Synthesis of some new quinazolin-4(3H)-one derivatives and evaluation of their anticonvulsant activity

Boshta, Nader M.; El‐Essawy, Farag A.; Ammar, Ramy M.; Ismail, Abd El‐Hamid; Wahba, Nancy E.

doi:10.1007/s00706-016-1710-1

Cited by 13 publications

(10 citation statements)

References 33 publications

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“…In this context, our main target was dedicated at the design and the synthesis of novel series of N-3 substituted quinazolone derivatives according to the synthetic methods showed in (Scheme 2). The starting material ethyl 2-(4-oxoquinazolin-3(4H)-yl)acetate (8) was synthesized via procedure as described in our earlier report [26]. Hydrazinolysis of (8) at room temperature afforded 2-(4-oxoquinazolin-3(4H)-yl)acetohydrazide (9) followed by the treatment with NaNO2 in the presence of HCl or acetic acid to form 2-(4-oxoquinazolin-3(4H)-yl)acetyl azide (10).…”

Section: Ethyl 5-amino-1-(quinazolin-4-yl)-1h-pyrazole-4-carboxylate mentioning

confidence: 99%

“…On the other hand, Pyrimidine, Triazole and pyrazole scaffolds attracted medicinal chemistry very much due to their biological and chemotherapeutic importance [14][15][16][17][18][19][20][21][22][23]. On this context and our research interest in the area of drug discovery as well as the synthesis of novel heterocyclic systems, [24][25][26][27] we became interested in the design and synthesis a series of novel quinazoline derivatives. Wherein the active pharmacophore triazole, pyrazole, pyrimidine heterocycles and others have been attached (fused/linkage) at the 3-and/or 4-positions of the quinazoline ring with enhanced biological significance ( fig.…”

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confidence: 99%

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Design, Synthesis, and Evaluation of Novel 3-, 4-substituted, and 3,4-di Substituted Quinazoline Derivatives as Antimicrobial Agents

El‐Essawy¹,

Alharthi²,

Alotaibi³

et al. 2020

Rev. Chim.

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A novel series of 3-, 4-substituted, and 3,4-di substituted quinazoline derivatives were prepared via various cyclized regents and most of the newly prepared compounds evaluated for their antimicrobial activities in vitro against Gram-positive, Gram-negative bacterial strains and fungi strains. The structures of the quinazoline derivatives have been confirmed using spectroscopic analyses (IR, NMR, and EI-MS). Some of the synthesized derivatives displayed a moderate antimicrobial activity in comparison with reference drugs, for example compounds 13d, 15a, 17b, 18b, 18d, 25, and 29a-c. Among the synthesized compounds, the pyrimidoqunazoline derivative 6c elicited the highest activity.

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Section: Ethyl 5-amino-1-(quinazolin-4-yl)-1h-pyrazole-4-carboxylate mentioning

confidence: 99%

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confidence: 99%

Design, Synthesis, and Evaluation of Novel 3-, 4-substituted, and 3,4-di Substituted Quinazoline Derivatives as Antimicrobial Agents

El‐Essawy¹,

Alharthi²,

Alotaibi³

et al. 2020

Rev. Chim.

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“…These drugs are effectively reducing the seizures, whereas their therapeutic efficacy is overcome by some unwanted side effects such as drowsiness, megaloblastic anemia, ataxia, gastrointestinal disturbance, etc. [2]. Despite the broad and growing array of antiepileptic drugs available for treatment, approximately 30% of epileptic patients have inadequate seizure control and a further 25% suffer from significant adverse effects.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Anticonvulsant Activity of Some Quinazoline Analogues

