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Mikrotalasno stimulisane transformacije prirodnih i sintetičkih karboksilnih kiselina i njihovih derivata / Microwave-assisted transformation of natural and synthetic carboxylic acids and their derivativesPavlović Ksenija 25 September 2014 (has links)
<p>Predviđena istraživanja u ovoj doktorskoj disertaciji su usmerena u pravcu <br />modifikacije klasičnih metoda i postupaka za transformaciju karboksilne grupe <br />prirodnih i sintetičkih karboksilnih kiselina. Modifikacije su rađene novim, <br />savremenim, ekonomski i ekološki opravdanim metodama rada u <br />mikrotalasnom reaktoru. Modifikovanim sintetskim postupcima u <br />mikrotalasnom reaktoru urađena je sinteza amida, hidroksamskih derivata, <br />kao i redukcija individualnih naftnih kiselina i smeše prirodnih naftnih kiselina <br />„Velebit“ do alkohola. Prirodne naftne kiseline korišćene u ovom radu su prvo <br />izolovane iz gasne frakcije (interval destilacije 168-290 °C) vojvođanske nafte <br />„Velebit“ a potom prečišćene i razdvojene na uže frakcije na osnovu različite <br />kiselosti. Nakon toga, izvršena je njihova karakterizacija GC-MS-EI analizom <br />(čime je potvrđeno da dolazi do strukturne diferencijacije kiselina). U radu je <br />takođe ispitana biološka aktivnost sintetizovanih derivata. Proučavan je uticaj <br />prirodnih naftnih kiselina „Velebit“ i njenih derivata na rast pet sojeva <br />Pseudomonas sp., kao i uticaj odabranih sintetisanih jedinjenja na proliferaciju <br />četiri ćelijske linije humanih tumora pri čemu je kao kontrola služila jedna <br />zdrava humana ćelijska linija.</p> / <p>The investigation of this doctoral dissertation is directed toward the modification of the transformation of the carboxylic group of natural and synthetic carboxylic acids. The dissertation takes into consideration the classical methods and procedures of the reaction and modifies them using microwave reactor. The synthesis of amides, hydroxamic derivatives, as well as the reduction of individual petroleum acids and acid mixtures of natural oil "Velebit" to alcohol were achieved by the modifications made to the synthetic methods in the microwave reactor. The natural oil acids used within this study were first isolated from the gas fraction (distillation interval 168-290 °C) of the Vojvodina's crude oil "Velebit", and then purified and separated by the narrow fractions under the different acidity. After that, their characterisation was made by the GC-MS-EI analysis which confirmed that the structural differentiation of acids had been achieved. Also, the biological activity of the synthesized derivatives are analysed. The impact of natural petroleum acids "Velebit" and its derivatives on the growth of five strains of Pseudomonas sp. was studied, as well as the impact of selected synthesized compounds on the proliferation of four human tumor cell lines wherein one healthy human cell lines used as the control.</p>
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Biološka aktivnost novosintetisanih D-seko i D-homo-estratrienskih derivata u in vivo i in vitro uslovima / Biological activity of the newly synthesized D-secoand D-homoestratriene derivatives in in vivo and in vitro experimentsJovanović-Šanta Suzana 08 October 2010 (has links)
