3-{[4-chloro-3-(3-chloro-5-cyanophenoxy)phenoxy]methyl}isoxazolo[5,4-b]pyridine-6-yl methanesulfonate | 1198161-36-2

• 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: 3-{[4-chloro-3-(3-chloro-5-cyanophenoxy)phenoxy]methyl}isoxazolo[5,4-b]pyridine-6-yl methanesulfonate
• 英文别名: [3-[[4-Chloro-3-(3-chloro-5-cyanophenoxy)phenoxy]methyl]-[1,2]oxazolo[5,4-b]pyridin-6-yl] methanesulfonate
• CAS: 1198161-36-2
• 化学式: C₂₁H₁₃Cl₂N₃O₆S
• 分子量: 506.323
• InChiKey: PKIVLGCLBVJXTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-{[4-chloro-3-(3-chloro-5-cyanophenoxy)phenoxy]methyl}isoxazolo[5,4-b]pyridine-6-yl methanesulfonate 、 甲胺 在 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以15%的产率得到3-chloro-5-(2-chloro-5-{[6-(methylamino)isoxazolo[5,4-b]pyridine-3-yl]methoxy}phenoxy)benzonitrile
  参考文献：
  名称：

  Biaryl Ethers as Novel Non-nucleoside Reverse Transcriptase Inhibitors with Improved Potency against Key Mutant Viruses

  摘要：

  Biaryl ethers were recently reported as potent NNRTIs. Herein we disclose a detailed SAR study that led to the biaryl ether 6. This compound possessed excellent potency against WT RT and key clinically observed RT mutants and had an excellent pharmacokinetic profile in rats, dogs, and rhesus macaques. The compound also exhibited a clean safety profile in preclinical safety studies.

  DOI：

  10.1021/jm901230r
• 作为产物：
  描述：

  3-氯-5-(2-氯-5-羟基苯氧基)苯甲腈 、 (6-fluoroisoxazolo[5,4-b]pyridine-3-yl)methanesulfonate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.67h， 以78%的产率得到3-{[4-chloro-3-(3-chloro-5-cyanophenoxy)phenoxy]methyl}isoxazolo[5,4-b]pyridine-6-yl methanesulfonate
  参考文献：
  名称：

  Biaryl Ethers as Novel Non-nucleoside Reverse Transcriptase Inhibitors with Improved Potency against Key Mutant Viruses

  摘要：

  Biaryl ethers were recently reported as potent NNRTIs. Herein we disclose a detailed SAR study that led to the biaryl ether 6. This compound possessed excellent potency against WT RT and key clinically observed RT mutants and had an excellent pharmacokinetic profile in rats, dogs, and rhesus macaques. The compound also exhibited a clean safety profile in preclinical safety studies.

  DOI：

  10.1021/jm901230r

文献信息

• Biaryl Ethers as Novel Non-nucleoside Reverse Transcriptase Inhibitors with Improved Potency against Key Mutant Viruses
  作者：Dai-Shi Su、John J. Lim、Elizabeth Tinney、Bang-Lin Wan、Mary Beth Young、Kenneth D. Anderson、Deanne Rudd、Vandna Munshi、Carolyn Bahnck、Peter J. Felock、Meiquing Lu、Ming-Tain Lai、Sinoeun Touch、Gregory Moyer、Daniel J DiStefano、Jessica A. Flynn、Yuexia Liang、Rosa Sanchez、Rebecca Perlow-Poehnelt、Mike Miller、Joe P. Vacca、Theresa M. Williams、Neville J. Anthony

  DOI：10.1021/jm901230r

  日期：2009.11.26

  Biaryl ethers were recently reported as potent NNRTIs. Herein we disclose a detailed SAR study that led to the biaryl ether 6. This compound possessed excellent potency against WT RT and key clinically observed RT mutants and had an excellent pharmacokinetic profile in rats, dogs, and rhesus macaques. The compound also exhibited a clean safety profile in preclinical safety studies.