• Bulletin of the Korean Chemical Society
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• v.33 no.1
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• pp.128-136
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• 2012

We report the solid-phase library construction of 222 number of a novel N-[alkyl sulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 1A and amine 1B derivatives. The polymer-bound N-[alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 9 and amine 10 derivatives were obtained by first diversity generation with various acid chlorides and alkyl halides. Further reactions on the resins 9 and 10 with substituted sulfonyl chlorides produced the desired N-[alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 1A and amine 1B analogues.

• Natural Product Sciences
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• v.28 no.1
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• pp.1-5
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• 2022

Two 2H-1-benzopyran derivatives, methyl 8-hydroxy-2,2-dimethyl-2H-1-benzopyran-5-carboxylate (1) and methyl 8-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carboxylate (2), including a new compound (1) were isolated from the twigs of Chaenomeles sinensis. Their chemical structures were characterized based on analysis of NMR data including ¹H and ¹³C, COSY, HSQC, and HMBC and HRMS data. The isolated compounds (1 and 2) were assessed for their anti-neuroinflammatory activity by measuring inhibition levels of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells and for their neurotrophic activity by the secretion of nerve growth factor (NGF) in C6 cells. Compounds 1 and 2 exhibited powerful anti-neuroinflammatory effects with IC₅₀ values of 17.14 and 19.30 μM, respectively, without cell toxicity, and also showed moderate effects on the stimulation of NGF secretion levels with 113.15 ± 3.54 and 130.20 ± 8.03%, respectively. The biosynthetic pathway of 1 and 2 was proposed that they would be derived from a protocatechuic acid and an isoprenyl unit.

• 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.

• Journal of the Korean Chemical Society
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• v.52 no.3
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• pp.249-256
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• 2008

3-Acetyl/Formyl 4-hydroxy-2H(1)-benzopyran-2-one on treatment with malonitrile and ethyl cyanoacetate yielded 1,1-dicyano-2-[4/-hydroxy-2/H(1)-benzopyran-2/-one-3/-yl] ethene/propene 2a-h and ethyl-2-cyano-3-[4/-hydroxy-2/H (1)-benzopyran-2/-one-3/-yl] propenoate/butenoate 3a-h respectively. The 1,3 dipolar reaction of 2a-h with NaN3 gave the tetrazole derivative 4a-h. 3a-h on cyclization with PPA gave 3-cyano-2H,5H-pyrano [3, 2-c] benzopyran-2,5-diones 5a-h which on 1,3 dipolar reaction with NaN3 to gave 3-(1/H-tetrazol-5/-yl)-2H,5H-pyrano[3, 2-c] benzopyran-2,5-diones 6a-h. The structures of the compounds have been established on the basis of the spectral and analytical data. All the compounds were screened for their antimicrobial activities and have been found to exhibited significant antibacterial activities. Compounds 2h and 4h showed the activity 50g/mL.

• YAKHAK HOEJI
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• v.44 no.2
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• pp.107-114
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• 2000

We have synthesized 4-isonitroso-4H-1-benzopyran and 4-amino-2,3-dihydro -4H-1-benzopyran of chromone derivatives by using condensation method. Physico-chemical properties of these compounds were measured and analyzed by UV and HPLC method. The correlation coefficient of their methanol solutions by UV were 0.9992 and 0.9994, respectively. And oxime compound was resolved within 4 min and had a detection limit of 3 ng at S/N=3 by HPLC using a reversed phase column with three solvents(MeOH, $H_2O$, HAc). The amino compound was resolved within 4.5 min and had a detection limit of 10 ng at S/N=3 by HPLC under the same conditions. Anti-diabetic effect of chromone derivatives were investigated in the streptozotocin (STZ)-induced diabetic rats. Diabetes was induced in male Sprague-Dawley rats by injections of STZ (45 mg/kg, i.v). The investigation of the hair growth effect of isonitrosobenzopyran and 4-aminobenzopyran on the hair of black mouse (C57BL/6) was also carried out. The administraion of their ethanol solution to the black mouse (C57BU/6) through skin them promoted the growth of hair.

• Journal of the Korean Chemical Society
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• v.52 no.6
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• pp.663-667
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• 2008

• Journal of the Korean Chemical Society
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• v.46 no.5
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• pp.462-483
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• 2002

• 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

• 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.

• Bulletin of the Korean Chemical Society
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• v.13 no.4
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• pp.351-352
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• 1992