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Review
. 2017 May 26:132:108-134.
doi: 10.1016/j.ejmech.2017.03.025. Epub 2017 Mar 19.

Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review

Ramandeep Kaur  1 , Sandeep Chaudhary  1 , Kapil Kumar  1 , Manish K Gupta  2 , Ravindra K Rawal  3
Affiliations
Review

Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review

Ramandeep Kaur et al. Eur J Med Chem. .

Abstract

Dihydropyrimidines are the most important heterocyclic ring systems which play an important role in the synthesis of DNA and RNA. Synthetically they were synthesized using Multi-component reactions like Biginelli reaction and Hantzschdihydropyridine. In the past decades, such Biginelli type dihydropyrimidones have received a considerable amount of attention due to the interesting pharmacological properties associated with this heterocyclic scaffold. In this review, we highlight recent developments in this area, with a focus on the DHPMs, recently developed as anti-inflammatory, anti-HIV, anti-tubercular, antifungal anticancer, antibacterial, antifilarial, antihyperglycemic, antihypertensive, analgesic, anti-convulsant, antioxidant, anti-TRPA1, anti-SARS, and anti-cancer activity and α1a binding affinity.

Keywords: Anti-HIV; Anticancer; Biginelli reaction; Dihydropyrimidinones; Hantzsch.

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Figures

Image 1
Graphical abstract
Fig. 1
Fig. 1
Dihydropyrimidinone skeleton containing drugs.
Fig. 2
Fig. 2
DHPM containing various natural and synthetic analogs.
Scheme 1
Scheme 1
Various approaches for synthesis of 3,4-dihydropyrimidinones.
Scheme 2
Scheme 2
Kappe and Sondhi's strategies for synthesis of 3,4-dihydropyrimidine.
Scheme 3
Scheme 3
Alternative synthetic approaches utilized for the synthesis of 3,4-dihydropyrmidin-2(1H)-ones.
Scheme 4
Scheme 4
Synthesis of 3,4-dihydropyrimidin-2(1H)-ones using different catalyst under solvent free conditions.
Scheme 5
Scheme 5
Enantioselective synthesis of 3,4-dihyropyrimidinones using chiral ligands.
Scheme 6
Scheme 6
O-arylation of 4-aryl-6-methyl-pyrimidin-2(1H)-one.
Scheme 7
Scheme 7
Synthesis of 3,4-dihyropyrimidinone derivatives.
Fig. 3
Fig. 3
Biological activities of dihydropyrimidines.
Fig. 4
Fig. 4
The structure of potent DHPMs having anti-inflammatory activity.
Fig. 5
Fig. 5
The structure of first generation anti-HIV compounds.
Fig. 6
Fig. 6
The structure of second generation Anti-HIV compounds.
Fig. 7
Fig. 7
The structure of potent antitubercular compounds.
Fig. 8
Fig. 8
The structure of potent antifungal compounds.
Fig. 9
Fig. 9
The structure of potent anti-bacterial compounds.
Fig. 10
Fig. 10
The structure of compounds possessing antibacterial activity.
Fig. 11
Fig. 11
The structure of potent anti-filarial compounds.
Fig. 12
Fig. 12
The structure of potent anti-hyperglycaemic compounds.
Fig. 13
Fig. 13
The structure of potent antihypertensive compounds.
Fig. 14
Fig. 14
The structure of potent analgesic compounds.
Fig. 15
Fig. 15
The structure of potent anticonvulsant compounds.
Fig. 16
Fig. 16
The structure of potent antioxidant compounds.
Fig. 17
Fig. 17
The structure of potent antioxidant compounds using DPPH assay.
Fig. 18
Fig. 18
The structure of potent antioxidant compounds using CUPRAC assay.
Fig. 19
Fig. 19
The structure of potent compounds against colon cancer.
Fig. 20
Fig. 20
The structure of potent molecules against breast cancer.
Fig. 21
Fig. 21
The structure of potent compound for blood cancer.
Fig. 22
Fig. 22
DHPM fatty acid compounds active against glioma cells.
Fig. 23
Fig. 23
The structure of potent TRPA1 antagonists.
Fig. 24
Fig. 24
The structure of potent anti SARS compounds.
Fig. 25
Fig. 25
Structure of MCH1 receptor antagonist.
Fig. 26
Fig. 26
Structure of active inhibitors against ROCK1.
Fig. 27
Fig. 27
Currently available α1 antagonists for prostate cancer.
Fig. 28
Fig. 28
Compounds tested for α1a binding affinity.
Fig. 29
Fig. 29
Compounds tested for α1a binding affinity.
Fig. 30
Fig. 30
The structure of compounds investigated for the in vitro and in vivo study.
See this image and copyright information in PMC

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