Metabolism of ipriflavone (TC-80) in rats

Metabolic studies of ipriflavone (TC-80) in rats by gas-liquid chromatography-mass spectrometry led to the characterization of the following metabolites: the parent compound, 7-hydroxy-3-phenyl-4H-1-benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 3-(4-hydroxyphenyl)-7-isopropoxy-4H-1-benzopyran-4-one, 2-(3-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxypropionic acid, 2-[3-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl]oxypropionic acid and 2-[3-(3-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl]oxypropionic acid. From the metabolites identified, TC-80 was shown to be metabolized primarily by oxidation. In vitro study using tissue slices of rats indicated that the above metabolic changes occurred exclusively in the liver. It was also demonstrated that the compound did not undergo metabolic conversion by gut flora of rats.     

Alpha-glucosidase inhibitory constituents from Cuscuta reflexa

Two new compounds, 7'-(3',4'-dihydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide (4), and 7'-(4'-hydroxy,3'-methoxyphenyl)-N-[(4-butylphenyl)ethyl]propenamide (5) have been isolated from Cuscuta reflexa along with five known compounds, 6,7-dimethoxy-2H-1-benzopyran-2-one (1), 3-(3,4-dihydroxyphenyl)-2-propen-1-ethanoate (2), 6,7,8-trimethoxy-2H-1-benzopyran-2-one (3), 3-(4-O-beta-D-glucopyranoside-3,5-dimethoxyphenyl)-2-propen-1-ol (6), 2-(3-hydroxy-4-methoxyphenyl)-3,5-dihydroxy-7-O-beta-D-glucopyranoside-4H-1-benzopyrane-4-one (7), reported for the first time from this species. Structures of these compounds were determined by spectral analysis. These compounds showed strong inhibitory activity against alpha-glucosidase.     

Triterpene and coumarins from Skimmia laureola

In the course of our studies on the chemical constituents of the leaves of Skimmia laureola, a new triterpene O-methyl cyclolaudenol (1) and a new coumarin, (+)-7-methoxy-6-(2'R-methoxy-3'-hydroxy-3'-methyl butyl) coumarin (2) were isolated. In addition five known coumarins, isogospherol (3), heraclenol (4), 5,8-dimethoxy coumarin-2H-1-benzopyran-2-one (5), 7-methoxy-6[2'-oxo-3'-methyl butyl] coumarin (6), and (+)-ulopterol (7) were also isolated for the first time from this plant. The structures were identified by spectroscopic studies and the stereochemistry at C-2' in compounds 3 and 4 were established by Horeau's procedure.     

Plant Coumarins. 2. Beckmann Rearrangement of Oreoselone <Emphasis Type="Italic">E</Emphasis>- and <Emphasis Type="Italic">Z</Emphasis>-Oximes

Oximation of oreoselone to produce a mixture the E- and Z-oximes was investigated. The crystal and molecular structures of oreoselone Z-oxime and the Beckmann rearrangement product of oreoselone E- or Z-oximes and PCl₅, 7-(1-chloro-2-methylpropoxy)-2-oxo-2H-1-benzopyran-6-carbonitrile, were established by XSA. Hydrolysis of the latter produced 7-hydroxy-2-oxo-2H-1-benzopyran-6-carbonitrile. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 541–545, November–December, 2005.     

A prenyloxycoumarin from Psiadia dentata

A new coumarin identified as 5-hydroxy-6-methoxy-7-(3-methyl-but-2-enyloxy)-2H-1-benzopyran-2-one (isoobtusitin) was isolated from Psiadia dentata. This compound showed, in vitro, a moderate inhibitory activity against poliovirus and a very weak activity against (HIV), whereas it was inactive against (HSV1), (VSV), and murine tumoral cell lines (3LL, L1210).     

