Synthesis and biological screening of novel 2-morpholinoquinoline nucleus clubbed with 1,2,4-oxadiazole motifs

Karad, Sharad C.; Purohit, Vishal B.; Thummar, Rahul P.; Vaghasiya, Beena K.; Kamani, Ronak D.; Thakor, Parth; Thakkar, Vasudev R.; Thakkar, Sampark S.; Ray, Avik; Raval, Dipak K.

doi:10.1016/j.ejmech.2016.12.016

Cited by 50 publications

(30 citation statements)

References 38 publications

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“…45 Some recent protocols have been described for the formation of O-acylamidoxime intermediates using coupling reagents. 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).…”

Section: Differences Between 124-and 134-oxadiazolesmentioning

confidence: 99%

“…Next, oxadiazoles (39) were obtained through reflux of the acylated intermediate in ethanol in the presence of sodium acetate for 3 h (Scheme 6). 46 Cao et al 47 used coupling reagent 1-[bis(dimethylamino) methylene]-1H-1,2,3-triazolo [4,5-b]pyridinium-3-oxidhexafluoro-phosphate (HATU) to obtain O-acylamidoxime intermediates. To do so, they first reacted differently substituted cyanamides (40) in the presence of hydroxylamine hydrochloride and diisopropylethylamine (DIPEA).…”

Section: Differences Between 124-and 134-oxadiazolesmentioning

confidence: 99%

“…39 Zhao et al 48 produced nonsymmetrical disulfides bearing a 1,3,4-oxadiazolic ring with antiproliferative activity. To build the 1,3,4-oxadiazole moiety the authors reacted differently substituted benzohydrazides (46) in the presence of carbon disulfide and potassium hydroxide in ethanol, yielding intermediates (47). Then, the oxadiazoles were reacted with the previously prepared S-alkyl-thioisothiourea intermediates (48), furnishing the disulfides (49) (Scheme 9).…”

Section: Synthesis Of 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: Synthesis Of 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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“…6 The literature reports a diverse set of applications for the 1,2,4-oxadiazole core in medicinal chemistry, 7,8 such as antiasthmatic, 9 antidiabetic, 10 antitumoral, 11 anti-inflammatory, 12 antioxidant, 12 and antimicrobial. 13 Different parameters are used to quantify these biological activities, such as half maximal inhibitory concentration (IC 50 ), half maximal effective concentration (EC 50 ) or minimum inhibition concentration (MIC) (Figure 2). In Materials Science, structures containing this heterocycle have technological applications in ionic liquids and liquid crystals, for example.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Evaluation of 3,5-Diaryl-1,2,4-oxadiazole Derivatives

Cunha¹,

Nogueira²,

Aguiar³

2018

J. Braz. Chem. Soc.

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This manuscript reports the synthesis of twenty 3,5-diaryl-1,2,4-oxadiazole derivatives, nine of which are novel compounds. The amidoxime reaction with acyl chlorides obtained from substituted benzoic acids was used. All compounds were tested against five standard (American Type Culture Collection (ATCC)) bacteria: Escherichia coli, Pseudomonas aeruginosa, Enterococcus faecalis, Proteus mirabilis and Staphylococcus aureus. Screening assays were carried out using agardiffusion technique, in which 100 μM heterocyclic compounds solutions (20% dimethylsulfoxide/ water) were employed. The minimum inhibitory concentrations (MIC) of the active compounds were determined by serial dilutions at decreasing concentrations in microtiter plates. The nitrated derivatives gave the best test results, where MIC = 60 μM (E. coli) was the lowest value found for an ortho-nitrated derivative. The activity of these compounds possibly involves a mechanism via free radicals. S. aureus and P. aeruginosa were resistant to all compounds.

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“…[1]. In the QSAR modeling the chloramphenicol, ciprofloxacin, ampicillin and norfloxacin were used as the standard antibacterial therapeutics.…”

mentioning

confidence: 99%

QSAR Analysis of Antibacterial and Antifungal Activity of Novel 2-Morpholinoquinoline Analogs

Kоvаčеvić

Karadžić

Jevrić

et al. 2017

Proceedings of the 1st Molecules Medicinal Chemistry Symposium, Barcelona, Spain

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The present study is focused on the chemometric QSAR analysis of antifungal and antibacterial activity of novel 2-morpholinoquinoline analogs and their molecular structure described by in silico molecular descriptors. The results of antifungal activity have taken into account Aspergillus fumigatus (MTCC 3008) . In the QSAR modeling the chloramphenicol, ciprofloxacin, ampicillin and norfloxacin were used as the standard antibacterial therapeutics. The QSAR modeling has been carried out on the basis of the in silico molecular descriptors (physicochemical, lipophilicity, topological and absorption, distribution, metabolism, excretion and toxicity-ADMET descriptors) applying linear and multiple linear regression methods, as well as a crossvalidation approach. The obtained high-quality models can be considered useful in prediction of the antifungal and antibacterial activity of not yet synthesized structurally similar compounds as well as a contribution to the development of new antimicrobial agents. The studied compounds have been ranked by the sum of ranking differences (SRD) method on the basis of the reference ranking, which was based on the strongest antibacterial and antifungal activities in order to see which compounds express the most potent antimicrobial activity.

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Synthesis and biological screening of novel 2-morpholinoquinoline nucleus clubbed with 1,2,4-oxadiazole motifs

Cited by 50 publications

References 38 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 Antibacterial Evaluation of 3,5-Diaryl-1,2,4-oxadiazole Derivatives

QSAR Analysis of Antibacterial and Antifungal Activity of Novel 2-Morpholinoquinoline Analogs

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