Effect of chloro-, cyano-, and amidino-substituted flavanoids on enterovirus infection in vitro

Genovese, D.; Conti, Cinzia; Tomao, Paola; Desideri, N.; Stein, M. L.; Catone, Stefania; Fiore, Lucia

doi:10.1016/0166-3542(95)00088-4

Cited by 38 publications

(32 citation statements)

References 20 publications

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“…Generally, the additional presence of a chlorine in the 6 position further increased the antiviral effect of 3-substituted flavones. These data confirm the importance of this halogen for good antiviral activity in vitro (Burali et al, 1987;Conti et al, 1990a;Desideri et al, 1990Desideri et al, , 1992Genovese et al, 1995). However, overall analysis of the activities of all these compounds indicates that substituted f1avones and f1avanones are less promising as anti-picornavirus agents than the previously synthesized flavanoids.…”

Section: Discussionsupporting

confidence: 49%

“…In recent years new derivatives of flavans, isoflavans and isoflavenes have been synthesized and tested against members of this virus family (Burali et al, 1987;Conti et al, 1988Conti et al, , 1990aConti et al, , 1990bSuperti et al, 1989;Desideri et al, 1990Desideri et al, , 1992Quaglia et al, 1991Quaglia et al, , 1992Quaglia et al, , 1993Genovese et al, 1995). Different substituents have been located in the 6 and 4' positions of the previously mentioned f1avanoids where chlorine, cyano, oxazoline and carboxy groups were found to be the most favourable for anti-picornavirus activity.…”

Section: Introductionmentioning

confidence: 99%

“…This inhibits the uncoating event after penetration of the resulting Virus-drug complex into cells (Conti et sl., 1988(Conti et sl., , 1992. Some other flavanoids interfere at an early stage between the uncoating of the viral genome and the initiation of viral protein synthesis (Conti et al, 1990b, Genovese et al, 1995. Natural flavonoids, characterized by a 4-carbonyl function, represent a broad group of compounds isolated from higher plants used in traditional medicine.…”

Section: Introductionmentioning

confidence: 99%

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In vitro Evaluation of the Anti-Picornavirus Activities of New Synthetic Flavonoids

Desideri

Conti

Sestili

et al. 1995

Antivir Chem Chemother

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SummarySubstituted oxazolinylflavons and oxazolinylflavanones were synthesized in order to compare their anti-picornavirus activities with those of related natural and synthetic compounds. The antiviral potencies of the new compounds were evaluated against rhinovirus type 1B and poliovirus type 2 by a plaque reduction assay in HeLa cell cultures. Among the substituted flavanones only 6-chloro-4'-oxazolinylflavanone showed activity against both viruses. A comparison of the effects of 3-substituted f1avones indicated that the presence of a 3-methoxy group enhances the activity against rhinovirus, while the presence of a 3-hydroxy group enhances the activity against poliovirus.

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Section: Discussionsupporting

confidence: 49%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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In vitro Evaluation of the Anti-Picornavirus Activities of New Synthetic Flavonoids

Desideri

Conti

Sestili

et al. 1995

Antivir Chem Chemother

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“…The concentration reducing cell viability by 50% was not measurable because of the very low solubility of compounds in the cell culture medium. All the derivatives tested were more toxic for HeLa cells than 4′,6-dichloroflavan (BW683C) (Bauer et al, 1981), which was utilized as a reference compound to allow a comparison of the results of this study with our preceding research on anti-picornavirus drugs (Burali et al, 1987;Conti et al, 1988Conti et al, , 1990aConti et al, ,b, 1992Desideri et al, 1990Desideri et al, , 1992Desideri et al, , 1995Desideri et al, , 1997Quaglia et al, 1991Quaglia et al, , 1992Quaglia et al, , 1993Genovese et al, 1995). The analysis of the values of the maximum nontoxic concentration for cell morphology and viability indicated that 3-acetoxyflavones (1c-d) were less toxic for HeLa cells than 3-hydroxyflavones (1a-b); they were also the least toxic compounds among all the substituted flavones utilized in this research.…”

