The new quinazoline derivative (N-methyl-N-[(thiophen-2-yl)methyl]quinazoline-2,4-diamine) vasodilates isolated mesenteric arteries through endothelium-independent mechanisms and has acute hypotensive effects in Wistar rats

Chatturong, Usana; Chootip, Krongkarn; Martin, Hélène; Tournier-Nappey, Maude; Ingkaninan, Kornkanok; Temkitthawon, Prapapan; Sermsenaphorn, Saharat; Somarin, Thanachon; Konsue, Adchatawut; Gleeson, M. Paul; Totoson, Perle; Demougeot, Céline

doi:10.1016/j.ejphar.2023.175829

Cited by 5 publications

(1 citation statement)

References 36 publications

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“… 3 Also, imide derivatives at 0.5 kg/ha preemergent gave slight (10–30%) control of weeds. 4 On the other hand, quinazoline derivatives cause vasodilation in animals, 5 , 6 and in vivo, testing showed that this in vitro activity translated to animal models predictive of chronic diseases such as depression and inflammation. 7 , 8 As well as, several advanced malignant bacterial forms have emerged because inappropriate antibiotic use in one patient can result in the establishment of a resistant strain that spreads to other people, each with varying levels of resistance to a therapeutic agent.…”

Section: Introductionmentioning

confidence: 99%

Powerful Approach for New Drugs as Antibacterial Agents via Molecular Docking and In Vitro Studies of Some New Cyclic Imides and Quinazoline-2,5-diones

Nasser Binjawhar,

Abu Ali,

Alqahtani

et al. 2024

ACS Omega

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We generated novel elven 1,2,3,6-tetrahydrophthalimides and tetrahydroquinazoline derivatives from 1,2,3,6-tetrahydrophthalic anhydride (1) in response to our interest in using the anhydrides to produce heterocyclic nitrogen compounds. The elemental and spectral analyses of the produced compounds validated the recommended configurations and MOE 2014.09 (Molecular Operating Environment) computations were used to perform their in silico analysis. The synthesized compounds have been analyzed and put through various experiments, including in vitro and in silico methods to assess their biological activity against Escherichia coli Penicillin-Binding Protein 3 (PBP3) and Staphylococcus aureus Penicillin-Binding Protein 2 (PBP2), among these compounds showing promising data as antibacterial drugs.

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Section: Introductionmentioning

confidence: 99%

Powerful Approach for New Drugs as Antibacterial Agents via Molecular Docking and In Vitro Studies of Some New Cyclic Imides and Quinazoline-2,5-diones

Nasser Binjawhar,

Abu Ali,

Alqahtani

et al. 2024

ACS Omega

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Dehydrogenative Coupling for Synthesis of Quinazolin‐4(3H)‐ones via Tandem Reaction using Ruthenium(II)‐Phenyl‐Azo‐Naphthaldoxime: An Experimental and Theoretical Investigation

Halder,

Naskar,

Jana

et al. 2024

Chemistry An Asian Journal

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The bidentate N, N, donor phenyl‐azo‐naphthaldoxime NpLH, 1 was used to synthesize the ruthenium(II) complex trans‐[Ru(NpL)(CO)Cl(PPh3)2], 2. It has been characterized by SCXRD, electrochemical and spectral studies. Computational analysis indicates that the low‐lying p*‐LUMO of the complex has substantial azo‐character of coordinated ligand. This property has been exploited to form an efficient electron transfer pre‐catalyst to effectuate dehydrogenative functionalization of a large number of benzyl alcohols to quinazolin‐4(3H)‐ones via condensation with diverse o‐amino benzamides as well as N‐substituted benzamides under aerobic conditions (57 entries). A reaction mechanism has been projected via isolation of intermediates and certain control experiments. Furthermore, it has been substantiated by theoretical scrutiny using density functional theory (DFT) calculation. The catalytic cycle involves stepwise hydrogen atom transfer (HAT) from benzyl alcohols to the Nazo atoms of the coordinated ligand with subsequent removal of the H‐atoms from the Nazo atoms to regenerate the active catalyst.

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Design, Synthesis, Antibacterial, and Antifungal Evaluation of a New Series of Quinazoline – Thiazole and/or Quinazoline – Triazole Hybrids as Bioactive Heterocycles

El‐Shahat,

Tawfek,

El‐Sofany

2024

Chemistry & Biodiversity

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Herein, a one‐pot reaction between cyclohexanone, thiourea, and 2,5‐dimethoxybenzaldehyde allowed to prepare hexahydroquinazoline‐2(1H)‐thione 4 firstly, which dollowed by reacting with hydrazine hydrate to produce the corresponding 2‐hydrazinylhexahydroquinazoline 6. Interesting analogs of thiazolo[3,2‐a]quinazoline 7‐13 where obtained when hexahydroquinazoline‐2(1H)‐thione 4 reacted with 1,2‐dibromoethane, chloroacetyl chloride, bromoacetic acid, bromoacetic acid/4‐chlorobenzaldehyde, 2‐bromopropionic acid, ethyl bromocyanoacetate, and/or bromomalononitrile; respectively. While triazolo[4,3‐a] quinazoline 14‐16 were created when 2‐hydrazinylhexahydroquinazoline 6 reacted with triethyl orthoformate, acetic anhydride, and carbon disulfide respectively. Additionally, the new analogs were examined for their antibacterial and antifungal properties against Escherichia coli, Staphylococcus aureus, and Candida albicans. It was discovered that triazolo[4,3‐a] quinazoline analogs 14‐16 have superior bacterial and fungal activity when compared to the corresponding conventional doses of Streptomycin and Griseofulvin. Towards Candida albicans; compounds 14, 15, and 16 increase activity with 1.14%, 1.15%, and 1.21%, respectively more than griseofulvin.While, for Staphylococcus aureus; compounds 14, 15, and 16 increase activity with 1.5%, 1.5%, and 1.7%, respectively more than streptomycin. Morever, for Escherichia coli; compounds 14, 15, and 16 increase activity with 1.19%, 1.21%, and 1.22%, respectively more than streptomycin. Finally, structure activity relationships show that quinazoline derivatives exhibit higher activity when fused to pyrazole ring 14–16 as compared when fused thiophene ring 7–13.

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The new quinazoline derivative (N-methyl-N-[(thiophen-2-yl)methyl]quinazoline-2,4-diamine) vasodilates isolated mesenteric arteries through endothelium-independent mechanisms and has acute hypotensive effects in Wistar rats

Cited by 5 publications

References 36 publications

Powerful Approach for New Drugs as Antibacterial Agents via Molecular Docking and In Vitro Studies of Some New Cyclic Imides and Quinazoline-2,5-diones

Powerful Approach for New Drugs as Antibacterial Agents via Molecular Docking and In Vitro Studies of Some New Cyclic Imides and Quinazoline-2,5-diones

Dehydrogenative Coupling for Synthesis of Quinazolin‐4(3H)‐ones via Tandem Reaction using Ruthenium(II)‐Phenyl‐Azo‐Naphthaldoxime: An Experimental and Theoretical Investigation

Design, Synthesis, Antibacterial, and Antifungal Evaluation of a New Series of Quinazoline – Thiazole and/or Quinazoline – Triazole Hybrids as Bioactive Heterocycles

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