- Novel 4-methylumbelliferone amide derivatives: Synthesis, characterization and pesticidal activities
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A series of novel 4-methylumbelliferone amide derivatives were designed, synthesized and characterized by 1H NMR, 13C NMR and HR-ESI-MS. The structures of compounds 4bd and 4be (compounds named by authors) were further confirmed by X-ray single crystal diffraction. The acaricidal, herbicidal and antifungal activities of the synthesized compounds were assayed for their potential use as pesticide. The results indicated that compounds 4bi, 4ac and 4bd were strong acaricidals against Tetranychus cinnabarinus, with 72h corrected mortalities of greater than 80% at 1000 mg/L. Meanwhile, compounds 4bh and 4bf exhibit the strongest inhibition against the taproot development of Digitaria sanguinalis and Chenopodium glaucum, and were even more potent than the commercial herbicide Acetochlor against D. sanguinalis. In addition, compounds 4bk, 4bh and 4bp showed the highest antifungal activity against the mycelium growth of Valsa Mali, which makes them more effective than commercial fungicide Carbendazim.
- Wei, Yan,Miao, Kai-Long,Hao, Shuang-Hong
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- Preparative-scale synthesis of amino coumarins through new sequential nitration and reduction protocol
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In contrast to the conventional deleterious approach for nitration (for example HNO3/H2SO4) and for reduction (for example Zn/HCl), we hypothesized that sensitive heterocycles such as coumarins could not withstand with those hard conditions. Hence, while studying this reaction sequence to prepare amino coumarins (which is our ongoing project to synthesize antitubercular coumarin agents), we came across mild and greener reagent for nitration using calcium nitrate (Ca(NO3)2·4H2O; lime nitrate), and reduction using D-glucose. These two mild, chemoselective, high yielding methods are discussed herein.
- Chaudhari, Hemchandra K.,Pahelkar, Akshata,Takale, Balaram S.
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supporting information
p. 4107 - 4110
(2017/09/28)
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- Understanding the Selectivity of a Multichannel Fluorescent Probe for Peroxynitrite over Hypochlorite
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Peroxynitrite is a prominent biological reactive nitrogen species from radical combination of nitric oxide and superoxide and fundamentally involved in broad spectrum physiological and pathological processes. Though redox-inert itself, peroxynitrite anion (OONO-) attacks various biological electrophiles to generate an array of potent 2-e- or 1-e- oxidants, which result in cell injuries. Development of fluorescent probes for peroxynitrite, free from interference from hypochlorite, has been an active endeavor of the chemical community. We previously reported a peroxynitrite probe (PN600), which could differentiate hypochlorite from peroxynitrite through a multichannel signaling mechanism. Herein, this intriguing selectivity was accounted for through a structure-reactivity relationship study. Also, this work, together with rich literature contributions, has allowed a qualitative guideline in the use of electron-rich aromatic moieties to design probes against peroxynitrite and/or hypochlorite. The viability of this guideline was further testified by development of another list of peroxynitrite selective probes.
- Zhang, Quanjuan,Zhang, Na,Long, Yi-Tao,Qian, Xuhong,Yang, Youjun
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p. 341 - 353
(2016/03/05)
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- Anti-inflammatory screening and molecular modeling of some novel coumarin derivatives
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Coumarin and their derivatives have drawn much attention in the pharmacological and pharmaceutical fields due to their broad range and diverse biological activities. In the present work, starting from the 6-amino-7-hydroxy-4-methyl-2H-chromen-2-one, a series of 6-(substituted benzylamino)-7-hydroxy-4-methyl-2H-chromen-2-ones 1-11 was synthesized and assessed for their anti-inflammatory activity using the carrageenan-induced hind paw edema method. Compounds 2, 3, 4 and 9 showed significant (p 0.001) reduction of rat paw edema volume after 1 h from the administration of the carrageenan compared to the reference drug, indomethacin. On the other hand, compounds 4 and 8 showed the highest anti-inflammatory activity, surpassing indomethacin after 3 h with 44.05% and 38.10% inhibition, respectively. Additionally, a molecular docking study was performed against the COX enzyme using the MOE 10.2010 software.
- El-Haggar, Radwan,Al-Wabli, Reem I.
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p. 5374 - 5391
(2015/05/13)
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- Oxazole light triggered protecting groups: Synthesis and photolysis of fused heteroaromatic conjugates
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Fused oxazole derivatives were synthesized and evaluated as new light triggered protecting groups by using amino acids as model bifunctional molecules. The photosensitivity of ester conjugates was tested under irradiation at 254, 300, and 350 nm. Oxazole
- Soares, Ana M.S.,Costa, Susana P.G.,Gonalves, M. Sameiro T.
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experimental part
p. 8189 - 8195
(2010/11/04)
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- Novel method for synthesis of some biologically active aminocoumarins
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Nitration of coumarin 4-methyl acetates using concentrated HNO3 in solvents like chloroform or dichloromethane at lower temperature 'Cheparon effect' was found to occur only on aromatic part of coumarin. Yields of nitrocoumarins are almost quantitative and isomers were separated using column chromatographic technique. Reduction of the nitrocoumarins was carried out in environmentally friendly hydride transfer system using Pd/C as catalyst and formic acid or phosphorous acid as hydride generating reagent. Functional groups like -OH, Br, COCH3, -CH2COOH3 and lactone were not interfering in the reduction of nitro group to amino.
- Mashelkar,Audi
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p. 258 - 261
(2008/09/21)
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- New Facile Synthesis of 7-Hydroxy-6-amino-4-substituted Benzopyran-2-ones
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A new facile synthesis of 6-amino-7-hydroxy-4-substituted benzopyranones is described through the von Pechmann reaction. The yields obtained were high, and the proposed methodology leads to pure products. The selectivity of formation of the desired products can be attributed to the formation of an intramolecular hydrogen bond, which leads to reduced reactivity of the 2-hydroxyl group.
- Gikas, Evagelos,Parissi-Poulou, Maria,Kazanis, Michael,Vavagianis, Andreas
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p. 4233 - 4242
(2007/10/03)
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- SYNTHESIS OF o-ACYLAMINO-4-METHYL-7-HYDROXYCOUMARINS (4-METHYLUMBELLIFERONES)
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Some acylated o-amino-7-hydroxycoumarins have been obtained which may be used as intermediates in the preparation of fluorogenic substrates for certain enzymes.
- Kozlova, I. K.
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p. 750 - 753
(2007/10/02)
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