Synthesis, biological evaluation and docking studies of 4-amino-tetrahydroquinazolino[3,2-e]purine derivatives

Verones, Valérie; Flouquet, Nathalie; Farce, Amaury; Carato, Pascal; Léonce, Stéphane; Pfeiffer, Bruno; Berthelot, Pascal; Lebegue, Nicolas

doi:10.1016/j.ejmech.2010.09.022

Cited by 7 publications

(4 citation statements)

References 37 publications

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“…On treatment with methanolic ammonia at 80 °C, 555 is converted into 556. This molecule treated with sodium nitrite affords 557, [420] which treated once again with methanolic ammonia at 150 °C gives 558. [418] Deprotection of this molecule yields 4'-selenoguanosine 553 as shown in Scheme 108.…”

Section: Selenium-containing Nucleosidesmentioning

confidence: 99%

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Sonego,

de Diego,

Szajnman

et al. 2023

Chemistry A European J

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Selenium, originally described as a toxin, turns out to be a crucial trace element for life that appears as selenocysteine and its dimer, selenocystine. From the point of view of drug developments, selenium‐containing drugs are isosteres of sulfur and oxygen with the advantage that the presence of the selenium atom confers antioxidant properties and high lipophilicity, which would increase cell membrane permeation leading to better oral bioavailability. In this article, we have focused on the relevant features of the selenium atom, above all, the corresponding synthetic approaches to access a variety of organoselenium molecules along with the proposed reaction mechanisms. The preparation and biological properties of selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, and other selenium‐containing compounds will be treated. We have attempted to condense the most important aspects and interesting examples of the chemistry of selenium into a single article.

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Section: Selenium-containing Nucleosidesmentioning

confidence: 99%

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Sonego,

de Diego,

Szajnman

et al. 2023

Chemistry A European J

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“…Compounds 9a-g were hydrolysed in aqueous HCl to afford the intermediates 11ag, which were then brominated to afford the 8-bromopurine intermediates 12a-g (Michael et al 1993). Finally, the brominated purines were transformed to the desired 8oxopurines 13a-g through hydrolysis of the bromo group, in low to good yields (6-85%) (Verones et al 2010).…”

Section: Design Of Novel Analogues and Synthetic Chemistrymentioning

confidence: 99%

The discovery of purine-based agents targeting triple-negative breast cancer and the αB-crystallin/VEGF protein–protein interaction

et al. 2018

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Oestrogen receptor-negative breast cancer, particularly subtypes such as triple-negative breast cancer (TNBC, around 10-15% of cases), are characterised by poor long-term survival, poor response to therapy and early progression to metastasis. Purine-based compounds represent a privileged scaffold in anticancer drug design, with several clinically approved and experimental agents in clinical development comprising a purine core structure. In this study, a series of new purine-based compounds were synthesised; seven of the new analogues were found to significantly reduce the in vitro viability of TNBC cell lines (MDA-MB-231 and MDA-MB-436) with IC 50 values of ≤50 μM. In previous work, we have proposed a new concept for targeting angiogenesis driving TNBC progression, by disrupting the protein-protein interaction between the molecular chaperone αB-crystallin (CRYAB) and VEGF. Since previous clinical studies applying anti-VEGF therapy to TNBC patients have met with limited success, we were interested to test our most promising purine analogues against CRYAB/VEGF, using a custom-designed cell-based CRYAB/VEGF 165 interaction assay platform. Analogues 4e and 4f significantly reduced the interaction between CRYAB/VEGF 165 , and compound 4e (100 μM) was also found to decrease the levels of soluble VEGF expressed by MDA-MB-231 cells by 40%. In conclusion, these promising early activity profiles warrant further investigation to validate this concept.

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“…Subsequent treatment with a primary amine or with hydrazine at elevated temperatures afforded the expected products in high yields. [22] The strategy consisted of bromination of the purine derivative 16 at the 8-position. The latter approach was also applicable for Nsubstituted BGs when primary amines were used rather than ammonia.…”

Section: Halogens As Functional Group Xmentioning

confidence: 99%

Synthetic Strategies for Preparing Bicyclic Guanidines

Lemrová

Soural

2015

Eur J Org Chem

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Different synthetic approaches leading to compounds containing bicyclic guanidine scaffolds are summarised. Because of the diversity within this group of target molecules and the wide range of individually reported synthetic routes, this review is divided into three subsections according to the key intermediate used to obtain the bicyclic structure. The first section is dedicated to strategies in which monocyclic guanidine derivatives are used as the key intermediates. The second section presents direct syntheses of bicyclic guanidines from acyclic or non‐guanidine starting materials. The last part of the text addresses the synthesis of target compounds through the use of polymer‐supported chemistry. The applicability of each synthetic approach for the preparation of target molecules with certain x+y combinations of individual cycles is specified.

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Synthesis, biological evaluation and docking studies of 4-amino-tetrahydroquinazolino[3,2-e]purine derivatives

Cited by 7 publications

References 37 publications

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

The discovery of purine-based agents targeting triple-negative breast cancer and the αB-crystallin/VEGF protein–protein interaction

Synthetic Strategies for Preparing Bicyclic Guanidines

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