Synthesis and evaluation of fused pyrimidine derivatives as anti-inflammatory, antiproliferative and antimicrobial agents

Vachala, Seekarajapuram Dinakaran; Srinivasan, K. K.; Prakash, Peralam Yegneswaran

doi:10.1007/s00044-011-9826-7

Cited by 7 publications

(3 citation statements)

References 9 publications

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“…Mouse macrophages J774.2 (2 × 10 5 cells /mL in HBSS) were seeded in 24-well plates (Corning, New York, NY, USA) in the presence of 1 mM NaN 3 as myeloperoxidase (MPO) inhibitor [24]. Cells were then incubated with the test compound (25 µg/mL) and activated with PMA (500 ng/mL) in a CO 2 incubator at 37 • C for 2 h. After incubation, the medium was removed and the cells were washed gently once, then carefully lysed using ice-cold 1% triton X-100.…”

Section: H 2 O 2 Determinationmentioning

confidence: 99%

Inhibitory Effects of Myrtucommuacetalone 1 (MCA-1) from Myrtus Communis on Inflammatory Response in Mouse Macrophages

et al. 2019

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1) Introduction: Reactive oxygen species (ROS) and nitric oxide (NO) are key signaling molecules that play important roles in the progression of inflammatory disorders. The objective of this study was to explore the use of myrtucommuacetalone-1 (MCA-1), as a novel compound of natural origin and a potential anti-inflammatory agent.(2) Methodology: The anti-inflammatory potential of MCA-1, which was isolated from Myrthus communis Linn, was determined by assaying superoxide, hydrogen peroxide, and nitric oxide production in macrophages. Furthermore, the effects of the compound were analyzed via phosphorylation and translocation of the transcription factor NF kappa B, which is a key regulator of iNOS activation. The effect of MCA-1 on the inducible nitric oxide synthase (iNOS) enzyme was also examined using in silico docking studies. The anticancer potential for MCA-1 was evaluated with an MTT cytotoxic assay. (3) Results: In stimulated macrophages, MCA-1 inhibited superoxide production by 48%, hydrogen peroxide by 53%, and nitric oxide (NO) with an IC 50 of <1 µg/mL. MCA-1 also showed a very strong binding pattern within the active site of the inducible nitric oxide synthase enzyme. Furthermore, 25 µg/mL of MCA-1 inhibited inducible nitric oxide synthase expression and abolished transcription factor (NFκB) phosphorylation and translocation to the nucleus. Cytotoxicity analyses of MCA-1 on 3T3 mouse fibroblasts, CC1 liver cell line, J774.2, macrophages and MDBK bovine kidney epithelial cell, yielded IC 50 values of 6.53 ± 1.2, 4.6 ± 0.7, 5 ± 0.8, and 4.6 ± 0.7, µg/mL, respectively. (4) Conclusion: Our results suggest that MCA-1, a major phloroglucinol-type compound, shows strong anti-inflammatory activity and has a potential to be a leading therapeutic agent in the future.

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Section: H 2 O 2 Determinationmentioning

confidence: 99%

Inhibitory Effects of Myrtucommuacetalone 1 (MCA-1) from Myrtus Communis on Inflammatory Response in Mouse Macrophages

et al. 2019

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“…[1] The antifungal, antiproliferative, antitumor, antihypertensive, cardiotonic, and anti-inflammatory actions of these different molecules have been identified for these substances. [2][3][4][5][6] The identification of the (±)-4-(3hydroxyphenyl)-2-thione derivative monasterol as a precursor anti-cancer medication that suppresses the mitotic kinesin-5 protein has elevated the prominence of this pharmacophore. [7] There are pyridimine core compounds like HEPT, MKC-442, and TNK-651 that have the greatest anti-HIV 1 effectiveness.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of ethyl‐6‐methyl‐2‐oxo‐4‐(3‐(2,4,5‐trifluorobenzamido)phenyl)‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylate. A DFT approach

Adaikalaraj,

Bhakiaraj,

Asha

et al. 2022

Vietnam Journal of Chemistry

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This study details the synthesis and spectrum analysis of ethyl‐6‐methyl‐2‐oxo‐4‐(3‐(2,4,5‐trifluorobenzamido)phenyl)‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylate (TFPPC). Hydrogen bonding between the carboxylate side chain and the dihydropyrimidine ring bearing the methyl group is caused via the C30–H31–O22 interaction. 2.475 and 2.236 are the intramolecular hydrogen bonds in these two O22H31 and O38H15 molecules, respectively. We were able to establish the optical characteristics of this unique (TFPPC) molecule using the polar relationship, which was utilized to forecast the change in hyperpolarizability. To study the optical band gap between valence and conduction bands and the electrostatic potential of the molecule, DFT simulations were used. The docking experiments were performed to theoretically assess the antibacterial capabilities of the chemical. Staphylococcus aureus is more efficient against Bacillus subtilis in terms of antibacterial activity. Feature drug development may take into account the compound's drug‐like properties. Toxicological predictions show that the molecule is less harmful, and its in‐silico properties are significant.

