Recent Trends in the Chemistry of Thienopyridines

Bakhite, Etify A.

doi:10.1080/10426500307855

Cited by 50 publications

(34 citation statements)

References 51 publications

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“…Accordingly, a number of powerful synthetic strategies have been developed to effectively access this heterocyclic family . Many thieno[2,3‐ b ]pyridines have been synthesized and investigated in relation to their biological and pharmacological importance . Some of them proved to possess antiviral, anti‐diabetic, antimicrobial, anti‐inflammatory, antitumor, antiparasitic and neurotropic activities .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of some new pyridines, thieno[2,3‐b] pyridines and pyrido[3′,2′:4,5]thieno[3,2‐d]pyrimidine‐4(3H)‐ones bearing styryl moiety

Al-Waleedy

Bakhite

Abbady

et al. 2020

Journal of Heterocyclic Chem

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3‐Cyano‐5‐ethoxycarbonyl‐6‐methyl‐4‐styrylpyridine‐2(1H)‐thione (3) was prepared by reaction of 2‐cyano‐5‐phenylpenta‐2,4‐dienethioamide (2) with ethyl acetoacetate or by multicomponent reaction of cinnamaldehyde (1), cyanothioacetamide and ethyl acetoacetate in a moderate yield. Reaction of compound 3 with some N‐aryl‐2‐chloroacetamides, in the presence of sodium acetate, gave the corresponding 2‐(N‐arylcarbamoylmethylsulfanyl)‐3‐cyano‐5‐ethoxycarbonyl‐6‐methyl‐4‐styrylpyridines 4a‐f. When compounds 4a‐f were subjected to Thorpe‐Ziegler reaction conditions, they converted into the corresponding 3‐amino‐5‐ethoxycarbonyl‐2‐(N‐arylcarbamoyl)‐6‐methyl‐4‐styrylthieno[2,3‐b]pyridines 5a‐f. Compounds 5a,e,f were reacted, in turn, with 2,5‐dimethoxytetrahydrofuran to furnish the corresponding 3‐(pyrrol‐1‐yl)thieno‐pyridines 6a,e,f. Reactions of 5a‐f with triethyl orthoformate or nitrous acid were also carried out and their products were identified. Structural formulas of all synthesized compounds was characterized and confirmed on the basis of their elemental and spectral analyses.

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of some new pyridines, thieno[2,3‐b] pyridines and pyrido[3′,2′:4,5]thieno[3,2‐d]pyrimidine‐4(3H)‐ones bearing styryl moiety

Al-Waleedy

Bakhite

Abbady

et al. 2020

Journal of Heterocyclic Chem

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“…The model compounds 7-9 were prepared by condensation of 3-aminothieno[2,3-b]pyridine-2-carboxamides 4-6 with cyclohexanone under acidic conditions (Scheme 2). Noteworthy, thieno[2,3-b]pyridines as well as polycyclic ensembles bearing thienopyridine core also represent promising candidates for the anticancer screening [35][36][37][38][39][40][41][42].…”

Section: Resultsmentioning

confidence: 99%

Spirocyclic thienopyrimidines: synthesis, new rearrangements under Vilsmeier conditions and in silico prediction of anticancer activity

et al. 2020

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Aim. To find novel anticancer lead molecules among easily available spiro-fused thieno[2,3-d] pyrimidines. Methods. Organic synthesis, spectral methods and molecular docking. Results. New spiro heterocycles were synthesized by condensation of 2-aminothiophene-3-carbonitriles with cyclic ketones via Gevald reaction. Other model spirocyclic compounds were prepared by the reaction of 3-aminothieno[2,3-b]pyridine-2-carboxamides with cyclohexanone under acidic conditions. According to the docking studies against the EGFR WT the synthesized compounds revealed good binding energies ranging from-8.4 to-10.2 kcal/mol. The compounds were tested as inhibitors of protein kinase CK; 7',8',9',10'-tetrahydro-1'H-spiro[cyclohexane-1,2'-pyrimido[4',5':4,5]thieno[2,3-b]quinolin]-4'(3'H)-one showed the best binding energy while be bound by a hydrogen bond to Val66 amino acid residue. This compound also showed good results as a potential inhibitor of B-Raf kinase. Conclusion. New spiro-fused thieno[2,3d]pyrimidines have been synthesized. The inhibition activity of novel compounds as potential inhibitors of the EGFR, CK2, FGFR1 and B-raf kinases was examined. We found that spirofused thieno[2,3-d]pyrimidines undergo the rearrangement under Vilsmeier-Haack conditions to afford hitherto undescribed thienopyrimidines and-quinolines. The docking studies revealed that the rearranged products do not tend to form hydrogen bonds with the kinase amino acid residues and show moderate binding energies. Therefore, in contrast to the spiro-fused thieno[2,3-d]pyrimidines, the rearranged products cannot be considered as perspective targets for further screening.

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“…On treatment of compound 7a with phenacyl bromide in boiling ethanol containing an equimolar amount of sodium acetate, the product was identified as 2H-pyrido[3'',2'':4',5']thieno [3',2':4,5]pyrimido [1,6-b] [1,2,4]triazine 12 rather than the related isomer 13 (Scheme 3). This assignment based on the spectral data of this product.…”

Section: Resultsmentioning

confidence: 99%

“…1,2 Some of them proved to possess antiviral, 3,4 anti-diabetic, 5 antimicrobial, 6,7 anti-inflammatory, 8 antitumor, 9 antiparasitic 10 and neurotropic activities. 11 Also, thienopyrimidine derivatives have been the subject of several chemical and biological studies on account of their wide spectrum of biological activity.…”

Section: Introductionmentioning

confidence: 99%

Fused thieno[2,3-b]pyridines: synthesis and characterization of new condensed pyridothienopyrimidines

Bakhite¹,

Abeed²,

Ahmed³

2017

Arkivoc

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Recent Trends in the Chemistry of Thienopyridines

Cited by 50 publications

References 51 publications

Synthesis and characterization of some new pyridines, thieno[2,3‐b] pyridines and pyrido[3′,2′:4,5]thieno[3,2‐d]pyrimidine‐4(3H)‐ones bearing styryl moiety

Synthesis and characterization of some new pyridines, thieno[2,3‐b] pyridines and pyrido[3′,2′:4,5]thieno[3,2‐d]pyrimidine‐4(3H)‐ones bearing styryl moiety

Spirocyclic thienopyrimidines: synthesis, new rearrangements under Vilsmeier conditions and in silico prediction of anticancer activity

Fused thieno[2,3-b]pyridines: synthesis and characterization of new condensed pyridothienopyrimidines

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