3H-Quinazolin-4-ones as a new calcilytic template for the potential treatment of osteoporosis

Shcherbakova, I. M.; Balandrin, Manuel F.; Fox, John; Ghatak, Anjan; Heaton, William L.; Conklin, Rebecca L.

doi:10.1016/j.bmcl.2005.01.078

Cited by 49 publications

(15 citation statements)

References 13 publications

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“…2). Similarly to in vivo effect of the quinazolinone calcilytics, 14 there were no changes in plasma Ca 2+ levels, probably because PTH levels were elevated for such a short time and/or because the study was only of 30 min duration.…”

mentioning

confidence: 58%

“…Also, in the pyrimidinone series 2, fluoro substitution in the 3-phenethyl fragment did not influence potency to the same extent as in the quinazolinone series 1. 12,14 Overall, the pyrimidinone compounds 2d-o demonstrated a noticeable potency improvement in comparison with the parent series, quinazolinone compounds 1 14 (Fig. 1).…”

mentioning

confidence: 89%

“…[12][13][14] Initial SAR of the quinazolinone series 1 rapidly revealed the key binding elements required to achieve a high level of potency and selectivity at CaR, and the 2-(2-hydroxy-phenyl) and 3-phenethyl substituents as essential for calcilytic activity. 12,14 Based on the SAR studies for compounds 1, design of the 3H-pyrimidin-4-one template 2 ( Fig. 1 15 PPAR agonists 16 and the atypical antipsychotic drug risperidone.…”

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confidence: 99%

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Design, new synthesis, and calcilytic activity of substituted 3H-pyrimidin-4-ones

Shcherbakova

Huang

Geoffroy

et al. 2005

Bioorganic & Medicinal Chemistry Letters

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confidence: 58%

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confidence: 89%

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confidence: 99%

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Design, new synthesis, and calcilytic activity of substituted 3H-pyrimidin-4-ones

Shcherbakova

Huang

Geoffroy

et al. 2005

Bioorganic & Medicinal Chemistry Letters

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“…Quinazolinones are heterocyclic compounds which have various biological effects including anticancer, sedative, anticompulsive, anti-inflammation, antibacterial, antifungal, anti-tuberculosis, antimalarial, antiviral, and anti HIV activities (34). Febrifugine (5), evodiamine (6), luotonin A (7), prazosin (8), methaqualone (9), and diproqualone (10) are some examples of quinazolinone-based drug which have good therapeutic effects. Gefitinib and erlotinib are the most important anticancer drugs in this category (11).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and cytotoxic evaluation of novel quinozalinone derivatives with substituted benzimidazole in position 3

et al. 2019

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Quinazolinone and benzimidazole are both fused heterocyclic compounds which have shown valuable biological properties including cytotoxic, antibacterial, and antifungal activities. In this study, a series of novel quinazolinone derivatives substituted with benzimidazole were synthesized in two parts. In the first part 2 - phenyl - 1 H - benzimidazol - 6 - amine ( 4 ) was synthesized from the reaction of 4-nitro-o-phenylenediamine and benzoic acid. In the second part, new 3-(2-phenyl-1 H benzoimidazol-5-yl)- 3H-quinazolin-4-one derivatives ( 8a-8f ) were also prepared. Finally compound 4 was reacted with the different benzoxazinone derivatives ( 8a-8f ) to give the target compounds. The structures of the synthesized compounds were confirmed by IR and 1 HNMR. Cytotoxic activities of the final compounds were assessed at 100, 200, 300, 400, and 500 μM against MCF-7 and HeLa cell lines using the MTT colorimetric assay. Almost all compounds exhibited good cytotoxic activity against both cell lines. Compound 9d demonstrated the highest cytotoxic activity against MCF7 and Hela cell lines with IC 50 70 μM and 50 μM, respectively.

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“…Some drugs have been synthesized with quinazoline structure such as chloroqualone (antitussive), diproqualone (analgesic) ( 17 ), gefitinib, lapatinib (anticancer) ( 1 ), piriqualone (anticonvulsant) ( 18 ), doxazocin (antihypertensive) ( 19 ), prazosin (antihypertensive) ( 20 ), trimetrexate (antibacterial), thymitaq (anticancer) ( 21 ) and raltitrexed (anticancer) ( 22 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and cytotoxic evaluation of some new 3-(2-(2-phenylthiazol-4-yl) ethyl)-quinazolin-4(3H) one derivatives with potential anticancer effects

et al. 2017

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Quinazolinones are a group of heterocyclic compounds that have important biological activities such as cytotoxicity, anti-bacterial, and anti-fungal effects. Thiazole-containing compounds have also many biological effects including antitumor, antibacterial, anti-inflammatory, and analgesic activities. Due to significant cytotoxic effects of both quinazoline and thiazole derivatives, in this work a group of quinazolinone-thiazol hybrids were prepared and their cytotoxic effects on three cell lines were evaluated using MTT assay. Compounds A3, A2, B4, and A1 showed highest cytotoxic activities against PC3 cell line. Compounds A3, A5, and A2 were most active against MCF-7 and A3, A5, and A6 showed good cytotoxic effect on HT-29 cell line. According to the results, A3 efficiently inhibited all cell growth tested in a dose dependent manner. The IC50 of A3 was 10 M, 10 μM, and 12 μM on PC3, MCF-7, and HT-29 cells, respectively.

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3H-Quinazolin-4-ones as a new calcilytic template for the potential treatment of osteoporosis

Cited by 49 publications

References 13 publications

Design, new synthesis, and calcilytic activity of substituted 3H-pyrimidin-4-ones

Design, new synthesis, and calcilytic activity of substituted 3H-pyrimidin-4-ones

Synthesis and cytotoxic evaluation of novel quinozalinone derivatives with substituted benzimidazole in position 3

Synthesis and cytotoxic evaluation of some new 3-(2-(2-phenylthiazol-4-yl) ethyl)-quinazolin-4(3H) one derivatives with potential anticancer effects

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