Design and Synthesis of 1,4-dihydropyridine Derivatives as Anti-cancer Agent

Viradiya, Denish J.; Mirza, Sheefa; Shaikh, Faraz; Kakadiya, Rajesh; Rathod, Anand; Jain, Nayan; Rawal, Rakesh; Shah, Anamik

doi:10.2174/1871520616666161206143251

Cited by 24 publications

(9 citation statements)

References 15 publications

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“…However, to gain better knowledge of their mode of action, further in-depth mechanistic validation is still needed for these types of compounds. 243 Naglaa et al recently designed a series of pyridinecontaining anticancer agents (Figure 59). The newly synthesized compounds were investigated for in vitro growth activity against mammary-gland carcinoma (MCF7) and human hepatocellular carcinoma (HepG2) cell lines.…”

mentioning

confidence: 99%

The Expanding Role of Pyridine and Dihydropyridine Scaffolds in Drug Design

Ling

Hao

Liang

et al. 2021

DDDT

216

114

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Pyridine-based ring systems are one of the most extensively used heterocycles in the field of drug design, primarily due to their profound effect on pharmacological activity, which has led to the discovery of numerous broad-spectrum therapeutic agents. In the US FDA database, there are 95 approved pharmaceuticals that stem from pyridine or dihydropyridine, including isoniazid and ethionamide (tuberculosis), delavirdine (HIV/AIDS), abiraterone acetate (prostate cancer), tacrine (Alzheimer's), ciclopirox (ringworm and athlete's foot), crizotinib (cancer), nifedipine (Raynaud's syndrome and premature birth), piroxicam (NSAID for arthritis), nilvadipine (hypertension), roflumilast (COPD), pyridostigmine (myasthenia gravis), and many more. Their remarkable therapeutic applications have encouraged researchers to prepare a larger number of biologically active compounds decorated with pyridine or dihydropyridine, expandeing the scope of finding a cure for other ailments. It is thus anticipated that myriad new pharmaceuticals containing the two heterocycles will be available in the forthcoming decade. This review examines the prospects of highly potent bioactive molecules to emphasize the advantages of using pyridine and dihydropyridine in drug design. We cover the most recent developments from 2010 to date, highlighting the ever-expanding role of both scaffolds in the field of medicinal chemistry and drug development.

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mentioning

confidence: 99%

The Expanding Role of Pyridine and Dihydropyridine Scaffolds in Drug Design

Ling

Hao

Liang

et al. 2021

DDDT

216

114

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“…In order to determine the cytotoxic effect of various compounds on the viability of MCF-7 cells, the MTT reduction assay was performed as described previously. [30][31][32] First MCF-7 cells were plated in 96-well microplates at a density of 1× 10 4 cells per well and were maintained overnight at 37 ºC to allow them to attach to the bottom of the wells. After cell attachment, the medium was removed and cells were treated with various compounds (9a-d, 10a-d and 11a-d) at…”

Section: Cell Viability Assay (Mtt)mentioning

confidence: 99%

“…The results of different studies have highlighted the fact that the DHPs are highly effective calcium antagonists and are used for treating various cardiovascular system (CVS) activities. [1][2][3] In addition to the CVS activities of DHPs, they possess a variety of biological activities including, cytotoxic activities, [4][5][6] anti-proliferative activities, 7 multidrug resistance activities 8,9 and anti-tumour activities. [10][11][12][13] However, synthesizing DHPs derivatives is an active and ongoing research area.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety

2021

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A number of 1,4-dihydropyridine derivatives (9a-d, 10a-d, and 11a-d) were designed and synthesized by the reaction of 1,3,4-oxadiazole-5-thiones and 1,2,4-triazole-5-thiones to 2,6-dibromomethyl-3,5-diethoxycarbonyl-4-(3-ni-trophenyl)-1,4-dihydropyridine. The synthesized compounds were characterrized using FT-IR, 1H-NMR, 13C-NMR spectral data, ESI-MS, and elemental analysis. The cytotoxicity of the synthesized compounds was evaluated in human breast cancer (MCF-7) cells based on the results of MTT assay. The results indicated that compound Diethyl 4-(3-nitrophenyl)-2,6-bis[((5-(3-nitrophenyl)-1,3,4-oxa-diazol-2-yl)thio)methyl]-1,4-dihydro pyridine-3,5-dicarboxylate (9b) with (IC50 = 23 ? 2.32 ?M) was the most potent derivative against MCF-7 cells. Based on the results, the use of oxadiazole moiety in the C2 and C6 positions of 1,4-di-hydropyridine ring system enhanced the cytotoxic potential of these derivatives. Therefore, some of the oxadiazole-substituted 1,4-DHPs may facilitate further modifications which result in the discovery of potent cytotoxic agents.

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“…Moreover, many heterocyclic hydrazones represents an interesting class of hetero compounds with a broad spectrum of biological activities, analgesic, anti-inflammatory, antimicrobial, antitubercular, antiplatelet, anticonvulsant, antimalarial and antiviral activities (19)(20)(21)(22)(23). It is quite interesting to note that the 1,4-dihydropyridine and hydrazine derivatives have gained prominence in the recent years for cancer chemotherapy (24)(25)(26)(27)(28)(29)(30). 1,4-Dihydropyridines have been proved to be a new class of multidrug resistance (MDR) reversals in cancer treatment (31).…”

Section: Introductionmentioning

confidence: 99%

Green synthesis, molecular docking and anticancer activity of novel 1,4-dihydropyridine-3,5-Dicarbohydrazones under grind-stone chemistry

Gomha

Muhammad

Abdel‐aziz

et al. 2020

Green Chemistry Letters and Reviews

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The reaction of 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarbohydrazide with variety of carbonyl compounds such as substituted benzaldehydes, cycloalkanones and hetero-cyclic ketones under grinding method under catalyst-and solvent-free conditions at room temperature, in the presence of catalytic drops of acetic acid gave a new series of 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarbohydrazone derivatives in good to excellent yields. The structures of new products were elucidated on the basis of their spectral data and elemental analysis. Most of the newly prepared compounds were evaluated towards HepG2 cell lines and showed good IC 50 for some compounds. Additionally, molecular docking of the novel chemical entities using Autodock Vina demonstrated their binding modes within the active site of DYRK1A.

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Design and Synthesis of 1,4-dihydropyridine Derivatives as Anti-cancer Agent

Abstract: Thus, synthesized 1,4-dihydropyridines can be considered as the encouraging molecules for further drug development as anticancer agents.

Cited by 24 publications

References 15 publications

The Expanding Role of Pyridine and Dihydropyridine Scaffolds in Drug Design

The Expanding Role of Pyridine and Dihydropyridine Scaffolds in Drug Design

Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety

Green synthesis, molecular docking and anticancer activity of novel 1,4-dihydropyridine-3,5-Dicarbohydrazones under grind-stone chemistry

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