• Bulletin of the Korean Chemical Society
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• v.26 no.4
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• pp.619-628
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• 2005

We attempted to replace a benzopyran ring of 4-[(N-imidazol-2-ylmethyl)-4-chloroanilino]benzopyran, previously discovered as anti-angiogenic agent with antitumor activity, with pyranopyridines. The [3,2-c]-, [3,2-b]-, [2,3-c]-, and [2,3-b]-pyranopyridines with -(imidazol-2-ylmethyl)aniline moiety at the 4-position, were synthesized respectively, and evaluated for primary anti-angiogenic properties through primary cultured HUVEC tube formation assay. From this study, we found that the pyranopyridine ring, especially [3,2-b]- and [2,3-c]-isomer, can replace the benzopyran ring of the compound 1 and can be optimized through the introduction of substituents both on the pyranopyridine ring and the aniline moiety for the identification of a novel anti-angiogenic agent.

• Journal of Applied Biological Chemistry
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• v.53 no.2
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• pp.99-104
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• 2010

The influences on antioxidant activities of the substituents ($R_1-R_4$) on benzo ring in 4-Methyl-2H-benzopyran-2-one analogues (1-23) were discussed quantitatively using three dimensional quantitative structure-activity relationships (3D-QSARs: Comparative molecular field analyses (CoMFA) and Comparative molecular similarity indice analyses (CoMSIA)) methods. The statistical qualities of CoMSIA models were better than those of CoMFA models and the CoMSIA 2 model was optimized model ($q^2$=0.700 & $r^2$=0.979). Also, the contribution ratios (%) of the optimized CoMSIA 2 model were H-bond donor field 43.5%, electrostatic field 41.8% and steric field 14.7% so that the antioxidant activity exhibited a strong correlation with H-bond donor and electrostatic factor of molecules. From the analytical results of the CoMSIA contour maps, if the positive charge favor group and H-bond donor disfavor group were placed in the $R_1-R_4$ positions on the benzo ring, it was predicted that the groups would raised the antioxidant activity.

• Archives of Pharmacal Research
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• v.21 no.6
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• pp.723-728
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• 1998

The chemical behaviours of 4-methyl-2-oxo-2H-benzopyran-7-yl oxoacetyl hydrazine (2) towards some different reagents such as anhydride compounds, aromatic aldehydes, carb on disulphide, and nitrous acid yielded the corresponding pathalazine derivatives (3, 4, 5), hydrazone derivative (6), 1,3,4-oxadiazole derivative (7, 8, 9) and acid azide (10) respectively. Treatmen of 10 with absolute alcohols, amines and ethyl amino acid ester gave the corresponding carbamate derivative (11), substituted urea derivative (12) and ethyl substituted alkyl acetate (13) respectively. The biological activity of some synthesized compounds was evaluated.

• Journal of the Korean Chemical Society
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• v.54 no.1
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• pp.9-12
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• 2010

• Bulletin of the Korean Chemical Society
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• v.33 no.8
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• pp.2647-2650
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• 2012

The total synthesis of biologically interesting ${\beta}$-hydroxypyranochalcones, purpurenone (1), its derivative 2, praecansone B (3), and pongapinone A (4) has been accomplished starting from commercially available 2,4-dihydroxyacetophenone or 6-methoxy-2,4-dihydroxyacetophenone in 3 steps by a convergent strategy through benzopyran formations, O-methylations, and coupling reactions.

• Archives of Pharmacal Research
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• v.18 no.1
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• pp.27-30
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• 1995

The Hantzsh reaction of 7-hydroxy-8-methoxy-2-oxo-2H-benzopyran-6-carboxaldehyde (1) with ethyl acetoacetate and ammonia yields the dihydropyridine derivative 2 together with the pyridine derivative 3 and the eight membred ring derivative 4. Reaction of 1 with ethyl cyanoacetate and malononitrile gives the iminodicoumarin derivatives 5 and 6 respectiely. The latter compound was reacted with butan-2-one and acetophenone to produce the Michael adduct 71, b and the 2-aminopyridine derivatives 8a, b.

• Bulletin of the Korean Chemical Society
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• v.35 no.8
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• pp.2385-2390
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• 2014

Novel 2,6-difuctionalized 2H-benzopyrans were synthesized and evaluated for a sphingosylphosphorylcholine(SPC) inhibitor. The synthetic 2H-benzopyrans 1c and 3a showed high potency in SPC-induced cell proliferation assay ($IC_{50}$ < 20 nM). Neither hERG $K^+$ channel binding (> $10{\mu}M$) nor CYP inhibitions (> $10{\mu}M$) were observed. Also, the simple structure-activity relationship (SAR) results were obtained from analysis of 2H-benzopyran derivatives 1-3 and the anti-SPC effect of 2H-benzopyran 1c was confirmed by a HUVEC tube formation assay.

• Korean Journal of Pharmacognosy
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• v.32 no.4 s.127
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• pp.302-306
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• 2001

The stem barks of Kalopanax septemlobus were extracted with MeOH, and successively partitioned with $CH_2Cl_2$, EtOAc, BuOH and water. Repeated column chromatographic separation of the $CH_2Cl_2$ fraction resulted in the isolation of four compounds. Their structures were identified as ${\beta}-sitosterol$ (1), oleanolic acid (2), 3,3'-bis(3,4-dihydro-4-hydroxy-6-methoxy-2H-1-benzopyran) (3) and (-)-balanophonin (4). This is the first report on the isolation of 3,3'-bis(3,4-dihydro-4-hydroxy-6-methoxy-2H-1-benzopyran) (3) and (-)-balanophonin (4) from Kalopanax spp.

• Bulletin of the Korean Chemical Society
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• v.22 no.9
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• pp.941-942
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• 2001

• Archives of Pharmacal Research
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• v.20 no.2
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• pp.194-196
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• 1997

A C-glycosyl chromone, named as 7-O-methylaloesinol, was newly isolated from the leaf exudate of Aloe capensis and identified as $8-C-{\beta}-D-glucopyranosyl$${\beta}-2-[2-(R)-hydroxypropyl]-7-methoxy-5-methyl-4H-1-benzopyran-4-one$ by chemical and spectral evidence.