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“…Quinazolines form a large family of compounds that are well recognized for their ability to show a broad range of biological activities, which are influenced significantly by the type of substituents and where they are placed around the quinazoline structure . Observed biological activities include, but are not limited to, CNS depressant , anti‐inflammatory , diuretic , antihypertensive , analgesic , anticancer , antihypoxic , hypoglycemic , and antimicrobial activities. The ability to synthesize and functionalize quinazolines is therefore of great importance, and the methods employed will reflect the structure of the desired quinazolines.…”

Section: Introductionmentioning

confidence: 99%

Functionalization of Quinazolin‐4‐Ones Part 2^#: Reactivity of 2‐Amino‐3, 4, 5, or 6‐Nitrobenzoic Acids with Triphenylphosphine Thiocyanate, Alkyl Isothiocyanates, and Further Derivatization Reactions

Heppell

Al‐Rawi

2014

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).2-amino-3, 4, 5, or 6-nitrobenzoic acids were reacted with PPh 3 (SCN) 2 and alkyl isothiocyanates to give 5, 6, 7, or 8-nitro-2-thioxo-3-substituted quinazolin-4-ones, respectively. The position of the nitro group was found to have significant influence on the outcome of the reactions. Similarly, the nature of the substituent at position 8 (NO 2 , NH 2 , NH(C═O)CH 3 ) in 8-substituted-2-methylthio quinazolin-4-ones was also found to significantly influence their reactivity towards morpholine. A selection of the products were also tested for in vitro antibacterial activity but little activity was observed. Scheme 3. Synthesis of 8-amino-2-morpholino quinazolines. (i) = morpholine, reflux, 3-72 h. (ii) = K 2 CO 3 , CH 3 I or benzyl bromide, acetone, reflux, 1.5 h. (iii) = SnCl 2 .

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Synthesis and evaluation of fused pyrimidine derivatives as anti-inflammatory, antiproliferative and antimicrobial agents

Cited by 7 publications

References 9 publications

Inhibitory Effects of Myrtucommuacetalone 1 (MCA-1) from Myrtus Communis on Inflammatory Response in Mouse Macrophages

Inhibitory Effects of Myrtucommuacetalone 1 (MCA-1) from Myrtus Communis on Inflammatory Response in Mouse Macrophages

Synthesis and characterization of ethyl‐6‐methyl‐2‐oxo‐4‐(3‐(2,4,5‐trifluorobenzamido)phenyl)‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylate. A DFT approach

Functionalization of Quinazolin‐4‐Ones Part 2^#: Reactivity of 2‐Amino‐3, 4, 5, or 6‐Nitrobenzoic Acids with Triphenylphosphine Thiocyanate, Alkyl Isothiocyanates, and Further Derivatization Reactions

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Synthesis and evaluation of fused pyrimidine derivatives as anti-inflammatory, antiproliferative and antimicrobial agents

Cited by 7 publications

References 9 publications

Inhibitory Effects of Myrtucommuacetalone 1 (MCA-1) from Myrtus Communis on Inflammatory Response in Mouse Macrophages

Inhibitory Effects of Myrtucommuacetalone 1 (MCA-1) from Myrtus Communis on Inflammatory Response in Mouse Macrophages

Synthesis and characterization of ethyl‐6‐methyl‐2‐oxo‐4‐(3‐(2,4,5‐trifluorobenzamido)phenyl)‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylate. A DFT approach

Functionalization of Quinazolin‐4‐Ones Part 2#: Reactivity of 2‐Amino‐3, 4, 5, or 6‐Nitrobenzoic Acids with Triphenylphosphine Thiocyanate, Alkyl Isothiocyanates, and Further Derivatization Reactions

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Functionalization of Quinazolin‐4‐Ones Part 2^#: Reactivity of 2‐Amino‐3, 4, 5, or 6‐Nitrobenzoic Acids with Triphenylphosphine Thiocyanate, Alkyl Isothiocyanates, and Further Derivatization Reactions