Synthesis and antioxidant evaluation of some new sulphadimidine incorporating thiophene moiety

Gouda, Moustafa A.; Eldien, Hadeer Fakhr; Girges, M. M.; Berghot, M. A.

doi:10.5155/eurjchem.5.4.595-600.1106

Cited by 15 publications

(16 citation statements)

References 26 publications

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“…6–14 In particular, substituted aminothiophenes, including 2-aminothiophene-3-carboxylate derivatives, appear to be of interest in medicinal chemistry and are represented in several classes of biologically active molecules. 15–17 …”

Section: Introductionmentioning

confidence: 99%

Copper-mediated N-arylation of methyl 2-aminothiophene-3-carboxylate with organoboron reagents

Karakaya

Heitz

Zubaır

et al. 2015

Tetrahedron Letters

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Section: Introductionmentioning

confidence: 99%

Copper-mediated N-arylation of methyl 2-aminothiophene-3-carboxylate with organoboron reagents

Karakaya

Heitz

Zubaır

et al. 2015

Tetrahedron Letters

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“…Condensation of 2‐amino‐4,5,6,7‐tetrahydrobenzo[ b ]thiophene‐3‐carboxamide (synthesised via the Gewald reaction) with a pyrazole derivative yielded an active methylene compound. Various aryl amines were diazotised and, coupled with pyridine at the active methylene site, afforded azo dyes 43 . These azo structures are in equilibrium with hydrazones.…”

Section: Synthesis Of Azo Dyesmentioning

confidence: 99%

The Gewald reaction in dye chemistry

Sabnis¹

2016

Coloration Technology

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This review presents the most elegant and promising set of synthetic routes for the synthesis of 2‐aminothiophenes by the Gewald reaction. This reaction has applications in several applied fields, such as pharmaceuticals/biomedicine, agrochemicals, carbohydrate conjugates, sugar cane ripeners, peptide analogues, dyestuffs, and electronic materials; however, the present review will focus on the use of Gewald chemistry in the synthesis of conventional and functional colourants. The Gewald reaction produces 2‐aminothiophene, which is a key intermediate for the diazotisation reaction and for the synthesis of azo dyes, and thus opened the door for new dye chemistry. The reaction produces electron‐withdrawing groups such as CN, COOEt, COOMe, CONH2, and COPh in the 3‐ and/or 5‐position, resulting in bathochromic shifts for the deeper colours of the dyes. The review further reveals the importance of this reaction in the synthesis of azo dyes, fluorescent dyes (coumarin dyes, styryl dyes, thieno[2,3‐d]pyrimidine dyes, bithiophene dyes), thiophene analogues of phthalocyanines, and fluorescent whitening agents.

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“…[7] Such type of scaffolds display attractive feature, due to their ability to act as intermediate for the synthesis of conjugates and hybrid biological active thiophene-containing heterocycles. [8,9] Many therapeutic products such as antipsychotic drug olanzapine I (Figure 1), the non-steroidal anti-inflammatory tinoridine II and the promising anticancer agent Raltitrexed (Tomudex) III are 2-aminothiophene derivatives which, appeared on the market or underwent wide-ranging pharmacological studies, [10][11][12][13][14] also 2-Aminothiophene derivatives exhibited a large spectrum of biological properties that include; Antiplatelet, [15] anxiolytic, [16] anti-diabetes, [15] antioxidant, [17] anti-inflammatory, [18] and antianxiety. [19] In light of the remarkable variety of biological activities realized in thiophene and attached heterocyclic compounds, we reported here the modification of thiophene ring into a variety of novels condensed thiophene derivatives incorporating thiazole, pyrazole, pyridazine, pyridine, and thiophene and investigated their activity as potent anticancer.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and cytotoxic activity of some new heterocycles incorporating cyclohepta[b]thiophene‐3‐carboxamide derivatives

Gouda

Al‐Ghorbani

Al‐Zaqri

2020

Journal of Heterocyclic Chem

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A series of 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide-heterocyclic hybrids were synthesized, characterized and their cytotoxic potencies were assessed on four human cell lines. Cyanoacetamide derivative (5) was used as the key synthetic intermediate for the synthesis many derivatives in this study, derivatives 9, 11, 12 were formed by coupled compound 5 with different aryl/heteryl diazonium chlorides, Gewald reaction and Knoevenagel condensation were used for synthesis derivatives 13, 14, 16 by treated cyanoacetamide (5) with different reagents. In another route, compound 5 treated with phenyl isothiocyanate give thiocarbamoyl derivative (7) which used as intermediate underwent oxidative cyclization with different moieties to offer the corresponding thiazoles and thiophene 18, 19, 20, 21, respectively. in vitro cytotoxic activity of prepared compounds were tested against four human tumor cell lines. The result revealed that compound 11a displayed promising cytotoxic activity against HepG2, HCT-116, MCF-7, and PC3 cancer cell lines comparing to the positive control (Doxorubicin).

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Synthesis and antioxidant evaluation of some new sulphadimidine incorporating thiophene moiety

Cited by 15 publications

References 26 publications

Copper-mediated N-arylation of methyl 2-aminothiophene-3-carboxylate with organoboron reagents

Copper-mediated N-arylation of methyl 2-aminothiophene-3-carboxylate with organoboron reagents

The Gewald reaction in dye chemistry

Synthesis and cytotoxic activity of some new heterocycles incorporating cyclohepta[b]thiophene‐3‐carboxamide derivatives

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