Structure—Activity Relationships of Some 3‐Substituted‐4‐hydroxycoumarins as HIV‐1 Protease Inhibitors.

Kirkiacharian, S; Thuy, Duong Thanh; Sicsic, Sames; Bakhchinian, Robert; Kurkjian, Raffi; Tonnaire, Thierry

doi:10.1002/chin.200304129

Cited by 17 publications

(22 citation statements)

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“…According to Semple et al (1998Semple et al ( ,1999, Pterocaulon sphacelatum has antiviral activity suggesting that other species from Pterocaulon genus may also have antiviral activity. Coumarins have been related to HIV-1 protease inhibitory activity (Kirkiacharian et al, 2002). Our results In vitro cytotoxic, antioxidant and antiviral effects of Pterocaulon alopecuroides and Bidens segetum extracts suggest that 7-(2',3'-dihidroxy-3'-methylbutyloxy)-6-methoxycoumarin can be responsible to the Herpes simplex virus inhibitory activity.…”

Section: Resultsmentioning

confidence: 54%

In vitro cytotoxic, antioxidant and antiviral effects of Pterocaulon alopecuroides and Bidens segetum extracts

Silveira¹,

Martins²,

Costa³

et al. 2009

Rev. bras. farmacogn.

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RESUMO: "Efeitos citotóxico, antioxidante e antiviral in vitro de extratos de Pterocaulon alopecuroides e Bidens segetum". Pterocaulon alopecuroides (Lamark) De Candolle e Bidens segetum Mart. ex Colla são duas espécies pertencentes à família Asteraceae. Os extratos dessas duas espécies foram avaliados quanto às suas atividades citotóxica, antioxidante e antiviral. Todos os extratos analisados apresentaram citotoxidade muito alta contra linhagens de células RBL-2H3. O ensaio de atividade antioxidante demonstrou uma alta atividade das frações em acetato de etila de B. segetum e P. alopecuroides. Isso pode ser parcialmente explicado pelo alto conteúdo de cumarinas, ao menos para P. alopecuroides. Nenhum dos extratos etanólicos totais de B. segetum mostraram atividade significativa contra o vírus Herpes simplex (Tipos 1 e 2 resistentes ao aciclovir). O extrato etanólico de P. alopecuroides também foi inativo contra o vírus Herpes simplex tipo 1 resistente ao aciclovir. Entretanto, este extrato apresentou atividade inibitória contra o vírus Herpes simplex tipo 2 resistente ao aciclovir. Do extrato etanólico bruto de P. alopecuroides foi possível isolar a 7-(2',3'-dihidroxi-3'-metilbutiloxi)-6-metoxicumarina, a qual foi testada nas mesmas condições, demonstrando um índice de inibição viral quase duas vezes maior do que o da amostra de P. alopecuroides para HSV-2-ACVr. A cumarina tabém foi ativa contra HSV-1-ACVr. Esses resultados evidenciam a importância de Pterocaulon alopecuroides e Bidens segetum como plantas medicinais.Unitermos: Pterocaulon alopecuroides, Bidens segetum, atividade antiviral, atividade citotóxica, atividade antioxidante, 7-(2',3'-dihidroxi-3'-metilbutiloxi)-6-metoxicumarina. ABSTRACT:Pterocaulon alopecuroides (Lamark) De Candolle and Bidens segetum Mart. ex Colla are two species belonging to the Asteraceae family. Extracts from those two species were evaluated to their cytotoxic, antioxidant and antiviral activities. All the extracts assayed have shown a very high cytotoxity against RBL-2H3 cell line. The antioxidant assay pointed out a really high activity of the ethyl acetate extracts for B. segetum and P. alopecuroides. This can be partially explained due to the high content of coumarins, at least for P. alopecuroides. None of the total ethanol extracts from B. segetum showed significant activity against the two strains of Herpes simplex virus (Types 1 and 2 resistant to acyclovir). P. alopecuroides ethanol extract was also inactive against the Herpes simplex virus type 1 resistant to acyclovir. However, this extract presented inhibitory activity against the Herpes simplex virus type 2 resistant to acyclovir. From the ethanol crude extract of P. alopecuroides, it was possible to isolate 7-(2',3'-dihidroxy-3'-methylbutyloxy)-6-methoxycoumarin, which was tested in the same conditions, showing a viral inhibitory rate almost twice bigger than the P. alopecuroides sample for HSV-2-ACVr. The coumarin was also active against HSV-1-ACVr. Those results provide further evidence of the importance of Pter...

