(4S,5R,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-3-(3,3-dioxo-1,3-dihydro-3λ6-naphtho[1,2-d]isothiazol-2-ylmethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester | 204843-51-6

• 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: (4S,5R,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-3-(3,3-dioxo-1,3-dihydro-3λ6-naphtho[1,2-d]isothiazol-2-ylmethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
• CAS: 204843-51-6
• 化学式: C₂₉H₃₀N₂O₈S
• 分子量: 566.632
• InChiKey: BPGACDWLMFRJCC-JSVJYBRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  40.0
• 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：
  119.52
• 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)-3-(3,3-dioxo-1,3-dihydro-3λ6-naphtho[1,2-d]isothiazol-2-ylmethyl)-4-methyl-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)-3-(3,3-dioxo-1,3-dihydro-3λ⁶-naphtho[1,2-d]isothiazol-2-ylmethyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[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：

  2,3-Dihydronaphth[1,2-d]isothiazol-1(2H)-one 3,3-dioxide 在 硼烷 、 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)-3-(3,3-dioxo-1,3-dihydro-3λ6-naphtho[1,2-d]isothiazol-2-ylmethyl)-4-methyl-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