Effect of aminophylline, butalamine and imolamine on human isolated smooth muscle

Coupar, Ian M.; Hedges, A.; Metcalfe, H; Turner, Paul

doi:10.1111/j.2042-7158.1969.tb08294.x

Cited by 21 publications

(15 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Although this scaffold remained poorly characterised until the early 1960s, their strong tendency of photochemical reactivity and rearrangements have later intensified the interest towards this heterocyclic compound 27,28 . However, 1,2,4-oxadiazole have also impacted the medicinal chemistry research after the launch of first-in-class marketed drug, oxolamine as a cough suppressant, and the subsequent discovery of commercial products like prenoxdiazine, fasiplon, pleconaril, proxazole, atalureri and butalamine [29][30][31] . 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 .…”

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

View full text Add to dashboard Cite

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.

show abstract

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

View full text Add to dashboard Cite

show abstract

“…1. Libexin and oxolamine are used as antitussive (cough) agents [14], butalamine is a coronary vasodilator and local anesthetic [15], and ataluren finds application for the treatment of fibrosis [16]. Often, oxadiazole derivatives act as inhibitors of bacterial phenylalanyl-tRNA-synthetase [17], phosphodiesterase 4B2 [18], y-secretase [19] and phenol-substituted 1,2,4-oxadiazoles exhibit powerful anti-oxidant properties [20].…”

Section: Introductionmentioning

confidence: 99%

Metal-free hydroarylation of the side chain carbon–carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid

Zalivatskaya

Ryabukhin

Tarasenko

et al. 2017

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

The metal-free reaction of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles with arenes in neat triflic acid (TfOH, CF3SO3H), both under thermal and microwave conditions, leads to 5-(2,2-diarylethyl)-3-aryl-1,2,4-oxadiazoles. The products are formed through the regioselective hydroarylation of the side chain carbon–carbon double bond of the starting oxadiazoles in yields up to 97%. According to NMR data and DFT calculations, N4,C-diprotonated forms of oxadiazoles are the electrophilic intermediates in this reaction.

show abstract

“…It is a particularly useful alternative when the instability of those groups is observed (e.g., when the hydrolysis may appear) [20,21]. Nowadays, there are a few commercially available drugs containing 1,2,4-oxadiazole nucleus such as Oxolamine, Prenoxdiazine (cough suppressant, Figure 3) Butalamine (vasodilator, Figure 3), Fasiplon (nonbenzodiazepine anxiolytic drug, Figure 3), Pleconaril (antiviral drug, Figure 3), Ataluren (Duchenne muscular dystrophy treatment drug, Figure 3) and Proxazole (a drug used for functional gastrointestinal disorders, Figure 3) [22][23][24]. It is worth noting that 1,2,4-oxadiazole ring, as the only one of all oxadiazole isomers, occurs in the structures of natural products.…”

Section: Historical Remarks-124-oxadiazolementioning

confidence: 99%

Novel 1,2,4-Oxadiazole Derivatives in Drug Discovery

et al. 2020

View full text Add to dashboard Cite

Five-membered 1,2,4-oxadiazole heterocyclic ring has received considerable attention because of its unique bioisosteric properties and an unusually wide spectrum of biological activities. Thus, it is a perfect framework for the novel drug development. After a century since the 1,2,4-oxadiazole have been discovered, the uncommon potential attracted medicinal chemists’ attention, leading to the discovery of a few presently accessible drugs containing 1,2,4-oxadiazole unit. It is worth noting that the interest in a 1,2,4-oxadiazoles’ biological application has been doubled in the last fifteen years. Herein, after a concise historical introduction, we present a comprehensive overview of the recent achievements in the synthesis of 1,2,4-oxadiazole-based compounds and the major advances in their biological applications in the period of the last five years as well as brief remarks on prospects for further development.

show abstract

Effect of aminophylline, butalamine and imolamine on human isolated smooth muscle

Cited by 21 publications

References 0 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

Metal-free hydroarylation of the side chain carbon–carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid

Novel 1,2,4-Oxadiazole Derivatives in Drug Discovery

Contact Info

Product

Resources

About