Literature DB >> 33860877

Synthesis of styryl-linked fused dihydropyridines by catalyst-free multicomponent reactions.

Rahul Yadav1, Tasneem Parvin2, Anoop Kumar Panday3, Lokman H Choudhury4.   

Abstract

Herein, we report a rapid catalyst-free three-component reaction of 2-hydroxy-1,4-naphthoquinone, cinnamaldehydes and 3-aminopyrazoles in ethanol medium under reflux conditions for the easy access of styryl-linked dihydropyridines fused with naphthoquinone and pyrazole moiety. A wide variety of cinnamaldehyde derivatives and 3-aminopyrazoles were found suitable for this three-component reaction. All the products were fully characterized by spectroscopic tools and by recording single crystal XRD of one of the product. Catalyst-free reaction conditions, short reaction time, good yields of the products, easy purification process, formation of three new bonds (Two C-C and one C-N) in one-pot and products having four different bioactive moieties are the notable features of this methodology.
© 2021. The Author(s), under exclusive licence to Springer Nature Switzerland AG.

Entities:  

Keywords:  Aminopyrazole; Fused dihydropyridines; Multicomponent reaction; Naphthoquinone-fused Heterocycles

Mesh:

Substances:

Year:  2021        PMID: 33860877     DOI: 10.1007/s11030-021-10216-4

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


  17 in total

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Authors:  Hebat-Allah S Abbas; Hend N Hafez; Abdel-Rahman B A El-Gazzar
Journal:  Eur J Med Chem       Date:  2010-10-08       Impact factor: 6.514

Review 2.  From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles.

Authors:  Santos Fustero; María Sánchez-Roselló; Pablo Barrio; Antonio Simón-Fuentes
Journal:  Chem Rev       Date:  2011-08-01       Impact factor: 60.622

3.  Fine structural tuning of styryl-based dyes for fluorescence and CD-based sensing of various ds-DNA/RNA sequences.

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Journal:  Org Biomol Chem       Date:  2019-08-29       Impact factor: 3.876

4.  QSAR models for inhibitors of physiological impact of Escherichia coli that leads to diarrhea.

Authors:  Andrey A Toropov; Alla P Toropova; Emilio Benfenati; Giuseppina Gini; Danuta Leszczynska; Jerzy Leszczynski; Gilberto De Nucci
Journal:  Biochem Biophys Res Commun       Date:  2013-02-10       Impact factor: 3.575

5.  Synthesis, anticonvulsant activity and molecular properties prediction of dialkyl 1-(di(ethoxycarbonyl)methyl)-2,6-dimethyl-4-substituted-1,4-dihydropyridine-3,5-dicarboxylates.

Authors:  G Prasanthi; K V S R G Prasad; K Bharathi
Journal:  Eur J Med Chem       Date:  2013-12-12       Impact factor: 6.514

6.  1,4-Dihydropyridine derivatives as calcium channel modulators: the role of 3-methoxy-flavone moiety.

Authors:  Roberta Budriesi; Alessandra Bisi; Pierfranco Ioan; Angela Rampa; Silvia Gobbi; Federica Belluti; Lorna Piazzi; Piero Valenti; Alberto Chiarini
Journal:  Bioorg Med Chem       Date:  2005-05-16       Impact factor: 3.641

7.  Molecular Tuning of Styryl Dyes Leads to Versatile and Efficient Plasma Membrane Probes for Cell and Tissue Imaging.

Authors:  Mayeul Collot; Emmanuel Boutant; Kyong Tkhe Fam; Lydia Danglot; Andrey S Klymchenko
Journal:  Bioconjug Chem       Date:  2020-02-26       Impact factor: 4.774

8.  A new cytotoxic 1-azaanthraquinone from the stems of Goniothalamus laoticus.

Authors:  Santi Tip-pyang; Yawistha Limpipatwattana; Suttira Khumkratok; Pongpan Siripong; Jirapast Sichaem
Journal:  Fitoterapia       Date:  2010-06-08       Impact factor: 2.882

Review 9.  Fused 1,4-dihydropyridines as potential calcium modulatory compounds.

Authors:  Cihat Safak; Rahime Simsek
Journal:  Mini Rev Med Chem       Date:  2006-07       Impact factor: 3.862

10.  Pyridopyrimidine derivatives as inhibitors of cyclic nucleotide synthesis: Application for treatment of diarrhea.

Authors:  Alexander Y Kots; Byung-Kwon Choi; Maria E Estrella-Jimenez; Cirle A Warren; Scott R Gilbertson; Richard L Guerrant; Ferid Murad
Journal:  Proc Natl Acad Sci U S A       Date:  2008-06-16       Impact factor: 11.205

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  2 in total

1.  One-pot multicomponent synthesis of benzophenazine tethered tetrahydropyridopyrimidine derivatives.

Authors:  Tasneem Parvin
Journal:  Mol Divers       Date:  2022-04-23       Impact factor: 2.943

2.  Rapid synthetic approaches to libraries of diversified 1,2-dihydrochromeno[2,3-c]pyrrole-3,9-diones and 3-(2-hydroxyphenyl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-ones.

Authors:  Roman N Vydzhak; Svitlana Ya Panchishin; Maryna V Kachaeva; Stepan G Pilyo; Viktoriia S Moskvina; Olga V Shablykina; Andriy V Kozytskiy; Volodymyr S Brovarets
Journal:  Mol Divers       Date:  2021-06-04       Impact factor: 3.364

  2 in total

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