使用多聚磷酸促进环缩合反应合成2-(N-苄基吡咯基)-苯并咪唑
Synthesis of 2-(N-Benzylpyrrolyl)-benzimidazoles Using Polyphosphoric Acid Prompted Cyclocondensation.
作者信息
Mochona Bereket, Le Laine, Gangapuram Madhavi, Mateeva Nelly, Ardley Tiffany, Redda Kinfe K
机构信息
Department of Chemistry, College of Arts and Sciences, Florida A&M University, Tallahassee, Florida 32307.
出版信息
J Heterocycl Chem. 2010 Nov 1;47(6):1367-1371. doi: 10.1002/jhet.480.
Abstract
Synthesis of a series of 2-substituted benzimidazoles was carried out for screening anti-inflammatory activities. 2-(N-benzylpyrrolyl)-benzimidazoles 9a-k were synthesized from N-benzyl-2-pyrrole carboxylic acids 8a-d and 4-substituted-1,2-phenylenediamines by cyclocondensation utilizing polyphosphoric acid (PPA) as condensing agent. The N-benzyl-2-pyrrole carboxylic acids were prepared by standard method of N-benzylation of 2-pyrrole carboxylate using NaH/DMF and appropriately substituted benzyl halides followed by alkaline hydrolysis.
摘要
为筛选抗炎活性，开展了一系列2-取代苯并咪唑的合成。以多磷酸（PPA）为缩合剂，通过环缩合反应，由N-苄基-2-吡咯羧酸8a-d和4-取代-1,2-苯二胺合成了2-(N-苄基吡咯基)-苯并咪唑9a-k。N-苄基-2-吡咯羧酸采用2-吡咯羧酸盐的N-苄基化标准方法制备，即使用NaH/DMF和适当取代的苄基卤化物，随后进行碱性水解。
相似文献
1
Synthesis of 2-(N-Benzylpyrrolyl)-benzimidazoles Using Polyphosphoric Acid Prompted Cyclocondensation.
J Heterocycl Chem. 2010 Nov 1;47(6):1367-1371. doi: 10.1002/jhet.480.
2
AlCl-Mediated CHF Transfer and Cyclocondensation of Difluoromethoxy Functionalized -Phenylenediamines to Access N-Substituted Benzimidazoles.
Org Lett. 2022 Aug 26;24(33):6142-6147. doi: 10.1021/acs.orglett.2c02231. Epub 2022 Aug 8.
3
Synthesis of new N-substituted 3,4,5-trihydroxypiperidin-2-ones from d-ribono-1,4-lactone.
Carbohydr Res. 2010 Sep 23;345(14):1983-7. doi: 10.1016/j.carres.2010.07.005. Epub 2010 Aug 6.
4
Synthesis of imidazo[1,5-]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes.
Beilstein J Org Chem. 2020 Nov 26;16:2903-2910. doi: 10.3762/bjoc.16.239. eCollection 2020.
5
Substituted phenyl[(5-benzyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetates/acetamides as alkaline phosphatase inhibitors: Synthesis, computational studies, enzyme inhibitory kinetics and DNA binding studies.
Bioorg Chem. 2019 Sep;90:103108. doi: 10.1016/j.bioorg.2019.103108. Epub 2019 Jul 3.
6
Synthesis and biological evaluation of N-substituted indole esters as inhibitors of cyclo-oxygenase-2 (COX-2).
Farmaco. 2002 Aug;57(8):677-83. doi: 10.1016/s0014-827x(02)01233-8.
7
TBAF-assisted copper-catalyzed N-arylation and benzylation of benzazoles with aryl and benzyl halides under the ligand/base/ solvent-free conditions.
J Org Chem. 2009 Aug 7;74(15):5675-8. doi: 10.1021/jo900752z.
8
Synthesis and structure of bifunctional N-alkylbenzimidazole phenylboronate derivatives.
