diphenyl methyl-7β-(2-thienyl)acetamido-3-<(4-methyl-thiazol-2-yl)sulphonylmethyl> ceph-3-em-4-carboxylate | 123445-97-6

• 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: diphenyl methyl-7β-(2-thienyl)acetamido-3-<(4-methyl-thiazol-2-yl)sulphonylmethyl> ceph-3-em-4-carboxylate
• 英文别名: benzhydryl (6R,7R)-3-[(4-methyl-1,3-thiazol-2-yl)sulfonylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 123445-97-6
• 化学式: C₃₁H₂₇N₃O₆S₄
• 分子量: 665.836
• InChiKey: JPXFYOMWBRDVDA-VAVYLYDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  213
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  diphenyl methyl-7β-(2-thienyl)acetamido-3-<(4-methyl-thiazol-2-yl)sulphonylmethyl> ceph-3-em-4-carboxylate 在 苯甲醚 、 三氟乙酸 作用下， 反应 0.33h， 生成 (6R,7R)-3-(4-Methyl-thiazole-2-sulfonylmethyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and in vitro antimicrobial activity of 3-heteroarylsulphonylmethyl cephems: a new class of cephalosporins

  摘要：

  A series of 3-heteroarylsulphonylmethyl and 3-heteroarylsulphenylmethyl cephems were prepared and tested for antimicrobial activities. In contrast to the adverse effect of oxidized ring sulphur of penams and cephems on antimicrobial activities, the oxidized side-chain sulphur of 3-mercaptoheteroaryl cephems retained Gram-negative and slightly decreased Gram-positive activity. The chemical nature of the moieties substituted at C-7 and C-3 positions also influenced the antibacterial activity and spectrum. Compounds with thienyl substitution at C-7 and sulphonylmethylthiazoles or sulphonylmethylthiadiazoles at C-3 exhibited good differentials in antibacterial activity vet-sus their unoxidized counterparts.

  DOI：

  10.1016/0223-5234(96)88221-3
• 作为产物：
  描述：

  diphenyl methyl-7β-(2-thienyl)acetamido-3-<(4-methyl-thiazol-2-yl)sulphonylmethyl> ceph-3-em-1β-oxide-4-carboxylate 在 吡啶 、 tetraphosphorus decasulfide 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以90.9%的产率得到diphenyl methyl-7β-(2-thienyl)acetamido-3-<(4-methyl-thiazol-2-yl)sulphonylmethyl> ceph-3-em-4-carboxylate
  参考文献：
  名称：

  Synthesis and in vitro antimicrobial activity of 3-heteroarylsulphonylmethyl cephems: a new class of cephalosporins

  摘要：

  A series of 3-heteroarylsulphonylmethyl and 3-heteroarylsulphenylmethyl cephems were prepared and tested for antimicrobial activities. In contrast to the adverse effect of oxidized ring sulphur of penams and cephems on antimicrobial activities, the oxidized side-chain sulphur of 3-mercaptoheteroaryl cephems retained Gram-negative and slightly decreased Gram-positive activity. The chemical nature of the moieties substituted at C-7 and C-3 positions also influenced the antibacterial activity and spectrum. Compounds with thienyl substitution at C-7 and sulphonylmethylthiazoles or sulphonylmethylthiadiazoles at C-3 exhibited good differentials in antibacterial activity vet-sus their unoxidized counterparts.

  DOI：

  10.1016/0223-5234(96)88221-3