154384-01-7Relevant academic research and scientific papers
3-Amino-thieno[2,3-b]pyridines as microtubule-destabilising agents: Molecular modelling and biological evaluation in the sea urchin embryo and human cancer cells
Eurtivong, Chatchakorn,Semenov, Victor,Semenova, Marina,Konyushkin, Leonid,Atamanenko, Olga,Reynisson, Jóhannes,Kiselyov, Alex
, p. 658 - 664 (2016/12/27)
A series of 3-amino-thieno[2,3-b]pyridines was prepared and tested in a phenotypic sea urchin embryo assay to identify potent and specific molecules that affect tubulin dynamics. The most active compounds featured a tricyclic core ring system with a fused cycloheptyl or cyclohexyl substituent and unsubstituted or alkyl-substituted phenyl moiety tethered via a carboxamide. Low nano-molar potency was observed in the sea urchin embryos for the most active compounds (1–5) suggestive of a microtubule-destabilising effect. The molecular modelling studies indicated that the tubulin colchicine site is inhibited, which often leads to microtubule-destabilisation in line with the sea urchin embryo results. Finally, the identified hits displayed a robust growth inhibition (GI50of 50–250?nM) of multidrug-resistant melanoma MDA-MB-435 and breast MDA-MB-468 human cancer cell lines. This work demonstrates that for the thieno[2,3-b]pyridines the most effective mechanism of action is microtubule-destabilisation initiated by binding to the colchicine pocket.
METHODS AND COMPOSITIONS FOR INHIBITING HUMAN COPPER TRAFFICKING PROTEINS ATOX1 AND CCS
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Page/Page column 69, (2014/08/07)
Compositions and methods concern organic molecules that bind to human Atox1 and CCS at the copper trafficking interface of these proteins. This binding suppresses copper trafficking, which leads to inhibition of cancer cell proliferation and tumor growth. In addition to serving as an effective treatment of cancer, these organic molecules inhibit cellular copper uptake and can be used as treatment of disorders of copper metabolism such as Wilson's disease, which is characterized by copper overload, as well as wound healing.
A synthetic strategy to a new class of cycloalkane ring-fused pyridine nucleosides as potential anti HIV agents
Elgemeie, Galal E. H.,Attia, Adel M. E.,Hussain, Badria A. W.
, p. 855 - 868 (2007/10/03)
Condensation of cyanothioacetamide or cyanoacetamide with sodium salts of 2-formyl-1-cycloalkanones afforded the corresponding cycloalkane ring fused pyridine-2(1H)-thiones and -2-pyridones. The latter compounds served as a key intermediates for the synthesis of a new class of cycloalkane ring fused pyridine glycosides.
A convenient synthesis of 5-deaza nonclassical antifolates: Reaction of cyanothioacetamide with sodium salts of 2-(hydroxymethylene)-1-cycloalkanones
Elgemeie, Galal E. H.,Hussain, Badria A. W.
, p. 199 - 204 (2007/10/02)
Condensation of cyanothioacetamide with sodium salts of 2-(hydroxymethylene)-1-cycloalkanones afforded the corresponding pyridine-2(1H)-thiones 4. Compounds 4 served as a key intermediate for the synthesis of condensed 2,4-diaminopyrido[2,3-d]pyridines 7. Compounds 7 were of interest as potential inhibitors of dihydrofolate reductase.
Regioselective synthesis of 5,6-polymethylene-3-cyanopyridine-2(1H)-thiones and fused heterocycles based on them
Rodinovskaya, L. A.,Belukhina, E. V.,Shestopalov, A. M.,Litvinov, V. P.
, p. 449 - 457 (2007/10/02)
Condensation of 2-hydroxymethylenecyclopentan-1-one or -cyclooctan-1-one sodium salts with cyanothioacetamide afforded 5,6-polymethylene-3-cyanopyridine-2(1H)-thiones which were regioselectively alkylated at the sulfur atom by alkyl halides.Derivatives of 3-cyanopyridine-2(1H)-thione and 2-alkylthio-3-cyanopyridine were used for regioselective synthesis of substituted heterocycles: 3-aminothienopyridines, pyridothienopyrimidines, and pyridothienooxazines. - Key words: fused heterocycles; 5,6-polymethylene-3-cyanopyridine-2(1H)-thiones; 2-alkylthio-3-cyanopyridines; 3-aminothienopyridines; pyridothienopyridines; pyridothienooxazines; regioselective synthesis.
