benzhydryl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate | 179034-64-1

• 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: benzhydryl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate
• 英文别名: benzhydryl (6R,7R)-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-carboxylate
• CAS: 179034-64-1
• 化学式: C₃₁H₂₆N₄O₄S₃
• 分子量: 614.77
• InChiKey: IXTZWIUUSFNTCN-VAVYLYDRSA-N

物化性质

• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  180
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzhydryl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate 在 吡啶 、 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以62%的产率得到benzhydryl 7β-amino-3-(5-methyl-1,3,4-thiadiasol-2-yl)thio-3-cephem-4-carboxylate hydrochloride
  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：

  3-羟基头孢 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.33h， 生成 benzhydryl 7β-(2-phenylacetamido)-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

文献信息

• Synthesis and anti-Helicobacter pylori activity of FR182024, a new cephem derivative
  作者：Yoshiki Yoshida、Keiji Matsuda、Hiroshi Sasaki、Yoshimi Matsumoto、Satoru Matsumoto、Hisashi Takasugi

  DOI：10.1016/s0960-894x(99)00549-1

  日期：1999.11

  The synthesis and anti-Helicobacter pylori activity of a novel cephem derivative FR182024 (1) are described. FR182024 having a (5-methyl-1,3,4-thiadiazol-2-yl)-thio moiety at the 3-position and a phenylacetamido at the 7-position was found to have extremely potent in vitro anti-H.pylori activity, superior therapeutic efficacy to AMPC and CAM, and low potential for causing diarrhea. (C) 1999 Elsevier Science Ltd. All rights reserved.