Synthesis and antiviral properties of 1-substituted 3-[ω-(4-oxoquinazolin-4(3h)-yl)alkyl]uracil derivatives

Paramonova, Maria P.; Khandazhinskaya, Anastasia L.; Озеров, А. А.; Kochetkov, Sergey N.; Snoeck, Robert; Andrei, Gracíela; Новиков, Михаил С.

doi:10.32607/actanaturae.10983

Cited by 10 publications

(5 citation statements)

References 25 publications

(25 reference statements)

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“…A number of analogues were synthesized to study the structure-antiviral activity dependence. In particular, 1-[5-(4-bromophenoxy)pentyl]-3-benzyl- (22) and -(anthracen-9-ylmethyl)uracil (23) derivatives were obtained by treating uracil 1 with benzyl chloride (20) or 9-(chloromethyl)anthracene (21) in DMF solution in the presence of K 2 CO 3 , the yield of which was 81 and 79%, respectively (Scheme 2). 8) was converted into the target compound 24 with a 77% yield (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

“…A suspension of 1-[ω-(4-bromophenoxy)alkyl]-uracil derivative 1-7 or 1-[5-(4-bromophenoxy)pentyl]quinazoline-2,4(1H,3H)-dione (25) (1.416 mmol) and freshly calcined potassium carbonate (0.3 g, 2.171 mmol) was incubated in a DMF solution (10 mL) at 80°C for 1 h with stirring, cooled to room temperature, and supplemented with a solution of bromomethylnaphthalene (8)(9)(10)(11), benzyl chloride (20), or 9-(chloromethyl)anthracene ( 21) (1.469 mmol) in DMF (5 mL). The obtained mixture was incubated at that temperature for 24 h with stirring and then evaporated under reduced pressure.…”

Section: General Methods For Obtaining 3-arylmethyl-1-[ω-(bromophenox...mentioning

confidence: 99%

“…We have recently discovered a series of uracil 1-cinnamyl derivatives containing benzyl and naphthalen-1-ylmethyl substituents at the nitrogen atom N 3 , which also exhibited activity against HIV-1 and HCMV [ 19 ]. In addition, a high anti-HCMV activity was shown for 1-[5-(4-bromophenoxy)pentyl]uracil derivatives, which had 3-(4-oxoquinazolin-3(4 H )-yl)propyl [ 20 ] or 3-[(4-methyl-2-oxo-2 H -chromen-7-yl)oxy]propyl substituent at the nitrogen atom N 3 [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 1-[ω-(Bromophenoxy)alkyl]-3-Naphthalenylmethyl Uracil Derivatives and Their Analogues as Probable Inhibitors of Human Cytomegalovirus Replication

Paramonova

Gureeva

Озеров

et al. 2022

Dokl Biochem Biophys

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A new series of 1-[ω-(bromophenoxy)alkyl]-uracil derivatives containing naphthalen-1-yl, naphthalen-2-yl, 1-bromonaphthalen-2-ylmethyl, benzyl, and anthracene-9-ylmethyl fragments in position 3 of uracil residue was synthesized. The antiviral properties of the synthesized compounds against human cytomegalovirus were studied. It was found that the compound containing a bridge consisting of five methylene groups exhibits a high anti-cytomegalovirus activity in vitro.

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Section: Resultsmentioning

confidence: 99%

Section: General Methods For Obtaining 3-arylmethyl-1-[ω-(bromophenox...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of 1-[ω-(Bromophenoxy)alkyl]-3-Naphthalenylmethyl Uracil Derivatives and Their Analogues as Probable Inhibitors of Human Cytomegalovirus Replication

Paramonova

Gureeva

Озеров

et al. 2022

Dokl Biochem Biophys

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“…There is a growing body of evidence that resistance to antiviral drugs has become a major ongoing clinical issue. Besides, the discovery of novel molecules to treat viral infections has attracted considerable attention due to the high prevalence of these diseases, the appearance of new viral strains and re-emergence of some viruses, and the limited treatments available. − It is worth mentioning that a plethora of research is dedicated toward the synthesis of novel Se derivatives of a wide range of antivirals and the study of their pharmacological activities. − …”