<p>Sintetisana su nova jedinjenja, 16- i 17-supstituisani 16,17-sekoestratrienski derivati i D-homoestranski derivati, polazeći od 3-benziloksi-17-hidroksi-16,17-sekoestra-1,3,5(10)-trien-16-nitrila. Ispitana je estrogena i antiestrogena aktivnost u eksperimentima <em>in vivo</em>, antiaromatazna aktivnost <em>in vitro</em>, antioksidantna aktivnost DPPH i TBA testom, kao i antiproliferativna aktivnost prema ćelijskim linijama MCF-7 ATCC, MDA-MB-231, HT-29 i MRC-5 novosintetisanih jedinjenja.</p> / <p>Some new compounds, 16- and 17-substituted 16,17-secoestratriene derivatives, as well as D-homoestratriene derivatives, were synthesized, starting from 3-benzyloxy-17-hydroxy-16,17-secoestra-1,3,5 (10)-triene-16-nitrile. The newly synthesized compounds were tested for their <em>in vivo </em>estrogenic and antiestrogenic activity, <em>in vitro </em>antiaromatase activity, antioxidative activity by DPPH and TBA tests, as well as antiproliferative activity against MCF-7 ATCC, MDA-MB-231, HT-29 i MRC-5 cell lines.</p>
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Prirodni stiril-laktoni, njihovi derivati i analozi kao potencijalni antitumorski agensi: Dizajn, sinteza i SAR ispitivanja / Natural styryl-lactones, their derivatives and analogues as potential antitumour agents: Design, synthesis and a SAR studyKovačević Ivana 29 April 2015 (has links)
<p>U radu je ostvarena sinteza četiri prirodna proizvoda, goniobutenolida A i B,<br />krasalaktona D i 3-deoksi-kardiobutanolida i 32 derivata i analoga polazeći iz<br />D-glukoze. Sinteza prirodnog stiril-laktona, kardiobutanolida i njegova 4<br />derivata je izvedena polazeći iz D-ksiloze. Ispitan je uticaj sintetizovanih<br />jedinjenja na inhibiciju rasta 10 tumorskih i jedne zdrave ćelijske linije.<br />Uspostavljene su i korelacije izmedju strukture i antiproliferativne aktivnosti (SAR) i ispitan je mehanzam antitumorskog dejstva.</p> / <p>Synthesis of four natural products: goniobutenolide A and B, crassalactone D, 3-deoxy-cardiobutanolide and their 32 analogues and derivatives is accomplished starting from D-glucose. Synthesis of natural styryl lactone cardiobutanolide and its four derivatives is achieved starting from D-xylose. Synthesized natural lactones, their analogues and derivatives were evaluated for their antiproliferative activity against ten malignant cell lines as well as against a single normal cell line. Influence of functional groups on antitumour activity was established by correlating structures of synthesized compounds with their biological activity (SAR). Also, mechanism of antitumour action was investigated.</p>
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Sinteza, strukturna, fizičko-hemijska i biološka karakterizacija novih N-heterocikličnih liganada i njihovih kompleksa sa jonima prelaznih metala / Synthesis, structural, physico-chemical and biological characterization of N-heterocyclic ligands and their complexes with transition metal ionsMađari Jožef 08 October 2018 (has links)
<p>Opisane su sinteze novih liganada bis(ftalazin-1hidrazon)-2,6-diacetilpiridna (Hz<sub>2</sub>DAP·2HCl), bis(3-hlorpiridazin-6-hidrazon)-2,6-diacetilpiridina (Hp<sub>2</sub>DAP), 3-hlorpiridazin-6-hidrazon di(2-piridil) ketona (HpDPK), ftalazin-1-hidrazon di(2-piridil)<br />ketona (HzDPK) i ftalazin-1-hidrazon piridin-2-karbaldehida (HzPY). Zajedničko svojstvo dobijenih liganada je što sadrže piridinski i diazinski prsten i sadrže samo donorne atome azota. Tokom nastajanja kompleksa dolazi do deprotonacije liganada. Svi ligandi su okarakterisani elementalnom analizom, termoanalitičkim metodama i metodom IR spektroskopije, dok neki i metodom NMR spektroskopije kao i rendgenskom strukturnom analizom.Za sintezu koordinacionih jedinjenja primenjeni soli Co(II), Ni(II), Cu(II) i Zn(II). Dobijeni kompleksi su okarakterisani elementalnom analizom, konduktomerijskim i magnetnim merenjima, IR spektroskopijom i termoanalitičkim metodama. Barem jedan kompleks iz svake serije je okarakterisan i rendgenskom strukturnom analizom. Urađena su i ispitivanja antimikrobne aktivnosti odabranih jedinjenja prema predstavnicima grampozitivnih i gram-negativnih bakterija i kulturu kvasca. Pored toga, urađena su i ispitivanja citotoksične,antiproliferativne i inhibitorne aktivnosti jedinjenja prema roditeljskim i multirezistentnim T-limfomnim ćelijama kancera. Utvrđeno je da neka jedinjenja pokazuju izrazito mikrobicidno, citotoksično, antiproliferativno i inhibitorno dejstvo.