The synthesized thienopyridines derivatives were evaluated for their in vitro antibacterial activity against two grampositive b. The thieno 2, 3 b thiophene moiety has been used in the design of a novel pharmaceutical therapies. Synthesis of some 2amino4carboxy3,4dihydro2h1benzopyranlactams from 4hydroxy5oxo4,5dihydropyrrole derivatives full text pdf 4 kb. Synthesis of new 4phenylaminothieno2,3bpyridines and derivatives of the novel benzobthieno. Thieno3,2bthiophene tt regarded as a star molecule is widely applied in the organic electronic domain. May 12, 2011 fluorescence properties of two new potential antitumoral tetracyclic thieno 3, 2 b pyridine derivatives were studied in solution and in liposomes of dppc dipalmitoyl phosphatidylcholine, egg lecithin phosphatidylcholine from egg yolk. Compounds 1 and 2 were prepared by heating 2 thienylcarboxaldehyde 23. Molecules free fulltext synthesis of some new thieno2,3b. Synthesis of some new thieno 2, 3b pyridines, pyrimidino 4, 5. Aminodiheteroarylamines in the thieno3,2bpyridine series.
The detailed synthetic procedures of kf 112 were previously reported and that of kf and kf 14 were described in supplementary material. Synthesis and characterization of novel thienofused. In the case of the thiazolo4, 5 b pyridines, the intermediate 5 2, 2 dicyanolphenylvinylthiazoles were separated. Furo3,2bpyridines and thieno3,2bpyridines as inhibitors. The newly synthesized compounds were elucidated by elemental analysis, spectral data, and alternative synthesis. Pdf reaction of cyanopyridine21hthiones 2a,b with chloroacetonitrile gave the.
Following the procedure described in example 1, steps 4 and 5, but replacing the 5bromomethylfuro3,2bpyridine from step 4 by 5methanesulonyloxymethylthieno3,2bpyridine as starting material, the title compound was obtained as a gum and purified by crystallisation in thfhexane 1. Formation of the thiazolo4,5 b pyridines was confirmed by xray analysis. Subsequent crosscoupling reactions proceed in excellent yields and demonstrate the potential of 4bromothieno2, 3 b pyridine as a building block for use in drug discovery research. Substituted 5hpyrano 2, 3 d thieno 3, 2 b pyridines were synthesized based on these thieno 3, 2 b pyridines. Molecules free fulltext synthesis of some new bisp. Furo3,2bpyridine and thieno3,2bpyridine full text pdf. Synthesis and anticancer evaluation of some novel thiophene, thieno3,2. Exploring the electrochromic properties of polythieno3,2. This invention relates to a process for the preparation of thienopyridine derivatives having the structural formula. Synthesis of the fused heterobicycles 5pyridin2ylthieno3,2bpyridine, 6pyridin2ylthieno2,3bpyridine and 6pyridin2ylthieno3,2cpyridine lasse j. Synthesis of some new thieno2,3bpyridines, pyrimidino4,5.
Fluorescence properties of two new potential antitumoral tetracyclic thieno3,2bpyridine derivatives were studied in solution and in liposomes of dppc dipalmitoyl phosphatidylcholine, egg lecithin phosphatidylcholine from egg yolk. Synthesis of kf derivatives thieno3,2bpyridine54hone derivatives general synthetic procedure for kf derivatives can be found in our previous report. Buy 3 bromothieno3,2 bpyridine cas 94191125, a product for proteomics research, from santa cruz. Thieno3,2bpyridine c7h5ns cid 12210218 structure, chemical names, physical and chemical properties, classification, patents, literature, biological. Synthesis and characterization of new condensed pyridothienopyrimidines article pdf available in archive for organic chemistry 20174. Sep, 2019 synthesis and anticancer evaluation of some novel thiophene, thieno3,2.
