3-(phthalimido)methylimidazo[5,1-b]thiazole | 165667-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-(phthalimido)methylimidazo[5,1-b]thiazole
• 英文别名: 2-(Imidazo[5,1-b][1,3]thiazol-3-ylmethyl)isoindole-1,3-dione
• CAS: 165667-44-7
• 化学式: C₁₄H₉N₃O₂S
• 分子量: 283.31
• InChiKey: SUIHVOSFWWPDRI-UHFFFAOYSA-N

物化性质

• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  82.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(phthalimido)methylimidazo[5,1-b]thiazole 在 氨基磺酰氯 、 N,N-二异丙基乙胺 、 sodium iodide 、 肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[3-(aminosulfonyl)aminomethylimidazo[5,1-b]thiazolium-6-yl]methyl-1-methyl-1-carbapen-2-em-3-carboxylate
  参考文献：
  名称：

  CP0569, A New Broad-Spectrum Injectable Carbapenem. Part 1: Synthesis and Structure–Activity Relationships

  摘要：

  A series of 10-methylcarbapenems bearing an (imidazo[5,1-b]thiazolium-6-yl)methyl moiety, a 5,5-fused heterobicycle, at the C-2 position was synthesized and evaluated for in vitro antibacterial activities. CP0569 (1r) and its analogues showed potent antibacterial activities against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA), and Gram-negative bacteria, including Pseudomonas aeruginosa. Moreover, CP0569 (1r) exhibited stronger antibacterial activity against MRSA and higher resistance to renal dehydropeptidase-1 (DHP-1) than any currently marketed carbapenems, that is, imipenem (IPM), panipenem (PAPM), and meropenem (MEPM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00304-3
• 作为产物：
  描述：

  ethyl 2-(formylamino)methylthiazole-4-carboxylate 在 sodium tetrahydroborate 、 三苯基膦 、 偶氮二甲酸二乙酯 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 3-(phthalimido)methylimidazo[5,1-b]thiazole
  参考文献：
  名称：

  CP0569, A New Broad-Spectrum Injectable Carbapenem. Part 1: Synthesis and Structure–Activity Relationships

  摘要：

  A series of 10-methylcarbapenems bearing an (imidazo[5,1-b]thiazolium-6-yl)methyl moiety, a 5,5-fused heterobicycle, at the C-2 position was synthesized and evaluated for in vitro antibacterial activities. CP0569 (1r) and its analogues showed potent antibacterial activities against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA), and Gram-negative bacteria, including Pseudomonas aeruginosa. Moreover, CP0569 (1r) exhibited stronger antibacterial activity against MRSA and higher resistance to renal dehydropeptidase-1 (DHP-1) than any currently marketed carbapenems, that is, imipenem (IPM), panipenem (PAPM), and meropenem (MEPM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00304-3

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
• CP0569, A New Broad-Spectrum Injectable Carbapenem. Part 1: Synthesis and Structure–Activity Relationships
  作者：K Aihara

  DOI：10.1016/s0968-0896(03)00304-3

  日期：2003.8.5

  A series of 10-methylcarbapenems bearing an (imidazo[5,1-b]thiazolium-6-yl)methyl moiety, a 5,5-fused heterobicycle, at the C-2 position was synthesized and evaluated for in vitro antibacterial activities. CP0569 (1r) and its analogues showed potent antibacterial activities against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA), and Gram-negative bacteria, including Pseudomonas aeruginosa. Moreover, CP0569 (1r) exhibited stronger antibacterial activity against MRSA and higher resistance to renal dehydropeptidase-1 (DHP-1) than any currently marketed carbapenems, that is, imipenem (IPM), panipenem (PAPM), and meropenem (MEPM). (C) 2003 Elsevier Ltd. All rights reserved.