2-Amino-6-chloro-3,4-dihydroquinazoline: A novel 5-HT3 receptor antagonist with antidepressant character

Dukat, Małgorzata; Alix, Katie; Worsham, Jessica; Khatri, Shailesh; Schulte, Marvin K.

doi:10.1016/j.bmcl.2013.08.072

Cited by 37 publications

(26 citation statements)

References 20 publications

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“…Rodent experiments show that the antidepressant-like effect should be attributed to postsynaptic, rather than presynaptic, 5-HT 3 antagonism, since the presynaptic and somatodendritic 5-HT 3 receptor blockade reduces serotonin levels [203]. The antidepressant and/or anxiolytic effects recently demonstrated by some 5-HT 3 receptor antagonists in animal models of depression may result from the modulation of the hypothalamic-pituitary-adrenal axis, interaction with the serotonergic system, or antioxidant properties [213][214][215][216][217][218].…”

Section: The 5-ht3 Receptorsmentioning

confidence: 99%

5-HT Receptors and the Development of New Antidepressants

Ślifirski

Król

Turło

2021

IJMS

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Serotonin modulates several physiological and cognitive pathways throughout the human body that affect emotions, memory, sleep, and thermal regulation. The complex nature of the serotonergic system and interactions with other neurochemical systems indicate that the development of depression may be mediated by various pathomechanisms, the common denominator of which is undoubtedly the disturbed transmission in central 5-HT synapses. Therefore, the deliberate pharmacological modulation of serotonergic transmission in the brain seems to be one of the most appropriate strategies for the search for new antidepressants. As discussed in this review, the serotonergic system offers great potential for the development of new antidepressant therapies based on the combination of SERT inhibition with different pharmacological activity towards the 5-HT system. The aim of this article is to summarize the search for new antidepressants in recent years, focusing primarily on the possibility of benefiting from interactions with various 5-HT receptors in the pharmacotherapy of depression.

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Section: The 5-ht3 Receptorsmentioning

confidence: 99%

5-HT Receptors and the Development of New Antidepressants

Ślifirski

Król

Turło

2021

IJMS

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“…2,3-dihydroquinazolin-4(1H)-one is one of the derivatives of quinazoline that possesses broad range of biological, medicinal and pharmacological activities such as anti-tumor, antibiotic, anti-tubercular, anti-defibrillatory, anti-pyretic, analgesic, anti-hypertonic, diuretic, anti-histamine, anti-depressant, vasodilating agents and many more [13][14][15][16][17][18][19][20][21][22]. Since 2,3dihydroquinazolin-4(1H)-one acquire different biological applications, in the present work, we made an attempt to synthesize some novel 2,3-dihydroquinazolin-4(1H)-ones with an aim to get probable novel anti-TB agent(s).…”

Section: Introductionmentioning

confidence: 99%

Anti-TB evaluation of novel 2,3-dihydroquinazolin-4(1H)-ones and in silico studies of the active compounds

et al. 2021

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In vitro anti-tubercular activity of a series of 15 novel 2,3-dihydroquinazolin-4(1H)-one analogues were evaluated against Mycobacterium tuberculosis H37Ra (ATCC 25177 strain). Among the series, seven compounds showed moderate to good anti-TB activity with minimum inhibitory concentration (MIC) values ranging from 25.0-12.5 μg/mL. Further, in silico experiments were carried out to identify the probable ligand-protein interaction. Molecular docking of the target compounds into the active site of enzymes 1DQY Antigen 85C from Mycobacterium Tuberculosis and 2NSD Enoyl Acyl Carrier Protein Reductase reveals notable information on the possible binding interactions.

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“…A majority of substituted quinazoline derivatives are known for their broad-spectrum biological activities including anticancer (tyrosine kinase inhibitors), antiviral, anti-inflammatory, antiprotozoan, antifungal, antibacterial, diuretics, antimalarial, antidepressant, muscle relaxants, antitubercular, anticonvulsant and many more. [1][2][3][4][5][6][7][8][9][10][11][12] Among the 4-substituted quinazolines, 4-amino and 4-phenoxy derivatives have been known to constitute an active class of drugs [13] and other materials, [14] while on the other hand, the 4-carbonyl derivatives of quinazoline such as quinazolin-4-carboxamides have not explored well so far despite exhibiting variety of biological properties such as potent inhibitor of AAKl, acetyl CoA carboxylase inhibitor, anti-disorders, adenosine receptors, anti-neurodegenerative, and anticancer have been described (Figure 1). [15][16][17][18][19][20] In the past few decades, the catalytic one-pot multicomponent reactions has become a powerful tool for the synthesis of N-containing biologically active heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Catalyst‐Free One‐Pot Multi‐Component Synthesis of 2‐Substituted Quinazolin‐4‐carboxamides from 2‐Aminophenyl‐2‐oxoacetamides, Aldehydes, and Ammonium Acetate

et al. 2021

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Herein, we report a simple and straightforward catalyst-free one-pot multi-component synthesis of quinazolin-4-carboxamides using 2-(2-aminophenyl)-N,N-dialkyl-2-oxoacetamide, aldehydes and ammonium acetate. As compared to the conventional approached for quinazolin-4-carboxamides synthesis, this transformation demonstrates very good reactivity by tolerating a large number of functional groups, and proceeds with good to moderate yields under mild conditions. Notably, the synthesized 6-bromoquinazolin-4-carboxamide was subjected to Suzuki-Miyaura cross-coupling and Buchwald-Hartwig CÀ N bond forming reactions providing a straightforward method to obtain structurally diverse and valuable quinazoline scaffolds. Furthermore, the reaction could be easily scaled up to gram scale.

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2-Amino-6-chloro-3,4-dihydroquinazoline: A novel 5-HT3 receptor antagonist with antidepressant character

Cited by 37 publications

References 20 publications

5-HT Receptors and the Development of New Antidepressants

5-HT Receptors and the Development of New Antidepressants

Anti-TB evaluation of novel 2,3-dihydroquinazolin-4(1H)-ones and in silico studies of the active compounds

Catalyst‐Free One‐Pot Multi‐Component Synthesis of 2‐Substituted Quinazolin‐4‐carboxamides from 2‐Aminophenyl‐2‐oxoacetamides, Aldehydes, and Ammonium Acetate

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