1-（取代苯甲酰基/磺酰氨基）-1,2,3,6-四氢吡啶-5-羧酸二乙酰胺作为潜在抗炎剂的合成
Synthesis of 1-(Substituted Phenylcarbonyl/sulfonylamino)-1,2,3,6-tetrahydropyridine-5-carboxylic acid diethylamides as Potential Anti-inflammatory Agents.
作者信息
Gangapuram Madhavi, Redda Kinfe K
机构信息
College of Pharmacy and Pharmaceutical Sciences, Florida A&M University, Tallahassee, FL 32307, USA.
出版信息
J Heterocycl Chem. 2006 May 1;43(3):709-718. doi: 10.1002/jhet.5570430327.
Abstract
Fifteen novel 1-(substituted phenylcarbonyl/sulfonylamino)-1,2,3,6-tetrahydro- pyridine-5-carboxylic acid diethylamide (7, 15) were synthesized in fair to good yields via sodium borohydride reduction of the corresponding 1-(substituted phenylcarbonyl/ sulfonylimino)-3-diethylcarbamoyl pyridinium ylides (6, 14) in absolute ethanol.
摘要
通过在无水乙醇中用硼氢化钠还原相应的1-（取代苯甲酰基/磺酰亚氨基）-3-二乙氨基甲酰基吡啶叶立德（6,14），以中等至良好的产率合成了15种新型的1-（取代苯甲酰基/磺酰氨基）-1,2,3,6-四氢吡啶-5-羧酸二乙酰胺（7,15）。
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本文引用的文献
1
The chemistry and pharmacology of tetrahydropyridines.
Curr Med Chem. 2005;12(5):551-71. doi: 10.2174/0929867310504050551.
2
Synthesis and anti-inflammatory activities of N-benzoylamino-1,2,3,6-tetrahydropyridine analogs.
Drugs Exp Clin Res. 2003;29(4):131-40.
3
A diastereoselective synthesis of 2,4-disubstituted piperidines: scaffolds for drug discovery.
Org Lett. 2000 Nov 16;2(23):3679-81. doi: 10.1021/ol006589o.
4
5
6
Synthesis of N-[[(substituted-phenyl)carbonyl]amino]-1,2,3,6-tetrahydropyridines with analgesic and hyperglycemic activity.
J Med Chem. 1982 Jun;25(6):720-3. doi: 10.1021/jm00348a021.
7
Dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine in mice.
Science. 1984 Jun 29;224(4656):1451-3. doi: 10.1126/science.6610213.
8
Trail of ironies to Parkinson's disease.
Science. 1984 Jun 8;224(4653):1083-5. doi: 10.1126/science.6426059.
9
Synthesis and dihydropteridine reductase inhibitory effects of potential metabolites of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine.
J Med Chem. 1985 Mar;28(3):311-7. doi: 10.1021/jm00381a009.
10
Synthesis and toxicity toward nigrostriatal dopamine neurons of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) analogues.
J Med Chem. 1986 Mar;29(3):424-7. doi: 10.1021/jm00153a019.
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