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1 RESEARCES ABOUT SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF SOME 4-QUINOLIN- 3-CARBOXYLIC ACID DERIVATIVES. CHEMICAL STRUCTURE -BIOLOGICAL ACTIVITY RELATIONSHIPS - BIOCHINOXO- Contract CEEX: 197/2006 Consortium parteners list Project coordinator: CO - National Institute for Chemical Pharmaceutical Research and development ICCF Calea Vitan, 112, Sector 3, Bucuresti Tel. : Parteners : P 1 Technical University Gh. Asachi Iasi UTI Gh. Asachi P 2 - "C. D. Nenitescu Institute of Organic Chemistry- CCOA Splaiul Independentei, 202B, Sector 6, Bucuresti - P 3 University of Medicine and Pharmacy Gr. T. Popa - UMFIS Strada Universitatii, 16, Iasi, Jud. Iasi Project Manager : Dr.ing. Pintilie Lucia Project Short Presentation Lately it has been observed that a certain resistance to the following bacteria, separated from infectious processes, has been acquired in Central Europe, where Ciprofloxacin has been widely utilized: Pseudomonas aeruginosa, Escherichia coli, Staphilococus aureus. Resistance to fluoroquinolones can be obtained by chromosomal mutation, which takes a long time to settle. Because of this, worldwide research for new fluoroquinolones was based on 2 desired outcomes: - the synthesis of new 4-oxo-1,4-dihydro-quinolones, active against pathogenetic germs which are resistant to first generation 4-oxo-1,4-dihydro-quinolones - enlarging the antibacterial spectrum of the 4-oxo-1,4-dihydro-quinolines on gram positive and anaerobic germs Taking these into account, the main objectives of this project are:: obtaining new biologically active (antibacterial, antitumoral and/or antiviral) derivatives of the 4-oxo-1, 4-dihydro-quinoline-3-carboxylic acid through synthesis; obtaining an original compounds with a large antibacterial spectrum, against both gram negative and gram positive germs; obtaining an original compound active against bacteria that has become immune to currently used antibiotics. The measurable objectives are : Synthesis of original compounds with quinolone structure; Physical chemical structured characterization of the synthesized original Determining the specific biological activity; Elaborating laboratory procedures for the most biologically active compound. Work Procedures The processes employed are:
2 - processing documentary and experiment data, saving project related information using software applications; - chemical reactions (substitution reactions, reduction, condensation, alkylation, arylation, amination, hydrolysis), laboratory operations :purification through crystallization, distillation at atmospheric pressure, at reduced pressure, fractionized distillation, extractions, filtering; - structural physical-chemical characterization of the intermediary and the active substance by elemental analysis, IR spectroscopy, UV spectroscopy, H-NMR, C-NMR, mass spectrometry, HPLC,.gas chromatography, CSS. - Molecular mechanics software and and prediction of specific activity. Identify the significant molecular fragments and the molecular features with great influence on biochemical activity value. Identify the molecules recommende for synthesis or un recommende for synthesis in the set molecules(new molecules,not yet synthesised) Proofing the sensitivity degree of the tested germs against the original substances will be done by establishing by minimum inhibitory concentration (MIC), by the CO Pharmaco Department in collaboration with P3. The tested strains are Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC The proofing will be performed by the twofold agar dilution method. The CMI will be determined using the twofold agar dilution method in a liquid environment. The bacteria inoculum is made up of a microbial suspension with a filter of UFC/ml. The chemotherapy agent dilution is obtained from a solution of 100 mcg/ml. the inferior limit of binary work solutions will be chosen so that it will allow the evaluation of the MIC for each strain separately. The work tubes containing the dilutions inoculated with the bacterial suspension for each microorganism separately will be incubated at 37 0 C for hours, after which the data readings will take place. The lowest concentration of antimicrobial agent that restrains the development of the microorganism represents the minimum inhibitory concentration (MIC). Estimated Results The following results are estimated for this research project: - obtaining original compounds with specific biological activity (antibacterial, antiviral, antitumoral); -identifying an original antibiotic with a large antimicrobial spectrum; it should also be active against bacteria which has acquired resistance to beta-lactamic antibiotics and other antibiotics used in anti infectious therapy; -the intermediaries used in the synthesis of 4-oxo-1,4-dihydro-quinolones derivatives will be also useful in the synthesis of other drugs; -elaborating the synthesis process in advantageous technical-economical conditions and by adhering to European quality and environmental norms for the selected product; -the possibility of inter-disciplinary collaboration with other Academy institutes, other research and development institutes or tertiary study institutes. Benefits: - An original product with pharmacological performance will be obtained either by micro production or by technological transfer to specialized factory; - The intermediaries will in turn be prime material for obtaining new drugs, e.g. quinolone drugs with antiviral activity (anti-hiv, antiherpetic, with inhibitory properties of HBV DNA ) quinolones drugs with antitumoral activity, or dyes: Dissemination of Results - The research results will be made public on each action and phase - At official communiqués and symposiums and conferences national and international. - Web page; - Boks, publications; - Articles in specialized journals from Romania and from abroad: Revue Romaine de Chemie, Quarterly Review, Revista de Chimie, Roumanian Biotehnological Letters, Antimicrobial Agents and Chemotherapy, Il Farmaco, Bioorganic and Medicinal Chemistry Letters. - The scientific results will be patented according to the law.
