Synthesis, Antitubercular and Antibacterial Activities of Some Quinazolinone Analogs Substituted with Benzothiophene

Rao, Gopal Krishna

doi:10.4172/2150-3494.100092

Cited by 20 publications

(8 citation statements)

References 4 publications

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“…Nonetheless, the foremost synthetic challenge in this field is to design and synthesize new polytopic ligands with appropriate donor groupings placed strategically in place for metal coordination. In general, pyrrole, thiophene, and their organic and metal cluster derivatives are recognized to present a wide range of biological activities [ 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 ]. Therefore, the design and synthesis of novel ligands containing the thiophene and pyrrole rings have attracted great interest.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

et al. 2022

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Polytopic organic ligands with hydrazone moiety are at the forefront of new drug research among many others due to their unique and versatile functionality and ease of strategic ligand design. Quantum chemical calculations of these polyfunctional ligands can be carried out in silico to determine the thermodynamic parameters. In this study two new tritopic dihydrazide ligands, N’2, N’6-bis[(1E)-1-(thiophen-2-yl) ethylidene] pyridine-2, 6-dicarbohydrazide (L1) and N’2, N’6-bis[(1E)-1-(1H-pyrrol-2-yl) ethylidene] pyridine-2, 6-dicarbohydrazide (L2) were successfully prepared by the condensation reaction of pyridine-2, 6-dicarboxylic hydrazide with 2-acetylthiophene and 2-acetylpyrrole. The FT-IR, 1H, and 13C NMR, as well as mass spectra of both L1 and L2, were recorded and analyzed. Quantum chemical calculations were performed at the DFT/B3LYP/cc-pvdz/6-311+ G (d, p) level of theory to study the molecular geometry, vibrational frequencies, and thermodynamic properties including changes of ∆H, ∆S, and ∆G for both the ligands. The optimized vibrational frequency and (1H and 13C) NMR obtained by B3LYP/cc-pvdz/6-311 + G (d, p) showed good agreement with experimental FT-IR and NMR data. Frontier molecular orbital (FMO) calculations were also conducted to find the HOMO, LUMO, and HOMO–LUMO gaps of the two synthesized compounds. To investigate the biological activities of the ligands, L1 and L2 were tested using in vitro bioassays against some Gram-negative and Gram-positive bacteria and fungus strains. In addition, molecular docking was used to study the molecular behavior of L1 and L2 against tyrosinase from Bacillus megaterium. The outcomes revealed that both L1 and L2 can suppress microbial growth of bacteria and fungi with variable potency. The antibacterial activity results demonstrated the compound L2 to be potentially effective against Bacillus megaterium with inhibition zones of 12 mm while the molecular docking study showed the binding energies for L1 and L2 to be −7.7 and −8.8 kcal mol−1, respectively, with tyrosinase from Bacillus megaterium.‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬

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Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

et al. 2022

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“…The aromatic protons resonated as multiplet signals in the region from δ 7.17 The molecular ion peak at m/z = 523.33 (M + ), which matches the compound's molecular formula C29H25N5O3S, was observed in the mass spectrum of compound 7a with a relative intensity of 43.1%. (17), which undergoes stirring with phenyl isothiocyanate in dimethyl formamide and potassium hydroxide to furnish 2-cyano-N'4-(2-(antipyrin-4-yl)-2-oxoethoxy)benzylidene)-3-mercapto-3-(phenylamino)-acrylohydrazide (18). The structures of 17 and 18 were elucidated by spectroscopic techniques and satisfactory elemental analysis.…”

Section: Resultsmentioning

confidence: 99%

“…They occupy a unique position because advances in their synthesis, availability, stability, and structural simplicity make them useful scaffolds in pharmaceuticals and other therapeutics, like the best-selling drugs Olanzepine and Tinoridine [1][2][3] (Figure 1). Furthermore, thiophene derived molecules displayed a variety of pharmacological properties, including anti-inflammatory [4], antimicrobial [5], antihypertensive [6], anti-atherosclerotic properties [7], cytotoxicity in several cancer cell lines [8,9], tubulin polymerization [10,11], antioxidant [12], inhibitor for acetyl-CoA carboxylase [13], STAT3 inhibitors [14], antidepressant [15], antidepressant, anti-diabetic [16], anti-tubercular [17], antifungal [18], enzyme inhibitor [19], anti-malarial drugs [20] and are used in the treatment of asthma [21]. On the other hand, thiophene derivatives are the largest class of industrial chemistry, thermal, optoelectronic properties and material science because of their wide utilized applications, such as materials for electroluminescence devices [22,23], corrosion inhibitors [24], organic semiconductors [25], organic field-effect transistors (OFETs), and in the fabrication of organic light-emitting diodes (OLEDs) [26], synthesis of fluorescent chemo sensors [27].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some new antipyrine-thiophene hybrids and their evaluations as antioxidant and antibacterial agents

Saleh¹,

Saeed²,

Ghani³

et al. 2022

Bull. Chem. Soc. Eth.

