412335-39-8Relevant academic research and scientific papers
4-hydroxy-2-quinolones. 202*. Synthesis, chemical and biological properties of 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3- carboxylic acid alkylamides
Ukrainets,Bevz,Mospanova,Savchenkova,Yankovich
, p. 320 - 326 (2012)
In continuation of the search for potential analgesics amongst 4-hydroxyquinol-2-one derivatives we have proposed and carried out a preparative method of synthesis of 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3- carboxylic acid alkylamides. It has been shown that bromination of 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid allylamide using an equivalent of molecular bromine occurs with a conventional addition of the halogen to the allyl double bond and not with halocyclization. The results of the study of the analgesic properties of the compounds prepared are presented.
Scaffold morphing leading to evolution of 2,4-diaminoquinolines and aminopyrazolopyrimidines as inhibitors of the ATP synthesis pathway
Tantry, Subramanyam J.,Shinde, Vikas,Balakrishnan, Gayathri,Markad, Shankar D.,Gupta, Amit K.,Bhat, Jyothi,Narayan, Ashwini,Raichurkar, Anandkumar,Jena, Lalit Kumar,Sharma, Sreevalli,Kumar, Naveen,Nanduri, Robert,Bharath, Sowmya,Reddy, Jitendar,Panduga, Vijender,Prabhakar,Kandaswamy, Karthikeyan,Kaur, Parvinder,Dinesh, Neela,Guptha, Supreeth,Saralaya, Ramanatha,Panda, Manoranjan,Rudrapatna, Suresh,Mallya, Meenakshi,Rubin, Harvey,Yano, Takahiro,Mdluili, Khisi,Cooper, Christopher B.,Balasubramanian,Sambandamurthy, Vasan K.,Ramachandran, Vasanthi,Shandil, Radha,Kavanagh, Stefan,Narayanan, Shridhar,Iyer, Pravin,Mukherjee, Kakoli,Hosagrahara, Vinayak P.,Solapure, Suresh,Hameed, P.Shahul,Ravishankar, Sudha
supporting information, p. 1022 - 1032 (2016/06/08)
The success of bedaquiline as an anti-tubercular agent for the treatment of multidrug-resistant tuberculosis has validated the ATP synthesis pathway and in particular ATP synthase as an attractive target. However, limitations associated with its use in the clinic and the drug-drug interactions with rifampicin have prompted research efforts towards identifying alternative ATP synthesis inhibitors with differentiated mechanisms of action. A biochemical assay was employed to screen AstraZeneca's corporate compound collection to identify the inhibitors of mycobacterial ATP synthesis. The high-throughput screening resulted in the identification of 2,4-diaminoquinazolines as inhibitors of the ATP synthesis pathway. A structure-activity relationship for the quinazolines was established and the knowledge was utilized to morph the quinazoline core into quinoline and pyrazolopyrimidine to expand the scope of chemical diversity. The morphed scaffolds exhibited a 10-fold improvement in enzyme potency and over 100-fold improvement in selectivity against inhibition of mammalian mitochondrial ATP synthesis. These novel compounds were bactericidal and demonstrated growth retardation of Mycobacterium tuberculosis in the acute mouse model of tuberculosis infection.
Syntheses and fluorescent properties of 6-methoxy-2-oxoquinoline-3,4- dicarbonitriles and 6,7-dimethoxy-2-oxoquinoline-3,4-dicarbonitriles
Enoua, Guy Crépin,Lahm, Günther,Uray, Georg,Stadlbauer, Wolfgang
, p. E263-E275 (2014/11/07)
4-Chlorocarbostyrils 3, 12, 17, 24, 26 with methoxy substituents in 6, 7, or 6,7-position react with potassium cyanide in a p-toluenesulfinate mediated reaction either to the highly fluorescent and stable 2-oxoquinoline-3,4- dicarbonitriles 6, 27, 29, 30 or at slightly lower temperatures to 4-monocarbonitriles 5, 13, 18. 4-Chlorocarbostyril 3 and lithium p-toluenesulfinate gave pure 4-toluenesulfonylquinolone 4, which reacted with potassium cyanide either to monocarbonitrile 5 or dicarbonitrile 6, depending on the reaction conditions. 4-Trifluoromethylquinolones 9 and 19 were prepared for fluorescence comparison from the appropriate methoxyaniline and 4,4,4-trifluoroacetoacetate. The fluorescence properties such as emission wavelengths and quantum yields of 6-methoxyderivatives 4, 5, 6, 9, 13 were studied and compared with those of 7-methoxy derivatives 18, 19 and 6,7-dimethoxyderivatives 27, 28, 29, 30. 6,7-Dimethoxy derivatives show best results, showing long-waved fluorescence spectra up to 520 nm and acceptable quantum yields up to 0.46 for 3,4-dicyano derivative 27 excited at 440 nm in acetonitrile.
4-Cyano-6,7-dimethoxycarbostyrils with solvent- and pH-independent high fluorescence quantum yields and emission maxima
Ahvale, Appasaheb B.,Prokopcova, Hana,Sefcovicova, Jana,Steinschifter, Waltraud,Taeubl, Anna E.,Uray, Georg,Stadlbauer, Wolfgang
, p. 563 - 571 (2008/09/18)
Highly fluorescent and stable 6,7-dimethoxy-2-oxoquinoline-4-carbonitriles (11) were synthesized starting from appropriate 4-hydroxyquinolones 3 via reactive 4-chloroquinolones 8 by using toluenesulfinates as catalysts. In contrast to the well-described 4-trifluoromethyl-substituted analogues 18, N-substituted derivatives 11 fluoresce in water, polar, and apolar solvents in a narrow 430-440-nm window with almost constant quantum yield of 0.5. Equal excitation is possible in the broad double maximum between 385 and 410 nm yielding identical data between pH 1 and 11. These properties could lead to a broadly usable fluorescence standard. N-Alkylation with bromoacetate yields ester 13 in good yields. Reactive succinimidoyl (OSu) ester 15 was prepared by saponification to acid 14. With amino acids or peptides, linking to labeled derivatives 17 was achieved under mild conditions in slightly basic aqueous media. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