Synthesis of new 4phenylaminothieno2,3bpyridines and. Their electropolymerization leads to electroactive conjugated polymers. A new highly selective method was developed for the synthesis of substituted thieno3,2bpyridines based on the domino reaction of monopotassium salt rather than dipotassium one of carbamoylcyanodithioacetic acid with ethyl 4chloroacetoacetate. Nurkkala, lasse j steen, robert o dunne, simon j synthesis of the fused heterobicycles 5pyridin 2 yl thieno 3, 2 b pyridine, 6pyridin 2 yl thieno 2, 3 b pyridine and 6pyridin 2 yl thieno 3, 2 c pyridine. Exploring the electrochromic properties of polythieno3,2 b. Thieno 3, 2 b pyridine c7h5ns cid 12210218 structure, chemical names, physical and chemical properties, classification, patents, literature, biological. Shirini, farhad silica triflate as an efficient catalyst for the solventfree synthesis of 3,4dihydropyrimidin21hones. Novel enaminone derived from thieno 2,3 b bmc chemistry. New method for the synthesis of substituted thieno3,2 b. Pdf novel synthesis of purines analougues and thieno2,3. Synthesis of new thieno3, 2bpyridines and thieno2, 3b. Synthesis and evaluation of tumor cell growth inhibition. Pdf synthesis of some new thieno2,3bpyridines, pyrimidino4.
Two novel thieno3,2bthiophene tt3,4ethylenedioxythiophene edotbased compounds of 2,5edotttedot type bearing electronwithdrawing side groups 4cyanophenyl or 4pyridyl at 3,6positions of the tt moiety have been synthesized. Aminodiheteroarylamines in the thieno 3, 2 b pyridine series. A new synthesis of thieno 3,2 b pyridine and studies on direct substitution into its thiophene ring. A novel regioselective synthesis of thieno 3, 2 blpyridines and thiazolo4,5blpyridines from 2 bromoiphenyl ethylidenemalononitrile is proposed. In the case of the thiazolo4, 5bpyridines, the intermediate 52, 2dicyanolphenylvinylthiazoles were separated. Trifluoromethylsubstituted pyridyl and pyrazolylboronic. The synthetic utility of 3,33,4dimethylthieno2,3bthiophene2,5diylbis 3oxopropanenitrile 1 in the synthesis of some novel bis1,3,4thiadiazole 6ag and bisthiazole 10 and derivatives with thieno2,3bthiophene moiety is reported. A new synthesis of thieno3,2 b pyridine and studies on direct substitution into its thiophene ring. Synthesis and evaluation of tumor cell growth inhibition of methyl 3amino6heteroarylethynylthieno3,2bpyridine2carboxylates. Oct 27, 2010 the synthesis started from 2 amino 3 thiophenecarbonitriles which were prepared in one step from ketones, malononitrile, and sulfur with morpholine as a catalyst in the refluxing ethanol via the classic gewald reaction.
The synthesis started from 2amino3thiophenecarbonitriles which were prepared in one step from ketones, malononitrile, and sulfur with morpholine as a catalyst in the refluxing ethanol via the classic gewald reaction. New potential antitumoral fluorescent tetracyclic thieno3,2. Us4127580a process for the preparation of thienopyridine. Synthesis of some quinolylpyrido2,3b1,4benzodiazepinones. Therapeutic importance of synthetic thiophene bmc chemistry. Novel synthesis of purines analougues and thieno 2, 3 b pyridine derivatives with anticancer and antioxidant activity. Thieno 2, 3 bpyridines 4ai were prepared in two steps from thioglycolic acid 5. Eggpc and dodab dioctadecyldimethylammonium bromide. The thieno 2,3b thiophene moiety has been used in the design of a novel pharmaceutical therapies. The first four thienopyridines were studied in detail in the literature. Us82176b2 process for preparing thieno3,4b pyrazine. A novel regioselective synthesis of thieno3, 2blpyridines and thiazolo4,5blpyridines from 2bromoiphenyl ethylidenemalononitrile is proposed. Additionally, its enaminones derivatives are versatile synthons and have a lot of synthetic. Dunne department of biology and chemical engineering, malardalen university, box 325, 631 05 eskilstuna, sweden.
