1-(3-methoxy-4-methylphenyl)-2-nitropropene | 132980-18-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3-methoxy-4-methylphenyl)-2-nitropropene
• 英文别名: 2-methoxy-1-methyl-4-[(E)-2-nitroprop-1-enyl]benzene
• CAS: 132980-18-8
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: ZRYYPPHIFHGUID-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-methoxy-4-methylphenyl)-2-nitropropene 在 W-2 Raney Ni sodium dihydrogenphosphate 、 acetate buffer 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以53.4%的产率得到1-(3-methoxy-4-methylphenyl)-2-propanone
  参考文献：
  名称：

  Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA)

  摘要：

  The racemate and the enantiomers of 1-(3-methoxy-4-methylphenyl)-2-aminopropane (6) and racemic 5-methoxy-6-methyl-2-aminoindan (11) were tested for stimulus generalization in the two-lever drug-discrimination paradigm. Both 6 and 11 were found to substitute with high potency in 3,4-(methylenedioxy)methamphetamine (1) and (S)-1-(1,3-benzodioxol-5-yl)-2-(methylamino)butane (2) trained rats. In the latter assay, both enantiomers of 6 had identical potencies, but their dose-response curves were not parallel. Racemic 6, but not 11, partially substituted for LSD. Racemic 6 and 11 did not substitute in (S)-amphetamine-trained rats. All of the test compounds were potent inhibitors of [H-3]-5-HT uptake into synaptosomes in vitro, with the S enantiomer of 6 being most active. Rat brain monoamine levels were unaltered 1 week following a single high dose (10 or 20 mg/kg, sc) of 6 or 11, or two weeks following a subacute dosing regimen (20 mg/kg, sc, twice a day for 4 days). In addition, radioligand-binding parameters in rat brain homogenate with the 5-HT uptake inhibitor [H-3]proxetine were unchanged after subacute dosing with either racemic 6 or 11. The results indicate that compounds 6 and 11 have animal behavioral pharmacology similar to the methylenedioxy compounds 1 and 2, but that they do not induce the serotonin neurotoxicity that has been observed for the latter two drugs.

  DOI：

  10.1021/jm00109a020
• 作为产物：
  描述：

  硝基乙烷 、 3-甲氧基-4-甲基苯甲醛 在 乙酸铵 作用下， 反应 2.5h， 以83.5%的产率得到1-(3-methoxy-4-methylphenyl)-2-nitropropene
  参考文献：
  名称：

  Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA)

  摘要：

  The racemate and the enantiomers of 1-(3-methoxy-4-methylphenyl)-2-aminopropane (6) and racemic 5-methoxy-6-methyl-2-aminoindan (11) were tested for stimulus generalization in the two-lever drug-discrimination paradigm. Both 6 and 11 were found to substitute with high potency in 3,4-(methylenedioxy)methamphetamine (1) and (S)-1-(1,3-benzodioxol-5-yl)-2-(methylamino)butane (2) trained rats. In the latter assay, both enantiomers of 6 had identical potencies, but their dose-response curves were not parallel. Racemic 6, but not 11, partially substituted for LSD. Racemic 6 and 11 did not substitute in (S)-amphetamine-trained rats. All of the test compounds were potent inhibitors of [H-3]-5-HT uptake into synaptosomes in vitro, with the S enantiomer of 6 being most active. Rat brain monoamine levels were unaltered 1 week following a single high dose (10 or 20 mg/kg, sc) of 6 or 11, or two weeks following a subacute dosing regimen (20 mg/kg, sc, twice a day for 4 days). In addition, radioligand-binding parameters in rat brain homogenate with the 5-HT uptake inhibitor [H-3]proxetine were unchanged after subacute dosing with either racemic 6 or 11. The results indicate that compounds 6 and 11 have animal behavioral pharmacology similar to the methylenedioxy compounds 1 and 2, but that they do not induce the serotonin neurotoxicity that has been observed for the latter two drugs.

  DOI：

  10.1021/jm00109a020

文献信息

• Novel dihydroquinolizinones for the treatment and prophylaxis of hepatitis B virus infection
  申请人：Hoffmann-La Roche Inc.

  公开号：US20150210682A1

  公开（公告）日：2015-07-30

  The invention provides novel compounds having the general formula: wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as described herein, compositions including the compounds and methods of using the compounds.

  这项发明提供了具有一般公式的新化合物： 其中R1、R2、R3、R4、R5和R6如本文所述，包括这些化合物的组合物和使用这些化合物的方法。
• JOHNSON, MICHAEL P.;FRESCAS, STEWART P.;OBERLENDER, ROBERT;NICHOLS, DAVID+, J. MED. CHEM., 34,(1991) N, C. 1662-1668
  作者：JOHNSON, MICHAEL P.、FRESCAS, STEWART P.、OBERLENDER, ROBERT、NICHOLS, DAVID+

  DOI：——

  日期：——
• NOVEL DIHYDROQUINOLIZINONES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION
  申请人：F. Hoffmann-La Roche AG

  公开号：EP3099685B1

  公开（公告）日：2018-04-18
• US9458153B2
  申请人：——

  公开号：US9458153B2

  公开（公告）日：2016-10-04
• US9949966B2
  申请人：——

  公开号：US9949966B2

  公开（公告）日：2018-04-24