Synthesis of new triazole fused imidazo[2,1-b]thiazole hybrids with emphasis on Staphylococcus aureus virulence factors

Shareef, Mohd Adil; Kanugala, Sirisha; Sayeed, Ibrahim Bin; Khan, Irfan; Ganapathi, Thipparapu; Akbar, Syed; Kumar, C. Ganesh; Kamal, Ähmed; Babu, Bathini Nagendra

doi:10.1016/j.bmcl.2019.08.025

Cited by 20 publications

(9 citation statements)

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“…Among hybrid heterocycles with bridgehead nitrogen, imidazo[2,1- b ]thiazole is one of the most vital nuclei owing to its wide range of applications as synthetic intermediates and promising biological applicability as anticancer, antiviral, antibacterial, antifungal, antitubercular, antioxidant, anthelmintic, and anti-inflammatory. − The supreme importance of imidazo[2,1- b ]thiazoles in medicinal chemistry and the pharmaceutical industry is validated by the well-known anthelmintic and immunomodulatory agent Levamisole ( i ), anxiolytic agent WAY-181187 (SAX-187) ( ii ), anticancer agent Tilomisole ( iii ), and antineoplastic agent Pifithrin-β ( iv ) (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Visible-Light-Prompted Synthesis and Binding Studies of 5,6-Dihydroimidazo[2,1-b]thiazoles with BSA and DNA Using Biophysical and Computational Methods

et al. 2022

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Fused heterocyclic systems containing a bridgehead nitrogen atom have emerged as imperative pharmacophores in the design and development of new drugs. Among these heterocyclic moieties, the imidazothiazole scaffold has long been used in medicinal chemistry for the treatment of various diseases. In this study, we have established a simplistic and environmentally safe regioselective protocol for the synthesis of 5,6-dihydroimidazo[2,1-b]thiazole derivatives from easily available reactants. The reaction proceeds through in situ formation of the α-bromodiketones ensuing trap with imidazolidine-2-thione to provide these versatile bicyclic heterocycles in excellent yields. The synthesized compounds were screened through the molecular docking approach for the most stable complex formation with bovine serum albumin (BSA) and calf thymus deoxyribonucleic acid (ctDNA). The selected compound was further studied using ex vivo binding studies, which revealed moderate interactions with BSA and ctDNA. The binding studies were performed using biophysical approaches including UV–visible spectroscopy, steady-state fluorescence, circular dichroism (CD), and viscosity parameters.

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Section: Introductionmentioning

confidence: 99%

Visible-Light-Prompted Synthesis and Binding Studies of 5,6-Dihydroimidazo[2,1-b]thiazoles with BSA and DNA Using Biophysical and Computational Methods

et al. 2022

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“…One of those medicines that are prevalent in the markets and proven effective is penicillin as antibiotic for bacterial diseases (Figure 1). It is an undeniable fact that many previous research shows that compounds that include the thiazole ring have high effectiveness such as antimicrobial [1][2][3][4][5], anti-diabetes [6][7][8], antitumor [9][10][11][12], anti-HIV [13,14], anticonvulsant [15,16], anti-oxidant [17,18], and antiinflammatory activities [19][20][21]. The continued resistance of microbes to antibiotics circulating in the market has contributed to intensifying efforts to search for new effective antimicrobial drugs [22].…”

Section: Introductionmentioning

confidence: 99%

Fluorinated hydrazonoyl chlorides as precursors for synthesis of antimicrobial azoles

Al‐Hussain

Alshehrei²,

Zaki

et al. 2020

Journal of Heterocyclic Chem

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Hydrazonoyl halides have been known for their ability to react with different reagents to afford wide range of bioactive heterocyclic systems as thiazoles and imidazopyrazoles. This research work focused on the synthesis of two new fluorinated hydrazonoyl chlorides and used them in synthesis of novel series of thiazole derivatives and two imidazopyrazole systems. The mechanistic pathways and the structures of all synthesized derivatives were discussed and assured based on the available spectral data. The results of antimicrobial activity of the tested thiazoles and imidazopyrazoles showed that some derivatives have moderate to no activity against tested fungi and bacteria strains. Only one derivative namely 2‐(2‐(3‐fluoro‐4‐methylphenyl)hydrazono)‐7‐(2‐oxoindolin‐3‐ylidene)‐2,7‐dihydro‐3H‐imidazo[1,2‐b]pyrazole‐3,6(5H)‐dione is the most active against Candida albicans (CA) with IZD = 20 mm, which was equipotent to ketoconazole. Furthermore, docking simulation was carried out to predict the binding pattern of the new compounds in the ATP binding site of the DNA gyrase B enzyme. The results of the docking simulation revealed that compounds 9a‐e, 12, and 13a,b fit well in the ATP binding site of DNA gyrase B with docking score values ranging from −5.883 to −6.833 kcal/mol.

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“…found that 2,6‐disubstituted imidazo[2,1‐ b ][1,3,4]thiadiazole derivatives ( 4 ) showed good antibacterial activity against S. aureus and Staphylococcus epidermidis with MIC values of 0.3 and 9.3 μg/mL, respectively. Shareef et al [31] . found that triazole‐fused imidazo[2,1‐ b ]thiazole hybrids ( 5 ) demonstrated broad‐spectrum antibacterial activity with MIC values between 1.9 and 7.8 μg/mL, and moderate antifungal activity with MIC values between 7.8 and 15.6 μg/mL.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity Evaluation of Imidazole‐Fused Imidazo[2,1‐b][1,3,4]thiadiazole Analogues

et al. 2021

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Three series of new imidazole‐fused imidazo[2,1‐b][1,3,4]thiadiazole analogues (compounds 20 a–g, 21 a–g, and 22 a–g) have been synthesized, and their antibacterial and antifungal activities have been evaluated. All the target compounds showed strong antifungal activity and high selectivity for the test fungus Candida albicans over Gram‐positive and ‐negative bacteria. N‐((4‐(2‐Cyclopropyl‐6‐(4‐fluorophenyl)imidazo[2,1‐b][1,3,4]thiadiazol‐5‐yl)‐5‐(6‐methyl‐pyridin‐2‐yl)‐1H‐imidazol‐2‐yl)methyl)aniline (21 a) showed the highest activity against C. albicans (MIC50=0.16 μg/mL), 13 and three times that of the positive control compounds gatifloxacin and fluconazole, respectively. Compounds 21 a and 20 e did not show cytotoxicity against human foreskin fibroblast‐1 cells, and compound 21 a was as safe as the positive control compounds in hemolysis tests. These results strongly suggest that some of the compounds produced in this work have value for development as antifungal agents.

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Synthesis of new triazole fused imidazo[2,1-b]thiazole hybrids with emphasis on Staphylococcus aureus virulence factors

Cited by 20 publications

References 38 publications

Visible-Light-Prompted Synthesis and Binding Studies of 5,6-Dihydroimidazo[2,1-b]thiazoles with BSA and DNA Using Biophysical and Computational Methods

Visible-Light-Prompted Synthesis and Binding Studies of 5,6-Dihydroimidazo[2,1-b]thiazoles with BSA and DNA Using Biophysical and Computational Methods

Fluorinated hydrazonoyl chlorides as precursors for synthesis of antimicrobial azoles

Synthesis and Antimicrobial Activity Evaluation of Imidazole‐Fused Imidazo[2,1‐b][1,3,4]thiadiazole Analogues

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