Synthesis of New Thiazole and Pyrazole Clubbed 1,2,3-Triazol Derivatives as Potential Antimycobacterial and Antibacterial Agents

Jagadale, Shivaji; Abhale, Yogita K.; Pawar, Hari R.; Shinde, Abhijit; Bobade, Vivek D.; Chavan, Abhijit P.; Sarkar, Dhiman; Mhaske, Pravin C.

doi:10.1080/10406638.2020.1857272

Cited by 18 publications

(7 citation statements)

References 52 publications

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“…were significantly inhibited by compounds 43 a-43 e. The structure-based activity study results displayed that the activity depends on the presence of various substituent groups like À H, À Cl, À Br, À F, hydroxyl methyl, and methyl connected to the 6-member aromatic ring (Figure 13). [86] A pyrazolyl thiazole hybrid containing 3-(4-chlorophenyl)-4substituted pyrazoles was designed, and 30 novel molecules were synthesized. Starting with 4-chloroacetophenone, an efficient approach for synthesizing the pyrazole moiety was developed.…”

Section: Pyrazolyl Thiazole Derivativesmentioning

confidence: 99%

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Thiazole Heterocycle: An Incredible and Potential Scaffold in Drug Discovery and Development of Antitubercular Agents

Bhanwala,

Gupta,

Chandrakar

et al. 2023

ChemistrySelect

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In 2020, 15 million people were diagnosed with tuberculosis (TB), and 2.4 million died. Additionally, the TB situation is worse with multidrug resistance (MDR) and extended‐drug resistance (XDR)‐TB. Research into innovative anti‐tubercular drugs with improved MDR‐TB activity, lower toxicity, and shorter therapy duration is crucial for solving this issue. Fortunately, numerous novel potential anti‐tubercular candidates are currently under clinical trials. Most of these candidates have five‐membered rings and are most likely effective against sensitive and resistant strains. This review discusses current developments in the five‐membered heterocyclic thiazole ring, emphasizing its anti‐tubercular properties, toxicity, structure‐activity relationship, and mechanism of action. Thiazole ring has a wide range of biological activities and thus gained much synthetic interest. Due to the popularity of thiazole as an anti‐tubercular moiety, it combined with other medicinally active chemical functionality and nuclei to design and synthesize novel hybrid analogues with maximum activity and minimal toxicity. In this review we have done the literature survey of the past 10 years, and compiled the structural and functional studies of thiazole as an anti‐tubercular agent with its potent chemical entities showing prominent pharmacological action.

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Section: Pyrazolyl Thiazole Derivativesmentioning

confidence: 99%

“…The structure‐based activity study results displayed that the activity depends on the presence of various substituent groups like −H, −Cl, −Br, −F, hydroxyl methyl, and methyl connected to the 6‐member aromatic ring (Figure 13). [86] …”

Section: Anti‐tubercular Potentialmentioning

confidence: 99%

Thiazole Heterocycle: An Incredible and Potential Scaffold in Drug Discovery and Development of Antitubercular Agents

Bhanwala,

Gupta,

Chandrakar

et al. 2023

ChemistrySelect

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“…Compounds 58a-e demonstrated significant effectiveness against the Mycobacterium TB H37Ra active strain and also against the Mycobacterium TB H37Ra dormant strain. The structure-based activity study indicated that the presence of different R and R 1 groups (H, Cl, Br, F, hydroxyl methyl, and methyl) attached to the phenyl ring is crucial for the activity [101]. Karale et al (2019) prepared and investigated tri-substituted thiazoles as anti-tubercular agents.…”