</p> / <p>The synthesis of new ligands dihydrochloride salt of 2,6-diacetylpyridne bis(phthalazine-1hydrazone) (Hz<sub>2</sub>DAP•2HCl), 2,6-diacetylpiridine bis(3- chloropyridazine-6-hydrazone) (Hp<sub>2</sub>DAP), di(2-pyridyl)ketone 3-chloropyridazine- 6-hydrazone (HpDPK), di(2-pyridyl)ketone phthalazine-1-hydrazone (HzDPK) and pyridine-2-carbaldehide phthalazine-1-hydrazone (HzPY) have been described. All the ligands contain pyridine and diazine core and all of them have only nitrogen donor atoms. During the complex formation the deprotonation of ligands takes places. All of the ligands have been characterized by elemental analysis,thermoanalytical methods and IR spectroscopy. In some cases also by NMR spectroscopy and X-ray structural analysis.Co(II), Ni(II), Cu(II) and Zn(II) salts were used for the synthesis of the coordinational compounds. The obtained complexes were characterized by elemental analysis, molar conductivity and magnetic measurements, IR spectroscopy and thermoanalytical methods. At least one complex of each series were characterized by X-ray structural analysis.The antimicrobial activity of some of the compounds toward Gram-positive/Gram- negative bacteria furthermore, the cytotoxic, antiproliferative and inhibitory activity toward sensitive parental andmultiresistant T-lymphoma cancer cells have also been carried out. It can be concluded that some of the compounds exhibit outstanding antimicrobial, cytotoxic, antiproliferative, and inhibitory activity.</p>
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Kompleksi nekih prelaznih metala sa Šifovim bazama aminogvanidina / Some transition metal complexes with Schiff bases of aminoguanidineRadanović Mirjana 29 October 2015 (has links)
<p> U ovoj doktorskoj disertaciji opisane su sinteze novih kompleksa prelaznih metala sa piridoksiliden- (PLAG), odnosno saliciliden-aminogvanidinom (SALAG). Dobijeni<br />kompleksi su okarakterisani elementalnom analizom, IR spektrima, konduktometrijskim i magnetnim merenjima, a većina i rendgenskom<br />strukturnom analizom. Osim toga, dobijene su i nove forme ovih Šifovih baza, i to u vidu monokristala, čime su omogućena ispitivanja njihovih molekulskih i kristalnih struktura, kao i uporedna analiza sa koordinovanim ligandima.<br /> Sa PLAG je sintetisano 7 novi kompleksa Cu(II), a pored toga po prvi put su<br />izolovani mono i bis(ligand) kompleksi Fe(III) i Co(III), mono(ligand) kompleksi V(V), kao i jedan kompleks Zn(II) u kojem ovaj potencijalno tridentatni <em> ONN </em> ligand, u<br />monoprotonovanoj formi, ima ulogu kontra-jona. Sa stanovišta geometrije zajedničko za izolovane komplekse Cu(II) i V(V) je da imaju kvadratno-piramidalnu strukturu, sa izuzetkom jednog kvadratno-planarnog kompleksa Cu(II), dok je u kompleksima Fe(III) i Co(III) nađeno očekivano oktaedarsko okruženje centralnog<br />jona. Pored ovih, sintetisano je i pet novih kompleksa sa SALAG, od kojih su dva<br />kompleksa Cu(II) i kompleks V(V) okarakterisani rendgenskom strukturnom<br />analizom, dok je mikrokristalnim bis(ligand) kompleksima Co(III) i Ni(III) na osnovu<br />fizičko-hemijskih karakteristika predložena odgovarajuća struktura.