Synthesis, photophysical, photochemical and biological properties of caged GABA, 4-[[(2H-1-benzopyran-2-one-7-amino-4-methoxy) carbonyl] amino] butanoic acid

The photorelease of a caged neurotransmitter can be used to investigate the function of neuronal circuits in tissues. We have designed and synthesized a stable, caged gamma-aminobutyric acid (GABA) derivative, 4-[[(2H-1-benzopyran-2-one-7-amino-4-methoxy)carbonyl]amino] butanoic acid (BC204), that releases the neurotransmitter in physiological medium when irradiated with UV light at 300-400 nm in PBS at pH 7.4. The release of GABA occurs with the formation of the major photoproduct, 7-amino-4-(hydroxymethyl)-2H-1-benzopyran-2-one, via a solvolytic photodegradation mechanism of the coumarin moiety and was confirmed by electrospray mass spectrometry/mass spectrometry (ESI MS/MS). BC204 is chemically stable and shows no intrinsic activity after many hours under physiological dark conditions. These properties suggest that BC204 is an excellent form of caged GABA that is well suited for long-term biological studies.     

Studies on the sequential claisen rearrangement of methyl-3-arlyloxy- 2-(aryloymethyl)prop-2-enolates

Claisen rearrangement of methyl-3-aryloxy-2-(aryloxymethyl)prop-2-enoates (4) in refluxing N,N-diethylaniline gave 3-(2-hydroxyphenylmethylene) -3,4-dihydro-2H-1-benzopyran-2-ones (6) and 3-methoxycarbonyl-2H-1-benzopyrans(7).     

Condensation Op 3-Acetyl-and 3-Acetyl-4-Methyl-2H-1-Benzopyran-2-One with Aromatic Adehydes

The reactivities of 3-acetyl-2H-1-benzo-pyran-2-one (2) and 3-acetyl-4-methyl-2H-1-benzopy-ran-2-one (3)are compared in the condensation with aromatic aldehydes. It is established that the benzopyrones 2 and 4 condense with various aromatic aldehydes in chloroform containing some drops of piperidine by boiling for 7 hours and azeotropic distillation of water, yielding 3-cinnamoyl-2H-1-benzopyran-2-ones (3a-g) and 4-(2-arylvinyl)-3-acetyl-2H-1-benzopyran-2-ones (6a-f), respectively. Evidence is provided that benzopyrone 4 participates in the condensation with the methyl group in position 4. A probable mechanism of the process is proposed.     

Aryloxyacetic acid diuretics with uricosuric activity. II. Substituted [(4-oxo-4H-1-benzopyran-7-yl)oxy]acetic acids and the related compounds.

Di- and tri-substituted [(4-oxo-4H-1-benzopyran-7-yl)oxy]acetic acids, and 4-oxo-3-phenyl-4H-furo[2,3-h]-[1]benzopyran-8-carboxylic acid were synthesized and tested for natriuretic and uricosuric activities. Among the compounds tested, 3,5-disubstituted [(4-oxo-4H-1-benzopyran-7-yl)oxy]acetic acids (6c-f, h, n and x) showed potent natriuretic and uricosuric activities, whereas 4-oxo-3-phenyl-4H-furo[2,3-h][1]benzopyran-8-carboxylic acid (6dd) possessed only potent natriuretic activity. The structure-activity relationships are also discussed.     

Five new peltogynoids from underground parts of Iris bungei: a Mongolian medicinal plant

Five new peltogynoids, irisoids A-E (1-5), have been isolated from the underground parts of Iris bungei. The structures of the new compounds were established on the basis of spectroscopic methods and were found to be 1,8,10-trihydroxy-9-methoxy-[1]benzopyrano-[3,2-c][2]-benzopyran-7(5H)-one (1), 1,8-dihydroxy-9,10-dimethoxy-[1]benzopyrano-[3,2-c][2]-benzopyran-7(5H)-one (2), 1,10-dihydroxy-8,9-dimethoxy-[1]benzopyrano-13,2-c][2]-benzopyran-7(5H)-one (3), 1,8-dihydroxy-9,10-methylenedioxy-[1]benzopyrano-[3,2-c][2]-benzopyran-7(5H)-one (4), and 1,8,11-trihydroxy-9,10-methylenedioxy-[1]benzopyrano-[3,2-c][2]-benzopyran-7(5H)-one (5). The structure of irisoid B (2) was established unambiguously by X-ray diffraction study.     

