(6R,7R)-3-(4-Carbamoylmethyl-thiazol-2-ylsulfanyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 194928-82-0

• 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-Carbamoylmethyl-thiazol-2-ylsulfanyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 英文别名: 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((4-(2-amino-2-oxoethyl)-2-thiazolyl)thio)-8-oxo-7-((phenylacetyl)amino)-, (6R-trans)-；(6R,7R)-3-[[4-(2-amino-2-oxoethyl)-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
• CAS: 194928-82-0
• 化学式: C₂₀H₁₈N₄O₅S₃
• 分子量: 490.585
• InChiKey: YINUFDSCPLNLPS-CRAIPNDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  222
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,3-二氢-2-硫代-4-噻唑乙酸乙酯 在 ammonium hydroxide 、 potassium tert-butylate 、 氯化铵 、 苯甲醚 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 生成 (6R,7R)-3-(4-Carbamoylmethyl-thiazol-2-ylsulfanyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[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

文献信息

• [EN] NEW CEPHEM COMPOUNDS AND PHARMACEUTICAL USE THEREOF<br/>[FR] NOUVEAUX COMPOSES DE CEPHEM ET LEUR UTILISATION PHARMACEUTIQUE
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1997029111A1

  公开（公告）日：1997-08-14

  (EN) This invention relates to new cephem compounds represented by general formula (I) wherein each symbol is as defined in the specification or a salt thereof, which has antimicrobial activity against $i(Helicobacter pylori), and are useful as anti-$i(Helicobacter pylori) agents, anti-gastritis agents, anti-ulcer agents and anti-cancer agents.(FR) Cette invention concerne un nouveau composé de céphem représenté par la formule générale (I) dans laquelle chaque symbole est tel que défini dans la description. Cette invention concerne également les sels de ce composé, lequel possède une activité antimicrobienne dirigée contre l'$i(Helicobacter pylori). Ce composé est utile en qualité d'agent de lutte contre l'$i(Helicobacter pylori), les gastrites, les ulcères et le cancer.

  该发明涉及新的头孢菌素化合物，由通式（I）表示，其中每个符号如规范中所定义或其盐，具有抗菌活性，可用作抗$ i（幽门螺杆菌）剂，抗胃炎剂，抗溃疡剂和抗癌剂。该化合物对$ i（幽门螺杆菌）具有抗菌活性，因此对于治疗幽门螺杆菌感染、胃炎、溃疡和癌症等方面具有重要作用。
• NEW CEPHEM COMPOUNDS AND PHARMACEUTICAL USE THEREOF
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0882052A1

  公开（公告）日：1998-12-09
• 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.