4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate | 432040-07-8

• 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: 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate
• 英文别名: (4-nitrobenzyl) (1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylate；(4-nitrophenyl)methyl (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[7-(pyridine-3-carbonyl)imidazo[5,1-b][1,3]thiazol-2-yl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 432040-07-8
• 化学式: C₂₈H₂₃N₅O₇S
• 分子量: 573.586
• InChiKey: LPHKOIYFLBATAB-CAPVFGHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  188
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate 在 palladium on activated charcoal sodium phosphate buffer 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以41 mg的产率得到(4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[7-(pyridine-3-carbonyl)imidazo[5,1-b][1,3]thiazol-2-yl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and SAR study of novel 7-(pyridinium-3-yl)-carbonyl imidazo[5,1-b]thiazol-2-yl carbapenems

  摘要：

  A new series of 10-methyl carbapenems, possessing a 7-substituted imidazo[5, 1-b]thiazol-2-yl group directly attached to the C-2 position of the carbapenem nucleus, was synthesized and evaluated for antibacterial activity. These compounds showed potent activities against Gram-positive bacteria, in particular methicillin-resistant Staphylococcus aureus (MRSA) and penicillin-resistant Streptococcus pneumoniae (PRSP). They also exhibited potent activity against beta-lactamase-negative ampicillin-resistant Haemophilus influenzae (BLNAR). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.049
• 作为产物：
  描述：

  (3S,4R)-3-[(1R)-1-hydroxyethyl]-4-{(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxoethyl}-1-[4-nitrobenzyl-oxycarbonyl(triphenylphosphoranylidene)-methyl]azetidin-2-one 在 methanol-dichloromethane 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以to give 23.1 mg of (4-nitrobenzyl) (1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylate的产率得到4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate
  参考文献：
  名称：

  Intermediates of 2-substituted carbapenem derivatives and process for production thereof

  摘要：

  本发明涉及由式（1）表示的化合物和其生产过程。使用这些化合物可以实现以安全和经济的方式生产具有强大的抗微生物活性和广泛抗微生物谱的碳青霉烯衍生物。

  公开号：

  US20090082571A1

文献信息

• Novel carbapenem derivatives
  申请人：——

  公开号：US20040038967A1

  公开（公告）日：2004-02-26

  An objective of the present invention is to provide carbapenem derivatives which have strong antibiotic activity also against MRSA, PRSP, Influenzavirus, and &bgr;-lactamase producing bacteria and are stable to DHP-1. The carbapenem derivatives according to the present invention are compounds represented by formulae (I) and (II) or pharmaceutically acceptable salts thereof: 1 wherein R 1 represents H or methyl, R 2 and R 3 each independently represent H; halogen; substituted or unsubstituted alkyl; cycloalkyl; substituted or unsubstituted alkylcarbonyl; carbamoyl; substituted or unsubstituted aryl; substituted or unsubstituted alkylthio; morpholinyl; alkylsulfonyl; or formyl, n is 0 (zero) to 4, and Hy represents a substituted or unsubstituted monocyclic or bicyclic heterocyclic group.

  本发明的目标是提供对MRSA、PRSP、流感病毒和β-内酰胺酶产生细菌具有强抗生素活性且稳定于DHP-1的头孢烯类衍生物。本发明的头孢烯类衍生物是由式(I)和(II)或其药学上可接受的盐所表示的化合物：其中R1代表H或甲基，R2和R3各自独立地代表H、卤素、取代或未取代的烷基、环烷基、取代或未取代的烷基羰基、氨基甲酰基、取代或未取代的芳基、取代或未取代的烷基硫代基、吗啉基、烷基磺酰基或甲酰基，n为0到4，Hy代表取代或未取代的单环或双环杂环基团。
• Intermediates of 2-Substituted Carbapenem Derivatives and Process for Production Thereof
  申请人：Sasaki Toshiro

  公开号：US20080076917A1

  公开（公告）日：2008-03-27

  The present invention relates to compounds represented by formula (1) and a process for producing the same. The use of these compounds can realize the production of carbapenem derivatives having potent antimicrobial activity and a wide antimicrobial spectrum in a safe and cost-effective manner.

  本发明涉及由公式（1）表示的化合物以及其制备方法。使用这些化合物可以以安全且具有成本效益的方式实现具有强大的抗微生物活性和广泛的抗微生物谱的碳青霉烯衍生物的生产。
• Carbapenem derivatives
  申请人：Kano Yuko

  公开号：US06908913B2

  公开（公告）日：2005-06-21

  An objective of the present invention is to provide carbapenem derivatives which have strong antibiotic activity also against MRSA, PRSP, Influenzavirus, and β-lactamase producing bacteria and are stable to DHP-1. The carbapenem derivatives according to the present invention are compounds represented by formulae (I) and (II) or pharmaceutically acceptable salts thereof: wherein R 1 represents H or methyl, R 2 and R 3 each independently represent H; halogen; substituted or unsubstituted alkyl; cycloalkyl; substituted or unsubstituted alkylcarbonyl; carbamoyl; substituted or unsubstituted aryl; substituted or unsubstituted alkylthio; morpholinyl; alkylsulfonyl; or formyl, n is 0 (zero) to 4, and Hy represents a substituted or unsubstituted monocyclic or bicyclic heterocyclic group.

  本发明的目的是提供对MRSA、PRSP、流感病毒和β-内酰胺酶产生菌也具有强抗生素活性且对DHP-1稳定的头孢烯类衍生物。根据本发明，头孢烯类衍生物是以下式(I)和(II)或其药学上可接受的盐所代表的化合物：其中，R1代表氢或甲基，R2和R3各自独立地代表氢、卤素、取代或未取代的烷基、环烷基、取代或未取代的烷基羰基、氨基甲酰基、取代或未取代的芳基、取代或未取代的烷基硫代基、吗啉基、烷基磺酰基或甲酰基，n为0到4，Hy表示取代或未取代的单环或双环杂环基团。
• INTERMEDIATE FOR 2-SUBSTITUTED CARBAPENEM DERIVATIVE AND PRODUCTION PROCESS
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：EP1582522A1

  公开（公告）日：2005-10-05

  The present invention relates to compounds represented by formula (1) and a process for producing the same. The use of these compounds can realize the production of carbapenem derivatives having potent antimicrobial activity and a wide antimicrobial spectrum in a safe and cost-effective manner.

  本发明涉及式（1）所代表的化合物及其生产工艺。使用这些化合物可以安全、经济地生产出具有强大抗菌活性和广泛抗菌谱的碳青霉烯类衍生物。
• EP1582522
  申请人：——

  公开号：——

  公开（公告）日：——