Synthesis of 3-(2H-Indazol-2-yl)-2H[1]-Benzopyran-2-Ones

Hitherto unknown 3-(2H-Indazol-2-yl)-2H[1] benzopyran-2-ones (4a-f) have been synthesized under the trithyl phosphite (TEP) mediated reaction conditions of 3-[[(2-nitro-phenyl)-methylene]amino]-2H-1-benzopyran-2-ones (3a-f), obtained by the condensation of 3-amino coumarins (1a-f) with 2-nitro-benzaldehyde (2).     

Isolation of tetraprenyltoluquinols from the brown alga Sargassum thunbergii

Thunbergols A (4) and B (5), tetraprenyltoluquinols, along with three known compounds (1-3) have been isolated from the brown alga Sargassum thunbergii. The structures of these two new compounds were determined to be 9-(3,4-dihydro-2,8-dimethyl-6-hydroxy-2H-1-benzopyran-2-yl)-6-methyl-2-(4-methyl-3-pentenyl)-(2E,6E)-nonadienoic acid (4) and 10-(2,3-dihydro-5-hydroxy-7-methyl-1-benzofuran-2-yl)-10-hydroxy-6-methyl-2-(4-methyl-3-pentenyl)-(2E,6E)-undecadienoic acid (5), respectively, by combined spectroscopic methods. Both of them exhibited significant scavenging activities on radical and potently inhibited generation of ONOO(-) from morpholinosydnonimine (SIN-1).     

PHOTOCHEMISTRY OF PESTICIDES, 13.1 SOME PHOTOREACTIONS OF O,O-DIETHYL-O-(4-METHYL-2-OXO-2H-1-BENZOPYRAN-7-YL)-PHOSPHOROTHIOATE (POTASAN®)

Abstract

UV-irradiation (δ > 313nm) of O,O-diethyl-O-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-phosphoro-thioate (Potasan®) la in chloroform and/or methanol with and without singlet oxygen results in the formation of the 2-oxo-2H-1-benzopyran-phosphate 2 the 3,3′-bipotasan dehydrodimer 3, and 7-ethoxy-4-methyl-2-oxo-2H-1-benzopyran 4: the mechanisms of formation, especially for 4 are discussed.     

Complex compounds of zinc and copper(ii) ions with dihydroquercetin and their antiviral activity

Russian Chemical Bulletin - Complex compounds of zinc and copper(ii) with trans-2R,3R-dihydro-2-(3,4-dihydroxy-phenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one (dihydroquercetin) were synthesized...     

A new homostilbene and two new homoisoflavones from the bulbs of Scilla scilloides

A new homostilbene, named scillabene A (2), and two new homoisoflavones, named scillavones A (3) and B (4), were isolated from the bulbs of Scilla scilloides DRUCE (Liliaceae) along with 13 known compounds comprising a homostilbene, seven homoisoflavones, a xanthone, a lignan, and three nortriterpenes. The structures of 2-4 were characterized as 3,5,4'-trihydroxy-3'-methoxy-4-methyl-trans-stilbene, (3R)-5,7,2'-trihydroxy-3',4'-dimethoxyspiro{2H-1-benzopyran-7'-bicyclo[4,2,0]octa[1,3,5]-trien}-4-one and (3S)-3-(3,4-dihydroxybenzyl)-5-hydroxy-6,7-dimethoxychroman-4-one, respectively, on the basis of spectroscopic data and X-ray crystallographic analysis.     

