Synthesis and Reactions of Substituted 3-amino-2-furyl(aryl)-thieno[2,3-b]pyridines

Kaigorodova, Ye. A.; Vasilin, V. K.; Konyushkin, L. D.; Usova, Ye. B.; Krapivin, G. D.

doi:10.3390/51001085

Cited by 15 publications

(7 citation statements)

References 6 publications

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“…Compound 11 in acetone was alkylated with ethyl bromoacetate in the presence of potassium carbonate and catalyst such as Adogen 464 at reflux for 4 h to give ethyl 3-((ethoxycarbonyl)methyl)-5-(bis((ethoxycarbonyl)methyl)amino)-4-cyano-thiophene-2-carboxylate (12), which is an intermediate of strontium ranelate (14), a medicine for the treatment of osteoporosis [7][8][9]. By making compound 12 undergo Thorpe-Ziegler cyclization, in the presence of potassium carbonate, using DMF as solvent, and refluxing at 150 • C [10], the expected thieno[2,3-b]pyrrole (13) was prepared. SCHEME 3…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Substituted Thieno[2,3‐b]pyrroles.

et al. 2007

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Section: Resultsmentioning

confidence: 99%

Synthesis of Substituted Thieno[2,3‐b]pyrroles.

et al. 2007

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“…While continuing our investigations into the reactivity of substituted 3-aminothieno [2,3-b]pyridines [1,2], we found a new reaction leading to closure of the pyridine ring during the formation of a pentacyclic heteroaromatic 22π-electronic system dipyridothienopyridine.…”

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confidence: 85%

The formation of the pyridine ring in the synthesis of dipyrido-[3′,2′:4,5]thieno[3,2-b: 3,2-d]pyridines

Vasilin

Lipunov

Konyushkin

et al. 2006

Chem Heterocycl Compd

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While continuing our investigations into the reactivity of substituted 3-aminothieno[2,3-b]pyridines [1, 2], we found a new reaction leading to closure of the pyridine ring during the formation of a pentacyclic heteroaromatic 22π-electronic system dipyridothienopyridine.During an attempt to reduce the carbonyl group of compounds 1a-d with sodium borohydride in ethanol the corresponding dipyrido[3',2':4,5]thieno[3,2-b:3,2-d]pyridines 3a-d were isolated from the reaction mixture instead of the expected amino alcohols 2. The mechanism of the transformations that occur is not quite clear and will be the subject of further investigations. N S Me NH 2 R O MeO NaBH 4 N S Me N S N Me R MeO OMe N S Me NH 2 R OH MeO 2 1a-d 3a-d 1, 3 a R = Ph; b R = C 6 H 4 Br-4; c R = C 6 H 3 Cl 2 -2,4; d R = MeThe 1 H NMR spectra were recorded in trifluoroacetic acid (compounds 3a-c) and DMSO-d 6 (compound 3d) on a Bruker DRX-500 instrument (500 MHz).Synthesis (General Procedure). Compound 1 (0.005 mol) was dissolved by heating in ethanol (20 ml), and sodium borohydride (7.5 mmol) was added while the reaction mixture was stirred. The obtained solution was boiled for 3 h, cooled, and neutralized with a 10% solution of hydrochloric acid. The flocculent precipitate was separated and washed with boiling DMF, water, and ethanol. The products were recrystallized from ethanol. __________________________________________________________________________________________

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“…Synthetic routes and structural analysis of thienopyridine derived molecules have also been described (Kaigorodova et al, 2000;El-Kashef et al, 2010;Testa et al, 2010) together with antiviral , anti-inflammatory (Moloney, 2001), antibacterial Pinheiro et al, 2008;Panchamukhi et al, 2011) and antiparasitic reports (Bernardino et al, 2006). Interestingly, thienopyridine derivatives are analogous to amodiaquine, and pyrazolopyridine derivatives (Mello et al, 2004;Dias et al, 2007), which have been described as antiprotozoa agents, acting against resistant Trypanosome and Leishmania strains (Silva et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

Searching for new antileishmanial lead drug candidates: Synthesis, biological and theoretical evaluations of promising thieno[2,3-b] pyridine derivatives

Pinheiro¹,

Tonioni²,

Sathler³

et al. 2012

J. Microbiol. Antimicrob.

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Cutaneous leishmaniasis is a parasitic disease associated with high morbidity and mortality rates. This work reports the synthesis, biological and theoretical evaluations of a new antileishmanial series of 5-(4,5-dihydro-1H-imidazol-2-yl)-4-(arylamino)thieno[2,3-b]pyridine derivatives -3 (H), 3a (m-CH 3 ), 3b (m-OCH 3 ), 3c (m-NO 2 ), 3d (m-F), 3e (m-Br), 3f (p-CH 3 ), 3g (p-OCH 3 ), 3h (p-NO 2 ), 3i (p-F), 3j (p-Br).Interestingly 3f and 3g showed a better profile against Leishmania amazonensis (EC 50 =29.49 and 32.23 μM, respectively) than glucantime, the current drug on the market (EC 50 =163.7 μM). The theoretical analysis pointed a correlation among the antileishmanial profile and the conformational and electrostatic features of these new molecules. ADMET and "Lipinski´s rule of 5" revealed higher theoretical biodisponibility, druglikeness and drugscore values for these derivatives compared to known antileishmanial drugs. Our results pointed these thieno[2,3-b]pyridine derivatives as lead compounds for designing new agents for treatment of cutaneous leishmaniasis.

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Synthesis and Reactions of Substituted 3-amino-2-furyl(aryl)-thieno[2,3-b]pyridines

Abstract: New substituted thieno [2,3-b]pyridines which contain 4-nitropehnyl and 5-nitro-, carboxy-, methoxycarbonyl-2-furyl groups in the 2 position have been obtained.

Cited by 15 publications

References 6 publications

Synthesis of Substituted Thieno[2,3‐b]pyrroles.

Synthesis of Substituted Thieno[2,3‐b]pyrroles.

The formation of the pyridine ring in the synthesis of dipyrido-[3′,2′:4,5]thieno[3,2-b: 3,2-d]pyridines

Searching for new antileishmanial lead drug candidates: Synthesis, biological and theoretical evaluations of promising thieno[2,3-b] pyridine derivatives

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