diphenylmethyl 7β-(o-hydroxybenzylideneamino)-3-hydroxymethyl-3-cephem-4-carboxylate | 90467-27-9

• 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: diphenylmethyl 7β-(o-hydroxybenzylideneamino)-3-hydroxymethyl-3-cephem-4-carboxylate
• 英文别名: benzhydryl (6R,7R)-3-hydroxymethyl-8-oxo-7-salicylideneamino-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；benzhydryl (6R,7R)-3-(hydroxymethyl)-7-[(2-hydroxyphenyl)methylideneamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 90467-27-9
• 化学式: C₂₈H₂₄N₂O₅S
• 分子量: 500.575
• InChiKey: OCOKTHICGVWWGL-YIXXDRMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  125
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diphenylmethyl 7β-(o-hydroxybenzylideneamino)-3-hydroxymethyl-3-cephem-4-carboxylate 在 咪唑 、 吉拉尔特试剂 T 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 diphenylmethyl 7β-formamido-3-t-butyldimethylsiloxymethyl-3-cephem-4-carboxylate
  参考文献：
  名称：

  Synthesis and β-Lactamase Inhibitory Activity of 3-Cyano-3-cephem Derivatives

  摘要：

  从 7β- 氨基头孢烷酸制备了两种新的 3-氰基-3-头孢衍生物，即 3-氰基-3-头孢-4-羧酸钾（2）和 7α-苯乙酰胺基-3-氰基-3-头孢-4-羧酸钾（3）。与 7α-[(1R)-1-羟乙基]-3-氰基-3-头孢-4-羧酸钠（1）相比，化合物 2 和 3 只显示出微弱的β-内酰胺酶抑制活性，这表明 7α-（1-羟乙基）取代基对β-内酰胺酶抑制活性起着重要作用。

  DOI：

  10.1246/bcsj.63.412
• 作为产物：
  描述：

  羟甲基-7-氨基头孢烷酸 以 甲醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 diphenylmethyl 7β-(o-hydroxybenzylideneamino)-3-hydroxymethyl-3-cephem-4-carboxylate
  参考文献：
  名称：

  Improvement of the synthesis of diphenylmethyl 7β-(o-hydroxy)benzylideneamino-3-hydroxymethyl-3-cephem-4-carboxylate

  摘要：

  The title product (I) is synthesized currently from 7-aminocephalosporanic acid, and diphenyldiazomethane (DDM) is used as a protective reagent of the acid function for further reactions. When DDM was prepared from benzophenone hydrazone by reaction with chloramine T, it was resulted impure by p-toluenesulfonamide, formed as side product, which cannot be removed during the final purification step carried out according to the literature procedure. Two simple methods are proposed here to obtain I with the suitable degree of purity necessary for a drug. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01115-6

文献信息

• Process for the preparation of 3-phosphoniummethyl-3-cephem compounds
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04705851A1

  公开（公告）日：1987-11-10

  The invention relates to a process for the preparation of 3-phosphoniummethyl-3-cephem compounds of the formula: ##STR1## wherein R.sub.3 is aryl, or a salt thereof, which is characterized by reacting one equimolar amount of a 3-hydroxymethyl-3-cephem compound of the formula: ##STR2## or a salt thereof, with two or a little over two equimolar amount of triarylphosphine and one or a little over one equimolar amount of iodine, said prepared compounds being useful as intermediates for manufacturing 3-vinyl-3-cephem compounds possessing potent antimicrobial activities.

  本发明涉及一种制备3-磷酸甲基-3-头孢菌素化合物的方法，其化学式为：##STR1## 其中R.sub.3为芳基或其盐。该方法的特点在于，将一摩尔的3-羟甲基-3-头孢菌素化合物的化学式：##STR2## 或其盐与两摩尔或略多于两摩尔的三芳基膦和一摩尔或略多于一摩尔的碘反应，制备的化合物可用作制造具有强效抗微生物活性的3-乙烯基-3-头孢菌素化合物的中间体。
• Synthesis and β-Lactamase Inhibitory Activity of 3-Cyano-3-cephem Derivatives
  作者：Shintaro Nishimura、Nobuyoshi Yasuda、Hiroshi Sasaki、Yoshimi Matsumoto、Toshiaki Kamimura、Kazuo Sakane、Takao Takaya

  DOI：10.1246/bcsj.63.412

  日期：1990.2

  Two new 3-cyano-3-cephem derivatives, potassium 3-cyano-3-cephem-4-carboxylate (2) and potassium 7α-phenylacetamido-3-cyano-3-cephem-4-carboxylate (3), were prepared from 7β-aminocephalosporanic acid. Compounds 2 and 3 showed only weak β-lactamase inhibitory activity in contrast to sodium 7α-[(1R)-1-hydroxyethyl]-3-cyano-3-cephem-4-carboxylate (1), indicating the important role of the 7α-(1-hydroxyethyl) substituent for β-lactamase inhibitory activity.

  从 7β- 氨基头孢烷酸制备了两种新的 3-氰基-3-头孢衍生物，即 3-氰基-3-头孢-4-羧酸钾（2）和 7α-苯乙酰胺基-3-氰基-3-头孢-4-羧酸钾（3）。与 7α-[(1R)-1-羟乙基]-3-氰基-3-头孢-4-羧酸钠（1）相比，化合物 2 和 3 只显示出微弱的β-内酰胺酶抑制活性，这表明 7α-（1-羟乙基）取代基对β-内酰胺酶抑制活性起着重要作用。
• Improvement of the synthesis of diphenylmethyl 7β-(o-hydroxy)benzylideneamino-3-hydroxymethyl-3-cephem-4-carboxylate
  作者：Miguel López、Zalua Rodrı́guez、Bárbara Valdés、Hermán Velez、Juan Agüero、Adamo Fini、Maritza González

  DOI：10.1016/s0014-827x(01)01115-6

  日期：2001.8

  The title product (I) is synthesized currently from 7-aminocephalosporanic acid, and diphenyldiazomethane (DDM) is used as a protective reagent of the acid function for further reactions. When DDM was prepared from benzophenone hydrazone by reaction with chloramine T, it was resulted impure by p-toluenesulfonamide, formed as side product, which cannot be removed during the final purification step carried out according to the literature procedure. Two simple methods are proposed here to obtain I with the suitable degree of purity necessary for a drug. (C) 2001 Elsevier Science S.A. All rights reserved.