• Title/Summary/Keyword: Coumarin derivatives

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Synthesis of Some Coumarin Derivatives and their Antimicrobial Activity

  • Hishmat, O.H.;Miky, J.A.A.;Farrag, A.A.;Fadl-Allah, E.M.
    • Archives of Pharmacal Research
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    • v.12 no.3
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    • pp.181-185
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    • 1989
  • When 3-acetyl coumarin derivatives are treated with bromine, 3-(w-bromoacetyl) coumarin derivatives are obtained. The reaction of 3-(w-bromoacetyl)coumarin derivatives with thiourea or with amines for two hours leads to the formation of 2-Amino-4-(3-coumarinyl) thiazole or 3-(w-aminoacetyl) coumarin derivatives, respectively. While 3-(w-bromoacetyl) coumarin derivatives react with amines for 5-8 hours to yield imino derivatives of 3-(w-aminoacetyl) coumarin. The antimicrobial activity of Ia-b, IIa-c, IVc-f, IVh and V$_{c}$, f, h, k, m, and q was studied.d.

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Solid Phase Synthesis of 3-(4-Hydroxyphenyl)coumarin: Preliminary Experiments for Combinatorial Synthesis of Substituted 3-Phenylcoumarin Derivatives

  • Bae, Hoon;Kim, Hak-Sung
    • Archives of Pharmacal Research
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    • v.27 no.8
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    • pp.811-815
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    • 2004
  • Coumarin and its derivatives occur widely in nature. Many attempts were made for synthesis of various coumarin derivatives because of their interesting biological activities. In this study, solid phase synthetic approach of 3-(4-hydroxyphenyl)coumarin was achieved for combinatorial synthesis of substituted 3-phenylcoumarin analogues. Starting from 4-hydroxyphenylacetic acid methyl ester, release of 3-(4-hydroxypnehyl)coumarin from polymer support was accom-plished.

Photosensitized Generation of ydroxyl Radical by Color Additive (색소 첨가제에 의한 히드록시 라디칼의 광증감 생성반응)

  • 김민식;성대동
    • The Korean Journal of Food And Nutrition
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    • v.10 no.1
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    • pp.6-13
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    • 1997
  • Reactivity and reaction mechanism for the photosensitized generation of hydroxyl radical by various coumarin derivatives are investigated by means of ESR and laser flash photolysis methods. The nine kinds of coumarin derivatives show to be proceeded through the OH·radical generation mechanism, however 1-ethyl-3-nitro-1-nitrosoguanidine decomposes and produces the carbene intermediate before OH·radical generation reaction occurs. The nine coumarin derivatives show the signals, which are corresponded to DMPO-OH spin adducts. NaN3, EtOH and HCOONa act as a strong photosensitizer to quench OH·radical. The decay rate constants of the hydrated electrons in the case of added N2O show higher than added K3Fe(CN)6.

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Synthesis of New 8-Formyl-4-methyl-7-hydroxy Coumarin Derivatives

  • Manidhar, D.M.;Rao, K. Uma Maheswara;Reddy, N. Bakthavatchala;Sundar, Ch. Syama;Reddy, C. Suresh
    • Journal of the Korean Chemical Society
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    • v.56 no.4
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    • pp.459-463
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    • 2012
  • 8-Formyl-4-Methyl-7-Hydroxy Coumarin Derivatives were synthesized via Penchem condensation followed by Duffs reaction. Treatment of this with N,N-di substituted cyano acetamides in the presence of piperdine afforded New 8-Formyl-4-Methyl-7-Hydroxy Coumarin Derivatives (7a-o). Their structures were characterized by IR, $^1H$ and $^{13}C$ NMR and Mass spectral and elemental analysis data.

Synthetic Studies of Coumarin Derivatives from o-Hydroxybenzophenones with Phenylacetic Acid and Acetic Anhydride (o-Hydroxybenzophenones와 Phenylacetic Acid, Acetic Anhydride에 의한 Coumarin 유도체 합성에 관한 연구)

  • Kang, Soon Hee;Yang, Sung Yun
    • Journal of the Korean Chemical Society
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    • v.43 no.1
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    • pp.92-103
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    • 1999
  • The 8 coumarin derivatives have been synthesized from 8 starting materials(2-hydroxy-benzophenone, 2,2'-dihydroxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-5-methylbenzophenone, 5-chloro-2-hydroxy-4-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-ethoxybenzophenone, 2-hydroxy-4,4'-dimethoxybenzophenone) with phenylacetic acid and $Ac_2$O/TEA in acetone at reflux temperature. The ratio of o-hydroxybenzophenone, phenylacetic acid, $Ac_2$O and TEA is 1 : 1: 8: 8 in acetone. Our results showed higher products yields of coumarin derivatives than Shama and Ray's method in previous papers. A new intermediate form was proposed to our mechanism of coumarin synthetic method.

