- Substituent effects on hydrogen bonding of aromatic amide-carboxylate
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N-(p-benzoyl)-anthranilic acid (BAA) derivatives have been synthesized with different substituents (X: Br, Cl, OCH3, CH3), and their crystal structures have been analyzed in order to understand the variations in their molecular geome
- Sen, Ibrahim,Kara, Hulya,Azizoglu, Akin
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- The base-catalyzed oxygenation of quinoline derivatives
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The base-catalyzed oxygenation of 1H-2-phenyl-3-hydroxy-4-oxoquinoline leads to cleavage products derived from either an endoperoxide or a 1,2-dioxetan intermediate. A persistent 1H-2-phenyl-3-oxy-4-oxoquinoline radical could also be detected by EPR in the reaction mixture.
- Czaun, Miklós,Speier, Gábor
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- A straightforward TBHP-mediated synthesis of 2-amidobenzoic acids from 2-arylindoles and their antimicrobial activity
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A simple and highly efficient strategy has been developed for the synthesis of 2-amidobenzoic acids through the tert-butyl hydroperoxide (TBHP)-mediated oxygenation and sequential ring opening of 2-arylindoles in a one-pot fashion under metal-free aerobic conditions. The developed synthetic protocol is operationally simple, tolerates a wide range of functional groups, and is amenable to the gram-scale. Radical trapping experiments revealed that the reaction involves a radical pathway. The synthesized compounds (2a-s) were tested for in vitro antimicrobial activity. Among all screened compounds, 2d showed the maximum antibacterial activity against P. aerugunosa (ZOI = 17 mm, MIC = 32 μg mL-1) and compounds 2d and 2p showed the maximum (32 μg mL-1) antifungal activity against A. flavus and C. albicans.
- Patel, Om P.S.,Dhiman, Shiv,Khan, Shahid,Shinde, Vikki N.,Jaspal, Sonam,Srivathsa, Manu R.,Jha, Prabhat N.,Kumar, Anil
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p. 5962 - 5970
(2019/06/24)
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- Kinetics and mechanism of the base-catalyzed oxygenation of 1H-2-phenyl-3-hydroxy-4-oxoquinolines in DMSO/H2O
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The oxygenation of 4′-substituted 1H-2-phenyl-3-hydroxy-4- oxoquinolines (PhquinH2) in a DMSO/H2O (50/50) solution leads to the cleavage products at the C2-C3 bond in about 75% yield at room temperature. The oxygenation, deduced from the product compositions, has two main pathways, one proceeding via an endoperoxide leading to CO-release, and the other through a 1,2-dioxetane intermediate without CO-loss. The reaction is specific base-catalyzed and the kinetic measurements resulted in the rate law -a...?[PhquinH2]/a...?t=kOH - [OH-] [PhquinH2] [O2]. The rate constant, activation enthalpy, and entropy at 303.16 K are as follows: kOH-=(2.42±0.03)×103mol -2L2s-1; ΔG?=73. 13±4.02 kJ mol-1; ΔH?=70.60±4. 04 kJ mol-1; ΔS?=-28±2 J mol -1 K-1. The reaction fits a Hammett linear free energy relationship for 4′-substituted substrates, and electron-releasing groups make the oxygenation reaction faster (ρ=-0.258). The EPR spectrum of the reaction mixtures showed the presence of the organic radical 1H-2-phenyl-3-oxyl-4-oxoquinoline and superoxide ion due to single electron transfer from the carbanion to dioxygen. The pathway via 1,2-dioxetane could be proved by chemiluminescence measurements.
- Czaun, Miklós,Speier, Gábor,Kaizer, József,El Bakkali-Taheri, Nadia,Farkas, Etelka
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p. 6666 - 6672
(2013/07/26)
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- Bio-inspired flavonol and quinolone dioxygenation by a non-heme iron catalyst modeling the action of flavonol and 3-hydroxy-4(1H)-quinolone 2,4-dioxygenases
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The mononuclear complex, FeIII(O-bs)(salen) (salenH2 = 1,6-bis(2-hydroxyphenyl)-2,5-diaza-hexa-1,5-diene; O-bsH = O-benzoylsalicylic acid) was synthesized as synthetic enzyme-depside complex, and characterized by spectroscopic methods and X-ray crystal analysis. The dioxygenation of flavonol (flaH) and 3-hydroxy-4-quinolone (quinH2) derivatives in the presence of catalytic amounts of FeIII(O-bs)(salen) results in the oxidative cleavage of the heterocyclic ring to give the corresponding O-benzoylsalicylic and anthranilic acid derivatives with concomitant release of carbon monoxide. These reactions can be regarded as biomimetic functional models with relevance to the iron-containing flavonol and the cofactor-independent 3-hydroxy-4(1H)-quinolone 2,4-dioxygenases.
- Pap, József S.,Matuz, Andrea,Baráth, Gábor,Kripli, Balázs,Giorgi, Michel,Speier, Gábor,Kaizer, József
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experimental part
p. 15 - 21
(2012/06/15)
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- A new synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones by cyanuric chloride cyclodehydration of N-benzoyl- and N-acylanthranilic acids
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A new and a convenient method for the synthesis of aryl- and alkyl-2-substituted 4H-3,1-benzoxazin-4-ones by cyclodehydration of N-benzoyl- and N-acylanthranilic acid by cyanuric chloride is described.
- Khajavi, Mohammad S.,Shariat, Seyed M.
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p. 1159 - 1165
(2007/10/03)
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- AMIDE DERIVATIVES AND THEIR USE AS CHLORIDE CHANNEL BLOCKERS
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The present invention relates to novel amide derivatives useful as chloride channel blockers. In other aspects the invention relates to the use of these compounds in a method for therapy, such as for the treatment of bone metabolic diseases, diseases resp
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