New potential antitumoral fluorescent tetracyclic thieno3,2bpyridine derivatives. Journal of heterocyclic chemistry 1984, 21 3, 785789. Therefore, the synthesis of highly substituted thieno 2, 3 b pyridine has attracted much attention and a number of procedures have been developed to prepare these compounds using a variety of protocols. New potential antitumoral fluorescent tetracyclic thieno3. Jun 19, 2006 the synthesis of thieno3,2 b pyridines was achieved using a threestep process allowing the construction of the thiophenic ring with 1734% overall yields. The first regioselective, mild bromination of thieno 2, 3 b pyridine is described herein.
Microwaveassisted novel synthesis of aminothieno3,2b. This invention relates to a process for the preparation of thieno pyridine derivatives having the structural formula. Feb 18, 2010 4chloro 3 phenyl thieno 2, 3 b pyridine 47 mg, 0. Fulltext utility of thieno2,3b pyridine derivatives.
Dec 20, 1994 following the procedure described in example 1, steps 4 and 5, but replacing the 5bromomethylfuro3,2bpyridine from step 4 by 5methanesulonyloxymethylthieno3,2bpyridine as starting material, the title compound was obtained as a gum and purified by crystallisation in thfhexane 1. Synthesis and cytotoxicity of thieno2,3bpyridine and. The reaction mixture was allowed to cool and the obtained solid was. S3 6trifluoromethyl3pyridylboronic acid 3 nbutyllithium 2. Our main focus is on synthesis of some new thieno2,3bpyridine derivatives. Whilst thieno 2, 3 b pyridine 2carboxamides such as 4 are often prepared through initial formation of 2substitutedthio. Compound 1 reacts also with the cinnamonitriles 3a,b to afford the thieno 2, 3. Compound 7 was identified as the active metabolite of 6 by hplc and mass spectral analysis. New thieno3,4bpyrazine copolymers are prepared by reacting 5,7functionalized thieno3,4bpyrazines with substituted aromatics in the presence of solvents, bases and polymerization catalysts, the copolymers thus prepared being employed preferably in the production of photovoltaic cells.
Exploration of syntheses and functions of higher ladder. Some of the new compounds show inhibitory effect to the production of mycotoxins and to. The key step was the regioselective lithiationbromination of the 3methylthiopyridine induced by bulilidmae superbase followed by sonogashira coupling and halogenocyclization producing the fused. Structureactivity relationships, effects on the cell cycle and apoptosis mariajoao r. The synthesis of thieno3,2 b pyridines was achieved using a threestep process allowing the construction of the thiophenic ring with 1734% overall yields.
Development of human serum albumin selective fluorescent. The key step was the regioselective lithiationbromination of the 3methylthiopyridine induced by bulilidmae superbase followed by sonogashira coupling and halogenocyclization producing the fused heterocycles. Synthesis and evaluation of tumor cell growth inhibition of. Synthesis, molecular engineering, and photophysical. The thieno2,3b pyridine derivatives occupy special place and have attracted considerable attention. In conclusion, we reported the synthesis of novel 1aryl34thieno3,2dpyrimidin4yloxyphenylureas 2a2f in high yields in two steps.
Due to their structural and therapeutic diversity, thienothiophene derivatives have attracted much synthetic interest because of their reactivity and biological activity. Exploring the electrochromic properties of polythieno3,2b. The vessel was sealed with a septum and placed in the microwave cavity. When visiting this website next time, the system will get back information on your previous session and facilitate navigation. After the reaction was complete, the mixture was cooled, acidified with 1.
