(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-({4-[(2S)-2-(hydroxymethyl)-2,5-dihydro-1H-pyrrol-3-yl]-1,3-thiazol-2-yl}sulfanyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid | 426253-22-7

• 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: (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-({4-[(2S)-2-(hydroxymethyl)-2,5-dihydro-1H-pyrrol-3-yl]-1,3-thiazol-2-yl}sulfanyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• 英文别名: (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[[4-[(2S)-2-(hydroxymethyl)-2,5-dihydro-1H-pyrrol-3-yl]-1,3-thiazol-2-yl]sulfanyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• CAS: 426253-22-7
• 化学式: C₁₈H₂₁N₃O₅S₂
• 分子量: 423.514
• InChiKey: UEPDTLJNMRAUGX-DLWRBLKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  177
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  allyl (4R,5S,6S)-3-({4-[(2S)-1-[(allyloxy)carbonyl]-2-(hydroxymethyl)-2,5-dihydro-1H-pyrrol-3-yl]-1,3-thiazol-2-yl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 、 溶剂黄146 、 三正丁基氢锡 、 磷酸肌酸 在 双三苯基磷二氯化钯 二氯甲烷 、 水 、 四氢呋喃 作用下， 以 二氯甲烷 为溶剂， 反应 0.05h， 以to give (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-({4-[(2S)-2-(hydroxymethyl)-2,5-dihydro-1H-pyrrol-3-yl]-1,3-thiazol-2-yl}sulfanyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (12.3 mg, 48%) as a white amorphous的产率得到(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-({4-[(2S)-2-(hydroxymethyl)-2,5-dihydro-1H-pyrrol-3-yl]-1,3-thiazol-2-yl}sulfanyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  β-lactam compounds and process for producing the same

  摘要：

  一种β-内酰胺化合物，其化学式为[1]；其中R1为较低的烷基，一种被羟基取代的较低烷基；R2为氢，较低的烷基；X为O、S、NH；m和n为0至4，Y1为卤素、氰基、羟基、氨基、较低的烷氧基、较低的烷基氨基、羧基、氨基甲酰基、较低的烷基等；Y2为氢、烷基、氰基、—C(R3)═NR4（其中R3和R4为氢、氨基、烷基等，或R3和R4可能互相结合形成一个5至7元杂环基），或其药学上可接受的盐或非毒性酯，对革兰氏阳性菌，特别是MRSA和MRCNS具有优异的抗菌活性。

  公开号：

  US07163936B2

文献信息

• Novel beta-lactam compounds and process for producing the same
  申请人：——

  公开号：US20040102433A1

  公开（公告）日：2004-05-27

  1. A &bgr;-lactam compound of the formula [1]; 1 wherein R 1 is a lower alkyl, a lower alkyl substituted by a hydroxy; R 2 is a hydrogen, a lower alkyl; X is O, S, NH; m and n are 0 to 4, Y 1 is a halogen, cyano, a hydroxy, an amino, a lower alkyloxy, a lower alkylamino, a carboxy, a carbamoyl, a lower alkyl, etc., Y 2 is hydrogen, an alkyl, cyano, —C(R 3 )═NR 4 (wherein R 3 and R 4 are hydrogen, an amino, an alkyl, etc., or R 3 and R 4 may combine each other together with the nitrogen atom to form a 5- to 7-membered heterocyclic group), or a pharmaceutically acceptable salt thereof, or a non-toxic ester thereof, which has an excellent antibacterial activity against Gram-positive bacteria, especially against MRSA and MRCNS.

  一种化学式为[1]的A &bgr;-内酰胺化合物，其中R1是低碳基，被羟基取代的低碳基; R2是氢，低碳基; X是O，S，NH; m和n为0至4，Y1是卤素，氰基，羟基，氨基，低碳基氧基，低碳基氨基，羧基，氨基甲酰基，低碳基等，Y2是氢，烷基，氰基，—C(R3)═NR4（其中R3和R4是氢，氨基，烷基等，或R3和R4可以相互结合形成5-至7成员杂环基的氮原子），或其药学上可接受的盐，或其非毒性酯，对革兰氏阳性菌，特别是对MRSA和MRCNS具有出色的抗菌活性。
• NOVEL BETA-LACTAM COMPOUNDS AND PROECSS FOR PRODUCING THE SAME
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：EP1340756A1

  公开（公告）日：2003-09-03

  1. A β-lactam compound of the formula [1];    wherein R1 is a lower alkyl, a lower alkyl substituted by a hydroxy; R2 is a hydrogen, a lower alkyl; X is O, S, NH; m and n are 0 to 4, Y1 is a halogen, cyano, a hydroxy, an amino, a lower alkyloxy, a lower alkylamino, a carboxy, a carbamoyl, a lower alkyl, etc., Y2 is hydrogen, an alkyl, cyano, -C(R3)=NR4 (wherein R3 and R4 are hydrogen, an amino, an alkyl, etc., or R3 and R4 may combine each other together with the nitrogen atom to form a 5- to 7-membered heterocyclic group), or a pharmaceutically acceptable salt thereof, or a non-toxic ester thereof, which has an excellent antibacterial activity against Gram-positive bacteria, especially against MRSA and MRCNS.

  1.一种式[1]的β-内酰胺化合物； 其中 R1 是低级烷基、被羟基取代的低级烷基；R2 是氢、低级烷基；X 是 O、S、NH；m 和 n 是 0 至 4；Y1 是卤素、氰基、羟基、氨基、低级烷氧基、低级烷氨基、羧基、氨基甲酰基、低级烷基等；Y2 是氢、烷基、氰基、-C(R3)＝NR4（其中 R3 和 R4 是氢、氨基、烷基等、或 R3 和 R4 可与氮原子相互结合形成 5 至 7 元杂环基团），或其药学上可接受的盐，或其无毒酯，对革兰氏阳性菌，尤其是 MRSA 和 MRCNS 具有优异的抗菌活性。
• NOVEL ANTIMICROBIAL MEDICINE
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：EP1797879A1

  公开（公告）日：2007-06-20

  An antimicrobial combination medicament for injection comprising a β-lactam compound represented by the formula [1], wherein R1 is lower alkyl or the like, R2 is H or lower alkyl group, X is O, S or NH; m and n are 0 to 4, provided that the sum of m and n is 0 to 4; Y1 is halogen or the like; and Y2 is hydrogen, optionally substituted lower alkyl group or the like; and carbapenems such as meropenem.

  一种注射用抗菌复方药物，包含由式[1]代表的β-内酰胺化合物、 其中 R1 为低级烷基或类似物，R2 为 H 或低级烷基，X 为 O、S 或 NH；m 和 n 为 0 至 4，但 m 和 n 之和为 0 至 4；Y1 为卤素或类似物；Y2 为氢、任选取代的低级烷基或类似物；以及碳青霉烯类，如美罗培南。
• NOVEL BETA-LACTAM COMPOUNDS AND PROCESS FOR PRODUCING THE SAME
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：EP1340756B1

  公开（公告）日：2007-10-10
• Novel Antimicrobial Medicament
  申请人：Sunagawa Makoto

  公开号：US20090018111A1

  公开（公告）日：2009-01-15

  An antimicrobial combination medicament for injection comprising a β-lactam compound represented by the formula [1], wherein R 1 is lower alkyl or the like, R 2 is H or lower alkyl group, X is O, S or NH; m and n are 0 to 4, provided that the sum of m and n is 0 to 4; Y 1 is halogen or the like; and Y 2 is hydrogen, optionally substituted lower alkyl group or the like; and carbapenems such as meropenem.