2-hydroxymethylimidazo[5,1-b]thiazole | 183066-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-hydroxymethylimidazo[5,1-b]thiazole
• 英文别名: imidazo[5,1-b][1,3]thiazol-2-ylmethanol
• CAS: 183066-71-9
• 化学式: C₆H₆N₂OS
• 分子量: 154.192
• InChiKey: XPEBFUABUNMQRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S(R))-3-(hydroxymethyl)-4-methyl-6-<1-<<(2-propenoxy)carbonyl>oxy>ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-enecarboxylic acid 2-propenyl ester 、 2-hydroxymethylimidazo[5,1-b]thiazole 以obtaining 3.3 mg of the title compound的产率得到(1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-(2-hydroxymethylimidazo[5,1-b]thiazolium-6-yl)methyl-1-methyl-1-carbapen-2-em-3-carboxylate
  参考文献：
  名称：

  Carbapenem derivatives

  摘要：

  本发明揭示了一种具有以下式(I)的取代或未取代的咪唑[5,1-b]噻唑-6-基甲基基团的新型碳青霉烯衍生物。公式（I）代表的化合物对从革兰氏阳性菌到革兰氏阴性菌包括铜绿假单胞菌在内的广谱细菌具有强效的抗菌活性，此外，它们对各种β-内酰胺酶产生的细菌和MRSA具有强效的抗菌活性，并且对DHP-1非常稳定。 ##STR1##

  公开号：

  US05990101A1
• 作为产物：
  描述：

  2-acetoxymethylimidazo[5,1-b]thiazole 在 silica gel 作用下， 以 甲醇 、 potassium carbonate 为溶剂， 反应 1.5h， 以to obtain 550 mg of the title compound的产率得到2-hydroxymethylimidazo[5,1-b]thiazole
  参考文献：
  名称：

  Carbapenem derivatives

  摘要：

  本发明揭示了一种具有以下式(I)的取代或未取代的咪唑[5,1-b]噻唑-6-基甲基基团的新型碳青霉烯衍生物。公式（I）代表的化合物对从革兰氏阳性菌到革兰氏阴性菌包括铜绿假单胞菌在内的广谱细菌具有强效的抗菌活性，此外，它们对各种β-内酰胺酶产生的细菌和MRSA具有强效的抗菌活性，并且对DHP-1非常稳定。 ##STR1##

  公开号：

  US05990101A1

文献信息

• Novel carbapenem derivatives of quarternary salt type
  申请人：——

  公开号：US20030022881A1

  公开（公告）日：2003-01-30

  An objective of the present invention is to provide carbapenem derivatives which have potent antibiotic activity against MRSA, PRSP, Influenzavirus, and &bgr;-lactamase-producing bacteria and are stable against DHP-1. The compounds according to the present invention are compounds represented by formula (I) or pharmaceutically acceptable salts thereof: 1 wherein R 1 represents H or methyl; R 2 and R 3 each independently represent H, halogen, lower alkyl or the like; R 4 represents optionally substituted lower alkylthio or the like; and R 5 represents optionally substituted lower alkyl or the like.

  本发明的目的在于提供对MRSA、PRSP、流感病毒和β-内酰胺酶产生菌具有强大抗生素活性的碳青霉烯衍生物，且对DHP-1稳定。根据本发明的化合物是由公式(I)表示的化合物或其药物可接受的盐：1其中R1代表H或甲基；R2和R3各自独立地代表H、卤素、低级烷基等；R4代表可选地取代的低级烷基亚磺酰基等；R5代表可选地取代的低级烷基等。
• NOVEL CARBAPENEM DERIVATIVES
  申请人：MEIJI SEIKA KABUSHIKI KAISHA

  公开号：EP0760370A1

  公开（公告）日：1997-03-05

  Novel carbapenem derivatives, represented by the following formula (I), having a substituted or unsubstituted imidazo[5,1-b]thiazolium-6-ylmethyl group at the 2-position are disclosed. The compounds represented by the formula (I) have potent antibacterial activity against a wide spectrum of bacteria from Gram-positive bacteria to Gram-negative bacteria including Pseudomonas aeruginosa and, in addition, have potent antibacterial activity against various β-lactamase-producing bacteria and MRSA and are very stable against DHP-1.

  本发明公开了由下式(I)表示的新型碳青霉烯类衍生物，其 2-位具有取代或未取代的咪唑并[5,1-b]噻唑鎓-6-基甲基。由式（I）代表的化合物对从革兰氏阳性菌到革兰氏阴性菌（包括铜绿假单胞菌）在内的广谱细菌具有强效抗菌活性，此外，还对各种产β-内酰胺酶细菌和 MRSA 具有强效抗菌活性，并且对 DHP-1 非常稳定。
• NOVEL CARBAPENEM DERIVATIVES OF QUATERNARY SALT TYPE
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：EP1251134A1

  公开（公告）日：2002-10-23

  An objective of the present invention is to provide carbapenem derivatives which have potent antibiotic activity against MRSA, PRSP, Influenzavirus, and β-lactamase-producing bacteria and are stable against DHP-1. The compounds according to the present invention are compounds represented by formula (I) or pharmaceutically acceptable salts thereof: wherein R1 represents H or methyl; R2 and R3 each independently represent H, halogen, lower alkyl or the like; R4 represents optionally substituted lower alkylthio or the like; and R5 represents optionally substituted lower alkyl or the like.

  本发明的目的是提供碳青霉烯类衍生物，它们对 MRSA、PRSP、流感病毒和产 β-内酰胺酶细菌具有强效抗生素活性，并且对 DHP-1 稳定。根据本发明的化合物是由式（I）代表的化合物或其药学上可接受的盐： 其中 R1 代表 H 或甲基；R2 和 R3 各自独立地代表 H、卤素、低级烷基或类似物；R4 代表任选取代的低级烷硫基或类似物；R5 代表任选取代的低级烷基或类似物。
• 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.
• US5990101A
  申请人：——

  公开号：US5990101A

  公开（公告）日：1999-11-23