diphenylmethyl 7-phenylacetamido-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate

• 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: diphenylmethyl 7-phenylacetamido-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate
• 英文别名: diphenylmethyl 7-phenylacetamido-3-trifluoromethylsulfonyloxy-3-cephem-4-carboxylate；diphenylmethyl 7-(phenylacetamido)-3-triflyloxy-3-cephem-4-carboxylate；Diphenylmethyl 7-phenylacetamido-3-triflyloxyceph-3-em-4-carboxylate；benzhydryl (6R)-8-oxo-7-[(2-phenylacetyl)amino]-3-(trifluoromethylsulfonyloxy)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• 化学式: C₂₉H₂₃F₃N₂O₇S₂
• 分子量: 632.638
• InChiKey: KWGRLVVNNGEQTA-IQHZPMLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  diphenylmethyl 7-phenylacetamido-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate 、 sodium 2-mercaptobenzothiazole 在 sodium chloride 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到Diphenylmethyl 7-phenylacetamido-3-(benzothiazol2,yl)thio-3-cephem-4-carboxylate
  参考文献：
  名称：

  Cephalosporin derivatives

  摘要：

  提供了新的抗菌剂头孢菌素衍生物，其具有一般式(I)：##STR1##其中R.sup.1是氢原子、较低的烷基或取代的较低的烷基，R.sup.2是氢原子或易于被消化道内酯酶裂解的酯基，R.sup.3和R.sup.4可以相同，且各自独立地是氢原子、卤原子、较低烷基、较低烯基、羟基、氨基或较低烷氧基，以及其药学上可接受的盐。公式(I)的头孢菌素衍生物可用作口服或注射给药的头孢菌素衍生物，其在结合上表现出高抗菌活性和有利特性，能够在给药时在血液中获得高浓度的化合物。

  公开号：

  US05461044A1
• 作为产物：
  描述：

  diphenylmethyl 7-(2-phenylacetamido)-3-hydroxy-3-cephem-4-carboxylate 、 三氟甲磺酸酐 以69%的产率得到
  参考文献：
  名称：

  BAKER, STEPHEN R.;FARINA, VITTORIO;SAPINO, CHESTER (JR)

  摘要：

  DOI：

文献信息

• Cephalosporin derivative
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：US05607927A1

  公开（公告）日：1997-03-04

  An aminothiazolyl- or aminothiadiazolyl-cephalosporin derivative represented by the following general formula (I) which has a condensed-ring thio group as a 3-positioned substituent group that contains a thiazolylthio group, an oxazolylthio group or a heterocyclic ring thereof as one of the ring components. The compound according to the present invention has excellent activities to inhibit growth of various bacteria, especially Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), and therefore, the antibacterial agent comprising, as an active ingredient, the inventive compound can be used as a therapeutic drug for the treatment of various bacterial infections. ##STR1##

  以下是通式(I)所代表的氨基噻唑基或氨基噻二唑基头孢菌素衍生物，其具有紧缩环硫基作为3位取代基，其中包含噻唑基硫基、噁唑基硫基或其杂环组分之一作为环组分之一。本发明的化合物具有抑制各种细菌生长的优异活性，特别是革兰氏阳性菌，包括耐甲氧西林金黄色葡萄球菌（MRSA），因此，将本发明化合物作为活性成分的抗菌剂可用作治疗各种细菌感染的治疗药物。 ##STR1##
• Processes for making cephems from allenylazetidinone derivatives
  申请人：Bristol-Myers Squibb Company

  公开号：US05162521A1

  公开（公告）日：1992-11-10

  This invention relates to a novel process for making a cephem of formula II from 2-(3-amino-2-oxo-azetidin-1-yl)-2,3-butadienoate of formula I. In another aspect, this invention is concerned with a process of further converting a compound of formula II into an antibacterial cephem of formula III. ##STR1## In formulae I, II and III, R.sup.1 is hydrogen, a conventional amino protecting group or an acyl group; R.sup.2 is an aromatic heterocyclic or aryl group; R.sup.3 is a conventional carboxy protecting group or --CO.sub.2 R.sup.3 taken together forms a physiologically hydrolyzable ester; and R.sup.4 is a group selected from the group consisting of C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, cyclic C.sub.3-6 alkyl, and aryl; and n is 0 or 2.

