64675-79-2Relevant academic research and scientific papers
Convenient Synthesis of Piperazine Substituted Quinolones
Fathalla, Walid,Pazdera, Pavel
, p. 3481 - 3489 (2017)
A series of 1-[(4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinolin-3-yl)carbonyl]-4-(substituted) piperazines 3a–c and methyl 2-[(4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinolin-3-yl)carbonylamino] alkanoates 5a–d has been developed by the direct condensation of ethyl [4-hydroxy-2-oxo-1-phenyl-1,2-dihydro-3-quinoline] carboxylate 2 with N1-monosubstituted piperazine hydrochlorides or amino acid ester hydrochloride in the presence of triethyl amine. The quinolone amino acid esters 5a–d were the key intermediate for the preparation of a series of 1-[2-((4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinolin-3-yl)carbonylamino)alkylcarbony]-4-substituted piperazine derivatives 8–11 (a-d) via azide coupling method with amino acid ester hydrochloride.
Synthesis of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl) carbonylamino] alkanoates and methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonyl-amino)alkanamido] alkanoate
Fathalla, Walid,Pazdera, Pavel
, p. 158 - 173 (2017/06/19)
A series of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino] alkanoates 7a-f has been developed by the direct condensation of ethyl [4-hydroxy-2-oxo-1-phenyl-1,2-dihydro-3-quinoline] carboxylate 4 with amino acid ester hydrochloride in the presence of triethylamine. The quinoline amino acid esters 7a-f were the key intermediate for the preparation of a series of methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino)alkanamido] alkanoate 10-13(a-f) via azide coupling method with amino acid ester. {figure presented}.
TUMOR NECROSIS FACTOR ALPHA INHIBITORS AND THEIR USE IN THE TREATMENT OF HUMAN DISEASES
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, (2008/12/06)
treatment of a variety of disorders, including the treatment of pathological conditions associated with tumor necrosis factor alpha. The inhibitors of tumor necrosis factor alpha have the following structures: including stereoisomers, pharmaceutically acceptable salts, and solvates thereof, wherein substituents are as defined herein. Compositions containing an inhibitor of tumor necrosis factor alpha in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.
A novel short-step synthesis of functionalized 4-hydroxy-2-quinolones using a 1-hydroxybenzotriazole methodology
Zikou, Lamprini,Athanasellis, Giorgos,Detsi, Anastasia,Zografos, Alexandros,Mitsos, Christos,Igglessi-Markopoulou, Olga
, p. 1505 - 1508 (2007/10/03)
A novel method for the synthesis of 3-substituted 4-hydroxy-1-methyl- and 1-phenyl-2-quinolones is presented. The compounds are produced in a one-step reaction in very good yields (51-76%). The major advantage of the methodology is the short time for the
Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders: Structure-Activity Relationship
J?nsson, Stig,Andersson, Gunnar,Fex, Tomas,Fristedt, Tomas,Hedlund, Gunnar,Jansson, Karl,Abramo, Lisbeth,Fritzson, Ingela,Pekarski, Olga,Runstr?m, Anna,Sandin, Helena,Thuvesson, Ingela,Bj?rk, Anders
, p. 2075 - 2088 (2007/10/03)
Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).
4-HYDROXY-2-QUINOLONES. 22. SYNTHESIS AND BIOLOGICAL PROPERTIES OF 1-ALKYL(ARYL)-2-OXO-3-CERBETHOXY-4-HYDROXYQUINOLINES AND THEIR DERIVATIVES
Ukrainets, I.V.,Gorokhova, O.V.,Taran, S.G.,Bezuglyi, P.A.,Turov, A.V.,et al.
, p. 829 - 836 (2007/10/02)
The presently known method for obtaining ethyl esters of 1-alkyl(or aryl)-2-oxo-4-hydroxyquinoline-3-carboxylic acids and their derivatives has been improved.Results are presented from an investigation of the anticoagulant, analgesic, and antiinflammatory activities of the synthesized compounds.
4-Hydroxy-2-quinolones. 3. Synthesis and Physicochemical Properties of 1-R-3-Carbethoxy-4-hydroxy-2-quinolones
Ukrainets, I. V.,Bezuglyi, P. A.,Treskach, V. I.,Turov, A. V.,Slobodzyan, S. V.
, p. 534 - 538 (2007/10/02)
1-R-3-Carbethoxy-4-hydroxy-2-quinolones were synthesized by intramolecular cyclization of N-R-2-carbalkoxymalonanilic acids by the Dieckmann reaction.The possibility and advantages of conducting this reaction in aqueous medium were demonstrated.The mutual
