5-(2-(3-chloropropoxy)-4-methoxyphenyl)-3-phenylisoxazole | 1186130-73-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(2-(3-chloropropoxy)-4-methoxyphenyl)-3-phenylisoxazole
• 英文别名: 5-[2-(3-chloropropoxy)-4-methoxyphenyl]-3-phenyl-1,2-oxazole
• CAS: 1186130-73-3
• 化学式: C₁₉H₁₈ClNO₃
• 分子量: 343.81
• InChiKey: GDVYBLFYHQBVHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基丁胺 、 5-(2-(3-chloropropoxy)-4-methoxyphenyl)-3-phenylisoxazole 在 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83.7%的产率得到N-(3-(5-methoxy-2-(3-phenylisoxazol-5-yl)phenoxy)propyl)-(N-methyl)butan-1-amine
  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：

  5-methoxy-2-(3-phenylisoxazol-5-yl)phenol 、 1-溴-3-氯丙烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以92.5%的产率得到5-(2-(3-chloropropoxy)-4-methoxyphenyl)-3-phenylisoxazole
  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.