Synthesis and antitubercular activity of new 1,3,4-oxadiazoles bearing pyridyl and thiazolyl scaffolds

Dhumal, Sambhaji T.; Deshmukh, A. R. A. S.; Bhosle, Manisha R.; Khedkar, Vijay M.; Nawale, Laxman; Sarkar, Dhiman; Mane, Ramrao A.

doi:10.1016/j.bmcl.2016.05.093

Cited by 67 publications

(41 citation statements)

References 49 publications

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“…Being so, it has typical interactions of aromatic systems, such as π-π stacking with hydrophobic amino acids such as tyrosine, phenylalanine and tryptophan. Dhumal et al 37 synthesized a series of 1,3,4-oxadiazoles aiming to inhibit the mycobacterial enoyl reductase (InhA) of Mycobacterium tuberculosis. Docking studies carried out by Dhumal et al 37 on InhA showed that the oxadiazole core of 16 interacts with Phe149 and Tyr158 through a π-π stacking, as shown in Figure 9.…”

Section: Differences Between 124-and 134-oxadiazolesmentioning

confidence: 99%

“…Dhumal et al 37 synthesized a series of 1,3,4-oxadiazoles aiming to inhibit the mycobacterial enoyl reductase (InhA) of Mycobacterium tuberculosis. Docking studies carried out by Dhumal et al 37 on InhA showed that the oxadiazole core of 16 interacts with Phe149 and Tyr158 through a π-π stacking, as shown in Figure 9. This kind of interaction also happens in other 1,3,4-oxadiazoles designed by the authors, 37 with relevant changes only at the level of the other structure decorations present, like a pyridine ring.…”

Section: Differences Between 124-and 134-oxadiazolesmentioning

confidence: 99%

“…In a recently published work, Karad et al 46 described the synthesis of 1,2,4-oxadiazoles as antimicrobial and antifungal agents. The properly substituted amidoximes (36) were obtained from the respective 2-morpholinoquinoline-3-carbonitriles (37). O-Acylation and cyclization steps were conducted in a one-pot reaction with the benzoic acids (38) in the presence of coupling reagent ethyl-(N',N'-dimethylamino)-propyl-carbodiimide hydrochloride (EDC.HCl).…”

Section: Differences Between 124-and 134-oxadiazolesmentioning

confidence: 99%

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1,2,4- and 1,3,4-Oxadiazoles as Scaffolds in the Development of Antiparasitic Agents

Pitasse-Santos¹,

Sueth-Santiago²,

Lima³

2017

J. Braz. Chem. Soc.

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In this review, we present the potential use of the heterocyclic oxadiazole rings in the design and synthesis of new drugs to treat parasitic infections. We intend to compare herein all the four isomeric forms of oxadiazole rings as well as discuss the differences and similarities between them. In addition, we discuss aspects on their reactivity that justify the great importance of both 1,2,4-and 1,3,4-oxadiazoles isomers when compared with their other two isomers. Although some oxadiazole isomers satisfy Hückel's rule, there are differences concerning their aromaticity, which have a great impact on the possible interactions of the oxadiazole ring with biological receptors. The set of works selected from the literature and discussed herein points out the oxadiazole core as an important and versatile scaffold in the development of new chemical entities potentially useful as antiparasitic drugs.

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Section: Differences Between 124-and 134-oxadiazolesmentioning

confidence: 99%

Section: Differences Between 124-and 134-oxadiazolesmentioning

confidence: 99%

Section: Differences Between 124-and 134-oxadiazolesmentioning

confidence: 99%

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1,2,4- and 1,3,4-Oxadiazoles as Scaffolds in the Development of Antiparasitic Agents

