Methyl 2-methyl-2-(4-phenylmethoxyphenyl)pent-4-enoate | 223405-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methyl 2-methyl-2-(4-phenylmethoxyphenyl)pent-4-enoate
• CAS: 223405-99-0
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: XRJRZDVQCOKUQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-methyl-2-(4-phenylmethoxyphenyl)pent-4-enoate 在 palladium dihydroxide 氢气 、 caesium carbonate 、 臭氧 、 溶剂黄146 、 sodium iodide 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.5h， 生成 (R)-2-{(S)-3-Methyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-2-oxo-pyrrolidin-1-yl}-propionic acid methyl ester
  参考文献：
  名称：

  Discovery of γ-Lactam Hydroxamic Acids as Selective Inhibitors of Tumor Necrosis Factor α Converting Enzyme:  Design, Synthesis, and Structure−Activity Relationships

  摘要：

  New gamma-lactam. TACE inhibitors were designed from known MMP inhibitors. A homology model of TACE was built and examined to identify the S1' site as the key area for TACE selectivity over MMPs. Rational exploration of the P1'-S1' interactions resulted in the discovery of the 3,5-disubstituted benzyl ether as a TACE-selective P1' group. Further optimization led to the discovery of IK682 as a selective and orally bioavailable TACE inhibitor.

  DOI：

  10.1021/jm0255670
• 作为产物：
  描述：

  4-苄氧基苯基乙酸甲酯 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 Methyl 2-methyl-2-(4-phenylmethoxyphenyl)pent-4-enoate
  参考文献：
  名称：

  Discovery of γ-Lactam Hydroxamic Acids as Selective Inhibitors of Tumor Necrosis Factor α Converting Enzyme:  Design, Synthesis, and Structure−Activity Relationships

  摘要：

  New gamma-lactam. TACE inhibitors were designed from known MMP inhibitors. A homology model of TACE was built and examined to identify the S1' site as the key area for TACE selectivity over MMPs. Rational exploration of the P1'-S1' interactions resulted in the discovery of the 3,5-disubstituted benzyl ether as a TACE-selective P1' group. Further optimization led to the discovery of IK682 as a selective and orally bioavailable TACE inhibitor.

  DOI：

  10.1021/jm0255670

文献信息

• Discovery of γ-Lactam Hydroxamic Acids as Selective Inhibitors of Tumor Necrosis Factor α Converting Enzyme:  Design, Synthesis, and Structure−Activity Relationships
  作者：James J.-W. Duan、Lihua Chen、Zelda R. Wasserman、Zhonghui Lu、Rui-Qin Liu、Maryanne B. Covington、Mingxin Qian、Karl D. Hardman、Ronald L. Magolda、Robert C. Newton、David D. Christ、Ruth R. Wexler、Carl P. Decicco

  DOI：10.1021/jm0255670

  日期：2002.11.1

  New gamma-lactam. TACE inhibitors were designed from known MMP inhibitors. A homology model of TACE was built and examined to identify the S1' site as the key area for TACE selectivity over MMPs. Rational exploration of the P1'-S1' interactions resulted in the discovery of the 3,5-disubstituted benzyl ether as a TACE-selective P1' group. Further optimization led to the discovery of IK682 as a selective and orally bioavailable TACE inhibitor.