5-methoxy-2-(3-phenylisoxazol-5-yl)phenol | 1186130-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-methoxy-2-(3-phenylisoxazol-5-yl)phenol
• 英文别名: 5-Methoxy-2-(3-phenylisoxazol-5-yl)phenol；5-methoxy-2-(3-phenyl-1,2-oxazol-5-yl)phenol
• CAS: 1186130-66-4
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: BZWWDJSLSIBSLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氯丙酸 、 5-methoxy-2-(3-phenylisoxazol-5-yl)phenol 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以90.65%的产率得到4-(5-methoxy-2-(3-phenylisoxazol-5-yl)phenoxy)butanoic acid
  参考文献：
  名称：

  Design and synthesis of 3,5-diarylisoxazole derivatives as novel class of anti-hyperglycemic and lipid lowering agents

  摘要：

  We have designed 1,3-disubstituted-5-membered heteroaromatic ring system as a common core motif from known anti-hyperglycemic agents. Designed compounds were synthesized and screened for in vivo anti-hyperglycemic activity in sucrose loaded model (SLM), sucrose-challenged streptozotocin-induced diabetic rat model (STZ-S) as well as db/db mice model. Some of the synthesized compounds showed promising in vivo anti-hyperglycemic as well as moderate lipid lowering activity. Synthesized Compounds were screened in various in vitro models of type-2 diabeties such as DPP-4, PTP1B and PPAR gamma to know the mechanism of their anti-hyperglycemic action. None of the synthesized compounds showed DPP-4 inhibitory as well as PPAR gamma activity. These compounds have shown promising PTP-1B inhibitory activity there by revealing that compounds exhibit anti-diabetic activity by PTP1B pathway. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.033
• 作为产物：
  描述：

  1-(2-羟基-4-甲氧基苯基)-3-苯基丙烷-1,3-二酮 在 吡啶 、 盐酸羟胺 作用下， 反应 0.5h， 以44.94%的产率得到5-methoxy-2-(3-phenylisoxazol-5-yl)phenol
  参考文献：
  名称：

  Design and synthesis of 3,5-diarylisoxazole derivatives as novel class of anti-hyperglycemic and lipid lowering agents

  摘要：

  We have designed 1,3-disubstituted-5-membered heteroaromatic ring system as a common core motif from known anti-hyperglycemic agents. Designed compounds were synthesized and screened for in vivo anti-hyperglycemic activity in sucrose loaded model (SLM), sucrose-challenged streptozotocin-induced diabetic rat model (STZ-S) as well as db/db mice model. Some of the synthesized compounds showed promising in vivo anti-hyperglycemic as well as moderate lipid lowering activity. Synthesized Compounds were screened in various in vitro models of type-2 diabeties such as DPP-4, PTP1B and PPAR gamma to know the mechanism of their anti-hyperglycemic action. None of the synthesized compounds showed DPP-4 inhibitory as well as PPAR gamma activity. These compounds have shown promising PTP-1B inhibitory activity there by revealing that compounds exhibit anti-diabetic activity by PTP1B pathway. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.033

文献信息

• Design and synthesis of 3,5-diarylisoxazole derivatives as novel class of anti-hyperglycemic and lipid lowering agents
  作者：Atul Kumar、Ram Awatar Maurya、Siddharth Sharma、Pervez Ahmad、A.B. Singh、A.K. Tamrakar、Arvind K. Srivastava

  DOI：10.1016/j.bmc.2009.05.033

  日期：2009.7

  We have designed 1,3-disubstituted-5-membered heteroaromatic ring system as a common core motif from known anti-hyperglycemic agents. Designed compounds were synthesized and screened for in vivo anti-hyperglycemic activity in sucrose loaded model (SLM), sucrose-challenged streptozotocin-induced diabetic rat model (STZ-S) as well as db/db mice model. Some of the synthesized compounds showed promising in vivo anti-hyperglycemic as well as moderate lipid lowering activity. Synthesized Compounds were screened in various in vitro models of type-2 diabeties such as DPP-4, PTP1B and PPAR gamma to know the mechanism of their anti-hyperglycemic action. None of the synthesized compounds showed DPP-4 inhibitory as well as PPAR gamma activity. These compounds have shown promising PTP-1B inhibitory activity there by revealing that compounds exhibit anti-diabetic activity by PTP1B pathway. (C) 2009 Elsevier Ltd. All rights reserved.