Section: Thiazoles As Anti-tubercular Agentsmentioning

confidence: 99%

Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents

Arshad¹,

Alam

Alshammari

et al. 2022

Molecules

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For many decades, the thiazole moiety has been an important heterocycle in the world of chemistry. The thiazole ring consists of sulfur and nitrogen in such a fashion that the pi (π) electrons are free to move from one bond to other bonds rendering aromatic ring properties. On account of its aromaticity, the ring has many reactive positions where donor–acceptor, nucleophilic, oxidation reactions, etc., may take place. Molecules containing a thiazole ring, when entering physiological systems, behave unpredictably and reset the system differently. These molecules may activate/stop the biochemical pathways and enzymes or stimulate/block the receptors in the biological systems. Therefore, medicinal chemists have been focusing their efforts on thiazole-bearing compounds in order to develop novel therapeutic agents for a variety of pathological conditions. This review attempts to inform the readers on three major classes of thiazole-bearing molecules: Thiazoles as treatment drugs, thiazoles in clinical trials, and thiazoles in preclinical and developmental stages. A compilation of preclinical and developmental thiazole-bearing molecules is presented, focusing on their brief synthetic description and preclinical studies relating to structure-based activity analysis. The authors expect that the current review may succeed in drawing the attention of medicinal chemists to finding new leads, which may later be translated into new drugs.

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“…The pyrazole ring clubbed with other heterocycles is a privileged pharmacophore for the development of new lead molecules. − The pyrazole-tethered thiazole (Figure ) has received much attention in recent years due to its remarkable biological activities such as antimicrobial, − antibiofilm, as an apoptosis inducer, anti-inflammatory, , antitubercular, and antimycobacterial activities. Considering the efficiency of pyrazole and thiazole clubbed derivatives, our studies have been focused on the synthesis and bioevaluation of these derivatives by a hybrid approach as possible bioactive molecules.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Screening of New 2-(5-Aryl-1-phenyl-1H-pyrazol-3-yl)-4-aryl Thiazole Derivatives as Potential Antimicrobial Agents

Nandurkar

Shinde²,

Bhoye

et al. 2023

ACS Omega

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A new series of 2-(5-aryl-1-phenyl-1H-pyrazol-3yl)-4-aryl thiazoles (10a−ab) have been synthesized by a cyclocondensation reaction of 5-aryl-1-phenyl-1H-pyrazole-3-carbothioamide (7a−d) with substituted phenacyl bromide (8a−f). The structure of newly synthesized 2-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-4-aryl thiazole (10a−ab) derivatives was characterized by spectroscopic analysis. The compounds 10a−ab were evaluated for in vitro antibacterial activity against Escherichia coli (NCIM 2574), Proteus mirabilis (NCIM 2388), Bacillus subtilis (NCIM 2063), Staphylococcus aureus (NCIM 2178), and in vitro antifungal activity against Aspergillus niger (ATCC 504) and Candida albicans (NCIM 3100). Among the twenty-eight pyrazolyl-thiazole derivatives, six compounds, 10g, 10h, 10i, 10j, 10o, and 10t, showed good activity against P. mirabilis; four compounds 10q, 10u, 10y, and 10z showed good activity against S. aureus; and twenty-four derivatives showed good antifungal activity against A. niger. Compounds 10g, 10q, 10r, 10s, and 10ab showed comparable activity with respect to the reference drug Ravuconazole. Thus, the significant antimicrobial activity of 2-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-4-aryl thiazole (10a−ab) derivatives prompted that these scaffolds could assist in the development of lead compounds to treat microbial infections.

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Synthesis of New Thiazole and Pyrazole Clubbed 1,2,3-Triazol Derivatives as Potential Antimycobacterial and Antibacterial Agents

Cited by 18 publications

References 52 publications

Thiazole Heterocycle: An Incredible and Potential Scaffold in Drug Discovery and Development of Antitubercular Agents

Thiazole Heterocycle: An Incredible and Potential Scaffold in Drug Discovery and Development of Antitubercular Agents

Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents

Synthesis and Biological Screening of New 2-(5-Aryl-1-phenyl-1H-pyrazol-3-yl)-4-aryl Thiazole Derivatives as Potential Antimicrobial Agents

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