3 Phase I: Synthesis for obtaining new compounds type I and II;QSAR studies evaluating worldwide research; establishing synthesis strategy for obtaining new 4- oxo- 1,4-dihydro-quinolones experimental synthesis studies ; the physical-chemical characterization of intermediaries and new QSAR studies pharmacological studies Were presented documentary studies about quinolones compounds. It was established the research strategy for obtaining key intermediates and new quinolones compounds. Were obtained by chemical synthesis using the modified Gould-Jacobs method 9 key intermediates and 6 new quinolones compounds. The modeling process was performed by obtaining a key intermediate using regression and neural networks The analysis was performed and the structural characterization and H-NMR, C-NMR, FT-IR, UV- Vis, MS and elemental analysis. Were carried out molecular mechanics calculations predict property and specific action Models were validated experimental pharmacological tests necessary original structures summarized. Phase II : Synthesis for obtaining new compounds type III ; QSAR studies evaluating worldwide research; establishing synthesis strategy for obtaining new 4- oxo- 1,4-dihydro-quinolones experimental synthesis studies; the physical-chemical characterization of intermediaries and new molecular mechanics software; QSAR studies; evaluating the specific biological activity of the new Were presented documentary studies about quinolones compounds. It was established the research strategy for obtaining key intermediates and new quinolones compounds. Were obtained by chemical synthesis using the modified Gould-Jacobs method 11 key intermediates and 14 new quinolones compounds. The analysis was performed and the structural characterization and H-NMR, C-NMR, FT-IR, UV-Vis, MS and elemental analysis. Were carried out molecular mechanics calculations predict property and specific action Pharmacological Studies were conducted on9 new quinolones compounds Phase III Synthesis for obtaining new compounds type IV and V ; QSAR studies. Final evaluation of the biological activity aimed at selecting the substance with the best biological activity evaluating worldwide research; establishing synthesis strategy for obtaining new 4- oxo- 1,4-dihydro-quinolones
4 experimental synthesis studies ; the physical-chemical characterization of intermediaries and new molecular mechanics software QSAR studies evaluating the specific biological activity of the new Final evaluation of the biological activity aimed at selecting the substance with the best biological activity Were presented documentary studies about quinolones compounds. It was established the research strategy for obtaining key intermediates and new quinolones compounds. Were obtained by chemical synthesis using the Gould-Jacobs method 22 key intermediates and 27 new quinolones compounds. Were presented QSAR studies Were carried out pharmacological studies on 12 new compounds. Phase IV: The synthesis process for the selected compound;expanding the pharmacological studies experimental laboratory studies in order to elaborate the synthesis process for the selected compound; structural physical-chemical characterization of the intermediaries and the new molecular mechanics software expanding the pharmacological studies identifying and granting the intellectual property rights over the results elaborating the synthesis process for the selected compound; Were made: - experimental