2-methyl-6-{[4-(methylsulfonyl)phenyl]oxy}-3-pyridinecarbaldehyde | 1150100-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-6-{[4-(methylsulfonyl)phenyl]oxy}-3-pyridinecarbaldehyde
• 英文别名: 2-Methyl-6-(4-(methylsulfonyl)phenoxy)nicotinaldehyde；2-methyl-6-(4-methylsulfonylphenoxy)pyridine-3-carbaldehyde
• CAS: 1150100-46-1
• 化学式: C₁₄H₁₃NO₄S
• 分子量: 291.328
• InChiKey: FSJBCLBRINVPNY-UHFFFAOYSA-N

物化性质

• 沸点：
  490.8±45.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-6-{[4-(methylsulfonyl)phenyl]oxy}-3-pyridinecarbaldehyde 、 2,4-difluoro-5-(2-oxo-4-phenyl-3-piperidin-4-ylimidazolidin-1-yl)benzamide 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到2,4-Difluoro-5-[3-[1-[[2-methyl-6-(4-methylsulfonylphenoxy)pyridin-3-yl]methyl]piperidin-4-yl]-2-oxo-4-phenylimidazolidin-1-yl]benzamide
  参考文献：
  名称：

  Discovery of a novel series of cyclic urea as potent CCR5 antagonists

  摘要：

  A novel series of cyclic urea-based CCR5 antagonists was designed aiming to resolve instability issue in the fasted simulated intestinal fluid (FSIF) associated with the acyclic urea moiety in 1. This class of CCR5 compounds demonstrated high antiviral activities against HIV-1 infection in both HOS and PBL assays. Further evaluation of these compounds indicated that 16-R not only substantially enhanced its stability, but also exhibited excellent pharmacokinetics properties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.096
• 作为产物：
  描述：

  2-甲基-6-[4-(甲磺酰基)苯氧基]-3-吡啶甲腈 在 二异丁基氢化铝 、 甲醇 、 水 、 柠檬酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 6.33h， 以85%的产率得到2-methyl-6-{[4-(methylsulfonyl)phenyl]oxy}-3-pyridinecarbaldehyde
  参考文献：
  名称：

  [EN] CCR5 ANTAGONISTS AS THERAPEUTIC AGENTS
  [FR] ANTAGONISTES DE CCR5 EN TANT QU'AGENTS THÉRAPEUTIQUES

  摘要：

  本发明涉及在治疗CCR5相关疾病和疾病中有用的化合物，例如，在抑制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（AIDS）方面有用。

  公开号：

  WO2009058919A1

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：WO2009058919A1

  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).

  本发明涉及在治疗CCR5相关疾病和疾病中有用的化合物，例如，在抑制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（AIDS）方面有用。
• Discovery of a novel series of cyclic urea as potent CCR5 antagonists
  作者：Maosheng Duan、Wieslaw M. Kazmierski、Matt Tallant、Jung Ho Jun、Mark Edelstein、Rob Ferris、Dan Todd、Pat Wheelan、Zhiping Xiong

  DOI：10.1016/j.bmcl.2011.08.096

  日期：2011.11

  A novel series of cyclic urea-based CCR5 antagonists was designed aiming to resolve instability issue in the fasted simulated intestinal fluid (FSIF) associated with the acyclic urea moiety in 1. This class of CCR5 compounds demonstrated high antiviral activities against HIV-1 infection in both HOS and PBL assays. Further evaluation of these compounds indicated that 16-R not only substantially enhanced its stability, but also exhibited excellent pharmacokinetics properties. (C) 2011 Elsevier Ltd. All rights reserved.