• 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

• 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.

• Bulletin of the Korean Chemical Society
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• 제22권8호
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• pp.917-920
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• 2001

• 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.

• Bulletin of the Korean Chemical Society
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• 제28권11호
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• pp.2061-2064
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• 2007

The first efficient synthesis of biologically interesting nigrolineabenzopyran A, blandachromene II, and daurichromene D with the benzopyran moiety has been accomplished using ethylenediamine diacetatecatalyzed reaction as a key step. The key step in these synthetic strategies involves the formation of benzopyran moiety via an electrocyclization reaction.

• Bulletin of the Korean Chemical Society
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• 제28권12호
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• pp.2549-2551
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• 2007

• 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

• 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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• 제47권2호
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• pp.137-146
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• 2003

3-하이드록시 벤조피란[3,2-c]-[1]-벤조피란-6,7-다이온(3)과 3-메톡시카보닐쿠마린을 소듐 메톡사이드 존재하에 화합물 1과 레조시놀을 축합시켜 합성하였으며 화합물 3의 아세트산 무수물, 알킬 할라이드, 다이아조니움 클로라이드와의 반응성에 대해 기술하였다. 화합물 4,5오 6a,b의 EI 질량분석에서는 89, 280, 91, 120 들의 주된 봉우리들이 각각의 분열 결과로 얻어짐을 볼 수 있었다. 화합물 3, 6b, 7a의 분자이온 봉우리로써 280, 366, 488을 각각 관찰할 수 있었다. 화합물 7a에서는 383과 77의 두 개의 안정한 조각을 가지는 특징적인 분역형태를 얻었다.