Synthesis of methyl 3azidothieno2,3bpyridine2carboxylates and. Chemistry on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Request pdf on sep 3, 2014, joy m hung and others published synthesis and cytotoxicity of thieno 2, 3 b pyridine and furo2, 3 b pyridine derivatives find, read and cite all the research you. In the case of the thiazolo4, 5 b pyridines, the intermediate 5 2, 2 dicyanolphenylvinylthiazoles were separated. Some methoxy compounds inhibited significantly the growth of human tumor cell lines. Synthesis of new thieno2,3bpyridine derivatives as pim.
Pdf reaction of cyanopyridine21hthiones 2a,b with chloroacetonitrile gave the corresponding 3aminothieno2. These compounds can also be used as scaffolds for further synthesis of more potent analogues. Namely diheteroarylamine derivatives of the thieno 3, 2 b pyridine skeleton, 1 substituted thieno 3, 2 b pyridine ureas, 2 and thieno 3, 2 c pyridine ureas 3 were shown to be inhibitors of the vascular endothelial growth factor receptor vegfr 2 mediator of the biological function of the vascular endothelial growth factor vegf, related to. Peixoto, daniela alexandra silva calhelha, ricardo c. Therefore, the synthesis of highly substituted thieno2,3bpyridine has attracted much attention and a number of procedures have been developed to prepare these compounds using a variety of protocols. In the case of the thiazolo4, 5bpyridines, the intermediate 52, 2dicyanolphenylvinylthiazoles were separated. Fluorescence studies on potential antitumor 6hetero. We describe a synthetic approach for a set of fluorescent thieno3,2bpyridine54hone derivatives and their photophysical properties. For this reason we have focused to prepare certain bisheterocycles containing thieno 2,3b thiophene derivatives. 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 new thieno 2, 3 b pyridine derivatives as pim1 inhibitors bassem h. General description thieno3,2bpyridin7ol is a thienopyridine derivative. Several novel 6heteroarylamino thieno 3, 2 b pyridines were prepared by palladiumcatalyzed cn buchwaldhartwig coupling of the methyl 3 amino6bromothieno 3, 2 b pyridine 2 carboxylate with. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided.
A series of pyridine and thieno 2, 3 b pyridine derivatives have been designed and synthesized as anticancer pim1 kinase inhibitors. Synthesis and anticancer evaluation of some novel thiophene, thieno 3,2. When visiting this website next time, the system will get back information on your previous session and facilitate navigation. Read fluorescence studies on potential antitumor 6 heteroarylthieno 3,2 b pyridine derivatives in solution and in nanoliposomes, journal of photochemistry and photobiology a. The compounds obtained were evaluated for their growth inhibitory activity on. Aminodiheteroarylamines in the thieno3,2bpyridine series. Thieno3,2bthiophene tt regarded as a star molecule is widely applied in the organic electronic domain. Compounds 1 were prepared in excellent yield, reacting the 3 fluoropicolinonitrile for 1a or the 5bromo 3 nitropicolinonitrile for 1b with methyl thioglycolate in dmf using an excess of kohaq, following a. Synthesis and characterization of novel thienofused bicyclic compounds through new enaminone containing thieno2,3bpyridine. New potential antitumoral diheteroarylether derivatives in. Synthesis and src kinase inhibitory activity of 2phenyl and 2thienyl7phenylaminothieno3,2 b pyridine6carbonitriles. The vascular endothelial growth factor receptor2 vegfr2 is a tyrosine kinase receptor involved in the growth and differentiation of endothelial cells that are implicated in tumorassociated angiogenesis.
Compounds 1 were prepared in excellent yield, reacting the 3fluoropicolinonitrile for 1a or the 5bromo3nitropicolinonitrile for 1b with methyl thioglycolate in dmf using an excess of. Synthesis, molecular engineering, and photophysical. Mar 28, 2012 aminodiheteroarylamines in the thieno 3, 2 b pyridine series. 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. Journal of heterocyclic chemistry 1984, 21 3, 785789. Antihepatocellular carcinoma activity using hepg2 cells. We describe a synthetic approach for a set of fluorescent thieno 3,2 b pyridine 54hone derivatives and their photophysical properties. 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. Compound 1 undergoes a electrophilic substitution at c. It is believed that the derivatives have the action to enhance gastric motor action and gastric emptying. Formation of the thiazolo4,5bpyridines was confirmed by xray analysis. Synthesis of new thieno3, 2bpyridines and thieno2, 3b.
