Synthesis and antiviral activity of 4'-hydroxy-5,6,7,8-tetramethoxyflavone

Burnham, W. S.; Sidwell, Robert W.; Tolman, Richard L.; Stout, M.G.

doi:10.1021/jm00280a023

Cited by 12 publications

(11 citation statements)

References 2 publications

(2 reference statements)

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“…1 A recent study on selective methylations of quercetin by Rolando et al gave the order of reactivity as 7 > 3 > 3′ > 5 for the phenol groups in tamarixetin (6). 13 We decided to confirm this theoretical order by a preliminary methylation study, carried out on a small scale (0.1 mM) with 6 and its 6,8-dibromo analogue (7). According to our previous studies 14,15 in the same field, attempts at bromination of 6 were undertaken with N-bromosuccinimide (2 equiv, rt) in a mixture of CH 2 Cl 2 -MeOH (2:1).…”

Section: Resultsmentioning

confidence: 89%

“…Thus, we turned to semisynthetic methods starting from readily available natural sources. Tangeretin ( 2 ) appeared of interest, since its alkaline degradation is known to provide in a single step 2′-hydroxy-3′,4′,5′,6′-tetramethoxyacetophenone ( 3 ), a key intermediate compound toward the synthesis of 1 . However, although 2 occurs in high concentration in the peel of various Citrus species such as sweet orange [ Citrus sinensis (L.) Pers.]…”

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confidence: 99%

“…Tangeretin (2) appeared of interest, since its alkaline degradation is known to provide in a single step 2′hydroxy-3′,4′,5′,6′-tetramethoxyacetophenone (3), a key intermediate compound toward the synthesis of 1. 7 However, although 2 occurs in high concentration in the peel of various Citrus species such as sweet orange [Citrus sinensis (L.) Pers.] and mandarin (Citrus reticulata Blanco), commercial sources are scarce and the product is expensive.…”

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confidence: 99%

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Semisynthesis of Natural Flavones Inhibiting Tubulin Polymerization, from Hesperidin

et al. 2010

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Semisynthesis of 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone (1), a natural flavone that binds with high affinity to tubulin, was performed from hesperidin, the very abundant Citrus flavanone, by a five-step sequence. The last step of the synthesis also gave rise to 5,3'-dihydroxy-3,6,7,4'-tetramethoxyflavone (= casticin or vitexicarpin) (10), 5,3'-dihydroxy-3,7,8,4'-tetramethoxyflavone (= gossypetin 3,7,8,4'-tetramethyl ether) (11), and, unexpectedly, 5,7,3'-trihydroxy-3,6,8,4'-tetramethoxyflavone (12) and 5,3'-dihydroxy-8-dimethylamino-3,6,7,4'-tetramethoxyflavone (= 8-dimethylaminocasticin) (13). Cytotoxicity and antitubulin activity of these five flavones, as well as 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (= ayanin) (14) and intermediate 6,8-dibromo-ayanin (8), were evaluated. Comparison of the responses confirmed and clarified the influence of the A-ring substitution pattern on the biological activity.

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confidence: 89%

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confidence: 99%

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Semisynthesis of Natural Flavones Inhibiting Tubulin Polymerization, from Hesperidin

et al. 2010

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“…Naturally occurring chalcones derived from general foods are phloretin and its glucoside phloridzin chalconaringenin, and arbutin. Most of the studies to date, regarding the synthetic approaches of chalcone derivatives [ 17 , 18 , 19 , 20 , 21 ],were reported by the organic and medicinal chemists through the formation of the 1,4-enones using acid- or base-catalysed condensation reactions of aldehyde and aryl methyl ketones in alcoholic solvents with variable yields.…”

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confidence: 99%

Practical Synthesis of Chalcone Derivatives and Their Biological Activities

et al. 2017

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Practical synthesis and biological activities of 4-hydroxy-3-methoxy-2-propene derivatives are described. The novel chalcone derivatives were prepared by acid catalysed one-step condensation of 1,3- or 1,4-diacetylbenzene and 1,3,5-triacetylbenzene with 4-hydroxy-3-methoxybenzaldehyde. They were then evaluated for free radical scavenging activity, suppression of lipopolysaccharides (LPS)-induced NO generation, and anti-excitotoxicity in vitro. It was found that all compounds showed good effects for 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging, LPS-induced NO generation, and anti-neurotoxicity. Compounds 6 and 7 were potent suppressor of NO generation with the concentration range 10 µM and especially compound 8 showed very potent anti-inflammatory activity with 1 µM. In addition, the di- and tri-acetylbenzyl derivatives 6, 7, and 8 showed enhanced anti-neurotoxicity activity in cultured cortical neurons. Molecular modelling studies to investigate the chemical structural characteristics required for the enhanced biological activities interestingly revealed that compound 8 has the smallest highest occupied molecular orbital-lowest energy unoccupied molecular orbital (HOMO-LUMO) gap, which signifies easy electron and radical transfer between HOMO and LUMO in model studies.

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“…Several compounds have been selected recently as inhibitors of the in vitro multiplication of rhinoviruses, namely guanidine [20], HBB and other benzimidazoles [9,18,20], a thiosemicarbazone derivative [8], 3-substituted triazinoindoles [3,8,10,11,14,15,21], some pyrimidine analogues [12,13,19], 4'-hydroxy-5,6,7,8-tetramethoxyflavone [4], and aromatic sulfonic acids [2]. Of all substances studied only some triazi-noindoles were active in vivo, in rhinovirus infections in primates [3,15] but not in humans [21].…”

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Antiviral Activity of N-Phenyl-N′-arylthiourea Derivatives against some Rhinoviruses

Galabov¹,

Velichkova²,

Vassilev³

1977

Chemotherapy

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The effect of 12 derivatives of N-phenyl-N′-aryl- or alkylthiourea, inhibitors of human enteroviruses and foot-and-mouth disease virus, on reproduction of some rhinoviruses (H-17, B-632) in HeLa Bristol cells was studied. As screening methods both the multicycle growth test in roller tube cultures and two variants of plaque inhibition tests were employed. The compounds selected were tested in one-step growth cycle set-up. We established that N-phenyl-N′-4-hydroxyphenyl-thiourea (V-24) and N-phenyl-N′-2-carboxyphenylthiourea (V-17) have a distinct inhibitory effect on the growth of rhinovirus H-17, and N-phenyl-N′-2-hydroxy-5-nitrophenylthiourea (V-25) inhibited strongly the multiplication of rhinovirus B-632.

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Synthesis and antiviral activity of 4'-hydroxy-5,6,7,8-tetramethoxyflavone

Cited by 12 publications

References 2 publications

Semisynthesis of Natural Flavones Inhibiting Tubulin Polymerization, from Hesperidin

Semisynthesis of Natural Flavones Inhibiting Tubulin Polymerization, from Hesperidin

Practical Synthesis of Chalcone Derivatives and Their Biological Activities

Antiviral Activity of N-Phenyl-N′-arylthiourea Derivatives against some Rhinoviruses

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