Synthesis, anti-HIV activity and molecular modeling study of some new pyrimidine analogues

Marich, Yossra A.; Al-Salihi, Niran J.; Al‐Masoudi, Najim A.

doi:10.5155/eurjchem.5.4.588-594.1109

Cited by 10 publications

(7 citation statements)

References 36 publications

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“…Hammerland et al (2006) showed that a 4-thiopyrimidine as a core linker is crucial for activity as an mGluR5 antagonist. In another article, it was found that compounds with alkyl-or arylthio substituents at the 4-position of the pyrimidine ring showed greater activity than those with alkyl-or arylamino substituents at the 4-position of the same ring against HIV-1 (Marich et al, 2014). In our previous publications, we indicated that 4-thiopyrimidines containing a disulfide or tetrasulfide bridge at the 4-position were interesting antibacterial and antifungal agents (Cieplik et al, 2015;Są siadek et al, 2016).…”

Section: Introductionmentioning

confidence: 97%

Synthesis, crystal structure and cytotoxic activity of novel 5-methyl-4-thiopyrimidine derivatives

et al. 2018

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This article presents the synthesis of three new 4-thiopyrimidine derivatives obtained from ethyl 4-methyl-2-phenyl-6-sulfanylpyrimidine-5-carboxylate as the starting material, namely, ethyl 4-[(4-chlorobenzyl)sulfanyl]-6-methyl-2phenylpyrimidine-5-carboxylate, C 21 H 19 ClN 2 O 2 S, (2), {4-[(4-chlorobenzyl)sulfanyl]-6-methyl-2-phenylpyrimidin-5-yl}methanol, C 19 H 17 ClN 2 OS, (3), and 4-[(4-chlorobenzyl)sulfanyl]-5,6-dimethyl-2-phenylpyrimidine, C 19 H 17 ClN 2 S, (4), which vary in the substituent at the 5-position of the pyrimidine ring. The compounds were characterized by 1 H NMR, 13 C NMR, IR and mass spectroscopies, and also elemental analysis. The molecular structures were further studied by single-crystal X-ray diffraction. Compound (2) crystallizes in the space group P1 with one molecule in the asymmetric unit, whereas compounds (3) and (4) crystallize in the space group P2 1 /c with two and one molecule, respectively, in their asymmetric units. The conformation of each molecule is best defined by the dihedral angles formed between the pyrimidine ring and the planes of the two aryl substituents attached at the 2-and 4-positions. The only structural difference between the three compounds is the substituent at the 5-position of the pyrimidine ring, but they present significantly different features in the hydrogenbond interactions. Compound (2) displays a one-dimensional chain formed by hydrogen bonds and the chains are further extended into a two-dimensional network. Molecules of (3) and (4) generate one-dimensional chains formed through intermolecular interactions. The study examines the cytotoxicity of compounds (3) and (4) against Human umbilical vein endothelial cells (HUVEC) and HeLa, K562 and CFPAC cancer cell lines. The presence of the hydroxymethyl and methyl groups in (3) and (4), respectively, offers an interesting new insight into the structures and behaviour of these derivatives. Compound (4) was found to be nontoxic against CFPAC and HUVEC; however, it shows weak activity against the HeLa and K563 cell lines. The presence of a hydroxy group in (3) significantly increases its cytotoxicity towards both, i.e. the cancer (HeLa, K562 and CFPAC) and normal (HUVEC) cell lines.

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Section: Introductionmentioning

confidence: 97%

Synthesis, crystal structure and cytotoxic activity of novel 5-methyl-4-thiopyrimidine derivatives

et al. 2018

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“…The mass spectrum of structure 19 revealed an ion peak at m/z 545 (M + , 82), while 13 C-NMR analysis showed two signals for the C 2 and C 4 carbons in the pyrimidine ring at δ 183.1 and 184.1 ppm. The IR spectrum revealed characteristic bands at 1150 and 1130 cm À 1 corresponding to two C=S groups.…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, the incorporation of heterocyclic groups such as azole, azine, and diazine was considered an interesting approach to accessing new biologically active derivatives. [13][14][15][16][17] N-Methyl-d-Glucamine consists of tertiary amine fragments and sorbitol and has structural characteristics similar to glycosides. One of the most important characteristics of this compound is its ability to form supramolecular adducts with lipophilic chemical molecules in water.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pyrazole, Pyridine, and Pyrimidine Derivatives Incorporating Glucaminoid Moiety and Their Antioxidant, Antitumor Activities and Docking Study

et al. 2023

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The reaction of N‐(4‐(phenyldiazenyl) phenyl) carbonohydrazonoyl dicyanide (2) with N‐methyl glucamine afforded 3‐amino‐3‐(methyl (2,3,4,5,6‐pentahydroxyhexyl)amino)‐2‐((4‐(phenyldiazenyl)phenyl)diazenyl)acrylonitrile (3). Additionally, compound 2 produced the pyrazole derivatives 4 and 6, respectively, by reactions with hydrazine hydrate and malononitrile. Moreover, when enaminonitrile 3 was treated with malononitrile, N,N‐Dimethylformamide ‐ dimethyl acetal, and thiourea, it generated the glucaminoid derivatives 9, 10, and 13, respectively. In pyridine, compound 19 was obtained when enaminonitrile 3 interacted with the carbon disulfide. While in sodium hydroxide in N,N‐Dimethylformamide, instead of pyridine, it afforded the methyl carbamodithioate 23. Finally, pyrimidinethione derivative 26 was produced when the enaminonitrile 3 and phenyl isothiocyanate interacted. All new compounds were well established by both spectral and elemental analyses. The antitumor activities were evaluated by testing their impact on the viability of four different cell lines: HepG2 (human hepatocellular liver carcinoma), WI‐38 (human lung fibroblast), VERO (African green monkey kidney epithelial), and MCF‐7 (human breast adenocarcinoma). The antitumor study showed that compound 23 has very strong antitumor activity against the HEPG‐2 cell line. The synthesized compounds were analyzed by docking studies that showed good binding scores against the diverse amino acids of the selected proteins B‐Cell Leukemia/Lymphoma‐2 (Bcl‐2). The conducted docking studies were found to be consistent with cytotoxic results.

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“…Experimental part). However, compound 11 has been selected for further NMR experiments [27][28][29]. The HSQC NMR spectrum [30] of compound 11 showed JC,H correlations between Harom.-3' together with Harom.-4' at the region δ 7.61-7.63 ppm and C-3' at δ 124.9 ppm as well as C-4' at δ 132.4 ppm.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of new derivatives of aryl-clonazepam via Suzuki Cross-coupling reaction

Salman

Abdul-Rida

2016

Eur. J. Chem.

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Synthesis, anti-HIV activity and molecular modeling study of some new pyrimidine analogues

Cited by 10 publications

References 36 publications

Synthesis, crystal structure and cytotoxic activity of novel 5-methyl-4-thiopyrimidine derivatives

Synthesis, crystal structure and cytotoxic activity of novel 5-methyl-4-thiopyrimidine derivatives

Synthesis of Pyrazole, Pyridine, and Pyrimidine Derivatives Incorporating Glucaminoid Moiety and Their Antioxidant, Antitumor Activities and Docking Study

Synthesis of new derivatives of aryl-clonazepam via Suzuki Cross-coupling reaction

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