sup.1 and R.sup.2 are, inter alia, hydrogen, alkyl, acyl, and can be joined to form a ring comprising 3 to 7 atoms; R.sup.a is hydrogen, a salt cation, a removable protecting group, or a pharmaceutically acceptable ester moiety. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

  本文披露了2-氮代取代的1-卡巴德硫杂吡啶-2-烯-3-羧酸I，其中通用的2-氮代基包括偶氮基、酰氨基、氨基、烷基氨基、二烷基胺基、三唑基、三唑啉基、氮杂环丙基等，以及它们的药用可接受的盐、酯、酐和酰胺衍生物，其可用作抗生素。还披露了从已知的适当取代的双环酮酯II经2-偶氮中间体III制备I的方法：其中R.sup.16为H或CH.sub.3，优选β-甲基；R.sup.6和R.sup.7独立地为氢、线性、支链或环状C.sub.1-C.sub.5烷基，可以用氟、羟基、保护羟基、亚砜基、氨基、保护氨基取代，其中R.sup.6和R.sup.7共同也可以是C.sub.2-C.sub.4烷基亚甲基，同样取代；但须注意R.sup.6和R.sup.7均不是未取代的烷基，R.sup.1和R.sup.2为氢、烷基、酰基等，可以连接形成包含3至7个原子的环；R.sup.a为氢、盐阳离子、可去除的保护基，或药用可接受的酯基。还披露了制备这类化合物的方法；包含这类化合物的药物组合物；以及在需要抗生素效果时，施用这类化合物和组合物的治疗方法。
• 2-aza-substituted 1-carbadethiapen-2-em-3-carboxylic acids
  申请人：Merck & Co., Inc.

  公开号：US04783453A1

  公开（公告）日：1988-11-08

  Disclosed are 2-aza-substituted 1-carbadethiapen-2-em-3-carboxylic acids I, where the generic 2-aza group includes azido, acylamino, amino, alkylamino, dialkylamino, triazolyl, triazolinyl, aziridinyl, and their pharmaceutically acceptable salt, ester, anhydride and amide derivatives which are useful as antibiotics. Also disclosed are processes for the preparation of I from the known, appropriately substituted bicyclic keto ester II via the 2-azido central intermediate III: ##STR1## wherein R.sup.16 is H or CH.sub.3, preferably beta-methyl; R.sup.6, and R.sup.7 are independently hydrogen, linear, branched or cyclic C.sub.1 -C.sub.5 alkyl, which can be substituted with fluoro, hydroxy, protected hydroxy, sulfoxy, amino, protected amino, wherein R.sup.6 and R.sup.7 taken together can also be C.sub.2 -C.sub.4 alkylidene, similarly substituted; with the proviso that both R.sup.6 and R.sup.7 are not unsubstituted alkyl, R.sup.1 and R.sup.2 are, inter alia, hydrogen, alkyl, acyl, and can be joined to form a ring comprising 3 to 7 atoms; R.sup.a is hydrogen, a salt cation, a removable protecting group, or a pharmaceutically acceptable ester moiety. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

  本文披露了2-氮代取代的1-卡巴德硫杂戊二烯-3-羧酸I，其中通用的2-氮代基包括偶氮基、酰胺基、氨基、烷基氨基、二烷基胺基、三唑基、三唑烯基、环氧丙基和它们的药用盐、酯、酐和酰胺衍生物，这些衍生物可用作抗生素。还披露了从已知的适当取代的双环酮酯II经2-偶氮中间体III制备I的方法：其中R.sup.16为H或CH.sub.3，最好是β-甲基；R.sup.6和R.sup.7独立地是氢、线性、支链或环状的C.sub.1-C.sub.5烷基，可以被氟、羟基、保护羟基、磺氧基、氨基、保护氨基取代，其中R.sup.6和R.sup.7共同也可以是C.sub.2-C.sub.4烷基亚甲基，同样被取代；条件是R.sup.6和R.sup.7都不是未取代的烷基，R.sup.1和R.sup.2是，其中包括氢、烷基、酰基，可以结合形成由3到7个原子组成的环；R.sup.a是氢、盐阳离子、可去除的保护基，或药用可接受的酯基团。还披露了制备这类化合物的方法；包含这类化合物的药物组合物；以及在需要抗生素效果时，通过给予这类化合物和组合物进行治疗的方法。
• CHRISTENSEN, BURTON G.;CHABALA, JOHN C.;RATCLIFFE, RONALD W.
  作者：CHRISTENSEN, BURTON G.、CHABALA, JOHN C.、RATCLIFFE, RONALD W.

  DOI：——

  日期：——