(4S,5R,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4-methyl-3-(3-methyl-2,2-dioxo-2,3-dihydro-2λ6-thia-1,3-diaza-phenalen-1-ylmethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester | 225531-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4S,5R,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4-methyl-3-(3-methyl-2,2-dioxo-2,3-dihydro-2λ6-thia-1,3-diaza-phenalen-1-ylmethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
• CAS: 225531-20-4
• 化学式: C₂₉H₃₁N₃O₈S
• 分子量: 581.646
• InChiKey: SAKYHKFIYGMYDN-JBGLNQESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  122.76
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4-methyl-3-(3-methyl-2,2-dioxo-2,3-dihydro-2λ6-thia-1,3-diaza-phenalen-1-ylmethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 在 四(三苯基膦)钯 、 2-乙基-己酸稀土盐 、 三苯基膦 、 sodium 2-ethylhexanoic acid 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 sodium;(4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(4-methyl-3,3-dioxo-3lambda6-thia-2,4-diazatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaen-2-yl)methyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Synthesis and activity of 2-(sulfonamido)methyl-carbapenems: Discovery of a novel, anti-MRSA 1,8-naphthosultam pharmacophore

  摘要：

  A series of 1 beta-methyl carbapenems substituted at the IL-position with lipophilic, acyclic and cyclic (sulfonamido)methyl groups was prepared and evaluated for activity against resistant gram-positive bacteria. From these studies, the 1,8-naphthosultamyl group emerged as a novel, PBP2a-binding, anti-MRSA pharmacophore worthy of further exploration. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00070-0
• 作为产物：
  描述：

  1H,3H-naphtho[1,8cd][1,2,6]thiadiazine-2,2-dioxide 在 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (4S,5R,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4-methyl-3-(3-methyl-2,2-dioxo-2,3-dihydro-2λ6-thia-1,3-diaza-phenalen-1-ylmethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
  参考文献：
  名称：

  Synthesis and activity of 2-(sulfonamido)methyl-carbapenems: Discovery of a novel, anti-MRSA 1,8-naphthosultam pharmacophore

  摘要：

  A series of 1 beta-methyl carbapenems substituted at the IL-position with lipophilic, acyclic and cyclic (sulfonamido)methyl groups was prepared and evaluated for activity against resistant gram-positive bacteria. From these studies, the 1,8-naphthosultamyl group emerged as a novel, PBP2a-binding, anti-MRSA pharmacophore worthy of further exploration. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00070-0