Modification of lead compound 7 by transformation of its noxide 66 biaryl ring system and fused aromatics produced a series of nonbasic fxa inhibitors with. Jul 15, 20 read fluorescence studies on potential antitumor 6 heteroarylthieno 3,2 b pyridine derivatives in solution and in nanoliposomes, journal of photochemistry and photobiology a. There are only a few recent literature reports which describe thieno3,2b and thieno3,4b. Synthesis and characterization of novel thienofused. Synthesis, effects in human tumor cells growth, cell cycle analysis, apoptosis and evaluation of toxicity using nontumor cells. Therefore, the compound of the present invention are effective for the prevention and. Bandgar bp, gawande ss, bodade rg, gawande nm, khobragade cn 2009 synthesis and biological evaluation of a novel series of pyrazole chalcones as antiinflammatory, antioxidant and antimicrobial agents. A novel regioselective synthesis of thieno 3, 2 blpyridines and thiazolo4,5blpyridines from 2 bromoiphenyl ethylidenemalononitrile is proposed. The molecule 5 that was prepared was found to be potent bacteria and fungus inhibitor. Application thieno 3, 2 b pyridin7ol may be used in the synthesis of 7bromothieno 3, 2 b pyridine. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided that echa is. New diheteroarylethers and diheteroarylamines in the. Modification of lead compound 7 by transformation of its noxide 66 biaryl ring system and fused aromatics produced a series of nonbasic fxa inhibitors with excellent potency in antifxa and anticoagulant assays.
Our main focus is on synthesis of some new thieno2,3bpyridine derivatives. In this study, novel 1aryl 3 4 thieno 3, 2 d pyrimidin4yloxyphenylureas were synthesized and evaluated for the vegfr 2 tyrosine kinase inhibition. Fulltext utility of thieno2,3b pyridine derivatives in the synthesis of. Exploring the electrochromic properties of polythieno3,2.
Pdf synthesis of some new thieno2,3bpyridines, pyrimidino4. Synthesis and cytotoxicity of thieno2,3bpyridine and. The thieno 2,3b thiophenes have been the focus of active research in recent years. New potential antitumoral fluorescent tetracyclic thieno3,2bpyridine derivatives. A new highly selective method was developed for the synthesis of substituted thieno 3, 2 b pyridines based on the domino reaction of monopotassium salt rather than dipotassium one of carbamoylcyanodithioacetic acid with ethyl 4chloroacetoacetate. Synthesis of a new class of cofacially oriented neutral donoracceptor thienothiophenes to probe the presence of throughspace charge. Substituted 5hpyrano 2, 3 d thieno 3, 2 b pyridines were synthesized based on these thieno 3, 2 b pyridines. Dunne department of biology and chemical engineering, malardalen university, box 325, 631 05 eskilstuna, sweden. Here we present the synthesis of two thieno3,2bpyridines 1a and 1b as components for palladiumcatalyzed couplings by reaction either on the pyridine or on the thiophene ring.
Synthesis of diheteroarylamines and ethers in the thieno3,2bpyridine series by metalcatalyzed couplings daniela peixoto, a. These altered the ncih460 cell cycle and increased the programmed death of cells. The well established method for their synthesis is via huisgens. Cookies are text snippets sent to your browser in order to provide you with a better user experience. Synthesis and fluorescence studies in solution and in nanoliposomes. Synthesis and characterization of new biologically active. Synthesis of new thieno 2, 3b pyridine derivatives as pim1 inhibitors. Diheteroarylethers and amines in the thieno3,2bpyridine series were prepared. Synthesis of some new thieno 2, 3b pyridines, pyrimidino 4, 5. Synthesis of some new thieno2,3bpyridines, pyrimidino4,5.
Synthesis of some new thieno2,3bpyridines, pyrimidino4. Several novel 6heteroarylamino thieno 3,2 b pyridines were prepared by palladiumcatalyzed cn buchwaldhartwig coupling of the methyl 3 amino6bromothieno 3,2 b pyridine 2carboxylate with. Chemical and photochemical synthesis of substituted. New diheteroarylethers and diheteroarylamines in the thieno 3,2bpyridine series. The thieno2,3bpyridine derivatives occupy special place and have attracted considerable attention because of their broad pharmacological. Application thieno3,2bpyridin7ol may be used in the synthesis of 7bromothieno3,2bpyridine. Compound 7 was identified as the active metabolite of 6 by hplc and mass spectral analysis. Chemical and photochemical synthesis of substituted dihydro. Substituted 5hpyrano2,3dthieno3,2bpyridines were synthesized based on these thieno3,2bpyridines.
Eggpc and dodab dioctadecyldimethylammonium bromide. Synthesis, effects in human tumor cells growth, cell cycle analysis, apoptosis and. New potential antitumoral diheteroarylether derivatives in the thieno3,2bpyridine series. New potential antitumoral diheteroarylether derivatives. Synthesis of new thieno3,2bpyridine derivatives by. Design, synthesis and docking study of pyridine and thieno. You also can through below form to request documents for moa,ros,1hnmr. Onepot synthesis of thieno3,2bpyridines thieme connect. Several novel 6heteroarylaminothieno3,2bpyridines were prepared by palladiumcatalyzed cn buchwaldhartwig coupling of the methyl 3amino6. New potential antitumoral diheteroarylether derivatives in the thieno3,2 b pyridine series.
