(8aS,8bR)-1-Eth-(E)-ylidene-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester | 209536-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (8aS,8bR)-1-Eth-(E)-ylidene-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester
• 英文别名: Allyl (8S,9R)-10-((E)-ethylidene)-11-oxo-1-azatricyclo-[7.2.0.03,8]undec-2-ene-2-carboxylate；prop-2-enyl (1E,8aS,8bR)-1-ethylidene-2-oxo-5,6,7,8,8a,8b-hexahydroazeto[1,2-b]isoindole-4-carboxylate
• CAS: 209536-89-0
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: FPXVLCFBHYTTKY-IQNCIHRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8aS,8bR)-1-Eth-(E)-ylidene-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester 在 四(三苯基膦)钯 、 三苯基膦 、 sodium 2-ethylhexanoic acid 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以94%的产率得到sodium (8S,9R,10E)-1-aza-10-ethylidene-11-oxo-tricyclo(7.2.0.0^3,8)undec-2-en-2-carboxylate
  参考文献：
  名称：

  Design, synthesis and bioactivity evaluation of tribactam β lactamase inhibitors

  摘要：

  Known carbapenem compounds with inhibitory effect towards P-lactamase enzymes are formed from bicyclical beta lactam structural scaffolds. On the basis of results from theoretical computational methods and molecular modelling we have designed and developed a synthetic route towards novel, biologically active tricyclic derivatives of carbapenems. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00061-6
• 作为产物：
  描述：

  4-乙酰氧基氮杂环丁酮 在 甲酸 四(三苯基膦)钯 、 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 对苯二酚 、 三苯基膦 、 偶氮二甲酸二乙酯 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (8aS,8bR)-1-Eth-(E)-ylidene-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester
  参考文献：
  名称：

  Design, synthesis and bioactivity evaluation of tribactam β lactamase inhibitors

  摘要：

  Known carbapenem compounds with inhibitory effect towards P-lactamase enzymes are formed from bicyclical beta lactam structural scaffolds. On the basis of results from theoretical computational methods and molecular modelling we have designed and developed a synthetic route towards novel, biologically active tricyclic derivatives of carbapenems. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00061-6

文献信息

• Ethylidene derivatives of tricyclic carbapenems
  申请人：LEK, tovarna farmacevtskih in kemicnih izdelkov, d.d.

  公开号：US06489318B1

  公开（公告）日：2002-12-03

  Disclosed are novel ethylidene derivatives of tricyclic carbapenems of the formula I wherein the ring marked C and X have the meaning as in the description, in the form of pure diastereoisomers and in the form of pure geometric isomers. Novel ethylidene derivatives of tricyclic carbapenems of the formula I are used as inhibitors of the action of the enzyme &bgr;-lactamase and/or as antibiotics in human and veterinary medicine. Also disclosed are pharmaceutical formulations for the treatment of bacterial infections of human and animal organisms comprising as an active ingredient a therapeutically effective amount of an ethylidene derivative of tricyclic carbapenems of the formula I in the form of an acid, a pharmaceutically acceptable salt or ester thereof and optionally in a combination with a &bgr;-lactam antibiotic, and usual pharmaceutically acceptable carriers and auxiliary substances. Also disclosed is a process for the preparation of novel ethylidene derivatives of tricyclic carbapenems of the formula I.

  本发明涉及公式I的新型三环羧甲青霉烷的乙烯基衍生物，其中标记为C和X的环具有如描述中的含义，以纯对映异构体和纯几何异构体的形式存在。公式I的新型三环羧甲青霉烷的乙烯基衍生物可用作酶β-内酰胺酶的作用抑制剂和/或人类和兽医学中的抗生素。还公开了用于治疗人类和动物有机体的细菌感染的制药配方，其包括作为活性成分的公式I的三环羧甲青霉烷的乙烯基衍生物的治疗有效量，以酸、药学上可接受的盐或酯的形式存在，并且可选地与β-内酰胺类抗生素组合，以及通常的药学上可接受的载体和辅助物质。还公开了制备公式I的新型三环羧甲青霉烷的乙烯基衍生物的方法。
• Design, synthesis and bioactivity evaluation of tribactam β lactamase inhibitors
  作者：Anton Copar、Tadeja Prevec、Borut Anžič、Tomaž Mesar、Lovro Selič、Mateja Vilar、Tom Solmajer

  DOI：10.1016/s0960-894x(02)00061-6

  日期：2002.3

  Known carbapenem compounds with inhibitory effect towards P-lactamase enzymes are formed from bicyclical beta lactam structural scaffolds. On the basis of results from theoretical computational methods and molecular modelling we have designed and developed a synthetic route towards novel, biologically active tricyclic derivatives of carbapenems. (C) 2002 Elsevier Science Ltd. All rights reserved.