N-methoxy-N-methyl-2-methyl-3-furamide | 220796-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: N-methoxy-N-methyl-2-methyl-3-furamide
• 英文别名: N-methoxy-N,2-dimethyl-3-furamide；N,2-dimethyl-N-(methyloxy)-3-furancarboxamide；N-methoxy-N,2-dimethylfuran-3-carboxamide
• CAS: 220796-18-9
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: VBXWJLBRCVALCA-UHFFFAOYSA-N

物化性质

• 沸点：
  288.7±28.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methoxy-N-methyl-2-methyl-3-furamide 在 氨 、 sodium 、 溶剂黄146 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 3-(1-hydroxypentyl)-2-methylfuran
  参考文献：
  名称：

  杂环化合物的桦木还原。IV †。3-酰基呋喃的桦木还原。环还原，羰基还原和二聚体形成之间的竞争

  摘要：

  描述了3-酰基呋喃1、3和10的桦木还原及其反应途径。

  DOI：

  10.1002/jhet.5570350608
• 作为产物：
  描述：

  2-甲基-3-糠酸 、 二甲羟胺盐酸盐 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以38%的产率得到N-methoxy-N-methyl-2-methyl-3-furamide
  参考文献：
  名称：

  Structure-Based Design of Potent Retinoid X Receptor α Agonists

  摘要：

  A series of tetrahydrobenzofuranyl and tetrahydrobenzothienyl propenoic acids that showed potent agonist activity against RXRalpha were synthesized via a structure-based design approach. Among the compounds studied, 46a,b showed not only very good potency against RXRalpha (K(i) = 6 nM) but was also found to be greater than 167-fold selective vs RARalpha (K(i) > 1000 nM). This compound profiled out as a full agonist in a cell-based transient transfection assay (EC(50) = 3 nM). The two antipodes were separated via chiral chromatography, and 46b was found to be 40-fold more potent than 46a. Interestingly, cocrystallization of 46a,b with the RXRalpha protein generated a liganded structure whereby the (S)-antipode was found in the binding pocket. Given orally in db/db mice or ZDF rats, 46a,b showed a significant glucose-lowering effect and an increase in liver mass. Triglycerides decreased significantly in db/db mice but increased in the ZDF rats. A dose-dependent decrease of nonesterified free fatty acids was seen in ZDF rats but not in db/db mice. These differences indicate a species specific effect of RXR agonists on lipid metabolism.

  DOI：

  10.1021/jm030565g

文献信息

• [EN] ALPHA-7 NICOTINIC RECEPTOR MODULATORS FOR THE TREATMENT OF PAIN, A PSYCHOTIC DISORDER, COGNITIVE IMPAIRMENT OR ALZHEIMER'S DISEASE<br/>[FR] MODULATEURS DU RÉCEPTEUR ALPHA-7 NICOTINIQUE POUR LE TRAITEMENT DE LA DOULEUR, D'UN TROUBLE PSYCHOTIQUE, D'UN DÉFICIT COGNITIF OU DE LA MALADIE D'ALZHEIMER
  申请人：PROXIMAGEN LTD

  公开号：WO2012055942A1

  公开（公告）日：2012-05-03

  Compounds are disclosed which modulate the α7 nicotinic acetyl choline receptor (nAChR), having the formula (I) wherein the variables are as specified in the description and claims.

  已披露了调节α7尼古丁乙酰胆碱受体（nAChR）的化合物，其化学式为（I），其中变量如描述和声明中所指定。
• Selective rxr ligands
  申请人：——

  公开号：US20040198980A1

  公开（公告）日：2004-10-07

  The present invention includes novel retinoid compounds that have selectivity as RXR agonists on one or more isoforms of RXR, currently, RXR&agr;, RXR&bgr;, or RXR&ggr;. The present compounds, and pharmaceutical compositions incorporating these compounds, therefore, are effective in treating conditions mediated by RXRs. Among other physiological responses, the compounds of the present invention reduce blood glucose and maintain body weight, and, thus, are useful for the treatment of diabetes (NIDDIM) and obesity.

  本发明涵盖了新型视黄醇化合物，其在RXR的一个或多个亚型上具有选择性作为RXR激动剂，目前包括RXRα、RXRβ或RXRγ。因此，本化合物及包含这些化合物的药物组合物在治疗由RXR介导的疾病方面是有效的。除其他生理反应外，本发明的化合物可降低血糖并维持体重，因此对于治疗糖尿病（NIDDIM）和肥胖症是有用的。
• SELECTIVE RXR LIGANDS
  申请人：HAFFNER Dale Curt

  公开号：US20070099991A1

  公开（公告）日：2007-05-03

  The present invention includes novel retinoid compounds that have selectivity as RXR agonists on one or more isoforms of RXR, currently, RXRα, RXRβ, or RXRγ. The present compounds, and pharmaceutical compositions incorporating these compounds, therefore, are effective in treating conditions mediated by RXRs. Among other physiological responses, the compounds of the present invention reduce blood glucose and maintain body weight, and, thus, are useful for the treatment of diabetes (NIDDIM) and obesity.

  本发明包括新型视黄醇类化合物，其具有对RXRα、RXRβ或RXRγ中一种或多种同工型具有选择性的RXR激动剂。因此，本化合物及包含这些化合物的制药组合物在治疗由RXR介导的疾病方面是有效的。除了其他生理反应外，本发明的化合物可以降低血糖并维持体重，因此，对于治疗糖尿病（NIDDIM）和肥胖症是有用的。
• ALPHA-7 NICOTINIC RECEPTOR MODULATORS FOR THE TREATMENT OF PAIN, A PSYCHOTIC DISORDER, COGNITIVE IMPAIRMENT OR ALZHEIMER'S DISEASE
  申请人：Dean David

  公开号：US20130310380A1

  公开（公告）日：2013-11-21

  Compounds are disclosed which modulate the α7 nicotinic acetyl choline receptor (nAChR), having the formula (I) wherein the variables are as specified in the description and claims.

  公开了一种调节α7尼古丁乙酰胆碱受体（nAChR）的化合物，其化学式为（I），其中变量如说明书和权利要求中所述。
• Alpha-7 nicotinic receptor modulators for the treatment of pain, a psychotic disorder, cognitive impairment or alzheimer'S disease
  申请人：Dean David

  公开号：US09133178B2

  公开（公告）日：2015-09-15

  Compounds are disclosed which modulate the α7 nicotinic acetyl choline receptor (nAChR), having the formula (I) wherein the variables are as specified in the description and claims.

  公开了一种调节α7尼古丁乙酰胆碱受体（nAChR）的化合物，其化学式为（I），其中变量如说明书和权利要求所述。