<br /> Zajedničko za obe opisane Šifove baze je da se koordinuju na <em> ONN </em>tridentatni način, i to preko atoma kiseonika deprotonovane fenolne grupe i atoma azota azometinske i imino grupe AG fragmeta. Posebno je naglašeno da su sa<br />PLAG izolovana dva dimerna kompleksa Cu(II) u kojima je po prvi put nađena tetradentatna koordinacija ovog liganda, u koju je dodatno uključen atom kiseonika hidroksimetil-grupe PL-ostatka. Za razliku od SALAG, koji je u izolovanim kompleksima koordinovan isključivo kao monoanjon, nastao deprotonacijom fenolne<br />OH-grupe, za PLAG je osim ove, potvđena koordinacija u neutralnoj, zwitter-jonskoj, ali i dvostruko deprotonovanoj formi. Zwitter-jonska forma liganda nastaje migracijom atoma vodonika sa fenolnog hidroksila na piridinski atom azota PL-ostatka, dok deprotonacijom piridinskog ili hidrazinskog atoma azota, odnosno oba pomenuta atoma nastaju monoanjon i dianjon helatnog liganda, respektivno.<br /> Na kraju, urađena su i ispitivanja antimikrobne aktivnosti odabranih jedinjenja<br />prema predstavnicima grampozitivnih i gramnegativnih bakterija, kao i dve kulture<br />kvasca. Tom prilikom nije utvrđena nikakva inhibitorna aktivnost prema primenjenim<br />bakterijskim sojevima, dok su u slučaju kvasaca izvesno mikrobicidno dejstvo pokazali samo kompleksi Cu(II).</p> / <p>This PhD thesis describes the syntheses of some new transition metal complexes with pyridoxilidene- (PLAG) and salicylideneaminoguanidine (SALAG). Obtained complexes are characterized by elemental analysis, IR spectroscopy, conductometric and magnetic measurements. Besides, the structural analysis of majority of the obtained complexes was performed. Some new forms of these Schiff bases are synthesized in form of single crystals, which made their X-ray analysis as well as comparison with coordinated forms possible.</p><p>With PLAG, 7 new Cu(II) complexes were obtained and for the first time mono and bis(ligand) complexes of Fe(III) and Co(III) as well mono(ligand) complexes of V(V) were isolated. Furthermore, the structure of Zn(II) complex in which PLAG in its monocationic form has a role of counter ion is presented. With the exception of one Cu(II) complex, all reported Cu(II) and V(V) complexes have a square-pyramidal geometry, whilst Fe(III) and Co(III) are situated in octahedral surroundings. Also, five new complexes of Cu(II), Co(III), Ni(II) and V(V) with SALAG were synthesized. In both Cu(II) complexes and V(V) complex the expected coordination mode and geometry were confirmed by X-ray analysis, while octahedral structure of bis(ligand) complexes with Co(III) and Ni(II) was proposed based on results of physico-chemical characterization.</p><p>Both PLAG and SALAG coordinate the metal ion in tridentate ONN manner, through the oxygen atom of deprotonated phenolic group and nitrogen atoms of azomethine and imino groups of AG moiety. It is also emphasized that in two dimeric Cu(II) complexes with PLAG tetradentate coordination mode was found, in which the oxygen atom of hydroxymethyl group of PL residue was additionally involved. Unlike SALAG, which is coordinated as monoanion in all of the examined complexes, PLAG can have one of three degrees of deprotonation. Zwitter-ion of PLAG is formed by migration of H-atom from phenolic oxygen to pyridine nitrogen, while the deprotonation of pyridine or/and hydrazine nitrogen, makes it mono-and dianion, respectively.</p><p>Also, microbiological tests on the selected compounds were preformed. Namely, antimicrobial activity of these compounds against some gram-positive and gram-negative bacteria, as well as some yeast cultures was examined and none of the samples showed antimicrobial activity against bacteria, whilst only Cu(II) complexes showed certain inhibitory effect against yeasts.</p>
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Strukturiranje polimernih mreža na osnovu akrilamida i akrilne kiseline / Structuring of polymer networks based on acrylamide and acrylic acidErceg Tamara 28 September 2019 (has links)
