• Title/Summary/Keyword: Benzopyran[3,2-c]-[1]-benzopyran-6

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Synthesis and Antibacterial Activity of New Tetrazole Derivatives (새로운 Tetrazole유도체의 합성과 항균활성)

  • Mulwad, V.V.;Pawar, Rupesh B;Chaskar, Atul C
    • 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.

Synthesis and Investigation of Mass Spectra of 3-(substituent)-benzopyran[3.2-c]-[1]-benzopyran-6,7-diones (3-치환-벤조피란[3,2-c]-[1]-벤조피란-6,7-다이온의 합성과 질량스펙트럼)

  • I. M. EI-Deen;H.K. Ibrahim
    • Journal of the Korean Chemical Society
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    • v.47 no.2
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    • pp.137-146
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    • 2003
  • 3-Hydroxybenzopyran[3,2-c]-[1]-benzopyran-6,7-diones (3) and 3-methoxycarbonylcoumarin (4) were prepared via condensation of 1 with resorcinol in the presence of sodium methoxide. The chemical behavior of 3 towards acetic anhydride, alkyl halides and diazonium chloride is described. The electron impact ionization mass spectra of compounds 4,5 and 6a,b show a weak molecular ion peak and a base peak of m/z 89, m/z 280. m/z 91 and m/z 120 resulting from a cleavage fragmentation respectively. The molecular ion of compounds 3, 6b, and 7a is a base peak of m/z 280, m/z 366 and m/z 488 respectively. Compound 7a give a characteristic fragmentation pattern with a two very stable fragmentation of m/z 383 and m/z 77.

Anti-inflammatory and Neurotrophic 2H-1-Benzopyran Derivatives of Chaenomeles sinensis

  • Ha, Young Jun;Lee, Tae Hyun;Subedi, Lalita;Kim, Hye Ryeong;Moon, Gyuri;Kim, Sun Yeou;Kim, Chung Sub
    • 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.

Properties and Activitiy Screening of Chromone Derivatives (크로몬 유도체의 물성 및 활성검색)

  • 김영로;이상현;김경순;정춘식;정재훈;김박광
    • 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.

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Discovery of a Novel 2,6-Difunctionalized 2H-Benzopyran Inhibitors Toward Sphingosylphosphorylcholine Synthetic Pathway as New Anti-inflammatory Target

  • Lee, Gee-Hyung;Lee, Seong Jin;Jeong, Dae Young;Kim, Ha-Young;Lee, Doohyun;Lee, Taeho;Hwang, Jong-Yeon;Park, Woo Kyu;Kong, Jae-Yang;Cho, Heeyeong;Gong, Young-Dae
    • 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.

Components of Potentilla Species -Isolation and Identification of 3, 3', 4-tri-O-methylellagic acid- (Potentilla속 식물의 성분연구 -3, 3', 4-tri-O-methylellagic acid의 분리 및 동정-)

  • Kim, Hack-Seang
    • YAKHAK HOEJI
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    • v.33 no.6
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    • pp.377-379
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    • 1989
  • The methylated compound of ellagic acid was isolated from Potentilla chinensis (Rosaceae). The isolated compound was 3, 3', 4-tri-O-methylellagic acid, [2, 3, 7-trimethoxy-8-hydroxy[1] benzopyrano-[5, 4, 3, cde][1] benzopyran-5, 10-dione], $C_{17}H_{12}O_8$, m.p. $293-295^{\circ}C$. The isolation of trimethylellagic acid was conducted by the column chromatography and the identification of the compound was carried out by the methods of IR, NMR and MS spectroscopy.

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Isolation of a New Herbicidal Compound Angelicin from Curly Dock (Rumex crispus L.) (소리쟁이(Rumex crispus L.)로부터 신규 살초활성물질 Angelicin의 분리)

