1-Benzyl derivatives of 5-(arylamino)uracils as anti-HIV-1 and anti-EBV agents

Новиков, Михаил С.; Buckheit, Robert W.; Temburnikar, Kartik; Khandazhinskaya, Anastasia L.; Ivanov, Alexander V.; Seley‐Radtke, Katherine L.

doi:10.1016/j.bmc.2010.09.070

Cited by 19 publications

(23 citation statements)

References 39 publications

(28 reference statements)

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“…The 5-halouracils and their derivatives have demostrated antitumor and antiviral properties [1][2][3][4]. For example, 5-uorouracil is known as one of the anticancer agents used clinically for the treatment of stomach, colorectal, and neck cancers [5,6].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of N,N-diethyl-5-bromo-3,4-dihydro-2,4-dioxopyrimidine-1(2H)-carboxamide, C₉H₁₂BrN₃O₃

Shi

Lian

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Discussionmentioning

confidence: 99%

Crystal structure of N,N-diethyl-5-bromo-3,4-dihydro-2,4-dioxopyrimidine-1(2H)-carboxamide, C₉H₁₂BrN₃O₃

Shi

Lian

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Uracil and its derivatives exhibit a broad spectrum of activity, and have been used as antitumor, antibacterial, and antiviral drugs [1][2][3]. For example, 5-fluorouracil was known one of the anticancer agents used clinically for the treatment of stomach, colorectal, and neck cancers [4,5].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 5-iodo-1-tosylpyrimidine-2,4(1H,3H)-dione, C11H9IN2O4S

Shao

et al. 2013

Zeitschrift Für Kristallographie - New Crystal Structures

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C 11 H 9 IN 2 O 4 S, monoclinic, P2 1 /c (no. 14), a = 14.771(3) Å,Source of material 5-Iodouracil (2.38 g,10 mmol), 4-methylbenzene-1-sulfonyl chloride (1.90 g,10 mmol), triethyl amine (0.25 mL) and acetone (30 mL) were added into a flask and stirred at 333 K for 2 hours. The solid was obtained after removal of acetone and washing by ethyl acetate (20 mL). The purified product was dissolved in ethanol and single crystals were separated after a few days. Experimental detailsAll H atoms were positioned geometrically and allowed to ride on their parent atoms at distances of C(sp 2 )-H = 0.93 Å with U iso = 1.2U eq (parent atom), N-H = 0.86 Å with U iso = 1.2U eq (parent atom) and C(methyl)-H = 0.96 Å with U iso = 1.5 U eq (C11).

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“…The literature also communicates very different structures of NNRTI containing the pyrimidine core and exhibiting very good anti-HIV activity, as seen from Figure 3 , the pyrimidine-catechol-diether compounds XIII and XIV, or compound XV and compound XVI (representative for a novel class of 2-pyrimidinylphenylamine derivatives) [ 39 , 40 , 84 , 85 , 86 ]. Similar compounds are 1,3-dibenzyl-uracil derivates, e.g., benzylated pyrimidines, being substituted in N1 and/or N3 position of pyrimidine nucleus by Maruyama et al [ 28 , 48 , 87 , 88 , 89 , 90 , 91 ]; they have been synthesized and tested as the compounds XVII and XX in Figure 3 (see Novikov et al [ 92 , 93 , 94 , 95 ]).…”

Section: Smiles Of Anti-hiv Pyrimidinesmentioning

confidence: 99%

Double Variational Binding—(SMILES) Conformational Analysis by Docking Mechanisms for Anti-HIV Pyrimidine Ligands

Putz

Dudaş

Isvoran

2015

IJMS

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Variational quantitative binding–conformational analysis for a series of anti-HIV pyrimidine-based ligands is advanced at the individual molecular level. This was achieved by employing ligand-receptor docking algorithms for each molecule in the 1,3-disubstituted uracil derivative series that was studied. Such computational algorithms were employed for analyzing both genuine molecular cases and their simplified molecular input line entry system (SMILES) transformations, which were created via the controlled breaking of chemical bonds, so as to generate the longest SMILES molecular chain (LoSMoC) and Branching SMILES (BraS) conformations. The study identified the most active anti-HIV molecules, and analyzed their special and relevant bonding fragments (chemical alerts), and the recorded energetic and geometric docking results (i.e., binding and affinity energies, and the surface area and volume of bonding, respectively). Clear computational evidence was also produced concerning the ligand-receptor pocket binding efficacies of the LoSMoc and BraS conformation types, thus confirming their earlier presence (as suggested by variational quantitative structure-activity relationship, variational-QSAR) as active intermediates for the molecule-to-cell transduction process.

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1-Benzyl derivatives of 5-(arylamino)uracils as anti-HIV-1 and anti-EBV agents

Cited by 19 publications

References 39 publications

Crystal structure of N,N-diethyl-5-bromo-3,4-dihydro-2,4-dioxopyrimidine-1(2H)-carboxamide, C₉H₁₂BrN₃O₃

Crystal structure of N,N-diethyl-5-bromo-3,4-dihydro-2,4-dioxopyrimidine-1(2H)-carboxamide, C₉H₁₂BrN₃O₃

Crystal structure of 5-iodo-1-tosylpyrimidine-2,4(1H,3H)-dione, C11H9IN2O4S

Double Variational Binding—(SMILES) Conformational Analysis by Docking Mechanisms for Anti-HIV Pyrimidine Ligands

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1-Benzyl derivatives of 5-(arylamino)uracils as anti-HIV-1 and anti-EBV agents

Cited by 19 publications

References 39 publications

Crystal structure of N,N-diethyl-5-bromo-3,4-dihydro-2,4-dioxopyrimidine-1(2H)-carboxamide, C9H12BrN3O3

Crystal structure of N,N-diethyl-5-bromo-3,4-dihydro-2,4-dioxopyrimidine-1(2H)-carboxamide, C9H12BrN3O3

Crystal structure of 5-iodo-1-tosylpyrimidine-2,4(1H,3H)-dione, C11H9IN2O4S

Double Variational Binding—(SMILES) Conformational Analysis by Docking Mechanisms for Anti-HIV Pyrimidine Ligands

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Crystal structure of N,N-diethyl-5-bromo-3,4-dihydro-2,4-dioxopyrimidine-1(2H)-carboxamide, C₉H₁₂BrN₃O₃

Crystal structure of N,N-diethyl-5-bromo-3,4-dihydro-2,4-dioxopyrimidine-1(2H)-carboxamide, C₉H₁₂BrN₃O₃