A Facile and Convenient Synthesis of some Novel Hydrazones, Schiff’s Base and Pyrazoles Incorporating Thieno[2,3-b]thiophenes

Mabkhot, Yahia N.; Barakat, Assem; Al‐Majid, Abdullah Mohammed; ALOthman, Zeid A.; Alamary, Abdullah Saleh

doi:10.3390/ijms12117824

Cited by 15 publications

(9 citation statements)

References 27 publications

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“…So, the low energy band may be assigned to spin-forbidden 3 MLCT and 3 LLCT transitions along with 1 MLCT transition [80]. The strong covalency of the carbon–metal bonds attributes to the mixed character of HOMO being delocalized on the metal and on the cyclometalating ligand [65–67]. The LUMOs are mainly (77.21–82.65%) composed of Schiff base ligand L1 and L2 and contributions from metal d-orbitals are not insignificant.…”

Section: Resultsmentioning

confidence: 99%

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Cyclometalated rhodium and iridium complexes with imidazole containing Schiff bases: Synthesis, structure and cellular imaging

et al. 2014

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Cyclometalated rhodium(III) and iridium(III) complexes (1–4) of two Schiff base ligands L1 and L2 with the general formula [M(ppy)2(Ln)]Cl {M = Rh, Ir; ppy = 2-phenylpyridine; n = 1, 2; L = Schiff base ligand} have been synthesized. The new ligands and the complexes have been characterized with spectroscopic techniques. Electrochemistry of the complexes revealed anodic behavior, corresponding to an M(III) to M(IV) oxidation. The X-ray crystal structures of complexes 2 and 4 have also been determined to interpret the coordination behavior of the complexes. Photophysical study shows that all the complexes display fluorescence at room temperature with quantum yield of about 3 × 10–2 to 5 × 10−2. The electronic absorption spectra of all the complexes fit well with the computational studies. Cellular imaging studies were done with the newly synthesized complexes. To the best of our knowledge, this is the first report of organometallic complexes of rhodium(III) and iridium(III) with Schiff base ligands explored for cellular imaging. Emphasis of this work lies on the structural features, photophysical behavior, cellular uptake and imaging of the fluorescent transition metal complexes.

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Section: Resultsmentioning

confidence: 99%

“…Selective hydrolysis of Schiff base by biological systems can generate alkylating agents for nucleic acids and at the same time the generated amines can act as antimetabolites. The Schiff bases are also active intermediaries for various heterocyclic systems of biological importance [65].…”

Section: Introductionmentioning

confidence: 99%

Cyclometalated rhodium and iridium complexes with imidazole containing Schiff bases: Synthesis, structure and cellular imaging

et al. 2014

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“…Recently, Mabkhot and co-workers have been involved in a research program aimed to development of new synthetic strategies for novel bioactive molecules and evaluation of their biological activity [22,23,24,25,26,27,28].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Anti-microbial and Molecular Docking Studies of Quinazolin-4(3H)-one Derivatives

et al. 2014

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Abstract:In this work, synthesis, antimicrobial activities and molecular docking studies of some new series of substituted quinazolinone 2a-h and 3a-d were described. Starting form 2-aminobenzamide derivatives 1, a new series of quinazolinone derivatives has been synthesized, in high yields, assisted by microwave and classical methods. Some of these substituted quinazolinones were tested for their antimicrobial activity against Gram-negative bacteria (Pseudomonas aeruginosa and Esherichia coli) and Gram-positive bacteria (Staphylococcus aureus, and Bacillus subtilis), and anti-fungal activity against (Aspergillus fumigatus, Saccharomyces cervevisiae, and Candida albicans) using agar well diffusion method. Among the prepared products, 3-benzyl-2-(4-chlorophenyl)quinazolin-4(3H)-one (3a) was found to exhibits the most potent in vitro anti-microbial activity with MICs of 25.6 ± 0.5, 24.3 ± 0.4, 30.1 ± 0.6, and 25.1 ± 0.5 µg/mL against Staphylococcus aureus, OPEN ACCESSMolecules 2014, 19 8726Bacillus subtilis, Pseudomonas aeruginosa and Esherichia coli, respectively. Compound 3a was found to exhibits the most potent in vitro anti-fungal activity with MICs of 18.3 ± 0.6, 23.1 ± 0.4, and 26.1 ± 0. 5 µg/mL against Aspergillus fumigatus, Saccharomyces cervevisiae, and Candidaal bicans, respectively.

