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The newly synthesized coumarin derivative with dopamine, 3-(1-((3,4-dihydroxyphenethyl)amino)ethylidene)-chroman-2,4-dione, was completely structurally characterized by X-ray crystallography. It was shown that several types of hydrogen bonds are present, which additionally stabilize the structure. The compound was tested in vitro against different cell lines, healthy human keratinocyte HaCaT, cervical squamous cell carcinoma SiHa, breast carcinoma MCF7, and hepatocellular carcinoma HepG2. Compared to control, the new derivate showed a stronger effect on both healthy and carcinoma cell lines, with the most prominent effect on the breast carcinoma MCF7 cell line. The molecular docking study, obtained for ten different conformations of the new compound, showed its inhibitory nature against CDKS protein. Lower inhibition constant, relative to one of 4-OH-coumarine, proved stronger and more numerous interactions with CDKS protein. These interactions were carefully examined for both parent molecule and derivative and explained from a structural point of view.

An efficient and simple approach for the synthesis of functionalized 4H-chromenes has been developed via acid catalyzed Michael addition of phenols to benzylidene oxobutanoates. Preliminary mechanistic studies were conducted, suggesting that intermediate chroman derivative is initially formed which on dehydration produces final 4H-chromene. The conversion of 4H-chromenes into linear and angular pyranocoumarins is also described. The structural arrangements between the pyran and coumarin rings have been established by X-ray crystallographic analysis and 2D NMR spectroscopy.

Gonadotropin-primed immature rats (GPIR) were used to study the anti-ovulatory effect of 4-(4-hydroxy-3-methyl-hex-5-enyl)-chroman-2,7-diol (chroman derivative) isolated from seeds of Ensete superbum on ovulation. Present results depicted dose-related anti-ovulatory effect of the chroman derivative at 2 mg/kg bw and 4 mg/kg bw. Chroman derivative showed dose-dependent anti-estrogenic activity on MCF-7 cell line. Attenuation of ovulation was associated with a lowered ovarian estrogen and progesterone levels along with reduced levels of some major cytokines, i.e. TNFα, VEGF, IL-6 and IL-1β, indicating the disrupted cytokinine signaling. Unruptured preovulatory follicles were found in all the ovaries extracted from animals treated with chroman derivative. Our findings demonstrated that chroman derivative has potential contraceptive activity through its anti-estrogenic activity which leads to inhibition in ovulation and attenuated ovarian cytokinine signaling.

Treatment of various 3-aryl-1-propanols with 1,3-diiodo-5,5-dimethylhydantoin (DIH) in ethyl acetate or 1,2-dichloroethane under irradiation with a tungsten lamp gave the corresponding chroman derivatives in good to moderate yields. The present reaction proceeds via the initial formation of an alkoxyl radical and the radical cyclization onto the aromatic ring, followed by the oxidation of the formed radical intermediate with DIH to provide the chroman derivative. The same treatment of o-biphenyldimethylcarbinol, o-phenylbenzoic acid, and o-alkylbenzoic acids with DIH provided the corresponding chroman derivatives and lactone derivatives in good yields, respectively.

Chemical and cytotoxicity examinations of the crude methanol extract of the aerial parts of Phyllanthus amarus. Schum. et Thonn. (Euphorbiaceae) were investigated. The cytotoxicity property of the P. amarus. was evaluated in vitro., using the human ovarian A2780 cancer cell. Bioassay-guided fraction of the crude extract (IC50 value of 31.2 µg/mL) showed that the dichloromethane fraction was most toxic with an IC50 value of 22.7 µg/mL, whereas the polar methanol fraction was least cytotoxic with an IC50 value of 31.2 µg/mL. This led to the isolation of a new chroman derivative from the dichloromethane fraction. On the basis of nuclear magnetic resonance and mass spectral data, the structure of the chroman was established as 4,4,8-trimethoxy chroman. The compound exhibited very little or no in vitro. cytotoxicity with an IC50 of 16.2 µg/mL, relative to actinomycin, the reference compound, with an IC50 of 2.0 ng/mL. It can therefore be concluded that the aerial parts of P. amarus., an extensively use...