<p style="text-align: justify;">U ovom radu sintetisani su hidrogelovi na osnovu akrilamida i akrilne kiseline, radikalnom polimerizacijom, primenom konvencionalne i mikrotalasne metode sinteze. Varirani su početni odnosi monomera i udeo umreživača, u cilju ispitivanja uticaja sastava reakcione smeše na svojstva dobijenih hidrogelova. Optimizovani su uslovi sinteze u mikrotalasnom polju kao brže, jednostavnije i ekonomičnije metode. U cilju uspostavljanja korelacije između mehanizma sinteze, strukture i svojstava dobijenih hidrogelova, primenom relevantnih metoda karakterizacije, upoređena su apsorpciona, reološka, toplotna i strukturna svojstva hidrogelova dobijenih dvema metodama. Ustanovljeno je da se mikrotalasnom metodom sinteze na brži i jednostavniji način uz smanjen utrošak vremena i energije dobijaju hidrogelovi konkurentni onima koji se dobijaju konvencionalnim zagrevanjem u vodenom rastvoru. Drugi deo doktorata obuhvata sintezu hidrofilnih polimernih mreža na osnovu natrijum karboksimetilceluloze (NaCMC) i karboksilnih kiselina, od kojih je jedna serija sintetisana prožimanjem linearnim kopolimerima akrilamida i akrilne kiseline u cilju povećanja potencijala primene u floku-lacione svrhe. Rezultati ispitivanja svojstava bubrenja, strukturnih toplotnih i flokulacionih svojstava pokazali su međusobno slaganje. Dobijeni rezultati pokazali su da od primenjenih karboksilnih kiselina, linunska kiselina u udelu od 15% u odnosu na masu NaCMC daje hidrogelove najboljih svojstava. Kombinacijom ove mreže sa kopolimerom akrilamida i akrilne kiseline u masenom odnosu 10/90, stvara se teorijska platforma za dobijanja flokulanta koji bi mogao da pokaže visoku efikasnost u prečišćavanju vode u kojoj dominiraju pozitivno naelektrisane čestice, pravilnim izborom parametara flokulacije.</p> / <p>In this paper, hydrogels based on acrylamide and acrylic acid were synthesized using conventional and microwave synthetic methods via free-radical polymerization. The initial monomers ratio and amount of crosslinking agent were varied in order to investigate the effect of the composition of the reaction mixture on the properties of the obtained hydrogels. The conditions of synthesis in the microwave field as faster simpler and more economical method have been optimized. In order to establish a correlation between the mechanism of synthesis, structure and properties of the obtained hydrogels using the relevant methods of characterization, the absorption, rheological, thermal and structural properties of the hydrogels obtained by the two methods were compared. It has been found that the microwave synthesis is a faster and simpler method, which enables reduced consumption of time and energy and produces hydrogels competitive to those ones obtained by conventional heating in aqueous solution. The second part of the thesis includes the synthesis of hydrophilic polymer networks based on sodium carboxymethylcellulose (NaCMC) and carboxylic acids, whereby one series is synthesized by interpenetration of the network using the linear acrylamide and acrylic acid copolymers in order to increase the potential application of hydrogels for flocculation purposes. The results of measurements of swelling, structural, thermal and flocculation properites have shown mutual agreement. The obtained results have shown that among applied carboxylic acids, citric acid in the amount of 15% per mass of NaCMC, has given the hydrogels with the best properties. The Combination of this network with a copolymer of acrylamide and acrylic acid in a mass ratio of 10/90 has created a theoretical platform for the production of flocculant which could show high efficacy in purifying of water dominated by positively charged particles.</p>
