benzhydryl 7β-[2-(phenylthio)acetamido]-3-methanesulfonyloxy-3-cephem-4-carboxylate | 179034-51-6

• 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: benzhydryl 7β-[2-(phenylthio)acetamido]-3-methanesulfonyloxy-3-cephem-4-carboxylate
• 英文别名: benzhydryl (6R,7R)-3-methylsulfonyloxy-8-oxo-7-[(2-phenylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 179034-51-6
• 化学式: C₂₉H₂₆N₂O₇S₃
• 分子量: 610.733
• InChiKey: YLHMTPBCGXRXMI-UFHPHHKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzhydryl 7β-[2-(phenylthio)acetamido]-3-methanesulfonyloxy-3-cephem-4-carboxylate 在 N,N-二异丙基乙胺 、 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 5.0h， 生成 (6R,7R)-8-Oxo-7-(2-phenylsulfanyl-acetylamino)-3-(4H-[1,2,4]triazol-3-ylsulfanyl)-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：

  苯硫基乙酸 在 五氯化磷 、 N-三甲基硅基乙酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 benzhydryl 7β-[2-(phenylthio)acetamido]-3-methanesulfonyloxy-3-cephem-4-carboxylate
  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

• [EN] CEPHEM COMPOUNDS AND PHARMACEUTICAL USE THEREOF<br/>[FR] COMPOSES DE CEPHEME ET LEUR UTILISATION PHARMACEUTIQUE
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1996017850A1

  公开（公告）日：1996-06-13

  (EN) This invention relates to a new use of a cephem compound of formula (I), wherein R1 is aryl(lower)alkyl which may have one or more suitable substituent(s), arylthio(lower)alkyl, lower alkenylthio(lower)alkyl which may have one or more suitable substituent(s), or a group of the formula: R4-A- or R4-S-A- in which R4 is heterocyclic group which may have one or more suitable substituent(s), and A is lower alkylene which may have one or more suitable substituent(s) or lower alkenylene, R2 is heterocyclic group which may have one or more suitable substituent(s), or heterocyclic(lower)-alkyl and R3 is carboxy or protected carboxy, and a pharmaceutically acceptable salt thereof, which have antimicrobial activity against $i(Helicobacter pylori), and are useful as anti-$i(Helicobacter pylori) agents, anti-gastritis agents, antiulcer agents and anticancer agents.(FR) La présente invention concerne une nouvelle utilisation d'un composé de céphème de formule (I) dans laquelle R1 est aryle alkyle(inférieur) pouvant posséder un ou plusieurs substituants appropriés, arylthio alkyle (inférieur), alcénylthio inférieur alkyle (inférieur) pouvant posséder un ou plusieurs substituants appropriés, ou bien un groupe de la formule R4-A- ou R4-S-A- dans laquelle R4 est un groupe hétérocyclique pouvant posséder un ou plusieurs substituants appropriés, et A est alkylène inférieur pouvant posséder un ou plusieurs substituants appropriés ou bien alcénylène inférieur, R2 est un groupe hétérocyclique pouvant posséder un ou plusieurs substituants appropriés, ou bien alkyle (inférieur) hétérocyclique et R3 est carboxy ou carboxy protégé, et son sel pharmaceutiquement acceptable, qui présentent une activité antimicrobienne contre $i(Helicobacter pylori), et sont utiles comme agents anti-$i(Helicobacter pylori), agents anti-gastrite, agents antiulcéreux et agents anticancéreux.

  本发明涉及一种新的使用方法，使用式(I)的头孢菌素化合物，其中R1是芳基（较低）烷基，可以具有一个或多个适当的取代基，芳硫（较低）烷基，较低烯基硫（较低）烷基，可以具有一个或多个适当的取代基，或者是公式R4-A-或R4-S-A-的基团，其中R4是杂环基团，可以具有一个或多个适当的取代基，A是较低烷基，可以具有一个或多个适当的取代基，或者是较低烯基，R2是杂环基团，可以具有一个或多个适当的取代基，或者是杂环（较低）烷基，R3是羧基或保护羧基，以及其药学上可接受的盐，具有抗菌活性，可用作抗$ i（幽门螺杆菌）剂，抗胃炎剂，抗溃疡剂和抗癌剂。
• CEPHEM COMPOUNDS AND PHARMACEUTICAL USE THEREOF
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0796263A1

  公开（公告）日：1997-09-24
• 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.