benzhydryl 7β-(3,5-di-t-butyl-4-hydroxybenzylideneamino)-7α-methoxy-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate | 308122-00-1

• 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: benzhydryl 7β-(3,5-di-t-butyl-4-hydroxybenzylideneamino)-7α-methoxy-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate
• CAS: 308122-00-1
• 化学式: C₃₉H₄₂N₄O₅S₃
• 分子量: 742.984
• InChiKey: WITBXHJMUPJMEK-RIEGYYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  51.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  114.21
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  benzhydryl 7β-(3,5-di-t-butyl-4-hydroxybenzylideneamino)-7α-methoxy-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate 在 吉拉尔特试剂 T 、 N-三甲基硅基乙酰胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 苯甲醚 为溶剂， 反应 10.0h， 生成 (6R,7S)-7-methoxy-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  studies on anti-helicobacter pylori agents. part 2: new cephem derivatives

  摘要：

  The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of cephem derivatives are described. Introduction of thio-heterocyclic groups containing N- and S-atoms to the 3-position and phenyl or thienyl acetamido groups to the 7-position of the cephem nucleus dramatically improved the activity. From this series of derivatives, compound 13i was Found to have extremely potent in vitro anti-H. pylori activity, superior therapeutic efficacy compared to AMPC and CAM, no cross-resistance between CAM or MNZ and low potential for causing diarrhea due to instability to beta-lactamase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00163-2
• 作为产物：
  描述：

  甲醇 、 benzhydryl 7β-(3,5-di-t-butyl-4-hydroxybenzylideneamino)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 反应 0.5h， 以54%的产率得到benzhydryl 7β-(3,5-di-t-butyl-4-hydroxybenzylideneamino)-7α-methoxy-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate
  参考文献：
  名称：

  studies on anti-helicobacter pylori agents. part 2: new cephem derivatives

  摘要：

  The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of cephem derivatives are described. Introduction of thio-heterocyclic groups containing N- and S-atoms to the 3-position and phenyl or thienyl acetamido groups to the 7-position of the cephem nucleus dramatically improved the activity. From this series of derivatives, compound 13i was Found to have extremely potent in vitro anti-H. pylori activity, superior therapeutic efficacy compared to AMPC and CAM, no cross-resistance between CAM or MNZ and low potential for causing diarrhea due to instability to beta-lactamase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00163-2