  本发明涉及一种从式I的2-(3-氨基-2-氧代-氮杂丁基)-2,3-丁二烯酸酯制备式II头孢菌素的新工艺。在另一个方面，本发明涉及一种将式II的化合物进一步转化为式III的抗菌头孢菌素的工艺。在公式I、II和III中，R1为氢、常规氨基保护基或酰基；R2为芳香杂环或芳基基团；R3为常规羧基保护基或--CO2R3，两者结合形成生理可水解的酯；R4为从C1-6烷基、C2-6烯基、C2-6炔基、环状C3-6烷基和芳基中选择的一组基团；n为0或2。
• 3-Unsaturated alkyl cephems from 3-triflyl cephems
  申请人：Bristol-Myers Company

  公开号：US04870168A1

  公开（公告）日：1989-09-26

  There is disclosed a process for the production of certain 3-hydrocarbyl-3-cephem derivatives wherein the hydrocarbyl group is selected from 1-alkenyl and conjugated and unconjugated 1-polyalkenyl, 1-alkynl, carbocyclic and heterocyclic aryl, and carbocyclic and heterocyclic arylmethyl and, in the case of the 1-alkenyl and conjugated 1-polyalkenyl derivatives, with substantially complete stereospecificity, by coupling a 3-triflyloxy cephem with a hydrocarbyltributylstannane in the presence of bis(dibenzylideneacetonyl)-palladium, a phosphine, and a metal halide such as, for example, zinc chloride. The 3-unsaturated alkyl-3-cephem derivatives so-produced are useful as broad-spectrum antibacterial agents.

  本发明揭示了一种制备某些3-羟基烃基-3-头孢菌素衍生物的方法，其中烃基被选自1-烯基和共轭和不共轭的1-多烯基、1-炔基、碳环和杂环芳基、碳环和杂环芳基甲基，并且在1-烯基和共轭1-多烯基衍生物的情况下，具有基本完整的立体特异性，方法是在双(二苯基乙酮)钯、膦和金属卤化物如氯化锌的存在下，将3-三氟甲基氧基头孢菌素与烃基三丁基锡烷偶联。由此产生的3-不饱和烷基-3-头孢菌素衍生物可用作广谱抗菌剂。
• Cephalosporins and homologues, preparations and pharmaceutical
  申请人：——

  公开号：US06001997A1

  公开（公告）日：1999-12-14

  .beta.-Lactam antibiotics of formula (I) or a salt thereof, wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acyl group; CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion, or R.sup.3 is a readily removable carboxy protecting group; R.sup.4 represents up to four substituents; X is S, SO, SO.sub.2, O or CH.sub.2 ; m is 1 or 2; and n is 0, useful in the treatment of bacterial infections. ##STR1##

  公式（I）或其盐的.beta.-内酰胺类抗生素，其中R.sup.1是氢，甲氧基或甲酰胺基；R.sup.2是酰基；CO.sub.2 R.sup.3是羧基或羧酸盐离子，或R.sup.3是易于去除的羧保护基；R.sup.4代表多达四个取代基；X是S，SO，SO.sub.2，O或CH.sub.2；m为1或2；n为0，有用于治疗细菌感染。##STR1##
• Cephaloporins and homologues, preparations and pharmaceutical
  申请人：Pzifer Inc.

  公开号：US06020329A1

  公开（公告）日：2000-02-01

  .beta.-Lactam antibiotics of formula (I) or a salt thereof, wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acy group; CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion, or R.sup.3 is a readily removable carboxy protecting group; R.sup.4 represents up to four substituents; X is S, SO, SO.sub.2, O or CH.sub.2 ; m is 1 or 2; and n is 0, useful in the treatment of bacterial infec ##STR1##

  式(I)的.beta.-内酰胺抗生素或其盐，其中R.sup.1为氢、甲氧基或甲酰胺基；R.sup.2为酰基；CO.sub.2R.sup.3为羧基或羧酸盐，或R.sup.3为易于去除的羧保护基；R.sup.4代表多达四个取代基；X为S、SO、SO.sub.2、O或CH.sub.2；m为1或2；n为0，有用于治疗细菌感染的作用。