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1-(4-三氟甲基苯基)-β-咔啉-3-酰肼的合成 被引量：1

Synthesis of 1-(4-trifluoromethyl-phenyl)-β-carboline-3-hydrazide
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摘要 以L-色氨酸为基础原料,经过Pictet-Spengler环合、酯化、钯/碳脱氢、亲核取代四步反应以62.5%收率合成β-咔啉中间体1-(4-三氟甲基苯基)-β-咔啉-3-酰肼化合物。 1-（4-trifluoromethyl-phenyl）-β-carboline-3-hydrazide as an important intermediate of β- carboline was synthesized using L-tryptophan as the basic raw material through the four steps such as Pictet-Spengler cyclization, esterization, palladium/carbon dehydrogenizatioo, nucleophilic substitution. The total yield was 62.5 %.
作者 陈泽宇 朱永松 张耀谋
机构地区 西双版纳出入境检验检疫局 华南农业大学理学院
出处 《广东化工》 CAS 2010年第7期8-9,共2页 Guangdong Chemical Industry
基金 华南农业大学"211工程"重点学科建设项目(2009B010100001)
关键词 β-咔啉 酰肼 合成 β-earboline hydrazide synthesis
分类号 TQ463.5 [化学工程—制药化工]
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参考文献17

  • 1Cao R,Peng W,Wang Z,et al.Curr.β-Carboline Alkaloids:Biochemical and Pharmacological Functions[J].J Med Chem,2007,14:479.
  • 2Cain M,Weber R W,Guzman F,et al.β-Carbolines:synthesis and neurochemical and pharmacological actions on brain benzodiazepine receptors[J].J Med Chem,1982,25:1081.
  • 3Dorey G Poissonnet G,Potier M C,et al.Synthesis and benzodiazepine receptor affinities of rigid analogs of 3-carboxy-.beta.-carbolines:demonstration that the benzodiazepine receptor recognizes preferentially the s-cis conformation of the 3-carboxy group[J].J Med Chem,1989,32:1799.
  • 4Cox E D,Diaz-Arauzo,H,Huang Q,et al.Synthesis and Evaluation of Analogues of the Partial Agonist 6-(Propyloxy)-4-(methoxymethyl)-β-carboline-3-carboxylic Acid Ethyl Ester (6-PBC) and the Full Agonist 6-(Benzyloxy)-4-(methoxymethyl)-β-carboline-3-carboxylic Acid Ethyl Ester (Zk 93423) at Wild Type and Recombinant GABAA Receptors[J].J Med Chem,1998,41:2537.
  • 5Sandrin,J S Hutchins L,RichfiedE,et al.Pictet-Spengler condensations in refluxing benzene[J].Heterocydes,1976,4:1101.
  • 6Sandrin J S,Mokry P,et al.Synthesis of 1,2,3,4-tetrahydro-β-carbolines[J].Heterocycles,1977,6(8):1133.
  • 7Soerens D,Sandrin J,Ungemach F,et al,Study of the Pictet-Spengler reaction in aprotic media:synthesis of the -galactosidase inhibitor,pyridindolol[J].J Org Chem,1979,44:535.
  • 8Sandrin J,Hollinshead S P,cook J.Pictet-Spengler reactions in aprotic media.Stereospecificity in the Pictet-Spengler reaction[J].J Org Chem,1989,54:5636-5640.
  • 9Bisehler B N.A new synthesis of isoquinoline[J].Ber.,1903,26:1893.
  • 10Tada H S,Tokura N.The Bischler-Napieralski reaction in liquid sulfur dioxide.Formation of N,N'-bis(-phenethyl)-acet-and benzamidines and N,N'-diphenylacet-and benzamidines[J].Bull Chem Soc Japan,1960,33:50.

二级参考文献18

  • 1Cox E D, Idiaz H, Huang Q, et al. Synthesis and evaluation of analogues of the Partial agonist 6-(propyloxy)-4-(methoxymethyl)-β-carboline -3-carboxylic acid ethyl ester(6-PBC) and the full agonist 6-(benzyloxy)-4- (methoxymethyl)-β-carboline-3-carboxylic acid ethyl ester(ZK 93423) at wild type and recombinant GABAAreceptors[J]. J. Med. Chem., 1998, 41: 2537-2552.
  • 2Cain M, Webev R W, Guzman E, et al. β-Carbolines: Synthesis and neurochemical and pharmacological actions on brain benzodiazepine receptors[J]. J. Med. Chem. 1982, 25: 1081-1091.
  • 3Guzman F, Cain M, Larscheid P, et al. Biomimetic approach to potential benzodiazepinereceptoragonists andAntagonists[J]. J. Med. Chem. 1984, 27(5): 564-570.
  • 4Dorey G, Poissonnet G, Potier M-C, et al. Synthesis and benzodiazepine receptor afinities of rigid analogs of 3-carboxy-β-cabolines: Demonstration that the benzodiazepine receptor recognizers preferentially the s-cis conformation ofthe3-carboxygroup[J]. J. Med. Chem. 1989, 32(8): 1799-1804.
  • 5Sandrin, J Soerens, D Hutchins, L Richfied, E Cook, J M Pictet-Spengler condensafionsinrefluxingbenzene[J]. Heterocydes, 1976, 4: 1101.
  • 6Sandrin J S D , Mokry P , Cook J M . Synthesis of 1,2,3,4-tetrahydro-β-carbolines. [J]. Heterocycles, 1977, 6(8): 1133.
  • 7Soerens, D., Sandrin, J., Ungemach, F., et al. Study of the Pictet-Spengler reaction in aprotic media: synthesis of the -galactosidase inhibitor, pyridindolol[J]. J. Org. Chem., 1979, 44: 535.
  • 8Pictet-Spengler reactions in apmtic media. Stereospecificity in the Pictet-Spengler reaction. Sandrin J, Hollinshead S P, Cook J. [J]. J. Org., Chem., 1989, 54: 5636-5640.
  • 9Bisehler, Napieralski B. A new synthesis of isoquinoline[J]. Ber., 1903, 26: 1893.
  • 10Sakuraba T H, Tokura N. The Bischler-Napieralski reaction in liquid sulfur dioxide. FormationofN, N'-bis(-phenethyl)-acet-andbenzamidinesandN, N'-diphenylacet-andbenzamidines[J]. Bull. Chem. Soc. Japan, 1960, 33: 50.

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广东化工
2010年 第7期

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