4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one dimethyl ketal | 153587-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one dimethyl ketal
• 英文别名: 1-(3-cyclopentyloxy-4-methoxyphenyl)-4,4-dimethoxycyclohexane-1-carbonitrile
• CAS: 153587-26-9
• 化学式: C₂₁H₂₉NO₄
• 分子量: 359.466
• InChiKey: BFYSIAHUJHBZHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one dimethyl ketal 在 sodium tetrahydroborate 、 二异丁基氢化铝 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 2.75h， 生成 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(hydroxymethyl)-cyclohexan-1-one dimethyl ketal
  参考文献：
  名称：

  1,4-Cyclohexanecarboxylates:  Potent and Selective Inhibitors of Phosophodiesterase 4 for the Treatment of Asthma

  摘要：

  Evaluation of a variety of PDE4 inhibitors in a series of cellular and in vivo assays suggested a strategy to improve the therapeutic index of PDE4 inhibitors by increasing their selectivity for the ability to inhibit PDE4 catalytic activity versus the ability to compete for high affinity [H-3]rolipram-binding sites in the central nervous system. Use of this strategy led ultimately to the identification of cis-4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1 -carboxylic acid (1, SB 207499, Ariflo(TM)), a potent second-generation inhibitor of PDE4 with a decreased potential for side effects versus the archetypic first generation inhibitor, (R)-rolipram.

  DOI：

  10.1021/jm970090r
• 作为产物：
  描述：

  在 对甲苯磺酸 、 sodium chloride 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one dimethyl ketal
  参考文献：
  名称：

  1,4-Cyclohexanecarboxylates:  Potent and Selective Inhibitors of Phosophodiesterase 4 for the Treatment of Asthma

  摘要：

  Evaluation of a variety of PDE4 inhibitors in a series of cellular and in vivo assays suggested a strategy to improve the therapeutic index of PDE4 inhibitors by increasing their selectivity for the ability to inhibit PDE4 catalytic activity versus the ability to compete for high affinity [H-3]rolipram-binding sites in the central nervous system. Use of this strategy led ultimately to the identification of cis-4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1 -carboxylic acid (1, SB 207499, Ariflo(TM)), a potent second-generation inhibitor of PDE4 with a decreased potential for side effects versus the archetypic first generation inhibitor, (R)-rolipram.

  DOI：

  10.1021/jm970090r

文献信息

• Compounds useful for treating allergic or inflammatory diseases
  申请人：SmithKline Beecham Corporation

  公开号：US05449686A1

  公开（公告）日：1995-09-12

  Novel cyclohexanes of Formulas (I) and (II) ##STR1## are described herein. They inhibit the production of Tumor Necrosis Factor and are useful in the treatment of disease states mediated or exacerbated by TNF production; these compounds are also useful in the mediation or inhibition of enzymatic or catalytic activity of phosphodiesterase V.

  本文描述了化学式（I）和（II）的新型环己烷化合物。它们抑制肿瘤坏死因子的产生，并可用于治疗由TNF产生介导或加重的疾病状态；这些化合物还可用于介导或抑制磷酸二酯酶V的酶活性。
• COMPOUNDS USEFUL FOR TREATING ALLERGIC OR INFLAMMATORY DISEASES
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0636025B1

  公开（公告）日：2001-07-18