ethyl 2-(2-biphenyl-4-ylethyl)tetrahydrothiophene-2-carboxylate 1,1-dioxide | 1354546-29-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(2-biphenyl-4-ylethyl)tetrahydrothiophene-2-carboxylate 1,1-dioxide
• 英文别名: Ethyl 1,1-dioxo-2-[2-(4-phenylphenyl)ethyl]thiolane-2-carboxylate
• CAS: 1354546-29-4
• 化学式: C₂₁H₂₄O₄S
• 分子量: 372.485
• InChiKey: LDBPMUQRUXPJFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-biphenyl-4-ylethyl)tetrahydrothiophene-2-carboxylate 1,1-dioxide 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 2-(2-biphenyl-4-ylethyl)-N-(tetrahydro-2H-pyran-2-yloxy)tetrahydrothiophene-2-carboxamide 1,1-dioxide
  参考文献：
  名称：

  Potent Inhibitors of LpxC for the Treatment of Gram-Negative Infections

  摘要：

  In this paper, we present the synthesis and SAR as well as selectivity, pharmacokinetic, and infection model data for representative analogues of a novel series of potent antibacterial LpxC inhibitors represented by hydroxamic acid 1a.

  DOI：

  10.1021/jm2014748
• 作为产物：
  描述：

  1,1-dioxo-tetrahydro-1λ⁶-thiophene-2-carboxylic acid ethyl ester 、 4-(2-iodoethyl)-1,1'-biphenyl 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以21%的产率得到ethyl 2-(2-biphenyl-4-ylethyl)tetrahydrothiophene-2-carboxylate 1,1-dioxide
  参考文献：
  名称：

  Potent Inhibitors of LpxC for the Treatment of Gram-Negative Infections

  摘要：

  In this paper, we present the synthesis and SAR as well as selectivity, pharmacokinetic, and infection model data for representative analogues of a novel series of potent antibacterial LpxC inhibitors represented by hydroxamic acid 1a.

  DOI：

  10.1021/jm2014748

文献信息

• Potent Inhibitors of LpxC for the Treatment of Gram-Negative Infections
  作者：Matthew F. Brown、Usa Reilly、Joseph A. Abramite、Joel T. Arcari、Robert Oliver、Rose A. Barham、Ye Che、Jinshan Michael Chen、Elizabeth M. Collantes、Seung Won Chung、Charlene Desbonnet、Jonathan Doty、Matthew Doroski、Juntyma J. Engtrakul、Thomas M. Harris、Michael Huband、John D. Knafels、Karen L. Leach、Shenping Liu、Anthony Marfat、Andrea Marra、Eric McElroy、Michael Melnick、Carol A. Menard、Justin I. Montgomery、Lisa Mullins、Mark. C. Noe、John O’Donnell、Joseph Penzien、Mark S. Plummer、Loren M. Price、Veerabahu Shanmugasundaram、Christy Thoma、Daniel P. Uccello、Joseph S. Warmus、Donn G. Wishka

  DOI：10.1021/jm2014748

  日期：2012.1.26

  In this paper, we present the synthesis and SAR as well as selectivity, pharmacokinetic, and infection model data for representative analogues of a novel series of potent antibacterial LpxC inhibitors represented by hydroxamic acid 1a.