• Bulletin of the Korean Chemical Society
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• 제33권1호
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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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• 제28권1호
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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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• 제18권1호
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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.

• 대한화학회지
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• 제52권3호
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• pp.249-256
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• 2008

3-Acetyl/Formyl 4-hydroxy-2H(1)-benzopyran-2-one를 malonitrile와 ethyl cyanoacetate로 처리하여 각각 1,1-dicyano-2-[4/-hydroxy-2/H(1)-benzopyran-2/-one-3/-yl] ethene/propene 2a-h와 ethyl-2-cyano-3-[4/-hydroxy-2/H (1)-benzopyran-2/-one-3/-yl] propenoate/butenoate 3a-h를 얻었다. NaN3와 2a-h의 1.3 dipolar 반응에서 4a-h인 tetrazole유도체를 얻었다. 3a-h는 PPA를 이용한 고리화 반응으로 3-cyano-2H,5H-pyrano [3, 2-c] benzopyran-2,5-diones 5a-h를 얻었다. 5a-h는 NaN3와1.3 dipolar 반응으로 -(1/H-tetrazol-5/-yl)-2H,5H-pyrano[3, 2-c] benzopyran-2,5-diones 6a-h얻었다. 화합물의 구조는 스펙트럼과 자료 분석을 기초로 입증했다.모든 화합물은 항균 활성을 검사하였고 의미있는 항균성을 가짐을 밝혔다. 2h화합물과 4h 화합물은 50 킽/mL에서 활성을 보였다

• 약학회지
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• 제44권2호
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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.

• 대한화학회지
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• 제52권6호
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• pp.663-667
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• 2008

• 대한화학회지
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• 제46권5호
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• pp.462-483
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• 2002

• 대한화학회지
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• 제54권1호
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• pp.9-12
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• 2010

• Archives of Pharmacal Research
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• 제21권6호
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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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• 제13권4호
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• pp.351-352
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• 1992