Reactions of 3-nitro-2H-chromenes with aminoenones derived from acetylacetone and cyclic amines proceed diastereoselectively to give functionalized 2,3,4-trisubstituted chromanes as a result of nucleophilic addition of the vinylogous β-methyl group at the C-4 atom of the chromene system. From these compounds, under acidic conditions, 5-(trifluoromethyl)-5H- chromeno[3,4-b]pyridines and 4-acetoacetonyl-3-nitro-2-(trichloromethyl/phenyl) chromanes, depending on the substituent at the 2-position, were obtained in moderate to good yields. © 2013 Elsevier Ltd. All rights reserved.

Synthesis of naturally occurring 6-(α,β-dihydrocinnamoyl)-3,4-dihydro-2H-chromanes has been carried out by the reaction of 6-acetyl-3,4-dihydro-2H--chromanes with methoxybenzaldehydes followed by hydrogenation of the resulting 6-cinnamoyl-3,4-dihydro-2H--chromanes.

A concise synthesis of the 2-[aminomethyl]chroman derivative BAY×3702 ( 3 ), a potent 5-hydroxytryptamine (5-HT 1A ) antagonist is described. Utilization of a Mitsunobu reaction of phenol ( 11 ) with the non-racemic allylic alcohol ( 12 ) and consequent ring-closing metathesis furnishes the chroman-2-yl framework of 3 in optically active form.

Electrochemical reduction of 4-alkoxy-3-bromochromans in acetonitrile led to a facile ring cleavage reaction yielding 2(α-alkoxy- allyl)phenols which are not easily accessible.

A new chroman derivative, named ruakuric acid, was isolated from a strain of Aspergillus fumigatus growing in conjunction with a coral lichen. The structure was determined as 6-acetyl-5-hydroxy-4-methoxy-chroman-2-carboxylic acid (mixture of 2,4-cis,trans isomers).

Grain is an important source of phytochemicals, which have potent antioxidant capacity. They have been implicated in the beneficial health effect of whole grains in reducing cardiovascular disease and type 2 diabetes. The aim of the present study was to identify the most important antioxidant fractions of wheat grain. It was found that the aleurone content of these fractions was highly correlated with the antioxidant capacity of the fractions (r = 0.96, p < 0.0001). Ferulic acid appeared to be the major contributor to the antioxidant capacity in fractions with higher antioxidant capacity. The contribution of protein was rather limited. It was concluded that the antioxidant potency of wheat grain fractions is predominantly determined by aleurone content, which can be attributed to the presence of relatively large amounts of phenolic compounds, primarily ferulic acid. © 2008 American Chemical Society. Chemicals / CAS: coumaric acid, 25429-38-3; ferulic acid, 1135-24-6, 24276-84-4; trolox C, 56305-04-5; 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid, 56305-04-5; Antioxidants; Chromans; Coumaric Acids; ferulic acid, 1135-24-6; Plant Extracts

Grain is an important source of phytochemicals, which have potent antioxidant capacity. They have been implicated in the beneficial health effect of whole grains in reducing cardiovascular disease and type 2 diabetes. The aim of the present study was to identify the most important antioxidant fractions of wheat grain. It was found that the aleurone content of these fractions was highly correlated with the antioxidant capacity of the fractions (r = 0.96, p < 0.0001). Ferulic acid appeared to be the major contributor to the antioxidant capacity in fractions with higher antioxidant capacity. The contribution of protein was rather limited. It was concluded that the antioxidant potency of wheat grain fractions is predominantly determined by aleurone content, which can be attributed to the presence of relatively large amounts of phenolic compounds, primarily ferulic acid. © 2008 American Chemical Society. Chemicals / CAS: coumaric acid, 25429-38-3; ferulic acid, 1135-24-6, 24276-84-4; trolox C, 56305-04-5; 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid, 56305-04-5; Antioxidants; Chromans; Coumaric Acids; ferulic acid, 1135-24-6; Plant Extracts

A new chroman derivative, named ruakuric acid, was isolated from a strain of Aspergillus fumigatus growing in conjunction with a coral lichen. The structure was determined as 6-acetyl-5-hydroxy-4-methoxy-chroman-2-carboxylic acid (mixture of 2,4-cis,trans isomers).