  • Cho, Nam-Kyu;Lee, Sa-Eun;Choi, Jung-Sup;Hwang, Ki-Hwan;Koo, Suk-Jin;Wang, Hai-Ying;Kim, Song-Mun
    • Korean Journal of Weed Science
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    • v.30 no.3
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    • pp.183-190
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    • 2010
  • The objective of this study was to isolate a herbicidally active compound from curly dock (Rumex crispus), a native weed in Korea and to identify its' chemistry. The $GR_{50}$ value of methanol extracts which is determined by a seed bioassay using rapeseed (Brassica napus) seedlings was $935\;{\mu}g\;g^{-1}$. Activity-directed isolation of ethylacetate extract led to the isolation of ECDA fraction with $GR_{50}$ value $53\;{\mu}g\;g^{-1}$. Based on data of GC-MS, $^1H$-NMR and $^{13}C$-NMR, the chemical structure of ECDA was determined as 2H-furo[2,3-H]-[1]-benzopyran-2-one which is known as angelicin. The $GR_{50}$ values of angelicin to barnyardgrass (Echinochloa crus-galli), southern crabgrass (Digitaria ciliaris), and indian jointvetch (Aeschynomene indica) were 426, 66 and $216\;{\mu}g\;g^{-1}$, respectively. Our results suggest that angelicin could be used as a lead compound for the development of new herbicides.

Removal Characteristics of Synthetic Musk Compounds in Water by Ozone Treatment (오존처리에 의한 수중의 인공 사향물질 제거특성)

  • Seo, Chang-Dong;Son, Hee-Jong;Yoom, Hoon-Sik;Lee, Sang-Won;Ryu, Dong-Chun
    • Journal of Korean Society of Environmental Engineers
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    • v.34 no.2
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    • pp.73-78
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    • 2012
  • In this study, three different synthetic musk compounds (SMCs) in the Nakdong river water (raw water) and rapid sand filtered water were treated by $O_3$ process. The experimental results showed that the removal efficiency of musk ketone (MK) was lower than removal efficiency of AHTN (7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene) and HHCB (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[c]-2-benzopyran) for both the raw water and the rapid sand filtered water. And in general, the removal efficiencies of three SMCs in the raw water were lower than that in the sand filtered water. Under the $O_3$ dose of 0.5~10.0 mg/L, the removal rate constants (k) of three SMCs for the raw and sand filtered waters increased rapidly with the increased $O_3$ dose. In the case of drinking water treatment plants (DWTPs) which were selected pre- and post-$O_3$ processes (located in the downstream of Nakdong River), operation conditions of pre- and post-$O_3$ process were $0.5{\sim}2.0mg{\cdot}O_3/L$ (2~4 min) and $0.5{\sim}2.5mg{\cdot}O_3/L$ (6~8 min). Therefore, $O_3$ doses and contact times of same conditions with above were very difficult to remove SMCs in DWTPs.

Fragrance Chemicals in the Essential Oil of Mentha arvensis Reduce Levels of Mental Stress (박하(Mentha arvensis) 향료의 향기성분이 정신적 스트레스 완화에 미치는 효과)

  • Cho, Haeme;Sowndhararajan, Kandhasamy;Jung, Ji-Wook;Jhoo, Jin-Woo;Kim, Songmun
    • Journal of Life Science
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    • v.23 no.7
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    • pp.933-940
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    • 2013
  • The aim of this work was to determine the chemical composition of essential oil from aerial partsof Mentha arvensis L. f. piperascens (MAO) and to evaluate the effect of its fragrant chemicals on electroencephalographic (EEG) activity of human brain. The MAO was obtained by supercritical $CO_2$ extraction. The maximum yield was 2.38% at conditions of $70^{\circ}C$ and 200 bar. There were 32 volatile chemicals with 6 alcohols (67.11%), 13 hydrocarbons (17.05%), 9 esters (11.50%), 2 ketones (7.16%), 1 oxide (2.77%), and 1 aldehyde (0.56%). The major components were (Z,Z,Z)-9,12,15-octadecatrien-1-ol (50.06%), 2-hydroxy-4-methoxyacetophenone (7.50%), and 3,4-dihydro-8-hydroxy-3-methyl-1H-2-benzopyran-1-one (6.60%). Results of the EEG study showed that inhalation of MAO significantly changed the EEG power spectrum values of relative gamma, relative fast alpha, and spectral edge frequency 90%. During the inhalation of MAO, the value of relative fast alpha was significantly increased (p<0.05). On the other hand, the values of gamma and the spectral edge frequency 90% were significantly decreased (p<0.05). The present study suggests that fragrant chemicals of essential oil of M. arvensis reduce the level of mental stress and that they could be used in the treatment of psychophysiological disorders.