p-nitrobenzyl (1R,5S,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-oxo-carbapanem-3-carboxylate | 90822-25-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: p-nitrobenzyl (1R,5S,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-oxo-carbapanem-3-carboxylate
• 英文别名: 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3carboxylate；p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate；(4-nitrophenyl)methyl (2R,4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 90822-25-6
• 化学式: C₁₇H₁₈N₂O₇
• 分子量: 362.339
• InChiKey: GUGYCHHWTVUBLV-KVTHKLIGSA-N

物化性质

• 沸点：
  596.6±50.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-nitrobenzyl (1R,5S,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-oxo-carbapanem-3-carboxylate 生成 杂氮双环磷酸酯
  参考文献：
  名称：

  Synthetic carbapenem antibiotics III. 1-Methyl thienamycin

  摘要：

  DOI：

  10.1016/s0040-4039(00)89154-6
• 作为产物：
  描述：

  (3S,4R)-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-methyl-3-diazo-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl]azetidin-2-one 在 rhodium(III) octanoate 作用下， 以 正己烷 、 乙酸乙酯 为溶剂， 反应 0.25h， 以95%的产率得到p-nitrobenzyl (1R,5S,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-oxo-carbapanem-3-carboxylate
  参考文献：
  名称：

  Shih, David H.; Baker, Florence; Cama, Lovji, Heterocycles, 1984, vol. 21, # 1, p. 29 - 40

  摘要：

  DOI：

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。
• Carbapenem derivatives
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：US06458780B1

  公开（公告）日：2002-10-01

  Disclosed is a novel carbapenem derivative having a substituted imidazo[5,1-b]thiazole group at the 2-position on the carbapenem ring have high anti-microbial activities against &bgr;-lactamase producing bacteria, MRSA, resistant-Pseudomonas aeruginosa, PRSP, enterococci, and influenza, and high stabilities to DHP-1. According to the present invention, there is provided a compound represented by the formula (I), or a pharmacologically acceptable salt thereof or an ester at the 3-position on the carbapenem ring thereof:

  公开了一种新的碳青霉烯衍生物，其在碳青霉烯环的2位置具有取代的咪唑[5,1-b]噻唑基团，对产生β-内酰胺酶的细菌、耐甲氧西林金黄色葡萄球菌(MRSA)、抗假单胞菌属铜绿假单胞菌、肺炎链球菌(PRSP)、肠球菌和流感具有高的抗菌活性，并对DHP-1具有高稳定性。根据本发明，提供了一种由公式(I)表示的化合物，或其药理上可接受的盐，或其碳青霉烯环上3位置的酯。
• Studies on the Synthesis and Structure-Activity Relationships of 2-(2 Functionalized Pyrrolidin-4-ylthio)-1.BETA.-methylcarbapenems.
  作者：Hong-Woo LEE、Eung-Nam KIM、Hoe-Joo SON、Soon-Kil AHN、Koo-Hun CHUNG、Jung-Woo KIM、Chong-Ryoul LEE

  DOI：10.1248/cpb.44.2326

  日期：——

  A series of new carbapenem derivatives, which have a pyrrolidin-4-ylthio group substituted with a hydroxyalkyl or carbamoyl group at the 2' position as the C-2 side chain, have been prepared. The antibacterial activity and the stability to renal dehydropeptidase-I of these compounds were investigated, and the structure-activity relationships were studied. Among these new carbapenems, (1R, 5S, 6S)-2-[(2S, 4S)-2-(2-hydroxy)ethylmercaptomethyl}pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid (1a) showed the most potent and well balanced activity and was selected as a candidate for further evaluation.

  一系列新的碳青霉烯衍生物已被制备出来，这些衍生物在C-2侧链位置上具有一个带有羟基烷基或氨甲酰基的吡咯烷-4-基硫醇基团。研究了这些化合物的抗菌活性和对肾脱氢肽酶I的稳定性，并探讨了构效关系。在这些新的碳青霉烯中，(1R, 5S, 6S)-2-[(2S, 4S)-2-(2-羟基)乙硫甲基}吡咯烷-4-基硫]-6-[(1R)-1-羟乙基]-1-甲基-1-碳青霉-2-烯-3-羧酸（1a）显示出最强的且平衡良好的活性，并被选为进一步评估的候选物。
• Process for producing 2-carbon-substituted carbapenem derivatives
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US05258509A1

  公开（公告）日：1993-11-02

  A process for producing a 2-(unsubstituted or carbon-substituted)-1-carbapen-2-em-3-carboxylic acid derivative, which comprises reacting a 2-trifluoromethanesulfonyloxy-1-carbapen-2-em-3-carboxylic acid derivative or the 1-carbapen-2-em-3-carboxylic acid derivative derived from a 2-oxo-1-carbapenam-3-carboxylic acid derivative and trifluoromethanesulfonic anhydride, and a stannane derivative in an inert solvent in the presence of a palladium compound and a salt.

  一种制备2-(未取代或碳取代)-1-卡巴喷-2-烯-3-羧酸衍生物的方法，包括在惰性溶剂中，在钯化合物和盐的存在下，通过反应2-三氟甲磺酰氧基-1-卡巴喷-2-烯-3-羧酸衍生物或由2-氧代-1-卡巴喷胺-3-羧酸衍生物得到的1-卡巴喷-2-烯-3-羧酸衍生物和一种锡烷衍生物制得，所述锡烷衍生物是指一种具有通式RnSnX4-n的化合物，其中R是烷基或芳香基，X是卤素。
• Novel carbapenum derivatives
  申请人：——

  公开号：US20030027809A1

  公开（公告）日：2003-02-06

  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 represent H, a halogen atom, alkyl or the like; and R 4 represents substituted lower alkylthio or the like.

  本发明的目标是提供一种对MRSA、PRSP、流感病毒和β-内酰胺酶产生菌有强效抗生素活性并且稳定对DHP-1的碳青霉烯衍生物。本发明的化合物是由式（I）或其药学上可接受的盐所表示的化合物：1其中R1代表H或甲基；R2和R3代表H、卤素原子、烷基或类似物；R4代表取代的低级烷基硫或类似物。