2-[2,5-dichloro-4-[(E)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]sulfanylacetic acid | 208512-39-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-[2,5-dichloro-4-[(E)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]sulfanylacetic acid
• CAS: 208512-39-4
• 化学式: C₁₅H₁₆Cl₂O₄S
• 分子量: 363.262
• InChiKey: QUTZMXGRKNWENG-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[2,5-dichloro-4-[(E)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]sulfanylacetic acid 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯甲醚 为溶剂， 反应 5.5h， 生成 (6R,7R)-7-[[2-[4-[(E)-2-carboxyethenyl]-2,5-dichlorophenyl]sulfanylacetyl]amino]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Anti-MRSA cephems. Part 2

  摘要：

  Forty-five novel cephalosporin derivatives with activity against methicillin-resistant Staphylococcus aureus (MRSA) are described. The compounds contain novel cinnamic acid moieties at C-7 that were synthesized using a key Heck reaction followed by nucleophilic aromatic substitution reactions. The most active compound (41) displayed an MIC90 against MRSA of 1.0 mug/mL, and a PD50 of 0.8 mg/kg. Compound 14 was found to be very safe in a mouse model of acute toxicity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00336-x
• 作为产物：
  描述：

  2,5-二氯苯酚 在 三乙烯二胺 、 氢氧化钾 、 sodium hydroxide 、 silver(II) sulfate 、 palladium(III) acetate 、 三正丁胺 、 碘 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 2-[2,5-dichloro-4-[(E)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]sulfanylacetic acid
  参考文献：
  名称：

  Anti-MRSA cephems. Part 2

  摘要：

  Forty-five novel cephalosporin derivatives with activity against methicillin-resistant Staphylococcus aureus (MRSA) are described. The compounds contain novel cinnamic acid moieties at C-7 that were synthesized using a key Heck reaction followed by nucleophilic aromatic substitution reactions. The most active compound (41) displayed an MIC90 against MRSA of 1.0 mug/mL, and a PD50 of 0.8 mg/kg. Compound 14 was found to be very safe in a mouse model of acute toxicity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00336-x

文献信息

• US6583133B1
  申请人：——

  公开号：US6583133B1

  公开（公告）日：2003-06-24
• Anti-MRSA cephems. Part 2
  作者：Dane M. Springer、Bing-Yu Luh、Jason Goodrich、Joanne J. Bronson

  DOI：10.1016/s0968-0896(02)00336-x

  日期：2003.1

  Forty-five novel cephalosporin derivatives with activity against methicillin-resistant Staphylococcus aureus (MRSA) are described. The compounds contain novel cinnamic acid moieties at C-7 that were synthesized using a key Heck reaction followed by nucleophilic aromatic substitution reactions. The most active compound (41) displayed an MIC90 against MRSA of 1.0 mug/mL, and a PD50 of 0.8 mg/kg. Compound 14 was found to be very safe in a mouse model of acute toxicity. (C) 2002 Elsevier Science Ltd. All rights reserved.