123413-84-3Relevant 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.
Synthesis and antiproliferative activity of 2-chlorophenyl carboxamide thienopyridines
van Rensburg, Michelle,Leung, Euphemia,Haverkate, Natalie A.,Eurtivong, Chatchakorn,Pilkington, Lisa I.,Reynisson, Jóhannes,Barker, David
supporting information, p. 135 - 138 (2016/12/27)
3-Amino-2-arylcarboxamide-thieno[2,3-b]pyridines are a known class of antiproliferative compounds with activity against the phospholipase C enzyme. To further investigate the structure activity relationships of these derivatives a series of analogues were prepared modifying key functional groups. It was determined that modification of the 3-amino and 2-aryl carboxamide functionalities resulted in complete elimination of activity, whilst modification at C-5 allowed compounds of greater activity to be prepared.
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.