The newly synthesized compounds were elucidated by elemental analysis, spectral data, and. The reaction proceeds with selectivity toward the 4position 87% isolated yield. These compounds have been investigated in relation. Buy 5trifluoromethylthieno3,2bpyridine6carboxylic acid cas 243977222, a product for proteomics research, from santa cruz. The synthesis began by preparing the mercaptoacetamides 6ac, with different substituted phenyl moieties, by heating the corresponding anilines and thioglycolic acid 5 without solvent.
Nucleosides obtained have been identified by their spectral analysis. The synthesis started from 2amino 3 thiophenecarbonitriles which were prepared in one step from ketones, malononitrile, and sulfur with morpholine as a catalyst in the refluxing ethanol via the classic gewald reaction. Dribofuranose and by using the silylation method, followed by debenzoylation by methanolic sodium methoxide to afford the corresponding free nnucleosides. Substituted 5hpyrano2,3dthieno3,2bpyridines were synthesized based on these thieno3,2. Synthesis and characterization of novel thieno3,2bthiophene based metalfree organic dyes with different heteroaromatic donor moieties as sensitizers for dyesensitized solar cells sara s. Thieno2,3bpyridines as potassium channel inhibitors. Nurkkala, lasse j steen, robert o dunne, simon j synthesis of the fused heterobicycles 5pyridin2ylthieno3,2bpyridine, 6pyridin2ylthieno2,3bpyridine and 6. The thieno2,3bpyridine derivatives occupy special place and have attracted considerable attention because of their broad pharmacological. The thieno2,3bpyridine derivatives occupy special place and have attracted. Synthesis, effects in human tumor cells growth, cell cycle analysis, apoptosis and evaluation of toxicity using nontumor cells by ricardo c. Design, synthesis, sar, and biological evaluation of new.
Pdf synthesis and antimicrobial studies of some novel. Synthesis of new thieno3, 2bpyridines and thieno2, 3bpyrazines by palladium crosscoupling article in chemistryselect 224. Synthesis and conformational analysis of a nonamidine factor xa inhibitor that incorporates 5methyl4,5,6,7tetrahydrothiazolo5,4c pyridine as s4 binding element. Suzuki coupling of 3,6dibromothieno 3, 2 b thiophenes 1 36 with 4cyanophenyl or 4pyridylboronic acids did not work well in dmf or toluene in contrast to the synthesis of 2a, but the reflux in dioxane with pdpph 3 4 as the catalyst gave us the desired compounds 2b,c. Synthesis of some quinolylpyrido2,3b1,4benzodiazepinones via mcr in solventfree conditions, and their biological studies the present chapter describes onepot synthesis of some new quinolylpyrido2,3b1,4benzodiazepinones via the mcr under solventfree conditions.
Compared to thiophene, the fused tt moiety possesses a larger extent of conjugation to give polymers with a lower band gap and higher charge carrier mobility. Synthesis and characterization of novel thienofused bicyclic. New thieno 3,4 b pyrazine copolymers are prepared by reacting 5,7functionalized thieno 3,4 b pyrazines with substituted aromatics in the presence of solvents, bases and polymerization catalysts, the copolymers thus prepared being employed preferably in the production of photovoltaic cells. All the methyl 6 heteroarylaminothieno3,2bpyridine2carboxylates obtained were studied as potential antitumor compounds using three human tumor cell lines, representative of different types of tumors, and it was possible to establish some structureactivity relationships. In continuation of our interest in the chemistry of thienofused bicyclic compounds 1821 to develop new library of pharmaceutical targets we started from new enaminone 3 as precursor for synthesis of new thienofused bicyclic compounds containing thieno2,3bpyridine core. Synthesis, effects in human tumor cells growth, cell cycle analysis, apoptosis and evaluation of toxicity using nontumor cells. Our main focus is on synthesis of some new thieno 2, 3 b pyridine derivatives. We describe a synthetic approach for a set of fluorescent thieno 3,2 b pyridine 54hone derivatives and their photophysical properties.
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