Synthesis of Pyrimidine, Dihydropyrimidinone, and Dihydroimidazole Derivatives under Free Solvent Conditions and Their Antibacterial Evaluation

Soliman, Ahmed M.; Mohamed, Shaaban K.; El‐Remaily, Mahmoud Abd El Aleem Ali Ali; Abdel‐Ghany, H.

doi:10.1002/jhet.1657

Cited by 27 publications

(15 citation statements)

References 30 publications

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“…Antibacterial activity: Andrews and Ahmed (2015) reported 5-(5-amino-1,3,4-thiadiazol-2-yl)-4-(4-hydroxy phenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one to be the most promising antibacterial among the series screened by them. 2-(1,3-benzothiazol-2-ylimino)-1,2-dihydro pyrimidine-4,6diamine excellent activity on both gram positive and negative isolate (Soliman et al, 2014). Other (Gulcan et al, 2014), pyrimidine-nucleotide (cGMP-AM) (Beckert et al, 2014), pyrrolidinyl-pyrimidine (Nguyen et al, 2014) and 5-amino-thiazolo[4,5-d]pyrimidine (Jang et al, 2011) as shown in Fig.…”

Section: Biological Activitiesmentioning

confidence: 88%

Exploration of the Chemistry and Biological Properties of Pyrimidine as a Privilege Pharmacophore in Therapeutics

Ajani¹,

Isaac²,

Owoeye³

et al. 2015

International J. of Biological Chemistry

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The pyrimidine moiety is one of the most widespread heterocycles in biologically occurring compounds, such as nucleic acids components (uracil, thymine and cytosine) and vitamin B1. Due to its prebiotic nature to living cells in biodiversity, it is an highly privileged motif for the development of molecules of biological and pharmaceutical interest. This present work deals with the exploration of chemistry and medicinal diversity of pyrimidine which might pave way to long await discovery in therapeutic medicine for future drug design.

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Section: Biological Activitiesmentioning

confidence: 88%

Exploration of the Chemistry and Biological Properties of Pyrimidine as a Privilege Pharmacophore in Therapeutics

Ajani¹,

Isaac²,

Owoeye³

et al. 2015

International J. of Biological Chemistry

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“…The reaction was performed in the presence of an excess of sulfuric acid in refluxing aqueous ethanol and led to modest yields. Similar conditions with hydrochloric acid were used later to form differently substituted 2-guanidinobenzimidazoles and 2-guanidinobenzothiazoles, respectively, with good to excellent yields (Scheme 11A) [30,31]. The efficiency of the reaction process usually follows the order: benzothiazole > benzimidazole > benzoxazole.…”

Section: Methodsmentioning

confidence: 99%

Synthetic accesses to biguanide compounds

Grytsai

Ronco

Benhida

2021

Beilstein J. Org. Chem.

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Biguanide is a unique chemical function, which has attracted much attention a century ago and is showing resurgent interest in recent years after a long period of dormancy. This class of compounds has found broad applications such as reaction catalysts, organic strong bases, ligands for metal complexation, or versatile starting materials in organic synthesis for the preparation of nitrogen-containing heterocycles. Moreover, biguanides demonstrate a wide range of biological activities and some representatives are worldwide known such as metformin, the first-line treatment against type II diabetes, or chlorhexidine, the gold standard disinfectant and antiseptic. Although scarcely represented, the number of “success stories” with biguanide-containing compounds highlights their value and their unexploited potential as future drugs in various therapeutic fields or as efficient metal ligands. This review provides an extensive and critical overview of the synthetic accesses to biguanide compounds, as well as their comparative advantages and limitations. It also underlines the need of developing new synthetic methodologies to reach a wider variety of biguanides and to overcome the underrepresentation of these compounds.

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“…The simplicity of their preparationusing Biginelli reaction as one pot protocol for the assembly of dihydropyrimidin-2-(1H )-one/thione (4,5)encouraged the scientific teams to discover different new members. Their pharmaceutical and biological activities include antiviral (6), potent-HIV pg-120-CD4 inhibitors (7,8), anticancer (9,10), anti-inflammatory (11,12), potent calcium channel blockers (4,13,14), antihypertensive (4), antibacterial (15,16) and antifungal agents (16,17). Monostrol and its analogues are effective antihuman kinesin Eg5 with a dihydropyrimidine nucleus (9,18).…”

Section: Introductionmentioning

confidence: 99%

Design, ecofriendly synthesis, anticancer and antimicrobial screening of innovative Biginelli dihydropyrimidines using β-aroylpyruvates as synthons

El‐Malah

Mahmoud

Salem

et al. 2021

Green Chemistry Letters and Reviews

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New ecofriendly Biginelli reaction procedures have been adapted to prepare new dihydropyrimidines (DHPMs) using a multicomponent one-pot reaction. All the synthesized compounds were evaluated for their anticancer activity against 59 human cancer cell lines and evaluated for their antimicrobial activities against representatives of both Gram-positive and Gram-negative bacteria. Compound 4 showed marked wide spectrum anticancer activity towards most of the tested cancer cell lines with a percentage of growth inhibition of 29.04-71.68% against leukemia cell line (K-562 and SR), lung cancer cell line (NCI-H522), five colon cancer cell lines (HCT-116, HCT-15, HT29, KM12 and SW-620), CNS cancer cell line (SF-295 and SNB-75), melanoma cell lines (MALME-3M and M14), renal cancer cell line (CAKI-1) and breast cancer cell lines (MCF7 and MDA-MB-468). The highest observed anticancer activity was against leukemia cell lines K-562 and SR with inhibition percentages of 64.97 and 71.68%, respectively. The renal cancer cell line (UO-31) was particularly sensitive towards all the evaluated compounds. Compounds including 2b and 5c exhibited antibacterial activity against S. aureus while 2a and 5b exhibited antifungal activity against C. albicans. The results also showed that compounds 2c and 5e exhibited both antibacterial and antifungal activity against S. aureus and C. albicans respectively.

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Synthesis of Pyrimidine, Dihydropyrimidinone, and Dihydroimidazole Derivatives under Free Solvent Conditions and Their Antibacterial Evaluation

Cited by 27 publications

References 30 publications

Exploration of the Chemistry and Biological Properties of Pyrimidine as a Privilege Pharmacophore in Therapeutics

Exploration of the Chemistry and Biological Properties of Pyrimidine as a Privilege Pharmacophore in Therapeutics

Synthetic accesses to biguanide compounds

Design, ecofriendly synthesis, anticancer and antimicrobial screening of innovative Biginelli dihydropyrimidines using β-aroylpyruvates as synthons

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