4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(fluoromethyl)cyclohexan-1-one dimethyl ketal | 153587-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(fluoromethyl)cyclohexan-1-one dimethyl ketal
• 英文别名: 2-cyclopentyloxy-4-[1-(fluoromethyl)-4,4-dimethoxycyclohexyl]-1-methoxybenzene
• CAS: 153587-29-2
• 化学式: C₂₁H₃₁FO₄
• 分子量: 366.473
• InChiKey: GWYBVXUDNNSHIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(fluoromethyl)cyclohexan-1-one dimethyl ketal 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.17h， 以24%的产率得到4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(fluoromethyl)cyclohexan-1-one
  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：

  1-[3-(环戊基氧基)-4-甲氧基苯基]-4-氧代环己烷甲腈 在 sodium tetrahydroborate 、 (diethylamido)sulfur trifluoride 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.51h， 生成 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(fluoromethyl)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：US05631286A1

  公开（公告）日：1997-05-20

  Novel cyclohexanes of formulas (I) and (II) 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 IV. ##STR1##

  本文描述了化学式(I)和(II)的新型环己烷化合物。它们能够抑制肿瘤坏死因子的产生，并且可用于治疗由TNF产生介导或加剧的疾病状态：这些化合物还可用于调节或抑制磷酸二酯酶IV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
• 1,4-Cyclohexanecarboxylates:  Potent and Selective Inhibitors of Phosophodiesterase 4 for the Treatment of Asthma
  作者：Siegfried B. Christensen、Aimee Guider、Cornelia J. Forster、John G. Gleason、Paul E. Bender、Joseph M. Karpinski、Walter E. DeWolf,、Mary S. Barnette、David C. Underwood、Don E. Griswold、Lenora B. Cieslinski、Miriam Burman、Steven Bochnowicz、Ruth R. Osborn、Carol D. Manning、Marilyn Grous、Leonard M. Hillegas、Joan O'Leary Bartus、M. Dominic Ryan、Drake S. Eggleston、R. Curtis Haltiwanger、Theodore J. Torphy

  DOI：10.1021/jm970090r

  日期：1998.3.1

  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.