Org Biomol Chem. 2006 Sep 7;4(17):3297-302. doi: 10.1039/b607127a. Epub 2006 Jul 26.
9
Synthesis, characterization and biological screening of N-substituted derivatives of 5-benzyl-1,3,4-oxadiazole-2yl-2"-sulfanyl acetamide.
Pak J Pharm Sci. 2013 May;26(3):455-63.
10
Anti-inflammatory, antiproteolytic, and antihemolytic properties of pyrrole carboxylic acids.
Pharmacology. 1981;23(5):287-92. doi: 10.1159/000137562.
引用本文的文献
1
Design and Synthesis of Non-Peptide Mimetics Mapping the Immunodominant Myelin Basic Protein (MBP) Epitope to Function as T-Cell Receptor Antagonists.
Int J Mol Sci. 2017 Jun 8;18(6):1215. doi: 10.3390/ijms18061215.
本文引用的文献
1
Synthesis of 1-(Substituted Phenylcarbonyl/sulfonylamino)-1,2,3,6-tetrahydropyridine-5-carboxylic acid diethylamides as Potential Anti-inflammatory Agents.
J Heterocycl Chem. 2006 May 1;43(3):709-718. doi: 10.1002/jhet.5570430327.
2
Synthesis of Substituted N-[4(5-Methyl/phenyl-1,3,4-oxadiazol-2-yl)-3,6-dihydropyridin-1(2H)-yl]benzamide/benzene Sulfonamides as Anti-Inflammatory and Anti-Cancer Agents.
J Heterocycl Chem. 2009 May 1;46(2):309-316. doi: 10.1002/jhet.62.
3
Studies on 1,2,4-triazole derivatives as potential anti-inflammatory agents.
Arch Pharm (Weinheim). 2007 Nov;340(11):586-90. doi: 10.1002/ardp.200700134.
4
Synthesis and antitumor activity of 1-substituted-2-methyl-5-nitrobenzimidazoles.
Bioorg Med Chem. 2006 Nov 1;14(21):7324-32. doi: 10.1016/j.bmc.2006.06.033. Epub 2006 Jul 24.
5
Synthesis, anti-inflammatory, analgesic and kinase (CDK-1, CDK-5 and GSK-3) inhibition activity evaluation of benzimidazole/benzoxazole derivatives and some Schiff's bases.
Bioorg Med Chem. 2006 Jun 1;14(11):3758-65. doi: 10.1016/j.bmc.2006.01.054. Epub 2006 Feb 9.
6
Novel cyano- and amidino-substituted derivatives of thieno[2,3-b]- and thieno[3,2-b]thiophene-2-carboxanilides and thieno[3',2':4,5]thieno- and thieno[2',3':4,5]thieno [2,3-c]quinolones: synthesis, photochemical synthesis, DNA binding, and antitumor evaluation.
Bioorg Med Chem. 2006 Apr 15;14(8):2859-68. doi: 10.1016/j.bmc.2005.12.004. Epub 2006 Jan 10.
7
Nonsteroidal anti-inflammatory drugs (NSAIDs): a comparative QSAR study.
Chem Rev. 2005 Sep;105(9):3235-71. doi: 10.1021/cr040708m.
8
Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1H-benzimidazole-5-carboxylates derivatives carrying amide or amidine groups.
Bioorg Med Chem. 2005 Mar 1;13(5):1587-97. doi: 10.1016/j.bmc.2004.12.025.
9
Synthesis of 4,5-diaryl-1H-pyrazole-3-ol derivatives as potential COX-2 inhibitors.
J Org Chem. 2004 Oct 15;69(21):7058-65. doi: 10.1021/jo049264k.
10
Synthesis and structure-activity relationships of indole and benzimidazole piperazines as histamine H(4) receptor antagonists.
Bioorg Med Chem Lett. 2004 Nov 1;14(21):5251-6. doi: 10.1016/j.bmcl.2004.08.035.
Zotero 插件