Syntheses and anti-allergic activity of 2-((bis(trimethylsilyl)methylthio/methylsulfonyl)methyl)-5-aryl-1,3,4-oxadiazoles

Reddy, Guda Dinneswara; Park, Sae-Jin; Lee, Minwoo; Kim, Tack-Joong; Lee, Myong Euy

doi:10.1016/j.ejmech.2012.12.035

Cited by 48 publications

(10 citation statements)

References 22 publications

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“…These clinical success in parallel gave an impetus to the synthetic chemists to design innovative strategies for the economic, ecofriendly and rapid synthesis of 1,2,4-oxadiazole chemical libraries to accelerate the drug discovery process 32 , 33 . In the past 40 years, 1,2,4-oxadiazole scaffold has been extensively investigated for diverse biological activities 34 including anti-inflammatory 35 , 36 , analgesic 37 , anaesthetic 38 , anthelmintic 39 , antiallergic 40 , anti-Alzheimer 41 , antibacterial 42 , 43 , anticancer 44–46 , anticonvulsant 47 , 48 , antidepressant 49 , antifungal 50 , anti-HIV 51 , antiparasitic 52 , antiplatelet and antithrombotic 53 , anti-tubercular 54 , antitussive 55 , antiviral 56 , 57 , insecticidal 58 , monoamine oxidase inhibition 59 , muscarinic receptor agonists 60 , selective G-protein bile acid receptor 1 (GPBAR1) agonists 61 and selective H 3 receptor antagonists 62 activities.…”

Section: Introductionmentioning

confidence: 99%

In vitro anti-TB properties, in silico target validation, molecular docking and dynamics studies of substituted 1,2,4-oxadiazole analogues against Mycobacterium tuberculosis

Deb

Al-Shar’i

Venugopala

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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The alarming increase in multi- and extensively drug-resistant (MDR and XDR) strains of Mycobacterium tuberculosis (MTB) has triggered the scientific community to search for novel, effective, and safer therapeutics. To this end, a series of 3,5-disubstituted-1,2,4-oxadiazole derivatives ( 3a–3i ) were tested against H37Rv, MDR and XDR strains of MTB. Of which, compound 3a with para-trifluorophenyl substituted oxadiazole showed excellent activity against the susceptible H37Rv and MDR-MTB strain with a MIC values of 8 and 16 µg/ml, respectively. To understand the mechanism of action of these compounds ( 3a–3i ) and identify their putative drug target, molecular docking and dynamics studies were employed against a panel of 20 mycobacterial enzymes reported to be essential for mycobacterial growth and survival. These computational studies revealed polyketide synthase (Pks13) enzyme as the putative target. Moreover, in silico ADMET predictions showed satisfactory properties for these compounds, collectively, making them, particularly compound 3a , promising leads worthy of further optimisation.

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Section: Introductionmentioning

confidence: 99%

In vitro anti-TB properties, in silico target validation, molecular docking and dynamics studies of substituted 1,2,4-oxadiazole analogues against Mycobacterium tuberculosis

Deb

Al-Shar’i

Venugopala

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Compounds bearing sulfonyl moiety with bis(trimethylsilyl)-1,3,4-oxadiazoles (45) showed better antiallergic activities (Fig. 8) [45].…”

Section: Miscellaneous Activitiesmentioning

confidence: 99%

1, 3, 4-Oxadiazole: A Versatile Therapeutic Heterocycle

Sharma¹

2014

abp

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1, 3, 4-oxadiazole emerged as an important heterocyclic nucleus for new drug development. These compounds have importance as biological targets. This article describes the various methods of synthesis and different bioactivity profiles of 1,3,4-oxadiazole ring system which have been reported within last five years and is helpful in the invention of newer compounds with antimicrobial, antimycobacterial, anti-tumor, antitubercular, anticonvulsant activities and so forth.

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“…On the other hand, compounds that contained oxadiazole ring in their structures also display many biological properties including anticancer [20], cytotoxic and antimicrobial [21], anticonvulsant [22], antiepileptic [23], anti-TB [24], and anti-allergic activities [25]. Both structural moieties are potent and their combination has been reported to have enhanced biological activity [26,27].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking and β-Glucuronidase Inhibitory Potential of Indole Base Oxadiazole Derivatives

et al. 2019

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β-glucuronidase is a lysosomal glycosidase enzyme which catalyzes the extracellular matrix of cancer and normal cells and the glycosaminoglycans of the cell membrane, which is important for cancer cell proliferation, invasion, and metastasis. Liver cancer, colon carcinoma, and neoplasm bladder are triggered by the increase of the level of β-glucuronidase activity. The most valuable structures are indole and oxadiazole which has gain immense attention because of its pharmacological behavior and display many biological properties. Twenty-two (1–22) analogs of indole based oxadiazole were synthesized and screened for their inhibitory potential against β-glucuronidase. Majority of the compounds showed potent inhibitory potential with IC50 values ranging between 0.9 ± 0.01 to 46.4 ± 0.9 µM, under positive control of standard drug d-saccharic acid 1,4 lactone (IC50 = 48.1 ± 1.2 µM). Structural activity relationship (SAR) has been established for all synthesized compounds. To shed light on molecular interactions between the synthesized compounds and β-glucuronidase, 1, 4, and 6 compounds were docked into the active binding site of β-glucuronidase. The obtained results showed that this binding is thermodynamically favorable and β-glucuronidase inhibition of the selected compounds increases with the number of hydrogen bonding established in selected compound-β-glucuronidase complexes.

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Syntheses and anti-allergic activity of 2-((bis(trimethylsilyl)methylthio/methylsulfonyl)methyl)-5-aryl-1,3,4-oxadiazoles

Cited by 48 publications

References 22 publications

In vitro anti-TB properties, in silico target validation, molecular docking and dynamics studies of substituted 1,2,4-oxadiazole analogues against Mycobacterium tuberculosis

In vitro anti-TB properties, in silico target validation, molecular docking and dynamics studies of substituted 1,2,4-oxadiazole analogues against Mycobacterium tuberculosis

1, 3, 4-Oxadiazole: A Versatile Therapeutic Heterocycle

Synthesis, Molecular Docking and β-Glucuronidase Inhibitory Potential of Indole Base Oxadiazole Derivatives

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