Section: Resultsmentioning

confidence: 99%

Anti-Picornavirus Activity of Synthetic Flavon-3-yl Esters

Conti

Mastromarino

Sgro

et al. 1998

Antivir Chem Chemother

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Members of the family Picornaviridae, which comprise rhinoviruses and enteroviruses, are responsible for several human diseases. It is estimated that over 100 serotypes of human rhinoviruses (HRV) cause approximately half of all cases of the common cold. Also, poliomyelitis still represents a relevant health problem in some countries of the world, despite a dramatic decrease in its incidence as a result of intensive vaccination programmes in developed countries. There therefore exists a need to search for effective chemotherapeutic agents for picornavirus infections.Several classes of flavonoids, isolated from plants utilized in traditional medicine, possess a well recognized anti-picornavirus activity (Van Hoof et al.,1984;Kaul et al., 1985;Tsuchiya et al., 1985). Among polyhydroxylated flavones, quercetin was originally described to reduce the infectivity and the intracellular replication of poliovirus type 1 (PV-1), but not of PV-2 or PV-3. Hesperetin, a flavanone, was able to interfere with PV-1 infection of cell monolayers without affecting virus infectivity (Kaul et al., 1985). 3-Methoxylated flavones, such as chrysosplenol B and C, and axillarin, were found to have potent anti-HRV activity, whereas flavones without a methoxyl group at the 3-position had no anti-rhinovirus activity (Tsuchiya et al., 1985). Beside an effect on HRVs, 4′,5-dihydroxy-3,3′,7-trimethoxyflavone (Ro-09-0179) also exerted an inhibitory activity against coxsackieviruses in tissue cultures (Kaul et al., 1985). The mechanism of action of flavonoids has been attributed to interference with an early stage of viral infection, probably represented by viral RNA synthesis (Castrillo et al., 1986;Gonzales et al., 1990).The study of various synthetic flavones, structurally related to natural flavonoids, confirmed the anti-picornavirus activity of this class of compounds (De Meyer et al., 1991;Desideri et al., 1995). Among the derivatives studied by us, flavanones were generally less effective against picornaviruses than flavones, and 3-hydroxy or 3-methoxyflavones were more active than 3-unsubstituted flavones. The presence of a 3-hydroxy group increased the anti-PV potency, whereas a 3-methoxy group enhanced the effect against HRV-1B ( Desideri et al., 1995). In order to further study the influence on anti-picornavirus activity of the substituent in position 3 of synthetic flavones, we extended our research to esters of chloroflavon-3-ols with natural occurring hydroxybenzoic and hydroxycinnamic acids, i.e. gallic, syringic, caffeic, vanillic and ferulic acids (compounds 2 a-h, 3 a-l). Materials and Methods: VirologyCells HeLa (Ohio) cells were routinely grown at 37°C in 75 cm 2 tissue culture flasks using Eagle's MEM supplemented with 100 µg/ml of streptomycin and 100 U/ml of penicillin G. Eight percent heat-inactivated fetal calf serum (FCS) was added for cell growth (growth medium); the concentration was reduced to 2% for cell maintenance (maintenance medium). The in vitro antiviral activity against picornaviruses (rhinovirus serotype 1B ...

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“…[6][7][8][9][10][11] Flavanoids inhibit xanthine-oxidase enzyme and have superoxide-scavenging activities. Therefore they could be a promising remedy for human gout and ischemia by decreasing both uric acid and superoxide concentration in human tissues.…”

mentioning

confidence: 99%

Synthesis, Biological Evaluation and In Silico Metabolic and Toxicity Prediction of Some Flavanone Derivatives

Moorthy

Singh

et al. 2006

Chem. Pharm. Bull.

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Flavones, which are also known as anthoxanthins, are widely distributed as yellow coloured plant pigment (flavus, latin meaning yellow) and occur either in the free state or as glycosides associated with tannins. The derivatives of phenol present as glycosidal form and chemically they are derivatives of phenyl benzo-Y-pyrone (chromone) ring.1,2) The basic flavanoid structure is a flavone nucleus, which consists of 15 carbon atom, arranged in 2 rings labeled as A, B, C. In nature, they are available as flavone, flavonol, flavanone, isoflavone, chalcone and their derivatives. In acidic medium, it forms oxonium salts, which are very unstable in water and are hydrolyzed back to freebase. [3][4][5] Natural and synthetic flavanoids and flavanones have attracted considerable attention because of their interesting biological activity, including, antioxidant, antifungal, antibacterial, anti-inflammatory, antiasthmatic, antihypertensive, antiviral, estrogenic and diuretic activity.6-11) Flavanoids inhibit xanthine-oxidase enzyme and have superoxide-scavenging activities. Therefore they could be a promising remedy for human gout and ischemia by decreasing both uric acid and superoxide concentration in human tissues. 12)There are number of methods available for the synthesis of flavanoids and flavanones like Kostanecki method, 13,14) Allan-Robinson method, 15) Mahal-Venkataraman method, 16) the Chalcone method, the Wheeler method and others. Almost all the methods of synthesis of flavanones and flavanoids required more amount of heating during the reaction and the yields of the products obtained was less (50-60% yield). 17-19)The metabolic fate and toxicity of a molecule is highly dependent upon its structural elements. Exogenous chemicals entering a living system can undergo a number of chemical modifications by a wide array of enzymes, which use these chemicals as substrates. Rarely does a compound simply produce a single metabolite, in general, complex metabolic pattern of competitive and sequential reactions occur. Synthesis, Biological Evaluation and In Silico Metabolic and Toxicity Prediction of Some Flavanone DerivativesNarayana Subbiah Hari Narayana MOORTHY,* Rahul Jitendra SINGH, Hemendra Pratap SINGH, and Sayan Dutta GUPTA School of Pharmaceutical Sciences, Rajiv Gandhi Proudyogiki Vishwavidyalaya; Airport Bypass Road, Gandhi Nagar, Bhopal-462036, Madhya Pradesh, India. Received May 8, 2006; accepted June 29, 2006 Flavones chemically are anthoxanthins, occur either in the free state or as glycosides associated with tannins (flavanoids). Flavanoids (derivatives of flavone) possess various pharmacological activities and due to its xanthine-oxidase enzyme inhibitory effect it also has superoxide-scavenging activities. A series of 2-phenyl-2,3-dihydrochromon-4-one derivatives (flavanone derivatives) were synthesized from chalcones by cyclization method and their activities were evaluated against some gram positive and gram-negative bacteria. IR, NMR and CHN analysis confirmed the structure of the synthesized comp...

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Effect of chloro-, cyano-, and amidino-substituted flavanoids on enterovirus infection in vitro

Cited by 38 publications

References 20 publications

In vitro Evaluation of the Anti-Picornavirus Activities of New Synthetic Flavonoids

In vitro Evaluation of the Anti-Picornavirus Activities of New Synthetic Flavonoids

Anti-Picornavirus Activity of Synthetic Flavon-3-yl Esters

Synthesis, Biological Evaluation and In Silico Metabolic and Toxicity Prediction of Some Flavanone Derivatives

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