(6R)-trans-3-(hydroxymethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenyl methyl ester | 52312-27-3

• 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: (6R)-trans-3-(hydroxymethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenyl methyl ester
• 英文别名: benzhydryl (6R,7R)-3-(hydroxymethyl)-7-[(2-methylpropan-2-yl)oxycarbonylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 52312-27-3
• 化学式: C₂₆H₂₈N₂O₆S
• 分子量: 496.584
• InChiKey: GVHBMBXWVKSEQI-AUSIDOKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6R)-trans-3-(hydroxymethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenyl methyl ester 在 吡啶 、 五氯化磷 、 碳酸氢钠 、 苯甲醚 、 sodium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (6R-trans)-7-amino-3-<<4-(3-carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid trifluoroacetic acid salt
  参考文献：
  名称：

  Albrecht; Beskid; Christenson, Journal of Medicinal Chemistry, 1994, vol. 37, # 3, p. 400 - 407

  摘要：

  DOI：
• 作为产物：
  描述：

  头孢呋辛杂质12 生成 (6R)-trans-3-(hydroxymethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenyl methyl ester
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Cephalosporin derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0550775A1

  公开（公告）日：1993-07-14

  Cephalosporin derivatives of the general formula    in which R³ is a group of the formula    R⁶⁰ and R⁶⁵ are hydrogen or lower alkyl, R¹⁵-R¹⁹ are each independently hydrogen, halogen or hydroxy, n is zero or 1, R⁴ and R⁵ are each hydrogen, halogen, lower alkyl, lower alkoxy or amino, R⁷ is hydrogen or lower alkyl and R⁸ is lower alkyl, halo- lower alkyl, C₃-C₇ cycloalkyl or mono-, di- or trihalophenyl, and Z is N or C-R⁹, where R⁹ is hydrogen, halogen, lower alkyl or lower alkoxy; and, when R⁴ is fluoro, R⁵ and R⁷ are hydrogen. R⁸ is cyclopropyl and Z is C-H, R³ can also be one of the groups    in which R⁶¹ and R⁶⁶ are hydrogen or methyl, R¹⁵-R¹⁹ are as above and R⁹⁰ is hydrogen, hydroxy, carboxy, amino or [[4-(lower alkyl)-2,3-dioxo-1-piperazinyl]carbonyl]amino; pharmaceutically acceptable acid or base addition salts thereof, hydrates of compounds of formula I and hydrates of such salts. The products have antibacterial activity.

  头孢菌素衍生物的一般公式如下，其中R³是一个具有公式R⁶⁰的基团，R⁶⁵是氢或较低烷基，R¹⁵-R¹⁹分别独立地是氢、卤素或羟基，n为零或1，R⁴和R⁵分别是氢、卤素、较低烷基、较低烷氧基或氨基，R⁷是氢或较低烷基，R⁸是较低烷基、卤代较低烷基、C₃-C₇环烷基或单、二或三卤苯基，Z是N或C-R⁹，其中R⁹是氢、卤素、较低烷基或较低烷氧基；当R⁴为氟时，R⁵和R⁷为氢。R⁸为环丙基，Z为C-H时，R³也可以是以下基团之一，其中R⁶¹和R⁶⁶为氢或甲基，R¹⁵-R¹⁹如上所述，R⁹⁰为氢、羟基、羧基、氨基或[[4-(较低烷基)-2,3-二氧代-1-哌嗪基]羰基]氨基；其药用上可接受的酸或碱盐，以及公式I化合物的水合物和此类盐的水合物。这些产品具有抗菌活性。
• Dual-action cephalosporins: cephalosporin 3'-quinolone carbamates
  作者：Harry A. Albrecht、George Beskid、Nafsika H. Georgopapadakou、Dennis D. Keith、Frederick M. Konzelmann、David L. Pruess、Pamela L. Rossman、Chung Chen Wei、James G. Christenson

  DOI：10.1021/jm00113a026

  日期：1991.9

  A series of cephalosporins has been prepared in which the 3'-position was linked to the nitrogen of the antibacterial quinolone ciprofloxacin through a carbamate function. Like the ester-linked and quaternary-linked dual-action cephalosporins reported earlier, these carbamate-linked compounds exhibited a broad antibacterial spectrum derived from both cephalosporin-like and quinolone-like activities, suggesting a dual mode of action. Studies to elucidate details of the mechanism of action have been inconclusive. Ciprofloxacin liberated as a consequence of bacterial enzyme-mediated reactions may contribute to the second mode of action, although some evidence indicates that the intact carbamate-linked bifunctional molecules may possess intrinsically both beta-lactam and quinolone activities.
• ——
  作者：NAGANO KEHNSE、 MURAKAMI YUKIYASU、 XARA RYUITIRO、 NAKANO KODZI、 KODA AKIO、+

  DOI：——

  日期：——
• US5189157A
  申请人：——

  公开号：US5189157A

  公开（公告）日：1993-02-23
• US5336768A
  申请人：——

  公开号：US5336768A

  公开（公告）日：1994-08-09