4-Methylsulfanyl-6-[4-(2-methylsulfanylethoxy)phenyl]-2-oxopyran-3-carbonitrile | 852360-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Methylsulfanyl-6-[4-(2-methylsulfanylethoxy)phenyl]-2-oxopyran-3-carbonitrile
• CAS: 852360-14-6
• 化学式: C₁₆H₁₅NO₃S₂
• 分子量: 333.432
• InChiKey: ZPRLNHYZLFARLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-Methylsulfanyl-6-[4-(2-methylsulfanylethoxy)phenyl]-2-oxopyran-3-carbonitrile 在 吡啶 、 sodium azide 、 氯化铵 、 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 5-{5-[4-(2-Methylsulfanyl-ethoxy)-phenyl]-1H-pyrazol-3-ylmethyl}-1H-tetrazole
  参考文献：
  名称：

  Synthesis and in vivo antihyperglycemic activity of 5-(1H-pyrazol-3-yl)methyl-1H-tetrazoles

  摘要：

  A series of 5-[(5-aryl-1H-pyrazol-3-yl)methyl]-1H-tetrazoles 3a-h have been synthesized and evaluated for their in vivo antihyperglycemic activity. Some of the synthesized compounds have shown significant glucose lowering activity in male Sprague-Dawley rats in sucrose loaded model. These compounds were also evaluated for their peroxisome proliferator activated receptor gamma agonistic property, but none of them displayed any significant activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.060
• 作为产物：
  描述：

  1-(4-(2-溴乙氧基)苯基)乙酮 、 2-氰-3,3-二(甲硫基)丙烯酸甲酯 在 氢氧化钾 作用下， 以48%的产率得到4-Methylsulfanyl-6-[4-(2-methylsulfanylethoxy)phenyl]-2-oxopyran-3-carbonitrile
  参考文献：
  名称：

  6-Aryl-4-methylsulfanyl-2H-pyran-2-one-3-carbonitriles as PPAR-γ activators

  摘要：

  Various 6-aryl-3-cyano/methoxycarbonyl-4-methylsulfanyl-2H-pyran-2-ones have been synthesized as a potential substitute of 2,4-thiazolidinedione head group to express potent PPAR-gamma transactivation response. Some of the screened compounds have shown promising PPAR-gamma agonistic activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.031

文献信息

• An efficient substituent dependent synthesis of congested pyridines and pyrimidines
  作者：Ramendra Pratap、Brijesh Kumar、Vishnu Ji Ram

  DOI：10.1016/j.tet.2007.07.062

  日期：2007.10

  An efficient and versatile synthesis of various congested pyridines 3a–h, 6a,b, 8a–n, 10a–g, and 16a,b, and (pyrimidin-4-yl)acetonitriles 13a–g has been delineated by base catalyzed ring transformation of suitably functionalized 2H-pyran-2-ones 1a–h, 5, 7, and 15 by formamidine acetate 2a, acetamidine hydrochloride 2b, S-methylisothiourea 9a, pyrazol-1-yl-carboxamidine 9b, and arylamidine hydrochloride

  碱催化的环转化描述了各种拥挤的吡啶3a - h，6a，b，8a - n，10a - g和16a，b以及（嘧啶-4-基）乙腈13a - g的高效通用合成方法。适当官能2 ħ -吡喃-2-酮1A - H ^，5，7，和15由乙酸甲脒2A，乙脒盐酸盐2b中，小号-methylisothiourea图9a，吡唑-1-基甲脒9B，和芳脒盐酸盐12分别在粉末KOH的无水DMF的存在。
• 6-Aryl-4-methylsulfanyl-2H-pyran-2-one-3-carbonitriles as PPAR-γ activators
  作者：Ashoke Sharon、Ramendra Pratap、Rit Vatsyayan、Prakas R. Maulik、Uma Roy、Atul Goel、Vishnu Ji Ram

  DOI：10.1016/j.bmcl.2005.05.031

  日期：2005.7

  Various 6-aryl-3-cyano/methoxycarbonyl-4-methylsulfanyl-2H-pyran-2-ones have been synthesized as a potential substitute of 2,4-thiazolidinedione head group to express potent PPAR-gamma transactivation response. Some of the screened compounds have shown promising PPAR-gamma agonistic activity. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and in vivo antihyperglycemic activity of 5-(1H-pyrazol-3-yl)methyl-1H-tetrazoles
  作者：Ashoke Sharon、Ramendra Pratap、Priti Tiwari、Arvind Srivastava、P.R. Maulik、Vishnu Ji Ram

  DOI：10.1016/j.bmcl.2005.02.060

  日期：2005.4

  A series of 5-[(5-aryl-1H-pyrazol-3-yl)methyl]-1H-tetrazoles 3a-h have been synthesized and evaluated for their in vivo antihyperglycemic activity. Some of the synthesized compounds have shown significant glucose lowering activity in male Sprague-Dawley rats in sucrose loaded model. These compounds were also evaluated for their peroxisome proliferator activated receptor gamma agonistic property, but none of them displayed any significant activity. (c) 2005 Elsevier Ltd. All rights reserved.