Pitasse-Santos¹,

Sueth-Santiago²,

Lima³

2017

J. Braz. Chem. Soc.

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“…Examples of com-pounds containing the 1, 3, 4-oxadiazole unit which are currently used in clinical medicine are: Raltegravir an antiretroviral drug and Zibotentan an anticancer agent, Vadrin a leprostatic drug and eudromil a hypnotic drug are a few examples. 1, 3, 4-oxadiazole derivatives have displayed a broad spectrum of biological activities such as antimicrobial 3 , antioxidant 4 , anticancer 5 , anticonvulsant 6 , antitubercular 7 , antiviral 8 , antimalarial 9 and analgesic and anti-inflammatory. 10 In addition to the various biological activities the 1, 3, 4-oxadiazoles are also found to possess potential agrochemical use 11 due to their wide spectrum of insecticidal 12 and acaricidal.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of 2-phenyl-5- (1-phenyl-3-(3, 4, 5-trimethoxyphenyl)-1H-pyrazol- 4-yl) - 1, 3, 4-oxadiazole Scaffolds for Assessing Their Medicinal Potentials

Chennapragada¹,

Palagummi²

2018

IJPER

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Objective: The present research is aimed at the discovery and development of 1-phenyl-3-(3,4,5-trimethoxyphenyl)-1H-pyrazole derivatives as a series of novel 1, 3, 4-oxadiazoles (7a-7h) through iodine-catalyzed oxidative cyclization of the hydrazone derivatives (6a-6h) in the presence of potassium carbonate as base and DMSO as solvent in good toexcellent yields. Methods: The structures of all the newly synthesized compounds (6a-6h) and(7a-7h) were well characterized by IR, 1H NMR, 13C NMR and HRMS. Furthermore, allthe synthesized compounds (6a-6h and 7a-7h) were evaluated for their antimicrobial andanti-oxidant activities. Results: The research results revealed that the compound 6d (Z)-2-bromo-N'-((1-phenyl-3-(3, 4, 5-trimethoxyphenyl)-1H-pyrazol-4-yl) methylene) benzohydrazide) has antimicrobial potent while the synthesized compounds 6a (

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“…[1][2][3][4] Thiazoles are present in a wide range of pharmacologically active compounds exhibiting antibacterial, [5][6][7][8] antimycobacterial, [9][10][11] antifungal, [5][6][7][8] anticancer [12][13][14] and antiviral 15,16 activity. Furthermore, thiazole derivatives are useful as chemosensors 17 and fluorescent sensors.…”

Section: Introductionmentioning

confidence: 99%

Green synthesis of highly functionalized octahydropyrrolo[3,4-c]pyrrole derivatives using subcritical water, and their anti(myco)bacterial and antifungal activity

Nural¹,

Gemili²,

Yabalak³

et al. 2018

Arkivoc

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A series of novel 2-(thiazol-2-yl)-octahydropyrrolo [3,4-c]pyrroles was synthesized by reaction of octahydropyrrolo [3,4-c]pyrrole N-benzoylthiourea derivatives and α-haloketones in subcritical water at 130 °C in 75-91% yield. Both the thiourea intermediates and the end products were synthesized in subcritical water, which proved a suitable green alternative to acetone by delivering the desired compounds in much shorter reaction times and practically the same yields. The antimicrobial activity of the compounds was determined against five bacterial strains and three fungal strains, and MIC values of 15.62-250 g/mL were observed. Moreover, the compounds exhibited antimycobacterial activity against M. tuberculosis H37Rv with MIC values of 7.81-62.5 µg/mL.

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Synthesis and antitubercular activity of new 1,3,4-oxadiazoles bearing pyridyl and thiazolyl scaffolds

Cited by 67 publications

References 49 publications

1,2,4- and 1,3,4-Oxadiazoles as Scaffolds in the Development of Antiparasitic Agents

1,2,4- and 1,3,4-Oxadiazoles as Scaffolds in the Development of Antiparasitic Agents

Synthesis and Characterization of 2-phenyl-5- (1-phenyl-3-(3, 4, 5-trimethoxyphenyl)-1H-pyrazol- 4-yl) - 1, 3, 4-oxadiazole Scaffolds for Assessing Their Medicinal Potentials

Green synthesis of highly functionalized octahydropyrrolo[3,4-c]pyrrole derivatives using subcritical water, and their anti(myco)bacterial and antifungal activity

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