165283-95-4Relevant articles and documents
Improving the solubility of anti-proliferative thieno[2,3-b]quinoline-2-carboxamides
Haverkate, Natalie A.,van Rensburg, Michelle,Kumara, Sisira,Reynisson, Jóhannes,Leung, Euphemia,Pilkington, Lisa I.,Barker, David
supporting information, (2021/03/16)
Thieno[2,3-b]pyridines are a class of compounds known for their potent anti-proliferative activities against a range of human cancer cell lines. In this research, a number of strategies to generate analogues that have improved aqueous solubility whilst retaining the potent anti-proliferative actions, compared to previously-explored compounds in this class, were made. Herein we report the synthesis of 80 novel compounds, comprising two series, all based on the thieno[2,3-b]pyridine core structure. Overall, it was found that introducing alternative heterocycles did not notably improve the solubility or retain anti-proliferative activity seen in previously-reported analogues. However, pleasingly it was discovered, that the best strategy for improving the solubility was the alteration of the appended alkyl ring to introduce polar groups such as alcohols, ketones and substituted amine groups. In addition to this finding, we have discovered a thieno[2,3-b]pyridine, 15e, with greater aqueous solubility that has ever been seen for this class of compounds that is also a potent inhibitor of cancer cell growth, with IC50′s in the nanomolar range. This new lead structure will form the basis of future explorations into this class of compounds.
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 facile one-pot synthesis of substituted thieno[2,3- b ]pyridines from enaminones
Gao, Baochang,Dong, Dewen,Zhang, Jie,Ding, Changjiang,Dong, Chunming,Liang, Yongjiu,Zhang, Rui
experimental part, p. 201 - 206 (2012/03/26)
A facile and efficient one-pot synthesis of substituted thieno[2,3-b]pyridines has been developed. Treatment of enamin-ones, such as 2-acetyl-3-(dimethylamino)propenamides and -propenoates, with 2-cyanothioacetamide in the presence of potassium carbonate in N,N-dimethylformamide at 80 C followed by addition of methylene-active bromides at room temperature provided, via intramolecular cyclization, 2,3,5,6-tetrasubstituted thieno[2,3-b]pyridines in yields of 78-90%. This protocol, which combines construction and modification of the thieno[2,3-b]pyridine ring, increases the structural diversity of the final products from readily available materials. Georg Thieme Verlag Stuttgart · New York.
New method of synthesis of 5-acetyl-3-cyano-6-methylpyridine-2(1H)-thione and its properties
Yakunin,Dyachenko,Litvinov
, p. 581 - 587 (2007/10/03)
5-Acetyl-3-cyano-6-methylpyridine-2(1H)-thione was obtained by the reaction of ethoxymethyleneacetylacetone with cyanothioacetamide in the presence of N-methylmorpholine. Its alkylation, bromination of the 2-methylthio derivative, and the conversions of its 5-bromoacetyl derivative have been studied.
Synthesis of 1-(β-D-glycopyranosyl)-3-deazapyrimidines from 2-hydroxy and 2-mercaptopyridines
Attia, Adel M.,Elgemeie, Galal H.,Alnaimi, Ibrahim S.
, p. 1355 - 1363 (2007/10/03)
The synthesis of new 4- and 5-substituted-3-cyanopyridine nucleosides has been performed by reacting the silylated pyridines and penta-O-aeetyl-α -Dglycopyranose in dichloroethane in the presence of SnCl4. The free nucleosides were tested for their potential activity against HIV and different types of tumor.
Synthesis of 2,3,5,6-tetrasubstituted pyridines from enamines derived from N,N-dimethylformamide dimethyl acetal
Abu-Shanab,Redhouse,Thompson,Wakefield
, p. 557 - 560 (2007/10/02)
Reactions of 1,3-dicarbonyl compounds with N,N-dimethylformamide dimethyl acetal, followed by cyanothioacetamide or cyanoacetamide and sodium hydride, then acidification, give 5,6-disubstituted 3-cyanopyridine-2(1H)-thiones or 5,6-disubstituted 3-cyanopyridin-2(1H)-ones 4. Analogous reactions with the malononitrile dimer give 5,6-disubstituted 3-cyano-2-(dicyanomethylene)-1,2-dihydropyridines 9.