Malpani¹,

Mohanty²,

Prasad³

2021

JPRI

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Aim: A new series of Quinazoline 4(3H)-one derivative were prepared by reacting quinazoline 4(3H)-one hydrazide with substituted aromatic aldehydes. Quinazoline is used as a potent pharmacological agent with various biological activities such as antimicrobial, antiviral, antitumor, convulsion, anxiety, anti-inﬂammatory, and analgesic. In this background, we have synthesized a series of Quinazoline 4(3H)-one derivatives (4a-4f) and screened for their anticonvulsant activity. Methods: In this work, Schiff bases were prepared by treating quinazoline 4(3H)-one hydrazide with aromatic aldehydes. Six compounds (4a-4f) were screened for anticonvulsant activity by Isoniazid (INH) and Pentylenetetrazole (PTZ) induced convulsions in mice. Results: All the compounds were given satisfactory reaction yields that representing the efficiency of the employed synthetic route. In INH induced convulsion model, delayed the onset of convulsion significantly 4a, 4b, 4d, 4e, 4f when compared to an induction control group. Whereas delayed onset of convulsion was non-significant for 4c. In PTZ induced convulsion model, delayed the onset of convulsion significantly 4a, 4d, 4e, 4f when compared to induction control group. Whereas delayed onset of convulsion was non-significant for 4b and 4c. Conclusion: This indicates the anticonvulsant activity to these derivatives which might be due to potentiating GABA activity in the CNS. This anticonvulsant activity was due to presence of electron-donating group like OH, NH2, OCH3 and electron-withdrawing group like CF3 at 2nd and 4th position of aromatic ring attached to hydrazide.

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“…It was reported that a series of quinazoline derivatives were designed and synthesized as potential CA inhibitors [ 10 ]. Moreover, a literature survey reveals that the chemistry of quinazolines and their derivatives has received considerable attention owing to their synthetic and effective anticonvulsant importance [ 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ]. Methaqualone and mecloqualone ( I , II ), as quinazoline analogues, approved as anticonvulsant drugs [ 1 ] and the 6-chloro derivative of ( I ) was found to possess remarkable anticonvulsant potency against electroshock-induced convulsions (1.5 times than phenytoin sodium) and against pentylenetetrazol (PTZ)-induced seizures (10 times than troxidone) [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Molecular Docking and Anticonvulsant Activity of Newly Synthesized Quinazoline Derivatives

et al. 2017

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A new series of quinazoline-4(3H)-ones are evaluated for anticonvulsant activity. After intraperitoneal (ip) injection to albino mice at a dose of 100 mg/kg body weight, synthesized quinazolin-4(3H)-ones (1–24) were examined in the maximal electroshock (MES) induced seizures and subcutaneous pentylenetetrazole (scPTZ) induced seizure models in mice. The Rotarod method was applied to determine the neurotoxicity. Most of the compounds displayed anticonvulsant activity in the scPTZ screen at a dose range of 0.204–0.376 mmol/mL. Out of twenty-four, compounds 8, 13 and 19 proved to be the most active with a remarkable protection (100%) against PTZ induced convulsions and four times more potent activity than ethosuximide. The structure-activity relationship concluded valuable pharmacophoric information, which was confirmed by the molecular docking studies using the target enzyme human carbon anhydrase II (HCA II). The studied quinazoline analogues suggested that the butyl substitution at position 3 has a significant effect on preventing the spread of seizure discharge and on raising the seizure threshold. However, benzyl substitution at position 3 has shown a strong anticonvulsant activity but with less seizure prevention compared to the butyl substitution.

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Synthesis of some new quinazolin-4(3H)-one derivatives and evaluation of their anticonvulsant activity

Cited by 13 publications

References 33 publications

Design, Synthesis, and Evaluation of Novel 3-, 4-substituted, and 3,4-di Substituted Quinazoline Derivatives as Antimicrobial Agents

Design, Synthesis, and Evaluation of Novel 3-, 4-substituted, and 3,4-di Substituted Quinazoline Derivatives as Antimicrobial Agents

Synthesis and Evaluation of Anticonvulsant Activity of Some Quinazoline Analogues

Molecular Docking and Anticonvulsant Activity of Newly Synthesized Quinazoline Derivatives

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