5-(aminosulfonyl)aminomethylimidazo[5,1-b]thiazole | 183066-41-3

• 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-(aminosulfonyl)aminomethylimidazo[5,1-b]thiazole
• 英文别名: 5-[(Sulfamoylamino)methyl]imidazo[5,1-b][1,3]thiazole
• CAS: 183066-41-3
• 化学式: C₆H₈N₄O₂S₂
• 分子量: 232.287
• InChiKey: JPEWVJAUTHNZNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(aminosulfonyl)aminomethylimidazo[5,1-b]thiazole 、 prop-2-enyl (4S,5R,6S)-3-(diphenoxyphosphoryloxymethyl)-4-methyl-7-oxo-6-[(1R)-1-prop-2-enoxycarbonyloxyethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 在 四(三苯基膦)钯 sodium iodide 、 2-乙基-己酸稀土盐 、 potassium 2-ethylhexanoate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 生成 (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[5-[(sulfamoylamino)methyl]imidazo[5,1-b][1,3]thiazol-6-ium-6-yl]methyl]-1-azabicyclo[3.2.0]hept-2-ene-2-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

文献信息

• Carbapenem derivatives
  申请人：Meiji Seika Kabushiki Kaisha

  公开号：US05990101A1

  公开（公告）日：1999-11-23

  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 .beta.-lactamase-producing bacteria and MRSA and are very stable against DHP-1. ##STR1##

  揭示了一种新型碳青霉烯衍生物，其化学式如下（I），在2-位具有取代或未取代的咪唑[5,1-b]噻唑-6-基甲基基团。化学式（I）代表的化合物对从革兰氏阳性细菌到革兰氏阴性细菌，包括铜绿假单胞菌在内的广谱细菌具有强效的抗菌活性，并且对各种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。
• 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。
• US5990101A
  申请人：——

  公开号：US5990101A

  公开（公告）日：1999-11-23