Synthesis of [1]Benzopyrano[3,4-c][2]benzazepine-6, 8, 13(7H)-triones

Hitherto unknown [1] benzopyrano [3,4-c] [2] benzazepine-6,8,13(7H)-triones (4a-e) have been synthesized by the intramolecular cyclodehydration of N-(2-oxo-2H-1-benzopyran-3-yl) phthalamic acids (3a-e) obtained by the reaction of 3-amino coumarins (1a-e) with phthalic anhydride (2)     

A study of the catalytic reductive products of 2,3-dihydro-6-methoxy-3-(6-nitroveratrylidene)-4H-benzopyran-4-one. Part II

Although the previously reported (1,2) chemical reduction of 2,3-dihydro-3-(6-nitroveratry-lidene)-4H-benzopyran-4-one with stannous chloride occurred with cyclization to the 6H-[1]-benzopyrano [4,3-b]quinoline ring system, the present study of the catalytic (palladium/carbon) reduction of 2,3-dihydro-6-methoxy-3-(6-nitroveratrylidene)-4H-benzopyran-4-one ( 1 ) (3) has indicated that other products in addition to the expected benzopyranoquinoline ( 3 ) may be isolated, depending upon the conditions of the reduction. The products of the reduction of 1 , isolated and structurally determined, include 2,9,10-trimethoxy-6H-[1]benzopyrano-[4,3-b]quinoline(3),2,9,10-trimethoxy-6a,7,12,12a-tetrahydro-6H-[1]benzopyrano[4,3-b]-quinoline (2), the N-oxide of 3 (6 ), and 6-hydroxy-2,9,10-trimethoxy-6H-[l]benzopyrano-[4,3-b Jquinoline ( 8 ).     

Synthesis,Characterization, and Antimicrobial Evaluation of New Imidazo[2,1-b][1,3,4]thiadiazoles Bearing a Chroman Moiety

Russian Journal of Organic Chemistry - A series of 6-aryl-2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)imidazo[2,1-b][1,3,4]thiadiazoles were synthesized through a two-step procedure. The structure...     

藤三七中一个新黄烷醇和抗HIV活性成分

利用各种色谱(硅胶和凝胶)方法, 从藤三七[Boussingaultia gracilis Miers var. pseudobaselloides Bailey]的70%(体积分数)的乙醇提取物中分离得到2个黄烷醇类化合物(1, 2)和4个黄酮类化合物(3~6). 采用UV, IR, MS 和1D, 2D NMR方法, 分别鉴定出如下化合物: 7-羟基-5-甲氧基-8-甲基-6-甲酰基-3,4-黄烷二醇, 命名为藤三七醇A(1); 4,7-二羟基-5-甲氧基-8-甲基-6-甲酰基黄烷(2); 7-O-methylunonal(3); 5,7-二羟基-6, 8-二甲基-2-苯基-4H-1-苯并吡喃-4-酮(4); Desmosflavone(5)和Demethoxymatteucinol(6). 其中化合物1是一个新的黄烷二醇化合物, 化合物2~6为首次从该植物中分离得到. 抗HIV-1活性筛选结果表明: 化合物1, 2, 5, 6对HIV-1诱导合胞体的形成具有一定的抑制作用, 其半数有效浓度(EC50)分别为45.09, 48.73, 55.47 和 82.75 μmol/L, 治疗指数(TI)分别为1.41, 1.20, 7.15 和>8.51.     

Total synthesis of quercetin 3-sophorotrioside

5,7-dihydroxy-3-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one (quercetin 3-sophorotrioside), a flavonol triglycoside, isolated from Pisum sativum shoots and showing protective effects on liver injury induced by chemicals, was synthesized for the first time. The target compound was successfully synthesized in eight linear steps and in 39% overall yield through a combination of phase-transfer-catalyzed (PTC) quercetin C-3 glycosylation and silver triflate (AgOTf) promoted carbohydrate chain elongation using both sugar bromide and trichloroacetimidate donors.