4-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenol | 63571-34-6

• 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-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenol
• 英文别名: 4-(5-Propan-2-yl-1,2,4-oxadiazol-3-yl)phenol
• CAS: 63571-34-6
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: WNYGMAQFYMJQBA-UHFFFAOYSA-N

物化性质

• 沸点：
  362.6±44.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenol 在 sodium hydride 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 18.67h， 生成 Tert-butyl 2-fluoro-4-(5-{(1R)-1-[4-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)benzoate
  参考文献：
  名称：

  AMIDE DERIVATIVE

  摘要：

  提供一种具有优异降血糖作用的化合物，或其药用盐，以及一种具有优异治疗作用和/或预防作用的药物组合物，对于引起血糖水平增高的糖代谢异常导致的1型糖尿病、2型糖尿病等具有良好疗效。公开了一种由通用式(I)表示的化合物，或其药用盐。

  公开号：

  US20120129832A1
• 作为产物：
  描述：

  4-羟基苯甲腈 在 吡啶 、 羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 32.0h， 生成 4-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenol
  参考文献：
  名称：

  3-Aryl-1,2,4-oxadiazole Derivatives Active Against Human Rhinovirus

  摘要：

  The human rhinovirus (hRV) is the causative agent of the common cold that often aggravates respiratory complications in patients with asthma or chronic obstructive pulmonary disease. The high rate of mutations and variety of serotypes are limiting the development of anti-hRV drugs, which emphasizes the need for the discovery of novel lead compounds. Previously, we identified antiviral compound 1 that we used here as the starting material for developing a novel compound series with high efficacy against hRV-A and -B. Improved metabolic stability was achieved by substituting an ester moiety with a 1,2,4-oxadiazole group. Specifically, compound 3k exhibited a high efficacy against hRV-B14, hRV-A21, and hRV-A71, with EC50 values of 66.0, 22.0, and 3.7 nM, respectively, and a relevant hepatic stability (59.6 and 40.7% compound remaining after 30 min in rat and human liver microsomes, respectively). An in vivo study demonstrated that 3k possessed a desirable pharmacokinetic profile with low systemic clearance (0.158 L.h(-1).Kg(-1)) and modest oral bioavailability (27.8%). Hence, 3k appears to be an interesting candidate for the development of antiviral lead compounds.

  DOI：

  10.1021/acsmedchemlett.8b00134

文献信息

• SULFONE DERIVATIVE
  申请人：Yamanoi Shigeo

  公开号：US20120129891A1

  公开（公告）日：2012-05-24

  Provided are a compound having an excellent hypoglycemic action, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition having an excellent therapeutic effect and/or prophylactic effect on type 1 diabetes, type 2 diabetes, and the like, which cause an increase in the blood sugar level due to abnormal sugar metabolism. A compound represented by general formula (I), or a pharmaceutically acceptable salt thereof, is disclosed.

  提供了一种具有优异降血糖作用的化合物，或其药用盐，以及一种具有优异治疗效果和/或预防效果的药物组合物，可用于治疗1型糖尿病、2型糖尿病等由于异常糖代谢导致血糖水平升高的疾病。公开了一种由通式（I）表示的化合物，或其药用盐。
• Substituted Phenylazole Derivatives
  申请人：DAIICHI SANKYO COMPANY, LIMITED

  公开号：US20140357675A1

  公开（公告）日：2014-12-04

  Compounds are provided having an excellent hypoglycemic effect and β cell- or pancreas-protecting effects, or pharmaceutically acceptable salts thereof, and a pharmaceutical composition having an excellent therapeutic effect and/or prophylactic effect on type 1 diabetes, type 2 diabetes, and the like, which cause hyperglycemia due to abnormal glucose metabolism. A compound represented by general formula (I), or a pharmaceutically acceptable salt thereof, is disclosed.

  提供具有出色降血糖效果和保护β细胞或胰腺的化合物，或其药学上可接受的盐，并提供具有出色治疗和/或预防1型糖尿病、2型糖尿病等导致由于异常葡萄糖代谢引起的高血糖的药物组合物。公开了一种由通式(I)表示的化合物或其药学上可接受的盐。
• SUBSTITUTED PHENYLAZOLE DERIVATIVE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2805941B1

  公开（公告）日：2016-08-17
• 4-(1,2,4-dioxazol-3-yl)benzamides for the treatment of diabetes and obesity
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2463279B1

  公开（公告）日：2014-02-12
• 2-PHENYL-1,3-OXAZOLE AND 5-PHENYL-1,2,4-OXADIAZOLE DERIVATIVES FOR THE TREATMENT OF DIABETES
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP3009433B1

  公开（公告）日：2017-06-21