7-amino-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid,diphenylmethyl ester | 53090-86-1

• 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: 7-amino-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid,diphenylmethyl ester
• 英文别名: diphenylmethyl 7-amino-3-<(1-methyl-1H-tetrazol-5-yl)thiomethyl>-3-cephem-4-carboxylate；7-amino-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-carboxylic acid,diphenylmethyl ester；7β-amino-3-(1-methyl-5-tetrazolylthiomethyl)-3-cephem-4-carboxylic acid diphenylmethyl ester；7-amino-3-(1-methyl-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid diphenylmethyl ester；7-amino-3-(1-methyl-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid benzhydryl ester；benzhydryl 7-amino-3-[(1-methyltetrazol-5-yl)-thio-methyl]-ceph-3-em-4-carboxylate；7-Amino-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester；benzhydryl 7-amino-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 53090-86-1
• 化学式: C₂₃H₂₂N₆O₃S₂
• 分子量: 494.598
• InChiKey: YDROWRWAIBYYQX-UHFFFAOYSA-N

物化性质

• 沸点：
  736.9±70.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  167
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (Z)-α-(2-tritylamino-4-thiazolyl)-α-[(2-tritylamino-4-thiazolyl)methoxyimino]acetic acid 、 7-amino-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid,diphenylmethyl ester 在 吡啶 、 五氯化磷 作用下， 以 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 生成 (Z)-7-{α-(2-tritylamino-4-thiazolyl)-α-[(2-tritylamino-4-thiazolyl)methoxyimino]acetamido}-3-[(1-methyl-5-tetrazolyl)thiomethyl]-3-cephem-4-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  Cephem compounds

  摘要：

  提供具有以下式子的新型头孢菌素化合物：##STR1## 其中，R代表低烷基，该低烷基可以被低酰氧基，低烷基硫基或含有5个或6个成员的杂环环的特定基团所取代。头孢菌素化合物及其盐对许多病原体表现出抗菌活性。还提供了一种生产头孢菌素化合物的方法。

  公开号：

  US04608373A1

文献信息

• [[[(2,4-Dioxo-1-imidazolidinyl)amino]carbonyl]amino]-acetylcephalosporin
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04063019A1

  公开（公告）日：1977-12-13

  [[[(2,4-Dioxo-1-imidazolidinyl)amino]carbonyl]amino]-acetylcephalosporin derivatives having the formula ##STR1## wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, diphenyl-lower alkyl, tri(lower alkyl)silyl, trihaloethyl, a salt forming ion, or the group ##STR2## R.sub.1 is hydrogen or methoxy; R.sub.2, R.sub.3 and R.sub.5 each is hydrogen or lower alkyl; R.sub.4 is hydrogen, lower alkyl, cyclo-lower alkyl, cyclo-lower alkenyl, cyclo-lower alkadienyl, phenyl, phenyl-lower alkyl, substituted phenyl, substituted phenyl-lower alkyl, or certain heterocyclic groups; R.sub.6 is lower alkyl; and X is hydrogen, lower alkanoyloxy, ##STR3## or certain heterothio groups; are useful as antibacterial agents.

  (2,4-二氧代-1-咪唑烷基)氨基甲酰氨基-头孢菌素衍生物具有以下结构式##STR1##其中R为氢、低烷基、苯基-低烷基、二苯基-低烷基、三(低烷基)硅基、三卤乙基、形成盐的离子，或基团##STR2##R.sub.1为氢或甲氧基；R.sub.2、R.sub.3和R.sub.5各自为氢或低烷基；R.sub.4为氢、低烷基、环-低烷基、环-低烯基、环-低烷二烯基、苯基、苯基-低烷基、取代苯基、取代苯基-低烷基，或某些杂环基团；R.sub.6为低烷基；X为氢、低烷酰氧基、##STR3##或某些杂硫基团；可用作抗菌剂。
• A new synthesis of 3-chloro-2-(thiazol-4-yl)propenoic acid and its application to cephalosporins.
  作者：KIYOHARU NISHIDE、MARIKO YAMAMURA、MAYUMI YAMAZAKI、TAKEO KOBORI、DAIEI TUNEMOTO、KIYOSI KONDO、KIYOSHI SATO

  DOI：10.1248/cpb.36.2346

  日期：——

  Three step transformations of α-formylation, chlorination and hydrolysis starting from ethyl 4-thiazoleacetate (1) afforded a new cephem 7-side chain acid, (E)-3-chloro-2-(thiazol-4-yl)propenoic acid (4-(E)). The presence of the corresponding 4-(Z) derived from photoisomerization of 4-(E) was confirmed by nuclear magnetic resonance analysis. Acylation of several 7-aminocephalosporins was conducted by two routes involving the photoisomerization of 4-(E) to 4-(Z) (method A) or the isomerization of the activated intermediate (formula III) of the carboxylic acid 4-(E) with Vilsmeier reagent by heating (method B). The synthesis and the antibacterial activities of a new series of geometrical isomers of 7-[3-chloro-2-(thiazol-4-yl)propenamido] cephalosporins (formula II) are described.