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ABSTRACT. A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemically synthesized through the cyclocondensation of 4-chloroacetylantipyrine with various 2-substituted-thioacetanilide scaffolds, including 3-arylazo-4-mercapto-4-phenylamino-buten-2-ones, ethyl 2-arylazo-3-mercapto-3-phenylamino-acrylate, 2-cyano-3-mercapto-3-(phenylamino)-N-arylacrylamide, 4-mercapto-4-(phenylamino)but-3-en-2-one, and/or ethyl-3-mercapto-3-(phenylamino)acrylate. Indeed, the reaction of 4-chloroacetylantipyrine with 4-hydroxybenzaldehyde followed by refluxing with 2-cyanoacetohydrazide yielded 2-cyano-N'-(4-(2-(antipyrin-4-yl)-2-oxoethoxy)benzylidene)-acetohydrazide 17 as a building compound, which was used consequentially to synthesize a set of new antipyrinyl thienyl hybrids 19a-d. The chemical structures of newly synthesised compounds were unambiguously confirmed using extensive elemental and spectral data analyses. The newly synthesized compounds were screened for their antioxidant and antimicrobial activities. Compared to the test reference (Ascorbic acid, 88.0%), the antipyrinyl thienyl ketones 13a and 13b substituted with methyl and/or hydroxyl groups at the thiophene ring system displayed excellent antioxidant properties, 87.8% and 87.2%, respectively. Additionally, antipyrinyl thienyl ketones 13a and 13b showed high antibacterial activities, and their relative activity index (which ranges from 68% to 91.7%) was close to that of a reference compound, Ampicillin. KEY WORDS: 4-Chloroacetylantipyrine, Thioacetanilide, Antipyrinyl thienyl ketones, Antioxidant, Antimicrobial Bull. Chem. Soc. Ethiop. 2023, 37(1), 123-140. a DOI:https://dx.doi.org/10.4314/bcse.v37i1.11

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“…However, the substituted phenyl ring in the side chain also facilitates the biological action of the molecules. 29 In their similar investigation of the substituted group of the aryl moiety towards antibacterial potency, they observe that more activity was found in electronwithdrawing moiety and less activity was shown in the group having electrons donating moiety. 30 Effect of electron-withdrawing groups present in the synthesized compounds on the result, is greater than our expectations.…”

Section: Chemistrymentioning

confidence: 97%

1,3,4-thiadiazole Attached 2, 3- disubstituted Thiazolidinones Derivatives: Synthesis and Biological Evaluation

Garg¹,

Garg²

2021

IJPER

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Background: Thiazolidinone derivatives are the subject of prominent importance since they have been seen as valuable intermediates for the formulating/synthesize of different heterocyclic derivatives and it gives various subsidiaries with every extraordinary kind of exercise. What're more, researches show that derivatives having 1,3,4-Thiadiazole core/ nucleus have a wide scope of pharmacological potential that incorporates antifungal, antibacterial, antiviral, anticancer, antitubercular, anticonvulsant, antidiabetic and antioxidant. From the literature reviewed, both the nucleus was found to be active as antimicrobials, anti-inflammatory as well as anticancer agents. Materials and Methods: It has been planned to synthesize "1,3,4-thiadiazolyl-thiazolidin-4-one" derivatives and evaluate their biological activities. The novel subordinates (4a-4j) of 2, 3-disubstituted Thiazolidinones were integrated into acceptable yield by the synthesis of benzaldehyde with thiosemicarbazide to provide thiosemicarbazones, 1,3,4-thiadiazoles is then produced by thiosemicarbazone cyclized by involving ferric chloride. By the reaction of various aromatic aldehyde with 1,3,4-thiadiazoles yielded different Schiff bases. The final derivative 2-aryl-3-(5-aryl-1,3,4-thiadiazol-2-yl)-1,3-thiazolidine-4-one was obtained by the reaction between the schiff base with thioglycolic acid. All subordinates/ derivatives were portrayed by spectral analysis examination (IR, 1H NMR) and elemental analysis and then screened for biological activities (in-vitro anticancer, antimicrobial, anti-inflammatory). Results and Conclusion: The analysis reveals that synthesized derivatives of thiazolidinone possessing methyl, hydro, nitro, hydroxyl, flouro, chloro, methoxy, dimethoxy and amino substitution through phenyl ring. All these groups help pharmacophore, to increase their pharmacological activities. However, the substituted phenyl ring in the side chain also facilitates the biological action of the molecules. The increased activity of the new derivatives explains that they act as a more powerful and potent bioactive molecule when compare with the standard drug. This significant activity may be due to the substitution in the 2 nd position of thiazolidinone nucleus. As result, all the tested compounds exhibit good activity and compounds 4i, 4b, 4f and 4a were established more noteworthy and outstanding as of all the derivatives.

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Synthesis, Antitubercular and Antibacterial Activities of Some Quinazolinone Analogs Substituted with Benzothiophene

Cited by 20 publications

References 4 publications

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

Synthesis of some new antipyrine-thiophene hybrids and their evaluations as antioxidant and antibacterial agents

1,3,4-thiadiazole Attached 2, 3- disubstituted Thiazolidinones Derivatives: Synthesis and Biological Evaluation

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