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Antifouling Activity of Coumarin and its Derivatives Isolated from the Cinnamon Tree Cinnamomum loureiroi (계피식물(Cinnamomum loureiroi)에서 분리한 coumarin과 유도체의 방오효과)

  • Kim, Young Do;Shin, Hyun Woung;Cho, Ji Young
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.46 no.1
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    • pp.53-58
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    • 2013
  • The active antifouling compounds coumarin and its derivatives were isolated from the cinnamon tree Cinnamomum loureiroi. The antifouling activities were determined using representative soft fouling organisms: the seaweed Ulvapertusa and diatom Navicula annexa. The chemical constituents with antifouling activities were identified as coumarin, hydroxylcoumarin, coumaric acid, and cinnamaldehyde by interpreting nuclear magnetic resonance, and high-resolution mass spectroscopy data. These compounds were isolated from 1.09 g of crude Cinnamomum sp. methanol extract, yielding approximately 18.4, 6.3, 9.8, and 14.7 mg of coumarin, hydroxylcoumarin, coumaric acid, and cinnamaldehyde, respectively. The compounds inhibited U. pertusa zoospores with $EC_{50}$ values of $0.13-0.25{\mu}g/mL$, and the diatom N. annexa with $EC_{50}$ of $0.21-0.81{\mu}g/mL$.

Spectrofluorometric Study of the Interaction of Coumarin Derivatives with Bovine Serum Albumin

  • Kamat, B.P.;Seetharamappa, J.;Kovala-Demertzi, D.
    • Journal of Photoscience
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    • v.11 no.32
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    • pp.65-69
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    • 2004
  • The mechanism of interaction of four coumarin derivatives (CDS) with bovine serum albumin (BSA) was studied using spectrofluorometric technique. It was found that the coumarin ring common to all CDS makes major contribution to interaction. Binding affinities could be related to parachor values of CDS. Stem-Volmer plots indicated the presence of static component in the quenching mechanism. Results also showed that both tryptophan residues of protein are accessible to CDS. The high magnitude of rate constant of quenching indicated that the process of energy transfer occurs by intermolecular interaction forces and thus CDS binding site is in close proximity to tryptophan residues of BSA. Binding studies in the presence of the hydrophobic probe, 8-anilino-l-naphthalein-sulfonic acid showed that there is hydrophobic interaction between CDS and the probe and they do not share common sites in BSA. Thermodynamic parameters obtained from data at different temperatures showed that the binding of CDS to BSA involve hydrophobic bonds predominantly. The effects of various metal ions on the binding of CDS with BSA were also investigated.

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Synthesis and Fluorescence Properties of New Rhodamine 6G Derivarives Containing Hydroxy Coumarin Moiety (새로운 로다민 6G 하이드록시 쿠마린 유도체의 합성과 형광특성)

  • Park, Seong Ho;Chang, Seung Hyun
    • Journal of Environmental Science International
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    • v.25 no.9
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    • pp.1283-1288
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    • 2016
  • In this study, we synthesized fluorescent sensors from rhodamine 6G derivatives and hydroxy coumarin. The synthetic routes to the rhodamine 6G derivatives containing hydroxy coumarin are shown in Fig. 1. Two derivatives were synthesized through Schiff base reactions. The structures of the new compounds were confirmed by melting point, $^1H$-NMR, and GC-MS analyses. The compounds were found to selectively bind to tin ($Sn^{2+}$) ion by fluorescence titration using various metal cations. Longer carbon chains gave more sensitivity. $Sn^{2+}$ ions exhibited the strongest fluorescence among the nime ions. The binding analysis using Job plots suggested that compounds form 1:1 complexes with the $Sn^{2+}$ ions.

Biochemical Studies on the Constitutents of Artemisia messer-schmidtiana Besser var. viricis Besser and their Derivatives. II. Cholagogic Activity of Coumarin Derivatives. (한국인진성분과 그 유도체에 관한 생물화학적연구 II Coumarin 유도체의 첨즙분필촉진작용)

  • 한덕룡
    • YAKHAK HOEJI
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    • v.10 no.2_3
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    • pp.25-29
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    • 1966
  • In the preceding paper, it was reported that two esculetin methyl ethers wre isolated from title plant, and exhibited good cholagogic activity. An experiment was made using the eleven coumarin compounds in order to know the relationship between the cholagogic activity and their chemical structure. The result obtained in this study shows that all compounds used possess cholagogic activity, among which daphnetin and esculin methylether are more potent.

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