5-((R)-1-formylamino-2-hydroxyethyl)imidazo[5,1-b]thiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-((R)-1-formylamino-2-hydroxyethyl)imidazo[5,1-b]thiazole
• 英文别名: N-[(1R)-2-hydroxy-1-imidazo[5,1-b][1,3]thiazol-5-ylethyl]formamide
• 化学式: C₈H₉N₃O₂S
• 分子量: 211.244
• InChiKey: IXGAHLFVGJNYKX-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-((R)-1-formylamino-2-hydroxyethyl)imidazo[5,1-b]thiazole 在 三氟乙酸 作用下， 以 苯甲醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-[5-((R)-1-formylamino-2-hydroxyethyl]imidazo[5,1-b]thiazolium-6-yl)methyl-3-cephem-4-carboxylate
  参考文献：
  名称：

  CP6679, a new injectable cephalosporin. Part1: Synthesis and structure–activity relationships

  摘要：

  A series of cephalosporins bearing a 5,5-fused ring system, an (imidazo/[5,1 -b]thiazolium-6-yl)methyl group, at the C-3 position were synthesized and evaluated for in vitro antibacterial activities. CP6679 (Is) and its analogues showed potent antibacterial activities against Gram-positive and Gram-negative bacteria, including Pseudomonas aeruginosa. They were also highly active against methicillin-resistant Staphylococcus aureus (MRSA). CP6679 (Is) showed more potent antibacterial activity than ceftazidime (CAZ) or cefpirome (CPR) against Pseudomonas aeruginosa and MRSA. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00214-5
• 作为产物：
  描述：

  5-[(R)-2-acetoxy-1-(trifluoroacetyl-amino)ethyl]imidazo[5,1-b]thiazole 、 sodium hydroxide 、 5-[(R)-1-amino-2-hydroxyethyl]imidazo[5,1-b]thiazole 、 乙酸酐 、 potassium carbonate 在 ice 、 二氯甲烷 、 magnesium sulfate 作用下， 以 甲醇 、 水 、 甲酸 、 二氯甲烷 为溶剂， 反应 16.17h， 以to give 0.200 g (quant.) of 5-((R)-1-formylamino-2-hydroxyethyl)imidazo[5,1-b]thiazole的产率得到5-((R)-1-formylamino-2-hydroxyethyl)imidazo[5,1-b]thiazole
  参考文献：
  名称：

  Cephem derivatives

  摘要：

  以下公式（I）所代表的化合物，即在头孢环的3位取代或未取代的咪唑[5,1-b]噻唑-6-基作为取代基的头孢菌素衍生物：##STR1## 其中X代表CH或N，R.sup.1代表H、烷基、烯基或类似物，而R.sup.2、R.sup.3、R.sup.4和R.sup.5代表H、烷基、氨基甲酰基、氨基或类似物。以上化合物具有优异的抗菌活性，并可用作治疗由细菌引起的各种传染病的药物。

  公开号：

  US05663162A1

文献信息

• NOVEL CEPHEM DERIVATIVE
  申请人：MEIJI SEIKA KABUSHIKI KAISHA

  公开号：EP0669336A1

  公开（公告）日：1995-08-30

  A compound represented by general formula (I), i.e., a cephem derivative having an (un)substituted imidazo-[5,1-b]thiazolium-6-yl group at the 3-position of the ring, wherein X represents CH or N; R1 represents H, alkyl, alkenyl, etc.; and R2, R3, R4 and R5 represent each H, alkyl, carbamoyl, amino, etc. This compound has an excellent antibacterial activity and is useful as a remedy for various types of microbism.

  一种由通式（I）代表的化合物，即在环的 3 位上具有一个（未）取代的咪唑并[5,1-b]噻唑鎓-6-基团的头孢衍生物，其中 X 代表 CH 或 N；R1 代表 H、烷基、烯基等；R2、R3、R4 和 R5 分别代表 H、烷基、氨基甲酰基、氨基等。这种化合物具有极佳的抗菌活性，可用于治疗各种微生物。
• NOVEL CEPHEM DERIVATIVES
  申请人：MEIJI SEIKA KABUSHIKI KAISHA

  公开号：EP0669336B1

  公开（公告）日：2000-05-17
• US5663162A
  申请人：——

  公开号：US5663162A

  公开（公告）日：1997-09-02
• Cephem derivatives
  申请人：Meiji Seika Kabushiki Kaisha

  公开号：US05663162A1

  公开（公告）日：1997-09-02

  Compounds represented by the following formula (I), that is, cephem derivatives having substituted or unsubstituted imidazo[5,1-b]thiazolium-6-yl as a substituent at the 3-position of the cephem ring: ##STR1## wherein X represents CH or N, R.sup.1 represents H, alkyl, alkenyl or the like, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 represent H, alkyl, carbamoyl, amino or the like. The above compounds have excellent antibacterial activity, and useful as medicines for the treatment of various infectious diseases caused by bacteria.

  具有下述通式（I）表示的化合物，即头孢烯环的3位上具有取代或未取代的咪唑并[5,1-b]噻唑鎓-6-基作为取代基的头孢烯衍生物：##STR1## 其中X代表CH或N，R1代表H、烷基、烯基等，R2、R3、R4和R5代表H、烷基、氨甲酰基、氨基等。上述化合物具有优异的抗菌活性，可作为治疗由细菌引起的各种感染性疾病的药物。
• CP6679, a new injectable cephalosporin. Part1: Synthesis and structure–activity relationships
  作者：Masaki Tsushima、Katsuyoshi Iwamatsu、Eijiro Umemura、Toshiaki Kudo、Yasuo Sato、Sojiro Shiokawa、Hiromasa Takizawa、Yuko Kano、Kazuko Kobayashi、Takashi Ida

  DOI：10.1016/s0968-0896(00)00214-5

  日期：2000.12

  A series of cephalosporins bearing a 5,5-fused ring system, an (imidazo/[5,1 -b]thiazolium-6-yl)methyl group, at the C-3 position were synthesized and evaluated for in vitro antibacterial activities. CP6679 (Is) and its analogues showed potent antibacterial activities against Gram-positive and Gram-negative bacteria, including Pseudomonas aeruginosa. They were also highly active against methicillin-resistant Staphylococcus aureus (MRSA). CP6679 (Is) showed more potent antibacterial activity than ceftazidime (CAZ) or cefpirome (CPR) against Pseudomonas aeruginosa and MRSA. (C) 2000 Elsevier Science Ltd. All rights reserved.