laboratory studies to optimize parameters for the synthesis steps involved in obtaining key intermediates and selected compounds - were developed laboratory methods for preparing compounds PQ 22, PQ 24, FPQ 25, FPQ 28. -new compounds were characterized by elemental analysis, melting point and FT-IR spectra, 1Hand 13C-RMN.Molecular mechanics SOFTWARE enabled the representation of the geometry of minimum energy of the quinolone most biologically active. Were calculated interatomics distances, the heat of formation and dipole moment of the molecule. -were carried out pharmacological studies on 12 compounds. -were selected from a number of the compounds tested, which have significant antibacterial activity and to be tested further for activity and other bacterial strains. Dissemination of Results Patents 1) Accession number - CBI A2008/00125 Noi derivati fluorochinolonpiperazinil-sulfonil-fenoxiacetici si procedeu de obtinere a acestora. Autori: Corneliu Oniscu, Lucia Pintilie, Corina Cernatescu, Anca Mocanu, Miron Teodor Caproiu 2) Accession number - CBI A2008/00663 NOI DERIVATI CHINOLONICI CU ACTIVITATE ANTIMICROBIANA SI PROCEDEUL DE PREPARARE AL LOR Pintilie Lucia, Negut Catalina, Oniscu Corneliu, Caproiu Miron Teodor, Nechifor Mihai Articles
5 1. New antimicrobial quinolones.1. Mathematical and neural modeling of diethylethoxymethylene malonate synthesys Oniscu C., Dumitrascu A., Pintilie L. Cernatescu C., Mocanu A., si Curteanu S., Roum.Biotechnol.Lett., 12(1), 3089 (2007). 2. QSARs on Bactericide Activity of 3 Carboxyl-4-Quinolones Tarko Laszlo,Lucia Pintilie,Catalina Negut,Oniscu Corneliu,Caproiu Miron Teodor Revista de Chimie (Bucuresti), 59(2), , Synthesis and Antibacterial Activity of Some Novel Quinolones - LUCIA PINTILIE, CATALINA CIOATES, C. ONISCU, M.T. CAPROIU, M. NECHIFOR, LUMINITA IANCU, CRISTINA GHICIUC, RAMONA URSU Roumanian Biotechnological Letters in press 4. Synthesis and Antibacterial Activity of Some Novel Desfluoroquinolones LUCIA PINTILIE, CATALINA CIOATES, C. ONISCU, M.T. CAPROIU, M. NECHIFOR, Revista de Chimie in press 5. New antimicrobial quinolones. II. Mathematical and neuronal modeling of 6- Fluoro-7-Chloro-4-oxo-quionolin-3-carboxilic acid synthesis C. ONISCU, L. PINTILIE, C. CERNATESCU, A. MOCANU, S. CURTEANU, Roumanian Biotechnological Letters in press 6. New antimicrobial quinolones. III. Mathematical and neuronal modeling of 6- Fluoro-7-morpholino-8-chloro-1-ethyl-4-oxo-quionolin-3-carboxilic acid synthesis C. ONISCU, L. PINTILIE, C. CERNATESCU, A. MOCANU, R. DIACONESCU Roumanian Biotechnological Letters in press Conference Titles 1) CERCETARI PRIVIND SINTEZA DE CHINOLONE NEFLUORURATE IN POZITIA 6 - comunicare Pintilie L, Oniscu C. Cocu F., Tanase C., Croitoru M., Albu F. Biraruti E.., Caproiu M.T, Draghici C al IV-lea Simpozion cu participare internationala Cercetarea Medicamentului intre informatie si stiintele vietii octombrie 2006, Bucuresti 2) CERCETARI PRIVIND SINTEZA DE NOI CHINOLONE FLUORURATE SUBSTITUITE IN NUCLEUL PIPERAZINIC - comunicare Oniscu C. Pintilie L. Mocanu A., Cernatescu C. al VIII-lea Simpozion International de produse cosmetice si odorizante mai 2007, Iasi 3) CERCETARI PRIVIND SINTEZA UNOR NOI AGENTI ANTIMICROBIENI DIN CLASA CHINOLONELOR -Poster PINTILIE LUCIA, ONISCU CORNELIU, NEGUT CATALINA, TANASE VIOREL, CAPROIU MIRON TEODOR, DRAGHICI CONSTANTIN, NECHIFOR MIHAI, LUPUSORU CATALINA, GHICIUC CRISTINA, CIUBOTARIU DIANA, CUCIUREANU MAGDA Simpozionul National de