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Enantiodivergentna totalna sinteza odabranih stiril laktona i preliminarno ispitivanje njihove citotoksičnosti / Enantiodivergent total synthesis of selected styryl lactones and preliminary evaluation of their cytotoxicityBenedeković Goran 11 October 2012 (has links)
<p>U radu je ostvarena enantiodivergentna totalna sinteza oba enantiomera goniofufurona, 7-epi-goniofufurona i krasalaktona C polazeći iz D-glukoze. Ključne faze u sintezi 7-epi-(+)-goniofufurona bile su stereoselektivna adicija fenilmagnezijum bromida na aldehidnu grupu pogodno zaštićene dialdoze, i stereospecifično formiranje furano-laktonskog prstena ciklokondenzacijom odabranog hemiacetalnog derivata sa Meldrum-ovom kiselinom. Sinteza (+)-goniofufurona i (+)-krasalaktona C zahtevala je inverziju konfiguracije na C-5<br />u zajedničkom intermedijeru, koja je efikasno ostvarena u uslovima Mitsunobu-ove reakcije, ili alternativno oksidacijom benzilne hidroksilne grupe u prohiralni keton, uz naknadnu stereoselektivnu redukcijom sa borohidridom. Sličan pristup je zatim primenjen za sintezu neprirodnih (−)-enantiomera goniofufurona, 7-epi-goniofufurona i krasalaktona C, dva nova konformaciono ograničena analoga (+)- i (−)-goniofufurona (oksetani 36 i ent-36), kao i odgovarajućih 7-deoksigenovanih derivata (31 i ent-31). Takodje je razvijena i prva totalna sinteza prirodnog (+)-krasalaktona B (3) i alternativna sinteza (+)-krasalaktona C (4) polazeći iz D-glukoze. Selektivni pristup molekulima 3, odnosno 4 omogućen je promenom uslova za TBDPS deprotekciju u finalnom intermedijeru 53. Osnovna karakteristika pomenutih pristupa je njihova generalnost i fleksibilnost. Na taj način je omogućena sinteza serije analoga i derivata (+)-goniofufurona, ili 7-epi-goniofufurona, uključujući i do sada nepoznate 7-epi-(+)-krasalaktone B (6) i C (7), 5,7-di-O-cinamoil derivate 8 i 9, 5,7-di-O-izopropilidenske derivate 5 i 10, kao i više lipofilnih derivata (jedinjenja 26, 30, 33, 65, ent-30 i ent-33). Konačno, u drugom delu rada, ispitan je uticaj sintetizovanih stiril-laktona na rast odabranih tumorskih ćelijskih linija in vitro.</p> / <p> Enantiodivergent total syntheses of both (+)- and (−)-enantiomers of goniofufurone, 7-epi-goniofufurone and crassalactone C have been accomplished starting from D-glucose. The key steps of the synthe-sis of 7-epi-(+)-goniofufurone were a stereo-selective addition of <br /> phenyl magnesium bromide to a protected dialdose, followed by a stereospecific furano-lactone ring formation by condensation of a partially protected lactole with Meldrum’s acid. The synthesis of (+)-goniofufurone and (+)-crassalactone C required a configurational inversion at C-5 in the common intermediate that was efficiently achieved under the standard Mitsunobu conditions, or alternatively through a sequential oxidation of the benzylic hydroxyl group followed by a stereo-selective reduction with borohydride. A similar approach was applied to the synthesis of the unnatural enantiomers of goniofufurone, 7-epi-goniofufurone and crassalactone C, two novel, conformationally constrained analogues of both (+)- and (−)-goniofufurone (oxetanes 34 and ent-34). as well as the corresponding 7-deoxygenated derivatives (31 and ent-31). We have also developed the first total synthesis of (+)-crassalactone B (2) and an alternative synthesis of (+)-crassalactone C (3) starting from D-glucose. Finally, the synthesized styryl-lactones were evaluated for their antiproliferative activity against a panel of human tumor cell lines.</p>
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