A simple and high yielding route to 3-alkylchromanones and 3-alkylchromones has been achieved from 3-alkyl-3-phenyl-sulphonyl-4-chromanones. A simple and high yielding route to 3-alkylchromanones and 3-alkylchromones has been achieved from 3-alkyl, 3-phenylsulphonyl-4-chromanones.

The condensation of 7-benzoyloxy-4′-hydroxyisoflavone with 2-methyl-3-buten-2-ol gave 7-benzoyloxy-4′-hydroxy-3′-(3-methyl-2-butenyl)isoflavone. The hydrolysis of the alkylated isoflavone with dilute alkali afforded neobavaisoflavone [7,4′-dihydroxy-3′-(3-methyl-2-butenyl)isoflavone], which was then converted into isoneobavaisoflavone on heating with formic acid. 7-Benzyloxy-4′-hydroxyisoflavone was condensed with 2-methyl-3-buten-2-ol to give a chroman derivative, which was then converted into isoneobavaisoflavone by hydrolysis. 3′-(3-Methyl-2-butenyl)-5,7,4′-trihydroxyisoflavone was also synthesized from 7-benzoyloxy-5,4′-dihydroxyisoflavone in a similar manner.

The condensation of 7-benzoyloxy-4′-hydroxyisoflavone with 2-methyl-3-buten-2-ol gave 7-benzoyloxy-4′-hydroxy-3′-(3-methyl-2-butenyl)isoflavone. The hydrolysis of the alkylated isoflavone with dilute alkali afforded neobavaisoflavone [7,4′-dihydroxy-3′-(3-methyl-2-butenyl)isoflavone], which was then converted into isoneobavaisoflavone on heating with formic acid. 7-Benzyloxy-4′-hydroxyisoflavone was condensed with 2-methyl-3-buten-2-ol to give a chroman derivative, which was then converted into isoneobavaisoflavone by hydrolysis. 3′-(3-Methyl-2-butenyl)-5,7,4′-trihydroxyisoflavone was also synthesized from 7-benzoyloxy-5,4′-dihydroxyisoflavone in a similar manner.

Condensation of 7-benzoyldaidzein (III) with 2-methyl-3-buten-2-ol gave 7-benzoyl-3′-(3-methyl-2-butenyl)daidzein (IV). Hydrolysis of IV with dilute alkali gave 3′-(3-methyl-2-butenyl)daidzein (neobavaisoflavone) (I), which was converted into isoneobavaisoflavone (VI) when heated with formic acid. 7-Benzyldaidzein (VII) was condensed with 2-methyl-3-buten-2-ol to give a chroman derivative (VIII), which was converted into VI by hydrogenolysis.

Chromanmethanol 2 , a chiral intermediate for the synthesis of α-tocopherol 1 , is prepared from α-hydroxy aldehyde 5 , which is obtained by an asymmetric synthesis in over 95% ee.

Condensation of 7-benzoyldaidzein (III) with 2-methyl-3-buten-2-ol gave 7-benzoyl-3′-(3-methyl-2-butenyl)daidzein (IV). Hydrolysis of IV with dilute alkali gave 3′-(3-methyl-2-butenyl)daidzein (neobavaisoflavone) (I), which was converted into isoneobavaisoflavone (VI) when heated with formic acid. 7-Benzyldaidzein (VII) was condensed with 2-methyl-3-buten-2-ol to give a chroman derivative (VIII), which was converted into VI by hydrogenolysis.

IN a recent publication1 we indicated that β-tocopherol, C28H48O2, might be a coumaran or chroman derivative bearing a long side chain in the heterocyclic nucleus.