Literature DB >> 31919737

Electro-organic synthesis of tetrahydroimidazo[1,2-a]pyridin-5(1H)-one via a multicomponent reaction.

Mohammad Reza Asghariganjeh1,2, Ali Asghar Mohammadi3, Elham Tahanpesar2, Ayeh Rayatzadeh2, Somayeh Makarem4.   

Abstract

Electro-synthesis through a one-pot three-component condensation of corresponding aldehydes, Meldrum's acid, and 2-(nitromethylene)imidazolidine resulted in a series of novel tetrahydroimidazo[1,2-a]pyridine-5(1H)-one derivatives containing an electronegative pharmacophore (=CNO2). The process was carried out in propanol medium with sodium bromide presented as electrolyte, inside an undivided cell with good to excellent yields. As a powerful entry into fused polycyclic structures related to bioactive heterocycles, this green protocol shows great potential.

Entities:  

Keywords:  2-(Nitromethylene)imidazolidine; Electro-organic synthesis; Imidazo[1,2-a]pyridine; Meldrum’s acid; Multicomponent reaction

Year:  2020        PMID: 31919737     DOI: 10.1007/s11030-019-10029-6

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  21 in total

Review 1.  Zolpidem and alpidem: two imidazopyridines with selectivity for omega 1- and omega 3-receptor subtypes.

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Journal:  Adv Biochem Psychopharmacol       Date:  1990

2.  Antiulcer agents. 6. Analysis of the in vitro biochemical and in vivo gastric antisecretory activity of substituted imidazo[1,2-a]pyridines and related analogues using comparative molecular field analysis and hypothetical active site lattice methodologies.

Authors:  J J Kaminski; A M Doweyko
Journal:  J Med Chem       Date:  1997-02-14       Impact factor: 7.446

Review 3.  Zolpidem: a review of its use in the management of insomnia.

Authors:  Tracy Swainston Harrison; Gillian M Keating
Journal:  CNS Drugs       Date:  2005       Impact factor: 5.749

4.  Influence of 2-substituent on the activity of imidazo[1,2-a] pyridine derivatives against human cytomegalovirus.

Authors:  Sylvie Mavel; Jean-Louis Renou; Christophe Galtier; Hassan Allouchi; Robert Snoeck; Graciella Andrei; Erik De Clercq; Jan Balzarini; Alain Gueiffier
Journal:  Bioorg Med Chem       Date:  2002-04       Impact factor: 3.641

Review 5.  Resistance of insect pests to neonicotinoid insecticides: current status and future prospects.

Authors:  Ralf Nauen; Ian Denholm
Journal:  Arch Insect Biochem Physiol       Date:  2005-04       Impact factor: 1.698

6.  Identification of biochemical markers linked to neonicotinoid cross resistance in Bemisia tabaci (Hemiptera: Aleyrodidae).

Authors:  Natascha Rauch; Ralf Nauen
Journal:  Arch Insect Biochem Physiol       Date:  2003-12       Impact factor: 1.698

7.  Antidepressants for the treatment of insomnia : a suitable approach?

Authors:  Michael H Wiegand
Journal:  Drugs       Date:  2008       Impact factor: 9.546

8.  6-Substituted 2-(N-trifluoroacetylamino)imidazopyridines induce cell cycle arrest and apoptosis in SK-LU-1 human cancer cell line.

Authors:  Miguel Angel Martínez-Urbina; Alejandro Zentella; Miguel Angel Vilchis-Reyes; Angel Guzmán; Omar Vargas; María Teresa Ramírez Apan; José Luis Ventura Gallegos; Eduardo Díaz
Journal:  Eur J Med Chem       Date:  2009-12-11       Impact factor: 6.514

9.  Improvement of cerebral blood flow by olprinone, a phosphodiesterase-3 inhibitor, in mild heart failure.

Authors:  Takashi Ueda; Katsufumi Mizushige; Kazushi Yukiiri; Tsutomu Takahashi; Masakazu Kohno
Journal:  Cerebrovasc Dis       Date:  2003       Impact factor: 2.762

10.  New potent imidazoisoquinolinone derivatives as anti-Trypanosoma cruzi agents: biological evaluation and structure-activity relationships.

Authors:  Mariela Bollini; Juan José Casal; Diego E Alvarez; Lucía Boiani; Mercedes González; Hugo Cerecetto; Ana María Bruno
Journal:  Bioorg Med Chem       Date:  2009-01-15       Impact factor: 3.641

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