  从 4-噻唑乙酸乙酯（1）开始，经过α-甲酰化、氯化和水解三个步骤的转化，得到了一种新的头孢 7 侧链酸，即(E)-3-氯-2-(噻唑-4-基)丙烯酸（4-(E)）。核磁共振分析证实了 4-(E)光异构化产生的相应 4-(Z)的存在。几种 7-氨基头孢菌素的酰化有两种途径，一种是 4-(E)光异构化成 4-(Z)（方法 A），另一种是羧酸 4-(E)的活化中间体（式 III）与 Vilsmeier 试剂加热异构化（方法 B）。本文介绍了 7-[3-氯-2-(噻唑-4-基)丙烯酰胺基]头孢菌素（式 II）的一系列新几何异构体的合成和抗菌活性。
• 3-Heterothio derivatives of (.alpha.-thiocarbonylamino) cephalosporins
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US03996219A1

  公开（公告）日：1976-12-07

  3-Heterothio(.alpha.-thiocarbonylamino)cephalosporin derivatives of the general formula ##STR1## wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, tri(lower alkyl)silyl, trihaloethyl, a salt forming ion or the group ##STR2## R.sub.1 is hydrogen, lower alkyl, cyclo-lower alkyl, unsaturated cyclo-lower alkyl, phenyl, substituted phenyl or thienyl; R.sub.2 and R.sub.5 each is hydrogen or lower alkyl; R.sub.3 is a five or six membered nitrogen, sulfur and/or oxygen containing ring system; and R.sub.4 is lower alkyl, phenyl or phenyl-lower alkyl; are useful as antibacterial agents.

  3-杂硫(.alpha.-硫代氨基)头孢菌素衍生物的一般式为##STR1##其中R为氢、低碳基、苯基-低碳基、三(低碳基)硅基、三卤乙基、盐形成离子或基团##STR2##R.sub.1为氢、低碳基、环-低碳基、不饱和环-低碳基、苯基、取代苯基或噻吩基；R.sub.2和R.sub.5各为氢或低碳基；R.sub.3为五元或六元含氮、硫和/或氧的环系统；R.sub.4为低碳基、苯基或苯基-低碳基；可用作抗菌剂。
• 3-HETEROTHIOMETHYL UREIDO CEPHALOSPORINS
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04127716A1

  公开（公告）日：1978-11-28

  L-Isomer compounds of the formula ##STR1## wherein R.sub.1 is phenyl, thienyl or furyl; R.sub.4 represents certain heterocyclic groups; R.sub.3 is hydrogen, lower alkyl, phenyl-lower alkyl, substituted phenyl-lower alkyl, diphenyl-lower alkyl, tri(lower alkyl)stannyl, tri(lower alkyl)silyl, a salt forming ion, or the group ##STR2## wherein R is lower alkyl, phenyl, phenyl-lower alkyl, or substituted phenyl and phenyl-lower alkyl are disclosed. These compounds are useful as antibacterial agents.

  化合物的L-异构体的化学式为##STR1## 其中R.sub.1为苯基，噻吩基或呋喃基; R.sub.4代表某些杂环基团; R.sub.3为氢，低碳基，苯基-低碳基，取代苯基-低碳基，二苯基-低碳基，三(低碳基)亚锡基，三(低碳基)硅基，形成盐的离子，或者是##STR2## 其中R为低碳基，苯基，苯基-低碳基，或者是取代苯基和苯基-低碳基。这些化合物可用作抗菌剂。
• SAKAGAMI, KENJI;ATSUMI, KUNIO;YOSHIDA, TAKASHI;NISHIHATA, KEN, YAKUGAKU DZASSI, 109,(1989) N, S. 377-387
  作者：SAKAGAMI, KENJI、ATSUMI, KUNIO、YOSHIDA, TAKASHI、NISHIHATA, KEN

  DOI：——

  日期：——