7-(allyloxycarbonylamino)cephalosporanic acid | 16901-30-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 7-(allyloxycarbonylamino)cephalosporanic acid
• 英文别名: (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-(prop-2-enoxycarbonylamino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 16901-30-7
• 化学式: C₁₄H₁₆N₂O₇S
• 分子量: 356.356
• InChiKey: GMWQWYDGFTYESU-BXKDBHETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-(allyloxycarbonylamino)cephalosporanic acid 在 四(三苯基膦)钯 吡啶 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 ammonium sulfate 、 对甲苯亚磺酸 、 acetylesterase 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 12.5h， 生成 benzhydryl (6R,7Z)-3-[[4-[(3R)-3-ethyl-2,6-dioxopiperidin-3-yl]phenyl]carbamoyloxymethyl]-7-[(4-methylphenyl)sulfonylamino]sulfanylimino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  Toward the Development of a Cephalosporin-Based Dual-Release Prodrug for Use in ADEPT

  摘要：

  In previous work we have shown that a cephalosporin structure bearing an S-aminosulfenimine at the 7-position behaved as a beta-lactamase-dependent dual-release prodrug. Scission of the beta-lactam ring of such a structure led to the rapid loss of the sulfur-attached side chain moiety via an intramolecular displacement, while the T-group was lost via the well-established elimination process at that position. In the present work we report on an evaluation of the scope and limitations of exploiting the S-aminosulfenimine functionality to generate a cephalosporin-based prodrug incorporating two biologically active components. Starting from 7-ACA, a viable synthetic cycle was put in place that avoided formation of the Delta(2) isomer throughout and that allowed incorporation of aminoglutethimide at the 3'-position and of a tosyl S-aminosulfenimine at the 7-position. The direct incorporation of a biologically active sulfonamide (ethoxzolamide) or a sulfamate (coumate) at this latter position was not achieved as a result of the difficulty of generating the corresponding sulfur diimides. An indirect route for the formation of an S-aminosulfenimine was put in place, as was a general method of alkylation (Mitsunobu reaction) of the tosyl S-ammosulfenimine following its incorporation.

  DOI：

  10.1021/jo048970i
• 作为产物：
  描述：

  benzhydryl 7-aminocephalosporanate 在 吡啶 、 4-二甲氨基吡啶 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 4.67h， 生成 7-(allyloxycarbonylamino)cephalosporanic acid
  参考文献：
  名称：

  Toward the Development of a Cephalosporin-Based Dual-Release Prodrug for Use in ADEPT

  摘要：

  In previous work we have shown that a cephalosporin structure bearing an S-aminosulfenimine at the 7-position behaved as a beta-lactamase-dependent dual-release prodrug. Scission of the beta-lactam ring of such a structure led to the rapid loss of the sulfur-attached side chain moiety via an intramolecular displacement, while the T-group was lost via the well-established elimination process at that position. In the present work we report on an evaluation of the scope and limitations of exploiting the S-aminosulfenimine functionality to generate a cephalosporin-based prodrug incorporating two biologically active components. Starting from 7-ACA, a viable synthetic cycle was put in place that avoided formation of the Delta(2) isomer throughout and that allowed incorporation of aminoglutethimide at the 3'-position and of a tosyl S-aminosulfenimine at the 7-position. The direct incorporation of a biologically active sulfonamide (ethoxzolamide) or a sulfamate (coumate) at this latter position was not achieved as a result of the difficulty of generating the corresponding sulfur diimides. An indirect route for the formation of an S-aminosulfenimine was put in place, as was a general method of alkylation (Mitsunobu reaction) of the tosyl S-ammosulfenimine following its incorporation.

  DOI：

  10.1021/jo048970i

文献信息

• NOVEL CEPHEM COMPOUND HAVING CATECHOL OR PSEUDO-CATECHOL STRUCTURE
  申请人：Shionogi & Co., Ltd.

  公开号：EP2703406A1

  公开（公告）日：2014-03-05

  The present invention provides a novel compound which has a wide antimicrobial spectrum, and in particular exhibits potent antimicrobial activity against beta-lactamase producing Gram negative bacteria. Specifically, the present invention provides a compound of the formula (I): wherein each symbol is as defined in the specification, or an amino-protected compound when the amino group is present on the ring in the 7-side chain, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising the same.

  本发明提供了一种新型化合物，它具有广泛的抗菌谱，特别是对β-内酰胺酶产生的革兰氏阴性菌具有强效抗菌活性。具体地说，本发明提供了一种式（I）化合物： 其中各符号如说明书中所定义、 或当氨基存在于 7 侧链的环上时的氨基保护化合物，或其药学上可接受的盐，以及由其组成的药物组合物。
• EP2703406
  申请人：——

  公开号：——

  公开（公告）日：——
• US9334289B2
  申请人：——

  公开号：US9334289B2

  公开（公告）日：2016-05-10