Synthesis and cardiotonic activity of 6,7-dimethoxyquinazoline derivatives

Morgalyuk, V. P.; Azimov, V. A.; Бондаренко, В. А.; Denisov, A. V.; Yuzhakov, S. D.; Mashkovskii, M. D.; Yakhontov, L. N.

doi:10.1007/bf00766359

Cited by 2 publications

(5 citation statements)

References 16 publications

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“…Refluxing the obtained ester derivatives IVa-d with hydrazine hydrate afforded the corresponding acid hydrazides Va-d [49,50], as shown in Scheme 1. The reaction of hydrazine hydrate with 2,4-dichloroquinazoline III in ethanol and in the presence of TEA at 0-5 • C afforded the target compound 2-chloro-4-hydrazinyl3,4-dihydroquinazoline VI [51,52]. The appropriate benzohydrazide derivatives Va-d were stirred with 2,4-dichloroquinazoline III in isopropanol at room temperature for 48 h and in the presence of TEA to afford the corresponding final compounds VIIa-d, as illustrated in Scheme 1.…”

Section: Chemistrymentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of New Potential Unusual Modified Anticancer Immunomodulators for Possible Non-Teratogenic Quinazoline-Based Thalidomide Analogs

Mabrouk

Abdallah

Mahdy

et al. 2023

IJMS

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Sixteen new thalidomide analogs were synthesized. The new candidates showed potent in vitro antiproliferative activities against three human cancer cell lines, namely hepatocellular carcinoma (HepG-2), prostate cancer (PC3), and breast cancer (MCF-7). It was found that compounds XII, XIIIa, XIIIb, XIIIc, XIIId, XIVa, XIVb, and XIVc showed IC50 values ranging from 2.03 to 13.39 µg/mL, exhibiting higher activities than thalidomide against all tested cancer cell lines. Compound XIIIa was the most potent candidate, with an IC50 of 2.03 ± 0.11, 2.51 ± 0.2, and 0.82 ± 0.02 µg/mL compared to 11.26 ± 0.54, 14.58 ± 0.57, and 16.87 ± 0.7 µg/mL for thalidomide against HepG-2, PC3, and MCF-7 cells, respectively. Furthermore, compound XIVc reduced the expression of NFκB P65 levels in HepG-2 cells from 278.1 pg/mL to 63.1 pg/mL compared to 110.5 pg/mL for thalidomide. Moreover, compound XIVc induced an eightfold increase in caspase-8 levels with a simultaneous decrease in TNF-α and VEGF levels in HepG-2 cells. Additionally, compound XIVc induced apoptosis and cell cycle arrest. Our results reveal that the new candidates are potential anticancer candidates, particularly XIIIa and XIVc. Consequently, they should be considered for further evaluation for the development of new anticancer drugs.

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Section: Chemistrymentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of New Potential Unusual Modified Anticancer Immunomodulators for Possible Non-Teratogenic Quinazoline-Based Thalidomide Analogs

Mabrouk

Abdallah

Mahdy

et al. 2023

IJMS

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“…Already, on early stages of the studies, chemotherapeutic, anti-inflammatory activity, and hypnotic and hypotensive actions were revealed [5].…”

Section: Introductionmentioning

confidence: 99%

“…Sixty to seventy years ago, more than 300 patents appeared in different countries, denoted synthesis and study of biological activity of this type of compounds. More than 20 medicinal preparations (analgesic, sedative, diuretic, hypotensive, cholegogue, bronchodilator, tranquilizer, chemotherapeutic action) of quinazoline derivatives are introduced in medicinal practice [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

“…2-Methyl-3-(o-tolyl) quinazolinone-4, named methaqualone, is broadly used in medicinal practice [5,8] as sedative and hypnotic. Aside from hypnotic action, methaqualone possesses the anticonvulsant and anti-cough properties and intensifies the action of barbiturates, analgesics, and neuroleptics [7].…”

Section: Introductionmentioning

confidence: 99%

“…Among compounds of this group, the most popular compounds that have been used in practical medicine are 2-methyl-З-(o-methyl-p-chlorphenyl)-5-chlorquinazolone-4 (SL-I64) as tranquilizer and 2-methyl-3-(о-methoxyp-nitrophenyl) quinazolone-4 (nitromethaqualone) as hypnotic [14]. Quinazolinones-4 render also hypothermic and spasmolytic action [5].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Introductory Chapter: The Newest Research in Quinazolinone and Quinazoline Derivatives

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2020

Quinazolinone and Quinazoline Derivatives

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Synthesis and cardiotonic activity of 6,7-dimethoxyquinazoline derivatives

Cited by 2 publications

References 16 publications

Design, Synthesis, and Biological Evaluation of New Potential Unusual Modified Anticancer Immunomodulators for Possible Non-Teratogenic Quinazoline-Based Thalidomide Analogs

Design, Synthesis, and Biological Evaluation of New Potential Unusual Modified Anticancer Immunomodulators for Possible Non-Teratogenic Quinazoline-Based Thalidomide Analogs

Introductory Chapter: The Newest Research in Quinazolinone and Quinazoline Derivatives

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