N-{4-[(5-cyano-6-methyl-2-pyridinyl)oxy]-3-methylphenyl}methanesulfonamide | 1150103-13-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-{4-[(5-cyano-6-methyl-2-pyridinyl)oxy]-3-methylphenyl}methanesulfonamide
• 英文别名: N-[4-(5-cyano-6-methylpyridin-2-yl)oxy-3-methylphenyl]methanesulfonamide
• CAS: 1150103-13-1
• 化学式: C₁₅H₁₅N₃O₃S
• 分子量: 317.368
• InChiKey: XOULPIBCMMIANA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-{4-[(5-cyano-6-methyl-2-pyridinyl)oxy]-3-methylphenyl}methanesulfonamide 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 N-{4-[(5-formyl-6-methyl-2-pyridinyl)oxy]-3-methylphenyl}methanesulfonamide
  参考文献：
  名称：

  Discovery of novel pyridyl carboxamides as potent CCR5 antagonists and optimization of their pharmacokinetic profile in rats

  摘要：

  A novel series of pyridyl carboxamide-based CCR5 inhibitors was designed, synthesized, and demonstrated to be highly potent against HIV-1 infection in both HOS and PBL assays. Attempts to evaluate this series of compounds in a rat PK model revealed its instability in rat plasma. A hypothesis for this liability was proposed, and strategies to overcome this issue were pursued, leading to discovery of highly potent 40 and 41, which featured dramatically improved rat PK profiles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.080
• 作为产物：
  描述：

  N-(4-hydroxy-3-methylphenyl)methanesulfonamide 、 6-氯-2-甲基-3-氰基吡啶 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-{4-[(5-cyano-6-methyl-2-pyridinyl)oxy]-3-methylphenyl}methanesulfonamide
  参考文献：
  名称：

  Discovery of novel pyridyl carboxamides as potent CCR5 antagonists and optimization of their pharmacokinetic profile in rats

  摘要：

  A novel series of pyridyl carboxamide-based CCR5 inhibitors was designed, synthesized, and demonstrated to be highly potent against HIV-1 infection in both HOS and PBL assays. Attempts to evaluate this series of compounds in a rat PK model revealed its instability in rat plasma. A hypothesis for this liability was proposed, and strategies to overcome this issue were pursued, leading to discovery of highly potent 40 and 41, which featured dramatically improved rat PK profiles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.080

文献信息

• [EN] CCR5 ANTAGONISTS AS THERAPEUTIC AGENTS<br/>[FR] ANTAGONISTES DE CCR5 EN TANT QU'AGENTS THÉRAPEUTIQUES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009058924A1

  公开（公告）日：2009-05-07

  The present invention relates to compounds useful in the treatment of CCR5-related diseases and disorders, for example, useful in the inhibition of HIV replication, the prevention or treatment of an HIV infection, and in the treatment of the resulting acquired immune deficiency syndrome (AIDS).

  本发明涉及用于治疗CCR5相关疾病和障碍的化合物，例如，可用于抑制HIV复制，预防或治疗HIV感染，以及治疗由此导致的获得性免疫缺陷综合症（艾滋病）。