Synthesis of new 1,3,4-oxadiazole and benzothiazolylthioether derivatives of 4-arylmethylidene-3-substituted-isoxazol-5(4H)-one as potential antimycobacterial agents

Chavan, Abhijit P.; Deshpande, Rujuta R.; Borade, Nandkumar A.; Shinde, Abhijit; Mhaske, Pravin C.; Sarkar, Dhiman; Bobade, Vivek D.

doi:10.1007/s00044-019-02420-7

Cited by 13 publications

(4 citation statements)

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“…P. Chavan and co-workers synthesized a new series of 4-(substituted benzylidene)-3-((benzo[ d ]thiazol-2-ylthio)methyl)isoxazol-5(4 H )-one 92a–g by the reaction of mercapto benzothiazole 44 with 4-[(4-methoxyphenyl)-methylidene-]-3-chloro-methyl-5(4 H )-isoxazolone 91a–g , prepared from 90 , in the presence of NaHCO 3 in ethanol in good yields (Scheme 24, Table 19). 62…”

Section: Recent Synthesis Of Benzothiazole Based Anti-tubercular Mole...mentioning

confidence: 99%

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Recent advances in the synthesis of new benzothiazole based anti-tubercular compounds

et al. 2023

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Section: Recent Synthesis Of Benzothiazole Based Anti-tubercular Mole...mentioning

confidence: 99%

“…19). 62 The anti-tubercular activity of synthesized compounds 92a-g was carried out against M. tuberculosis H 37 Ra (ATCC 25177) using XTT reduction menadione assay (XRMA). Among the synthesized derivatives compound 92b was found to be most potent against M. tuberculosis and all compounds from 92a-g were found to be non-cytotoxic (Table 19).…”

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confidence: 99%

Recent advances in the synthesis of new benzothiazole based anti-tubercular compounds

et al. 2023

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“…A series of 4‐{(substituted benzylidene)−3‐[(5‐(pyridine‐4‐yl)−1,3,4‐oxadiazole‐2‐ylthio]‐methyl}isoxazol‐5(4 H )‐ones were reported by Chavan et al [ 92 ] The compound 39 showed excellent antitubercular activity against MTB H 37 Ra and M. bovis BCG with MIC values of 7.46 and 15.01 µg/ml, respectively. Furthermore, compound 39 possessed excellent antibacterial activity against Gram‐negative strains like E. coli (MIC = 2.93 µg/ml) and P. flurescence (MIC = 7.17 µg/ml).…”

Section: Medicinal Attributes Of Oxadiazole Derivativesmentioning

confidence: 99%

Oxadiazole: A highly versatile scaffold in drug discovery

Desai

Monapara

Jethawa

et al. 2022

Archiv der Pharmazie

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As a pharmacologically important heterocycle, oxadiazole paved the way to combat the problem associated with the confluence of many commercially available drugs with different pharmacological profiles. The present review focuses on the potential applications of five-membered heterocyclic oxadiazole derivatives, especially 1,2,4-oxadiazole, 1,2,5-oxadiazole, and 1,3,4-oxadiazole, as therapeutic agents. Designing new hybrid molecules containing the oxadiazole moiety is a better solution for the development of new drug molecules. The designed molecules may accumulate a biological profile better than those of the drugs currently available on the market. The present review will guide the way for researchers in the field of medicinal chemistry to design new biologically active molecules based on the oxadiazole nucleus. Antitubercular, antimalarial, anti-inflammatory, anti-HIV, antibacterial, and anticancer activities of various oxadiazoles have been reviewed extensively here.

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“…7 The isoxazole-5(4H)-one fragment is a significant framework that has gained special attention in organic synthesis from the point of view of their applications as active synthetic intermediates in organic transformations. 8 Isoxazol-5(4H)-ones show myriads of attractive physiological activities such as including anti-obesity, 9 antitumor, 10 anti-HIV-1, 11 anti-inflammatory, 12 antitubercular, 13 anti-androgen, antibacterial, 15 tyrosinase inhibitory, 16 antimycobacterial, 17 analgesic, 18 anti-Alzheimer's disease, antifungal, 20 and antioxidant 21 activities. This class of heterocyclic molecules can also be found in donor−acceptor Stenhouse adducts (DASAs) as new generation of photochromic compounds.…”

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Efficient and Aqoues Synthesis of 3,4-Disubstituted Isoxazol-5(4H)-one Derivatives Using Piperazine under Green Conditions

Kiyani¹,

Daroughezadeh²

2022

HETEROCYCLES

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The one-pot, three-component, as well as expeditious synthesis of 3,4-disubstitted isoxazol-5(4H)-ones has been attained from the heterocyclization of various aryl/heteroaryl aldehydes, active methylene compounds, and hydroxylamine hydrochloride in the presence of piperazine as the efficient, low-cost, commercially available, and eco-friendliness basic organocatalyst. This double secondary amine catalyst was found that catalyzed the synthesis of isoxazol-5(4H)-ones under green conditions. The additional features of the present catalyst include readily available starting materials, relatively low catalyst loading, using water as a green solvent, broad substrate scope, simplicity, good to excellent reaction yields, faster synthesis, and avoiding the hazardous organic solvents.The piperazine is a special secondary heterocyclic diamine containing two nitrogen atoms at 1 and 4 positions, which present in pharmaceutical and biological active compounds. 1 Piperazine ranks as the third most common nitrogen heterocycle in drug discovery, 2 and it is an important pharmaceutical intermediate for the synthesis of anticancer, antituberculosis, antibacterial, antipsychotic, antimalarial, antioxidant, antihistamine, antidepressant, antifungal, and antidiabetic drug candidates. 3 This heterocyclic molecule acts as a transmitter of γ-aminobutyric acid receptor inhibitor, succinic acid formation by parasites inhibitor, 4 and a promoter for CO2 absorption. 5 Piperazine citrate organosalt as a derivative of piperazine is also used in the treatment, control, and prevention of several worm infections as threadworm, roundworm and pinworm in both human and animals. It is also helps in the treatment of chicken naturally infected with gastrointestinal helminths and can be used in the treatment of ascaris lumbricoides infestation and bacterial infections. 6 Literature survey

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Synthesis of new 1,3,4-oxadiazole and benzothiazolylthioether derivatives of 4-arylmethylidene-3-substituted-isoxazol-5(4H)-one as potential antimycobacterial agents

Cited by 13 publications

References 40 publications

Recent advances in the synthesis of new benzothiazole based anti-tubercular compounds

Recent advances in the synthesis of new benzothiazole based anti-tubercular compounds

Oxadiazole: A highly versatile scaffold in drug discovery

Efficient and Aqoues Synthesis of 3,4-Disubstituted Isoxazol-5(4H)-one Derivatives Using Piperazine under Green Conditions

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