Section: Selenized Small Molecule Drugsmentioning

confidence: 99%

Selenization of Small Molecule Drugs: A New Player on the Board

Morán-Serradilla,

Plano,

Sanmartín

et al. 2024

J. Med. Chem.

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There is an urgent need to develop safer and more effective modalities for the treatment of a wide range of pathologies due to the increasing rates of drug resistance, undesired side effects, poor clinical outcomes, etc. Throughout the years, selenium (Se) has attracted a great deal of attention due to its important role in human health. Besides, a growing body of work has unveiled that the inclusion of Se motifs into a great number of molecules is a promising strategy for obtaining novel therapeutic agents. In the current Perspective, we have gathered the most recent literature related to the incorporation of different Se moieties into the scaffolds of a wide range of known drugs and their feasible pharmaceutical applications. In addition, we highlight different representative examples as well as provide our perspective on Se drugs and the possible future directions, promises, opportunities, and challenges of this ground-breaking area of research. ■ SIGNIFICANCE • Significance: The development of novel compounds for the treatment of numerous pathologies has become a priority due to the lack of effective therapeutic options. • Impact: This work highlights the potential of incorporating Se moieties into the scaffold of several drugs to develop novel safer bioactive compounds. • Innovation: This Perspective discusses the development of selenoderivatives of a wide array of drugs and their biological applications and proposes novel avenues to continue exploring this outstanding research area.

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“…Paramonova et al [ 45 ] synthesized a set of (ω-p-bromophenoxyalkyl) uracil derivatives with various acetamide moieties. The authors demonstrated that a molecule with a dodecane-1,12-diyl linker ( Figure 3 , 7) has a potent antiviral activity against HCMV.…”

Section: Novel Inhibitors Targeting Viral Proteinsmentioning

confidence: 99%

Small Molecules—Prospective Novel HCMV Inhibitors

Bogner

Egorova

Makarov

2021

Viruses

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Human cytomegalovirus (HCMV), a member of the betaherpesvirinae, can cause life-threatening diseases. HCMV is globally widespread, with a seroprevalence in adults varying from 50 to 100%. HCMV infection is rarely of significant consequence in immunocompetent individuals. However, although immune control is efficient, it cannot achieve the clearance of the virus. HCMV persists lifelong in the infected host and reactivates in certain circumstances. In neonates and in immunocompromised adults, HCMV is a serious pathogen that can cause fatal organ damage. Different antiviral compounds alone or in combination have been used for the treatment of HCMV diseases. In clinical use, mutations in the viral DNA polymerase or the terminase confer resistance to ganciclovir, foscarnet, cidofovir, and letermovir. There is an urgent need to find new well-tolerated compounds supporting different modes of action. The list of novel small molecules that might have anti-HCMV activity has grown in recent years. In this short review, a selection of compounds in clinical trials and novel inhibitors targeting host-cell factors or viral proteins is presented, and their modes of action, described.

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Synthesis and antiviral properties of 1-substituted 3-[ω-(4-oxoquinazolin-4(3h)-yl)alkyl]uracil derivatives

Cited by 10 publications

References 25 publications

Synthesis of 1-[ω-(Bromophenoxy)alkyl]-3-Naphthalenylmethyl Uracil Derivatives and Their Analogues as Probable Inhibitors of Human Cytomegalovirus Replication

Synthesis of 1-[ω-(Bromophenoxy)alkyl]-3-Naphthalenylmethyl Uracil Derivatives and Their Analogues as Probable Inhibitors of Human Cytomegalovirus Replication

Selenization of Small Molecule Drugs: A New Player on the Board

Small Molecules—Prospective Novel HCMV Inhibitors

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