(6R,7R)-3-(4-Carboxymethyl-thiazol-2-ylsulfanyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester | 194929-94-7

• 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: (6R,7R)-3-(4-Carboxymethyl-thiazol-2-ylsulfanyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• 英文别名: 2-[2-[[(6R,7R)-2-benzhydryloxycarbonyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]sulfanyl]-1,3-thiazol-4-yl]acetic acid
• CAS: 194929-94-7
• 化学式: C₃₃H₂₇N₃O₆S₃
• 分子量: 657.792
• InChiKey: LMLVMDOAAYSJOS-DLFZDVPBSA-N

物化性质

• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  205
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (6R,7R)-3-(4-Carboxymethyl-thiazol-2-ylsulfanyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 在 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (6R,7R)-3-[[4-(carboxymethyl)-1,3-thiazol-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 3: A novel, efficacious cephem derivative, FR193879

  摘要：

  The synthesis, therapeutic efficacy against H. pylori, and preliminary safety of the novel cephem. derivative, FR193879 (8a) are described. Compound 8a having a (4-carbamoylmethylthiazol-2-yl)thio moiety at the 3-position and a phenylacetamido at the 7-position was found to have good safety showing a nontoxic dose of >100 mg/kg in dogs in a 4-week repeat dose toxicity study and extremely potent therapeutic efficacy against H. pylori, showing 30 times superior activity compared to AMPC, and did not display cross-resistance with CAM or MNZ. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.068
• 作为产物：
  描述：

  2,3-二氢-2-硫代-4-噻唑乙酸乙酯 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙二醇二甲醚 为溶剂， 生成 (6R,7R)-3-(4-Carboxymethyl-thiazol-2-ylsulfanyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  Studies on anti-Helicobacter pylori agents. Part 3: A novel, efficacious cephem derivative, FR193879

  摘要：

  The synthesis, therapeutic efficacy against H. pylori, and preliminary safety of the novel cephem. derivative, FR193879 (8a) are described. Compound 8a having a (4-carbamoylmethylthiazol-2-yl)thio moiety at the 3-position and a phenylacetamido at the 7-position was found to have good safety showing a nontoxic dose of >100 mg/kg in dogs in a 4-week repeat dose toxicity study and extremely potent therapeutic efficacy against H. pylori, showing 30 times superior activity compared to AMPC, and did not display cross-resistance with CAM or MNZ. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.068

文献信息

• US6150351A
  申请人：——

  公开号：US6150351A

  公开（公告）日：2000-11-21
• Studies on anti-Helicobacter pylori agents. Part 3: A novel, efficacious cephem derivative, FR193879
  作者：Yoshiki Yoshida、Keiji Matsuda、Hiroshi Sasaki、Yoshimi Matsumoto、Satoru Matsumoto、Shuichi Tawara、Hisashi Takasugi

  DOI：10.1016/j.bmcl.2004.02.068

  日期：2004.5

  The synthesis, therapeutic efficacy against H. pylori, and preliminary safety of the novel cephem. derivative, FR193879 (8a) are described. Compound 8a having a (4-carbamoylmethylthiazol-2-yl)thio moiety at the 3-position and a phenylacetamido at the 7-position was found to have good safety showing a nontoxic dose of >100 mg/kg in dogs in a 4-week repeat dose toxicity study and extremely potent therapeutic efficacy against H. pylori, showing 30 times superior activity compared to AMPC, and did not display cross-resistance with CAM or MNZ. (C) 2004 Elsevier Ltd. All rights reserved.