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Section: Resultsmentioning

confidence: 54%

In vitro cytotoxic, antioxidant and antiviral effects of Pterocaulon alopecuroides and Bidens segetum extracts

Silveira¹,

Martins²,

Costa³

et al. 2009

Rev. bras. farmacogn.

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“…Because of their sweet scent, readily recognized as the scent of newly-mown hay, coumarins have been used in perfumes since 1882. In addition to their use in perfumes, coumarins also constitute an important class of natural and synthetic products [4,5]. For instance, warfarin, a synthetic derivative of coumarin and also known under the brand names "Coumadin," "Jantoven," "Marevan," "Lawarin," and "Waran" is commonly used as an anticoagulant.…”

Section: Coumarin Dyesmentioning

confidence: 99%

Discovery of New Fluorescent Dyes: Targeted Synthesis or Combinatorial Approach?

Kim

Park

2010

Springer Series on Fluorescence

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Because of their advantageous properties, fluorescent organic molecules have been used extensively in various applications. Despite the high demand for fluorophores, there are only a limited number of fluorescent organic core skeletons with sufficient flexibility in their synthetic strategies. The rational design of fluorescent probes having desirable photophysical properties is still far from being achieved because of the complexity of underlying photophysical phenomena of fluorescent small molecules. To study and improve the photophysical properties of fluorescent core skeletons, many efforts have been pursued. Traditionally, targeted approach had been used to rationally study the photophysical properties of known fluorescent core skeleton. On the other hand, recent studies showed that combinatorial approach can act as a powerful tool to discover or develop novel fluorescent probes. Through a comparison between targeted synthesis and combinatorial approach in the study of fluorescent organic compounds, we can conclude that the targeted synthesis with rational design and systematic modification using combinatorial approach are complementary to each other for the discovery of novel, small molecules with desired photophysical properties.

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“…The results demonstrated that any hydroxyl group nearer to the 4hydroxyl group interfere with the hydrogen bond between this group and Asp25/Asp25 0 of HIV-1 protease however, distant 7hydroxy derivatives were most active anti-HIV agents. Replacement of 3-phenyl with benzyl group indicates that flexibility did not lead to any significant change in activity [39]. Similarly, another scientist Stanchev et al also reported some 4-HC derivatives as HIV-1 protease inhibitors.…”

Section: Introductionmentioning

confidence: 98%

Therapeutic potential of coumarins as antiviral agents

Hassan

Osman

Ali

et al. 2016

European Journal of Medicinal Chemistry

309

126

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Coumarins have received a considerable attention in the last three decades as a lead structures for the discovery of orally bioavailable non-peptidic antiviral agents. A lot of structurally diverse coumarins analogues were found to display remarkable array of affinity with the different molecular targets for antiviral agents and slight modifications around the central motif result in pronounced changes in its antiviral spectrum. This manuscript thoroughly reviews the design, discovery and structure-activity relationship studies of the coumarin analogues as antiviral agents focusing mainly on lead optimization and its development into clinical candidates.

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Structure—Activity Relationships of Some 3‐Substituted‐4‐hydroxycoumarins as HIV‐1 Protease Inhibitors.

Cited by 17 publications

References 1 publication

In vitro cytotoxic, antioxidant and antiviral effects of Pterocaulon alopecuroides and Bidens segetum extracts

In vitro cytotoxic, antioxidant and antiviral effects of Pterocaulon alopecuroides and Bidens segetum extracts

Discovery of New Fluorescent Dyes: Targeted Synthesis or Combinatorial Approach?

Therapeutic potential of coumarins as antiviral agents

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