trichloroethyl 2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate | 138976-46-2

• 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: trichloroethyl 2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate
• 英文别名: trichloroethyl 2α-[(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl]-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate；2,2,2-trichloroethyl (2S,3S,5R,6R)-3-methyl-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 138976-46-2
• 化学式: C₂₁H₂₁Cl₃N₄O₅S₃
• 分子量: 611.979
• InChiKey: DELBZFTUMVDZAI-DOHHPOSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  110.72
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  trichloroethyl 2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate 在 溶剂黄146 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以87%的产率得到2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylic acid
  参考文献：
  名称：

  Synthesis and in vitro antibacterial activity of 2β and 2α-(substituted methyl) phenoxymethylpenicillins and an oxidation product

  摘要：

  The effect of stereochemical changes on the antibacterial activity of a series of 2-substituted methyl-6-beta-phenoxyacetamido penams synthesized in our laboratory was studied. The 2-alpha-heteroarylthiomethyl penams were found to be more active than the 2-beta-substituted derivatives against a range of Gram-positive and Gram-negative microorganisms. Both the isomers of 2-substituted methyl derivatives were found to be less active than the unsubstituted compound, the phenoxymethyl penicillin. The oxidized product of the 2-alpha-isomer was less active than the unoxidized compound.

  DOI：

  10.1016/0223-5234(91)90005-8
• 作为产物：
  描述：

  trichloroethyl 2β-(chloromethyl)-2α-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate 在 palladium on activated charcoal 氢气 、 sodium acetate 、 三溴化磷 、 dinitrogen tetraoxide 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 60.0 ℃ 、41.38 kPa 条件下， 反应 30.58h， 生成 trichloroethyl 2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate
  参考文献：
  名称：

  Synthesis and in vitro antibacterial activity of 2β and 2α-(substituted methyl) phenoxymethylpenicillins and an oxidation product

  摘要：

  The effect of stereochemical changes on the antibacterial activity of a series of 2-substituted methyl-6-beta-phenoxyacetamido penams synthesized in our laboratory was studied. The 2-alpha-heteroarylthiomethyl penams were found to be more active than the 2-beta-substituted derivatives against a range of Gram-positive and Gram-negative microorganisms. Both the isomers of 2-substituted methyl derivatives were found to be less active than the unsubstituted compound, the phenoxymethyl penicillin. The oxidized product of the 2-alpha-isomer was less active than the unoxidized compound.

  DOI：

  10.1016/0223-5234(91)90005-8