Design, Synthesis, In Vitro Evaluation and Docking Studies of Pyrazole‐Thiazole Hybrids as Antimicrobial and Antibiofilm Agents

Gondru, Ramesh; Sirisha, K.; Raj, Sneha; Gunda, Shravan Kumar; Kumar, C. Ganesh; Pasupuleti, Mukesh; Rajitha, B.

doi:10.1002/slct.201801391

Cited by 38 publications

(51 citation statements)

References 57 publications

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“…Gondru and co-workers adopted the hybridization approach for the design of the new molecules 45a – g ( Table 15 ), which bear simultaneously in one molecular framework the four pharmacophores pyrazole, thiazole, coumarin, and benzothiazole. 100 …”

Section: Antibiofilm Compoundsmentioning

confidence: 99%

Thiazoles, Their Benzofused Systems, and Thiazolidinone Derivatives: Versatile and Promising Tools to Combat Antibiotic Resistance

et al. 2020

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Thiazoles, their benzofused systems, and thiazolidinone derivatives are widely recognized as nuclei of great value for obtaining molecules with various biological activities, including analgesic, anti-inflammatory, anti-HIV, antidiabetic, antitumor, and antimicrobial. In particular, in the past decade, many compounds bearing these heterocycles have been studied for their promising antibacterial properties due to their action on different microbial targets. Here we assess the recent development of this class of compounds to address mechanisms underlying antibiotic resistance at both bacterial-cell and community levels (biofilms). We also explore the SAR and the prospective clinical application of thiazole and its benzofused derivatives, which act as inhibitors of mechanisms underlying antibiotic resistance in the treatment of severe drug-resistant infections. In addition, we examined all bacterial targets involved in their antimicrobial activity reporting, when described, their spontaneous frequencies of resistance.

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Section: Antibiofilm Compoundsmentioning

confidence: 99%

Thiazoles, Their Benzofused Systems, and Thiazolidinone Derivatives: Versatile and Promising Tools to Combat Antibiotic Resistance

et al. 2020

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“…The pyrazole‐containing coumarin–thiazole hybrids 27 (MIC: 1.9 to >125 µg/ml) exhibited considerable activity against S. aureus , B. subtilis , M. luteus , Klebsiella planticola ( K. planticola ), E. coli , and E. aerogenes , and the SAR revealed that the introduction of the second coumarin moiety was also tolerated, as evidenced by hybrids 28 (MIC: 3.9 to >125 µg/ml) that displayed the similar activity. [ 72 ] Three hybrids, 27a,b (MIC: 1.9–7.8 µg/ml) and 28a (MIC: 3.9–7.8 µg/ml), possessed broad‐spectrum activity against all tested strains, but the activity was lower than that of ciprofloxacin (MIC: 0.9 µg/ml). The coumarin–thiadiazole hybrid 29 (inhibition zone: 15.2–17.1 mm), which was also less potent than the references ampicillin (inhibition zone: 23.8–27.4 mm) and ciprofloxacin (inhibition zone: 20.6–23.0 mm), still needs to be modified.…”

Section: Coumarin–thi(adi)azole Hybridsmentioning

confidence: 99%

Coumarin‐containing hybrids and their antibacterial activities

Feng

Zhang

Yang

et al. 2020

Archiv der Pharmazie

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Infections caused by Gram-positive and -negative bacteria are one of the foremost causes of morbidity and mortality globally. Antibiotics are the mainstay of therapy for bacterial infections, but the emergence and wide spread of drug-resistant pathogens have already become a huge issue for public healthcare systems. The coumarin moiety, which is ubiquitous in nature, could bind to the B subunit of DNA gyrase in bacteria and inhibit DNA supercoiling by blocking the ATPase activity; hence, coumarin derivatives possess potential antibacterial activity. Several coumarin-containing hybrids such as coumermycin A1, clorobiocin, and novobiocin have already been used in clinical practice for the treatment of various bacterial infections; thus, it is conceivable that hybridization of the coumarin moiety with other antibacterial pharmacophores may provide opportunities for the development of novel antibiotics. This review outlines the advances in coumarin-containing hybrids with antibacterial potential in the recent 5 years and the structure-activity relationships are also discussed. K E Y W O R D S antibacterial, coumarin, hybrid compounds, structure-activity relationships

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“…Gondru et al . developed the preparation of pyrazole‐thiazole hybrids ( 216 ) in excellent yield by treating aldehyde ( 215 ) with thiosemicarbazide ( 178 ) and various α ‐bromoketones ( 173 ) under reflux conditions (Scheme ).…”

Section: Synthesis Of Thiazolesmentioning

confidence: 99%

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

et al. 2020

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Thiazole frame work represents a vital pharmacophore in several areas of chemistry. Consequently, several synthetic protocols to construct and functionalize this core, in an attempt to generate diverse thiazole containing architectures have been developed by various researchers across the globe. These wide range of methodologies developed will allow the access to fully decorated thiazole containing new chemical entities that can find various application in the field of medicinal chemistry, agrochemicals and material science. This review will provide an insight in to the various synthons used in construction and diversification of this core. Diversely functionalized thiazole analogs are considered as a vital azole framework present in many natural products. This prominent heterocycle also constitutes an important pharmacophore in medicinal chemistry, in agrochemicals and in molecules for material science applications. All these above‐mentioned features of thiazole necessitates the continuous development of efficient methods to access this heterocycle. Accordingly, various researchers across the globe have come up with efficient synthetic protocols in an attempt functionalize different positions of this important scaffold. This review aims at highlighting some of the latest synthetic approaches to di/tri‐substituted thiazole analogs which are known to possess a wide spectrum of biological activities.

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Design, Synthesis, In Vitro Evaluation and Docking Studies of Pyrazole‐Thiazole Hybrids as Antimicrobial and Antibiofilm Agents

Cited by 38 publications

References 57 publications

Thiazoles, Their Benzofused Systems, and Thiazolidinone Derivatives: Versatile and Promising Tools to Combat Antibiotic Resistance

Thiazoles, Their Benzofused Systems, and Thiazolidinone Derivatives: Versatile and Promising Tools to Combat Antibiotic Resistance

Coumarin‐containing hybrids and their antibacterial activities

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

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