Cercetare Stiintifica Medicala de Excelenta : octombrie 2007 Sibiu 4) Fluorochinolonele-de la cercetare preclinica la progrese in terapie Nichifor Mihai,Catalina Elena Lupusoru,Chelarescu Dan-Ioan,Cristina Ghiciuc, Magda Cuciureanu, Diana Ciubotaru, Roxana Iancu, Lucia Pintilie, Oniscu Corneliu,Caproiu Miron Teodor,Draghici Constantin Congresul Nationat de Terapeutica,si Toxilogie clinica,mg.mures mai ) SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF SOME 4-OXO-QUINOLIN-3- CARBOXILIC ACID DERIVATIVES Poster Pintilie Lucia, Oniscu Corneliu, Nechifor Mihai, Negut Catalina, Tanase Constantin, Caproiu Miron Teodor, Draghici Constantin, Lupusoru Catalina, Ghiciuc Cristina, Chelarescu Dan, Ciubotariu Diana, Cuciureanu Magda XXth International Symposium on Medicinal Chemistry Viena, Austria, ) SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF SOME NOVEL QUINOLONES Poster
6 Pintilie Lucia, Oniscu Corneliu, Nechifor Mihai, Cocu Florea, Negut Catalina, Tanase Constantin, Caproiu Miron Teodor, Draghici Constantin, Maganu Maria, Lupusoru Catalina, Ghiciuc Cristina, Chelarescu Dan, Ciubotariu Diana, Cuciureanu Magda. Sixth International Conferance of Chemical Societies of South-Eastern European Countries Sofia, Bulgaria, septembrie ) RESEARCES ABOUT SYNTHESIS OF SOME 4-OXO-QUINOLINE-3-CARBOXYLIC ACID DERIVATIVES WITH BIOLOGICAL ACTIVITY -Poster Pintilie Lucia, Oniscu Corneliu, Nechifor Mihai, Cocu Florea, Negut Catalina, Tanase Constantin, Caproiu Miron Teodor, Draghici Constantin, Maganu Maria, Lupusoru Catalina, Ghiciuc Cristina, Chelarescu Dan, Ciubotariu Diana, Cuciureanu Magda. 2nd EuCheMS Chemistry Congress, Torino, Italia, septembrie ) Cercetari privind sinteza si activitatea antibacteriana a unor noi derivati de acid 4-oxochinolin-3-carboxilic Lucia Pintilie, Corneliu Oniscu, Constantin Tanase, Catalina Negut, Miron Teodor, Caproiu, Draghici Constantin, Nechifor Mihai, Catalina Lupusoru, Cristina Ghiciuc, Luminita Iancu, Ramona Ursu, Brandusa Copacianu, Dan Chelarescu Simpozion National VIASAN-CEEX (Modul 1) Septembrie Hotel Sinaia, Sinaia -Poster 9) Modelarea matematica si neuronala a procesului de obtinere a esterilor acizilor 1-R-6- fluoro-7-cloro-1,4-dihidro-4-oxo-chinolin-3-carboxilici Corneliu Oniscu, Lucia Pintilie, Miron Teodor Caproiu, Anca Mocanu, Corina Cernatescu Simpozion National VIASAN-CEEX (Modul 1) Septembrie Hotel Sinaia, Sinaia -Poster 10) Cercetari farmacologice aupra unor derivati ai acidului 4-oxo-chinolin-3-carboxilic Comunicare Mihai Nechifor, Luminita Iancu, Lucia Pintilie, Catalina Lupusoru, Cristina Ghiciuc, Dan Chelarescu, Ramona Ursu, Diana Ciubotariu Simpozion National VIASAN-CEEX (Modul 1) Septembrie Hotel Sinaia, Sinaia -Poster PERSPECTIVES Four compounds presented notable antimicrobial activity in vitro against E. Coli ATC25922and S. aureus respectively, PQ 22, PQ 24, FPQ 25, FPQ 28. For these compounds would be useful to further research and preclinical pharmacological trials in the event of possible future developments as medicines. Also, the results obtained in this phase, namely the development of laboratory methods for the synthesis of intermediates and quinolone compounds may be used: -in developing a process and Single Pilot + Laboratory on getting a new compound with antimicrobial activity - elaboration of new methods of synthesis of new derivatives quinolon-3-carboxylic acid with antitumoral or antiviral activity
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