• Title/Summary/Keyword: coumarin synthesis

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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.

The Synthesis and Light Absorption Behaviour of Novel Coumarin Chromophores

  • An, Kyoung Lyong;Shin, Seung Rim;Jun, Kun;Park, Soo Youl
    • Journal of the Korean Chemical Society
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    • v.58 no.3
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    • pp.297-302
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    • 2014
  • The synthetic route to coumarin systems is well established and one approach of particular interest leads to the intermediate 7-diethylamino-3-formylcoumarin. A combination of the N,N-diethylamino-coumarin donor with a wide range of acceptor groups of varying electron withdrawing strength should permit the synthesis of a series of extended coumarin dyes with absorption maxima range from 500 to 600 nm, or even beyond. In this communication, a novel efficient synthesis of indoles, benzothiazole and benzoxazole based on coumarin chromophores were achieved and the coloristic and fluorophoric properties of these chromophores were studied.

Synthesis and Biological Investigations of New Thiazolidinone and Oxadiazoline Coumarin Derivatives

  • Abd Elhafez, Omaima Mohamed;El Khrisy, Ezz El Din Ahmed Mohamed;Badria, Farid;Fathy, Alaa El Din Mohamed
    • Archives of Pharmacal Research
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    • v.26 no.9
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    • pp.686-696
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    • 2003
  • Ethyl (coumarin-4-oxy)acetate 1 was prepared through the reaction of 4-hydroxycoumarin with ethyl bromoacetate. Compound 1 was allowed to react with hydrazine hydrate to produce coumarin-4-oxyacetic hydrazide 2. The synthesis of N-(arylidene and alkylidene)-coumarin-4-oxyacetic hydrazones 3-20 was performed. The preparation of 2-substituted-3-[(coumarin-4-oxy) acetamido]thiazolidinones 21-26 and 2-[(coumarin-4-oxy )methyl]-4-acetyl-5-substituted-$\Delta^2$-1,3,4-oxadiazolines 27-33 was performed by the reaction of the hydrazones 3, 4, 7, 9, 12, 14 with mercaptoacetic acid and the hydrazones 3, 4, 5, 7, 12, 15, 16 with acetic anhydride, respectively. The antiviral activities, cytotoxicities and structure-activity relationship (SAR) towards different microorganisms of the prepared compounds were studied.

Synthesis of 4-Hydroxycoumarion Derivatives-1: An Efficient Synthesis of Flocoumafen

  • Park, Oee-Sook;Jang, Bong-Suek
    • Archives of Pharmacal Research
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    • v.18 no.4
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    • pp.277-281
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    • 1995
  • An anticoagulant, 4-hydroxy-3-[1, 2, 3, 4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyll-1 -naphthyl]coumarin (Flocoumafen) was synthesized in 8 steps starting from phenylacetyl shloride and anisole. The key step in the synthesis involves the reaction of 3-(4-methoxyphenyl)-1-teralol with 4-hydroxycoumarin to give 4-hydroxy-3 [1, 2, 3, 4-tetrahydro-3-[4-emthoxyphenyl]-1-naphthyl]coumarin.

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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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Synthesis and Biological Evaluation of Decursin, Prantschimgin and Their Derivatives

  • Xia, Yan;Min, Kyung-Hoon;Lee, Kyeong
    • Bulletin of the Korean Chemical Society
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    • v.30 no.1
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    • pp.43-48
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    • 2009
  • The synthesis of coumarin-based natural products and their derivatives is described. In vitro MDR reversal activities of the synthesized compounds were evaluated in P-glycoprotein over-expressing human sarcoma cell line MES-SA/DX5. Some of the coumarin derivatives were found to show potent MDR reversal activity. In particular, pyridyl derivative (15e) exhibited more potency than verapamil.

Synthesis of Poly(cinnam-4'-yl methyl methacrylate) Derivatives and Their Thermal Stability as Photoalignment Layer

  • Lee, Jong U;Kim, Hak Won;Kim, Hong Du
    • Bulletin of the Korean Chemical Society
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    • v.22 no.2
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    • pp.179-182
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    • 2001
  • Photocyclizable poly(cinnam-4'-yl methyl methacrylate) derivatives bearing methoxy benzene (PMCMMA), anthracene (PACMMA), and coumarin (PCCMMA) have been synthesized via Heck type reaction. Three different types of polymers are photoreactable usin g linearly polarized UV light and applicable as liquid crystal alignment layer. Anthracence and coumarin containing polymers (PACMMA, PCCMMA) have better thermal stability than PMCMMA. This observation may be attributed to the glass transition temperature elevation due to the bulky size and another photocrosslinking site provided by anthracene or coumarin group.