Synthesis and antimycobacterial screening of new thiazolyl-oxazole derivatives

Abhale, Yogita K.; Sasane, Amit V.; Chavan, Abhijit P.; Shekh, Saddam Husen; Deshmukh, Keshav K.; Bhansali, Sujit G.; Nawale, Laxman; Sarkar, Dhiman; Mhaske, Pravin C.

doi:10.1016/j.ejmech.2017.03.065

Cited by 47 publications

(19 citation statements)

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“…The syntheses of compounds 1a – d to 7a – d are reported in our previous papers. Ethyl 2‐arylthiazole‐4‐carboxylate, 1a – d on reduction of carboethoxy group followed by selective oxidation using iodoxy benzoic acid furnished 2‐arylthiazole‐4‐carbaldehyde 2a – d . Aldehyde 2a – d on reaction with iodine and ammonia in tetrahydrofuran gave 2‐arylthiazole‐4‐carbonitrile 3a – d .…”

Section: Resultsmentioning

confidence: 99%

“…In our previous communication, 4,5′‐bisthiazole, 2,5′‐bisthiazole, thiazole substituted thiosemicarbazideand thiazolyl‐oxazole derivatives were shown as potent antitubercular and antibacterial agents . Encouraged by the observed biological activities of the various thiazole derivatives and as part of our ongoing search for compounds as potential antimicrobial agents, employing molecular simplification, the synthesis and antimicrobial screening of uncommon 4″‐methyl‐2,2″‐diphenyl‐4,2′:4′,5″‐terthiazole derivatives is reported.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization, and Antimicrobial Screening of 4″‐methyl‐2,2″‐diaryl‐4,2′:4′,5″‐terthiazole Derivatives

Nalawade

Mhaske

Shinde

et al. 2018

Journal of Heterocyclic Chem

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A series of novel 4″‐methyl‐2,2″‐diaryl‐4,2′:4′,5″‐terthiazole (8a‐p) derivatives has been synthesized and screened for antibacterial activity against four pathogenic bacteria, Escherichia coli, Pseudomonas flurescence, Staphylococcus aureus, and Bacillus subtilis. Among them, compounds 8a and 8j exhibited excellent antibacterial activity with minimum inhibitory concentration range of 1.0 to 5.3 μg/mL and compounds 8m and 8p exhibited moderate to good antibacterial activity with minimum inhibitory concentration range of 16.9 to 29.7 μg/mL against all tested strains. All the synthesized compounds were screened for their in vitro antifungal activity against Cocinida candida. Most of the compounds reported moderate antifungal activity. This study provides valuable directions to our ongoing endeavor of rationally designing more potent antimicrobial agent.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antimicrobial Screening of 4″‐methyl‐2,2″‐diaryl‐4,2′:4′,5″‐terthiazole Derivatives

Nalawade

Mhaske

Shinde

et al. 2018

Journal of Heterocyclic Chem

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“…Particularly, compound 12e , which had a 4‐fluorobenzyl substitution on the thiazole group, exhibited the most outstanding activity against MTB H37Ra, and the MIC 90 value of 12e (0.64 μg/ml) was lower than that of the control medicine RIF (0.75 μg/ml). The selectivity index (SI) of compound 14e against H37Ra on Hela, A549, and PANC‐1 was 148, 391, and 391, respectively (Abhale et al, ).…”

Section: Five‐membered Ring Compoundsmentioning

confidence: 99%

Opportunities and challenges of using five‐membered ring compounds as promising antitubercular agents

Wang

et al. 2020

Drug Development Research

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Tuberculosis (TB), a chronic infectious disease, is one of the greatest risks to human beings and 10 million people were diagnosed with TB and 1.6 million died from this disease in 2017. In addition, with the emergence of multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB), the TB situation has become even worse, which has aggravated the mortality and spread of this disease.To overcome this problem, research into novel antituberculosis agents with enhanced activities against MDR-TB, reduced toxicity, and shortened duration of therapy is of great importance. Fortunately, many novel potential anti-TB drug candidates with five-membered rings, which are most likely to be effective against sensitive and resistant strains, have recently entered clinical trials. Different five-membered rings such as furans, pyranoses, thiazoles, pyrazolines, imidazoles, oxazolidinone, thiazolidins, isoxazoles, triazoles, oxadiazoles, thiadiazoles, and tetrazoles have been designed, prepared, and evaluated for their antimycobacterial activity against Mycobacterium tuberculosis. In this article, we highlight the recent advances made in the discovery of novel five-membered ring compounds and focus on their antitubercular activities, toxicity, structure-activity relationships, and mechanisms of action. K E Y W O R D Santi-TB drug, antitubercular activities, five-membered ring, MDR-TB, tuberculosis

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“…On the account of structural and chemical diversity, oxazole-based molecules, as a central scaffold, not only enable different types of interactions with various receptors and enzymes, showing broad biological activities, but also occupy a core position in medicinal chemistry, showing their enormous development value and they favored the discovery of newer potential therapeutic agents [1][2][3][4][5]. Consequently, a wide variety of oxazole-containing compounds, as clinical drugs or candidates, have been frequently employed, which play a vital role in the treatment of diverse types of diseases like antibacterial [6][7][8], antifungal [9][10][11], anti-inflammatory [12][13][14], antiviral [15][16][17], anti-tubercular [18][19][20], anticancer [21][22][23], anti-parasitic [24][25][26], antidiabetic [27][28][29], and so on. The marketed drugs containing the oxazole ring system with medicinal value are being actively exploited worldwide.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Synthesis of Oxazole-Based Molecules via van Leusen Oxazole Synthesis

2020

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Oxazole compounds, including one nitrogen atom and one oxygen atom in a five-membered heterocyclic ring, are present in various biological activities. Due to binding with a widespread spectrum of receptors and enzymes easily in biological systems through various non-covalent interactions, oxazole-based molecules are becoming a kind of significant heterocyclic nucleus, which have received attention from researchers globally, leading them to synthesize diverse oxazole derivatives. The van Leusen reaction, based on tosylmethylisocyanides (TosMICs), is one of the most appropriate strategies to prepare oxazole-based medicinal compounds. In this review, we summarize the recent advances of the synthesis of oxazole-containing molecules utilizing the van Leusen oxazole synthesis from 1972, aiming to look for potential oxazole-based medicinal compounds, which are valuable information for drug discovery and synthesis.

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Synthesis and antimycobacterial screening of new thiazolyl-oxazole derivatives

Cited by 47 publications

References 50 publications

Synthesis, Characterization, and Antimicrobial Screening of 4″‐methyl‐2,2″‐diaryl‐4,2′:4′,5″‐terthiazole Derivatives

Synthesis, Characterization, and Antimicrobial Screening of 4″‐methyl‐2,2″‐diaryl‐4,2′:4′,5″‐terthiazole Derivatives

Opportunities and challenges of using five‐membered ring compounds as promising antitubercular agents

Recent Advances in the Synthesis of Oxazole-Based Molecules via van Leusen Oxazole Synthesis

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