(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

• 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: (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
• 英文别名: (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[3-[(sulfamoylamino)methyl]imidazo[5,1-b][1,3]thiazol-6-ium-6-yl]methyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• 化学式: C₁₇H₂₁N₅O₆S₂
• 分子量: 455.516
• InChiKey: XIWFPNLARDNJSW-NYHSCFHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  198
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  ethyl 2-(formylamino)methylthiazole-4-carboxylate 在 sodium tetrahydroborate 、 氨基磺酰氯 、 N,N-二异丙基乙胺 、 三苯基膦 、 sodium iodide 、 肼 、 偶氮二甲酸二乙酯 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 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

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##

  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##
• 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
• 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.