(2,5-dioxopyrrolidin-1-yl) (E)-3-[2,5-dichloro-4-(2-methoxy-2-oxoethyl)sulfanylphenyl]prop-2-enoate | 208512-47-4

• 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: (2,5-dioxopyrrolidin-1-yl) (E)-3-[2,5-dichloro-4-(2-methoxy-2-oxoethyl)sulfanylphenyl]prop-2-enoate
• CAS: 208512-47-4
• 化学式: C₁₆H₁₃Cl₂NO₆S
• 分子量: 418.254
• InChiKey: FDBRMZYIRHCJLS-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2,5-dioxopyrrolidin-1-yl) (E)-3-[2,5-dichloro-4-(2-methoxy-2-oxoethyl)sulfanylphenyl]prop-2-enoate 在 N-甲基吗啉 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-({4-[(1E)-2-{[2-(tert-butoxy)-2-oxoethyl]carbamoyl}eth-1-en-1-yl]-2,5-dichlorophenyl}sulfanyl)acetic 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 、 silver(II) sulfate 、 palladium(III) acetate 、 三正丁胺 、 碘 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 苯甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.5h， 生成 (2,5-dioxopyrrolidin-1-yl) (E)-3-[2,5-dichloro-4-(2-methoxy-2-oxoethyl)sulfanylphenyl]prop-2-enoate
  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

• Singh, Janak; Kim, Oak K.; Kissick, Thomas P., Organic Process Research and Development, 2000, vol. 4, # 6, p. 488 - 497
  作者：Singh, Janak、Kim, Oak K.、Kissick, Thomas P.、Natalie, Kenneth J.、Zhang, Bo、Crispino, Gerard A.、Springer, Dane M.、Wichtowski, John A.、Zhang, Yunhui、Goodrich, Jason、Ueda, Yasutsugu、Luh, Bing Y.、Burke, Brian D.、Brown, Matthew、Dutka, Anthony P.、Zheng, Bin、Hsieh, Dau-Ming、Humora, Michael J.、North, Jeffrey T.、Pullockaran, Anne J.、Livshits, Juliya、Swaminathan, Shankar、Gao, Zhinong、Schierling, Peter、Ermann, Peter、Perrone, Robert K.、Lai, Mei C.、Gougoutas, Jack Z.、DiMarco, John D.、Bronson, Joanne J.、Heikes, James E.、Grosso, John A.、Kronenthal, David R.、Denzel, Theodor W.、Mueller, Richard H.

  DOI：——

  日期：——
• 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.