(6R,7R)-3-Mercapto-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester | 134737-46-5

• 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: (6R,7R)-3-Mercapto-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• 英文别名: Diphenylmethyl-3-mercapto-7beta-phenylacetamidoceph-3-em-4-carboxylate；benzhydryl (6R,7R)-8-oxo-7-[(2-phenylacetyl)amino]-3-sulfanyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 134737-46-5
• 化学式: C₂₈H₂₄N₂O₄S₂
• 分子量: 516.642
• InChiKey: WPGVODJIKWERNZ-YIXXDRMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (6R,7R)-3-Mercapto-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 在 三氟乙酸 作用下， 以 二氯甲烷 、 苯甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 (6R,7R)-8-Oxo-7-phenylacetylamino-3-(thiazol-2-ylsulfanylmethylsulfanyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  studies on anti-helicobacter pylori agents. part 2: new cephem derivatives

  摘要：

  The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of cephem derivatives are described. Introduction of thio-heterocyclic groups containing N- and S-atoms to the 3-position and phenyl or thienyl acetamido groups to the 7-position of the cephem nucleus dramatically improved the activity. From this series of derivatives, compound 13i was Found to have extremely potent in vitro anti-H. pylori activity, superior therapeutic efficacy compared to AMPC and CAM, no cross-resistance between CAM or MNZ and low potential for causing diarrhea due to instability to beta-lactamase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00163-2
• 作为产物：
  描述：

  3-羟基头孢 在 sodium hydrogensulfide 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (6R,7R)-3-Mercapto-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  studies on anti-helicobacter pylori agents. part 2: new cephem derivatives

  摘要：

  The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of cephem derivatives are described. Introduction of thio-heterocyclic groups containing N- and S-atoms to the 3-position and phenyl or thienyl acetamido groups to the 7-position of the cephem nucleus dramatically improved the activity. From this series of derivatives, compound 13i was Found to have extremely potent in vitro anti-H. pylori activity, superior therapeutic efficacy compared to AMPC and CAM, no cross-resistance between CAM or MNZ and low potential for causing diarrhea due to instability to beta-lactamase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00163-2

文献信息

• Cephalosporin derivatives and pharmaceutical compositions
  申请人：Beecham Group p.l.c.

  公开号：US05158946A1

  公开（公告）日：1992-10-27

  .beta.-Lactam compounds of the formula (I) including pharmaceutically acceptable salts and in vivo hydrolysable esters, processes for their preparation and their use as antibiotics: ##STR1## wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acyl group, in particular that of an antibacterially active cephalosporin; R.sup.3 is hydrogen or a readily removable carboxy protecting group (such as a pharmaceutically acceptable in-vivo hydrolysable ester group); R.sup.4 is a .gamma.- or .delta.-lactone ring optionally containing one or (where applicable) two endocyclic double bonds, which ring is optionally substituted at any carbon atom by alkyl, dialkylamino, alkoxy, hydroxy, halogen or aryl, which in the case of more than one substituent may be the same or different, or is optionally di-substituted at two adjacent carbon atoms, which are available for substitution, to form an aromatic fused bicyclic system; x and y are independently 0 or 1; X is S, SO, SO.sub.2, O or CH.sub.2 ; and Y is O or S.

  .beta.-内酰胺化合物的化学式（I），包括药学上可接受的盐和体内水解酯，其制备过程和用作抗生素的方法：##STR1## 其中R.sup.1是氢，甲氧基或甲酰胺基; R.sup.2是酰基，特别是抗菌活性头孢菌素的酰基; R.sup.3是氢或易于去除的羧基保护基（例如药学上可接受的体内水解酯基）; R.sup.4是含有一个或（适用时）两个内环双键的γ-或δ-内酯环，该环在任何碳原子上均可选择性地取代为烷基，双烷基氨基，烷氧基，羟基，卤素或芳基，在存在多个取代基的情况下，可能相同或不同，或者在两个相邻的可取代碳原子处选择性地双取代，以形成芳香融合的双环系统; x和y独立地为0或1; X为S，SO，SO.sub.2，O或CH.sub.2; Y为O或S。
• Cephalosporinderivatives, process for their preparation and pharmaceutical compositions
  申请人：BEECHAM GROUP PLC

  公开号：EP0418020A2

  公开（公告）日：1991-03-20

  β-Lactam compounds of the formula (I) including pharmaceutically acceptable salts and in vivo hydrolysable esters, processes for their preparation and their use as antibiotics: wherein R1 is hydrogen, methoxy or formamido; R2 is an acyl group, in particular that of an antibacterially active cephalosporin; R3 is hydrogen or a readily removable carboxy protecting group (such as a pharmaceutically acceptable in-vivo hydrolysable ester group); R4 is a y- or δ-lactone,ring optionally containing one or (where applicable) two endocyclic double bonds, which ring is optionally substituted at any carbon atom by alkyl, dialkylamino, alkoxy, hydroxy, halogen or aryl, which in the case of more than one substituent may be the same or different, or is optionally di-substituted at two adjacent carbon atoms, which are available for substitution, to form an aromatic fused bicyclic system; x and y are independently 0 or 1; x is S, SO, S02, 0 or CH2; and Y is 0 or S.

  式 (I) 的 β-内酰胺化合物，包括药学上可接受的盐类和体内可水解的酯类，其制备工艺及其作为抗生素的用途： 其中 R1 是氢、甲氧基或甲酰胺基； R2 是酰基，特别是抗菌活性头孢菌素的酰基； R3 是氢或易于去除的羧基保护基团（如药学上可接受的体内可水解酯基）； R4是y-或δ-内酯环，可选择含有一个或（适用时）两个内环双键，该环可选择在任何碳原子上被烷基、二烷基氨基、烷氧基、羟基、卤素或芳基取代，在多个取代基相同或不同的情况下，也可选择在两个相邻碳原子上被二取代，这两个碳原子可用于取代，以形成芳香族融合双环体系；x 和 y 独立地为 0 或 1；x 为 S、SO、S02、0 或 CH2；Y 为 0 或 S。
• US5158946A
  申请人：——

  公开号：US5158946A

  公开（公告）日：1992-10-27
• studies on anti-helicobacter pylori agents. part 2: new cephem derivatives
  作者：Yoshiki Yoshida、Keiji Matsuda、Hiroshi Sasaki、Yoshimi Matsumoto、Satoru Matsumoto、Shuichi Tawara、Hisashi Takasugi

  DOI：10.1016/s0968-0896(00)00163-2

  日期：2000.9

  The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of cephem derivatives are described. Introduction of thio-heterocyclic groups containing N- and S-atoms to the 3-position and phenyl or thienyl acetamido groups to the 7-position of the cephem nucleus dramatically improved the activity. From this series of derivatives, compound 13i was Found to have extremely potent in vitro anti-H. pylori activity, superior therapeutic efficacy compared to AMPC and CAM, no cross-resistance between CAM or MNZ and low potential for causing diarrhea due to instability to beta-lactamase. (C) 2000 Elsevier Science Ltd. All rights reserved.