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“…The promising results of previous studies [20,36-38] prompted us to further extend our research towards the synthesis of annulation of heterocyclic systems of potential biological application. In continuation of our previous work we are reporting here the synthesis of some more analogues of thieno[2,3- b ]thiophene moiety as a base unit and their in vitro anti-oxidant activity, including α -glucosidase and β -glucuronidase inhibition and anticancer activity against PC-3 cell lines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, reactions and biological activity of some new bis-heterocyclic ring compounds containing sulphur atom

Mabkhot

Barakat

Al‐Majid

et al. 2013

Chemistry Central Journal

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BackgroundThe derivatives of thieno[2,3-b]thiophene belong to a significant category of heterocyclic compounds, which have shown a wide spectrum of medical and industrial application.ResultsA new building block with two electrophilic center of thieno[2,3-b]thiophene derivatives 2 has been reported by one-pot reaction of diketone derivative 1 with Br2/AcOH in excellent yield. A variety of heteroaromatics having bis(1H-imidazo[1,2a] benzimidazole), bis(1H-imidazo[1,2-b][1,2,4]triazole)-3-methyl-4-phenylthieno[2,3-b]thiophene derivatives, dioxazolo-, dithiazolo-, and 1H-imidazolo-3-methyl-4-phenylthieno[2,3-b]thiophene derivatives as well pyrrolo, thiazolo -3-methyl-4-phenylthieno[2,3-b]thiophene derivatives have been designed, synthesized, characterized, and evaluated for their biological activity. Compounds 3–9 showed good bioassay result. These new derivatives were evaluated for anti-cancer activity against PC-3 cell lines, in vitro antioxidant potential and β-glucuronidase and α-glucosidase inhibitory activities. Compound 3 (IC50 = 56.26 ± 3.18 μM) showed a potent DPPH radical scavenging antioxidant activity and found to be more active than standard N-acetylcystein (IC50 = 105.9 ± 1.1 μM). Compounds 8a (IC50 = 13.2 ± 0.34 μM) and 8b (IC50 = 14.1 ± 0.28 μM) found as potent inhibitor of α-glucusidase several fold more active than the standard acarbose (IC50 = 841 ± 1.73 μM). Most promising results were obtained in β-glucuronidase enzyme inhibition assay. Compounds 5 (IC50 = 0.13 ± 0.019 μM), 6 (IC50 = 19.9 ± 0.285 μM), 8a (IC50 = 1.2 ± 0.0785 μM) and 9 (IC50 = 0.003 ± 0.09 μM) showed a potent inhibition of β-glucuronidase. Compound 9 was found to be several hundred fold more active than standard D-Saccharic acid 1,4-lactone (IC50 = 45.75 ± 2.16 μM).ConclusionsSynthesis, characterization, and in vitro biological activity of a series of thieno[2,3-b]thiophene have been investigated.

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A Facile and Convenient Synthesis of some Novel Hydrazones, Schiff’s Base and Pyrazoles Incorporating Thieno[2,3-b]thiophenes

Cited by 15 publications

References 27 publications

Cyclometalated rhodium and iridium complexes with imidazole containing Schiff bases: Synthesis, structure and cellular imaging

Cyclometalated rhodium and iridium complexes with imidazole containing Schiff bases: Synthesis, structure and cellular imaging

Synthesis, Anti-microbial and Molecular Docking Studies of Quinazolin-4(3H)-one Derivatives

Synthesis, reactions and biological activity of some new bis-heterocyclic ring compounds containing sulphur atom

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