4-[2-(2-cyclopentylethyl)oxazol-5-yl]benzenesulfonyl chloride | 182251-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[2-(2-cyclopentylethyl)oxazol-5-yl]benzenesulfonyl chloride
• 英文别名: 4-[2-(2-cyclopentylethyl)-1,3-oxazol-5-yl]benzenesulfonyl chloride
• CAS: 182251-96-3
• 化学式: C₁₆H₁₈ClNO₃S
• 分子量: 339.843
• InChiKey: FZYWDBAMXCJWRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[2-(2-cyclopentylethyl)oxazol-5-yl]benzenesulfonyl chloride 在 吡啶 、 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (R)-N-[4-[2-[[2-Hydroxy-2-(pyridin-3-yl)ethyl]amino]ethyl]phenyl]-4-[2-(2-cyclopentylethyl)oxazol-5-yl]benzenesulfonamide
  参考文献：
  名称：

  Substituted oxazole benzenesulfonamides as potent human β3 adrenergic receptor agonists

  摘要：

  As a part of our investigation into the development of orally bioavailable beta(3) adrenergic receptor agonists, we have identified a series of substituted oxazole derivatives that are potent beta(3) agonists with excellent selectivity against other beta receptors. Several of these compounds showed excellent oral bioavailability in dogs. One example, cyclopentylethyloxazole 5f is a potent beta(3) agonist (EC50 = 14 nM, 84% activation) with 340-fold and 160-fold selectivity over beta(1) and beta(2) receptors, respectively, and has 38% oral bioavailability in dogs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00277-8
• 作为产物：
  描述：

  2-azido-1-phenylvinyl 3-cyclopentylpropionate 在 氯磺酸 、 亚磷酸三乙酯 作用下， 以 环己烷 为溶剂， 反应 3.0h， 生成 4-[2-(2-cyclopentylethyl)oxazol-5-yl]benzenesulfonyl chloride
  参考文献：
  名称：

  Substituted oxazole benzenesulfonamides as potent human β3 adrenergic receptor agonists

  摘要：

  As a part of our investigation into the development of orally bioavailable beta(3) adrenergic receptor agonists, we have identified a series of substituted oxazole derivatives that are potent beta(3) agonists with excellent selectivity against other beta receptors. Several of these compounds showed excellent oral bioavailability in dogs. One example, cyclopentylethyloxazole 5f is a potent beta(3) agonist (EC50 = 14 nM, 84% activation) with 340-fold and 160-fold selectivity over beta(1) and beta(2) receptors, respectively, and has 38% oral bioavailability in dogs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00277-8

文献信息

• Substituted sulfonamides as selective .beta..sub.3 agonists for the
  申请人：Merck & Co., Inc.

  公开号：US05561142A1

  公开（公告）日：1996-10-01

  Substituted sulfonamides are selective .beta..sub.3 adrenergic receptor agonists with very little .beta..sub.1 and .beta..sub.2 adrenergic receptor activity and as such the compounds are capable of increasing lipolysis and energy expenditure in cells. The compounds thus have potent activity in the treatment of Type II diabetes and obesity. The compounds can also be used to lower triglyceride levels and cholesterol levels or raise high density lipoprotein levels or to decrease gut motility. In addition, the compounds can be used to reduced neurogenic inflammation or as antidepressant agents. The compounds are prepared by coupling an aminoalkylphenyl-sulfonamide with an appropriately substituted epoxide. Compositions and methods for the use of the compounds in the treatment of diabetes and obesity and for lowering triglyceride levels and cholesterol levels or raising high density lipoprotein levels or for increasing gut motility are also disclosed.

  磺胺代替物是选择性的β3肾上腺素受体激动剂，几乎没有β1和β2肾上腺素受体活性，因此这些化合物能够增加细胞内的脂肪分解和能量消耗。因此，这些化合物在治疗2型糖尿病和肥胖症方面具有强效活性。这些化合物还可以用于降低甘油三酯水平和胆固醇水平，或提高高密度脂蛋白水平，或降低肠道蠕动。此外，这些化合物可以用于减少神经源性炎症或作为抗抑郁剂。这些化合物是通过将氨基烷基苯磺胺与适当取代的环氧化合物偶联而制备的。还公开了这些化合物在治疗糖尿病和肥胖症，降低甘油三酯水平和胆固醇水平，提高高密度脂蛋白水平或增加肠道蠕动的组合物和方法。
• US5561142A
  申请人：——

  公开号：US5561142A

  公开（公告）日：1996-10-01
• Substituted oxazole benzenesulfonamides as potent human β3 adrenergic receptor agonists
  作者：H.O. Ok、L.B. Reigle、M.R. Candelore、M.A. Cascieri、L.F. Colwell、L. Deng、W.P. Feeney、M.J. Forrest、G.J. Hom、D.E. MacIntyre、C.D. Strader、L. Tota、P. Wang、M.J. Wyvratt、M.H. Fisher、A.E. Weber

  DOI：10.1016/s0960-894x(00)00277-8

  日期：2000.7

  As a part of our investigation into the development of orally bioavailable beta(3) adrenergic receptor agonists, we have identified a series of substituted oxazole derivatives that are potent beta(3) agonists with excellent selectivity against other beta receptors. Several of these compounds showed excellent oral bioavailability in dogs. One example, cyclopentylethyloxazole 5f is a potent beta(3) agonist (EC50 = 14 nM, 84% activation) with 340-fold and 160-fold selectivity over beta(1) and beta(2) receptors, respectively, and has 38% oral bioavailability in dogs. (C) 2000 Elsevier Science Ltd. All rights reserved.