- A green multicomponent synthesis of tocopherol analogues with antiproliferative activities
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A one-pot efficient, practical and eco-friendly synthesis of tocopherol analogues has been developed using water or solvent free conditions via Passerini and Ugi multicomponent reactions. These reactions can be optimized using microwave irradiation or ultrasound as the energy source. Accordingly, a small library of 30 compounds was prepared for biological tests. The evaluation of the antiproliferative activity in the human solid tumor cell lines A549 (lung), HBL-100 (breast), HeLa (cervix), SW1573 (lung), T-47D (breast), and WiDr (colon) provided lead compounds with GI50 values between 1 and 5 μM. A structure–activity relationship is also discussed. One of the studied compounds comes up as a future candidate for the development of potent tocopherol-mimetic therapeutic agents for cancer.
- Ingold, Mariana,Dapueto, Rosina,Victoria, Sabina,Galliusi, Germán,Batthyàny, Carlos,Bollati-Fogolín, Mariela,Tejedor, David,García-Tellado, Fernando,Padrón, José M.,Porcal, Williams,López, Gloria V.
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- Chroman/catechol hybrids: Synthesis and evaluation of their activity against oxidative stress induced cellular damage
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Three series of chromans substituted at positions 2 or 5 by catechol derivatives were synthesized, and their activity against oxidative stress induced cellular damage was studied. Specifically, the ability of the new molecules to protect cultured cells fr
- Koufaki, Maria,Theodorou, Elissavet,Galaris, Dimitrios,Nousis, Lambros,Katsanou, Efrosini S.,Alexis, Michael N.
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p. 300 - 306
(2007/10/03)
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- Synthesis and biological evaluation of CX-659S and its related compounds for their inhibitory effects on the delayed-type hypersensitivity reaction
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In order to find novel nonsteroidal compounds possessing an inhibitory activity against delayed-type hypersensitivity (DTH) reactions, we conducted random screening using a picryl chloride (PC)-induced contact hypersensitivity reaction (CHR) in mice, and found compound 1 as a lead compound. Then we synthesized and evaluated an extensive series of 5-carboxamidouracil derivatives focused on both the uracil and the antioxidative moieties. Among them, we found that the hindered phenol moiety was necessary to exhibit the activities; especially, compounds 28a-28c having the partial structure of vitamin E were found to exert potent activities against the DTH reaction by both oral and topical administration. And compound 28c showed antioxidative activity against lipid peroxidation with an IC50 of 5.9μM. Compound 28c (CX-659S) was chosen as a candidate drug for the treatment of cutaneous disorders such as atopic dermatitis and allergic contact dermatitis. Copyright (C) 2000 Elsevier Science Ltd.
- Tobe, Masanori,Isobe, Yoshiaki,Goto, Yuso,Obara, Fumihiro,Tsuchiya, Masami,Matsui, Junko,Hirota, Kosaku,Hayashi, Hideya
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p. 2037 - 2047
(2007/10/03)
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- Preparative Separation of the Enantiomers of a Chroman-2-carboxylic Acid via Chromatography of Glucose Derivatives
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Starting from the commercially available racemic carboxylic acid 2a,b (S)-Trolox methyl ether (1a), useful as a chiral reagent for capillary gas chromatography and supercritical fluid chromatography, was obtained in enantiomerically pure form (e.e. > 99.9
- Netscher, Thomas,Gautschi, Iwan
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p. 543 - 546
(2007/10/02)
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