Synthesis, effects in human tumor cells growth, cell cycle analysis, apoptosis and evaluation of toxicity using nontumor cells ricardo c. Pdf synthesis and src kinase inhibitory activity of. Synthesis and characterization of novel thienofused bicyclic. Pdf synthesis and src kinase inhibitory activity of 2phenyl. General description thieno 3, 2 b pyridin7ol is a thienopyridine derivative. New potential antitumoral fluorescent tetracyclic thieno3.
Furo 3, 2 b and thieno 3, 2 b pyridine derivatives as tbk1 and ikk inhibitors download pdf info publication number wo20117285a1. The vascular endothelial growth factor receptor 2 vegfr 2 is a tyrosine kinase receptor involved in the growth and differentiation of endothelial cells that are implicated in tumorassociated angiogenesis. 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. Here we present the synthesis of two thieno 3,2 b pyridines 1a and 1b as components for palladiumcatalyzed couplings by reaction either on the pyridine or on the thiophene ring. Here we present the synthesis of tetracyclic compounds and also urea and thiourea. Formation of the thiazolo4,5 b pyridines was confirmed by xray analysis. Jul 18, 2019 synthesis and anticancer evaluation of some novel thiophene, thieno3,2.
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 of new 4phenylaminothieno2,3bpyridines and. Elnassan2 1pharmaceutical chemistry department, faculty of pharmacy, the british university in egypt, cairo, egypt and 2pharmaceutical organic chemistry. 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. Synthesis, effects in human tumor cells growth, cell cycle analysis, apoptosis and evaluation of toxicity. Jan 07, 2015 synthesis of some new thieno 2, 3 b pyridines, pyrimidino4,5. A new synthesis of thieno 3,2 b pyridine and studies on direct substitution into its thiophene ring. Synthesis and anticancer evaluation of some novel thiophene, thieno3,2. The thieno 2, 3 b thiophenes have been the focus of active research in recent years. Our dedicated information section provides allows you to learn more about mdpi. On heating of 14 in the presence of a catalytic amount of rh2cf3cf2cf2co24 in phh for 4.
Synthesis, molecular engineering, and photophysical properties of. There are only a few recent literature reports which describe thieno 3, 2 b and thieno 3,4 b thiophenes with different features 1 3 and applications 4,5. Thieno3,2 bpyridine c7h5ns cid 12210218 structure, chemical names, physical and chemical properties, classification, patents, literature, biological. Jun 17, 2004 on heating of 14 in the presence of a catalytic amount of rh2cf3cf2cf2co24 in phh for 4. Utility of thieno2,3b pyridine derivatives in the synthesis of some condensed heterocyclic compounds with expected biological activity. Synthesis of the fused heterobicycles 5pyridin2ylthieno3,2bpyridine, 6pyridin2ylthieno2,3bpyridine and 6pyridin2ylthieno3,2cpyridine lasse j.
New potential antitumoral fluorescent tetracyclic thieno3,2. For this reason we have focused to prepare certain bisheterocycles containing thieno 2, 3 b thiophene derivatives. Omran chemistry department, faculty of science, kuwait university, p. A read is counted each time someone views a publication summary such as the title, abstract, and list of authors, clicks on a figure, or views or downloads the fulltext.
Synthesis, growth inhibitory activity on human tumor cell lines and nanotumor cells, effects on cell cycle and on apoptosis. Thirtyseven compounds were selected by nci to be tested initially at a single dose 10 m in the full nci 60 cell line panel. New method for the synthesis of substituted thieno3,2 b. Specifically, 7substituted thieno3, 2bpyridines are noted for their ability to inhibit kinases. In this study, novel 1aryl34thieno3,2 d pyrimidin4yloxyphenylureas were synthesized and evaluated for the vegfr2 tyrosine kinase inhibition. Synthesis and anticancer evaluation of some novel thiophene. Antihepatocellular carcinoma activity using hepg2 cells and. A novel regioselective synthesis of thieno3, 2blpyridines and thiazolo4,5blpyridines from 2bromoiphenyl ethylidenemalononitrile is proposed. Abstractthree series of 5bromothieno2,3bpyridines bearing amide or benzoyl groups at position 2 were prepared as pim1 inhibitors. Structure, properties, spectra, suppliers and links for. N s oh n s br n s hn r1 r2 r3 n s o r1 r2 r3 rn h unless stated r1 ome or f r2 ome or f r3 ome or f cn coupling co coupling pobr3 i ii i pdoac2 6mol%, binap 8mol%, cs2co3. Aminodiheteroarylamines in the thieno 3, 2 b pyridine series.
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