Synthesis and biological activity evaluation of cytidine-5′-deoxy-5-fluoro-N-[(alkoxy/aryloxy)] carbonyl-cyclic 2′,3′-carbonates

Rani, V. Jhansi; Aminedi, Raghavendra; Kishore, P. R. S.; Yellapu, Nanda Kumar; Kumar, K.; Jagadeeswarareddy, K.

doi:10.1016/j.ejmech.2012.06.023

Cited by 15 publications

(4 citation statements)

References 11 publications

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“…The chemical structures of the new compounds were confirmed using: IR, 1 H NMR, 13 C NMR spectral data and HRMS, the data for which are presented in the Experimental Protocols section. We observed characteristic IR absorption readings in regions at: 3475–3371 cm −1 and 3342–3330 −1 , for: N–H [37, 38], O–H [39, 40], respectively. In the 1 H NMR spectra of compounds 3a–e & 4a–e , the chemical shifts of aromatic hydrogen’s on the phenyl ring appeared as doublets in region and multiplets of 6.96–7.92 and 6.75–7.94 respectively [41, 42].…”

Section: Resultsmentioning

confidence: 99%

Identification of human presequence protease (hPreP) agonists for the treatment of Alzheimer's disease

Vangavaragu

Valasani

Gan

et al. 2014

European Journal of Medicinal Chemistry

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Amyloid-β (Aβ), a neurotoxic peptide, is linked to the onset of Alzheimer’s disease (AD). Increased Aβ content within neuronal cell mitochondria is a pathological feature in both human and mouse models with AD. This accumulation of Aβ within the mitochondrial landscape perpetuates increased free radical production and activation of the apoptotic pathway. Human Presequence Protease (hPreP) is responsible for the degradation of mitochondrial amyloid-β peptide in human neuronal cells, and is thus an attractive target to increase the proteolysis of Aβ. Therefore, it offers a potential target for Alzheimer’s drug design, by identifying potential activators of hPreP. We applied structure-based drug design, combined with experimental methodologies to investigate the ability of various compounds to enhance hPreP proteolytic activity. Compounds 3c & 4c enhanced hPreP-mediated proteolysis of Aβ (1–42), pF1β (2–54) and fluorogenic-substrate V. These results suggest that activation of hPreP by small benzimidazole derivatives provide a promising avenue for AD treatment.

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Section: Resultsmentioning

confidence: 99%

Identification of human presequence protease (hPreP) agonists for the treatment of Alzheimer's disease

Vangavaragu

Valasani

Gan

et al. 2014

European Journal of Medicinal Chemistry

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“…For PB1 to BP6, the results were in line with data previously reported for human breast cancer cell line. [40,41,42] All molecules proved to be much more active than 5-Fluorouracil against CaCo-2 cells. Under the conditions tested, the less active molecule inhibits the growth and replication of cancer cells at a concentration corresponding to 1/5 of that required for 5 Fluorouracil.…”

Section: Discussionmentioning

confidence: 97%

Heteroaryl-Ethylenes as New Lead Compounds in the Fight against High Priority Bacterial Strains

Bongiorno¹,

Musso²,

Bonacci³

et al. 2021

Preprint

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The widespread use of antibiotics has led to a gradual increase in drug-resistant bacterial infections, which severely weakens the clinical efficacy of antibacterial therapies. In recent decades, stilbenes aroused great interest because of their high bioavailability, as well as for their manifold biological activity. Our research efforts are focused on synthetic heteroaromatic stilbene deriva-tives as they represent a potentially new type of antibiotic with a wide antibacterial spectrum. Herein, a preliminary molecular modeling study and a versatile synthetic scheme allowed us to define eight heteroaromatic stilbene derivatives with potential antimicrobial activity. In order to evaluate our compound’s activity spectrum and antibacterial ability, Minimum Inhibitory Con-centration (MIC) and Minimum Bactericidal Concentration (MBC) tests have been performed on Gram-positive and Gram-negative ATCC strains. Compounds PB4, PB5, PB7 and PB8 showed the best values in terms of MIC and were also evaluated for MBC, which however was found to be greater than MIC, confirming a bacteriostatic activity. For all compounds, we evaluated toxici-ty on colon-rectal adenocarcinoma cells tumor cells (CaCo2), once established that the whole se-lected set was more active than 5-Fluorouracil in reducing CaCo-2 cells viability. To the best of our knowledge, the biological assays have shown for these derivatives an excellent bacteriostatic activity, compared to similar molecular structures previously reported, thus paving the way for a new class of antibiotic compounds.

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“…20 Various capecitabine derivatives have been designed and synthesized to date. 21,22 Recently, the PCC0208037 conjugate containing the haptophoric groups of irinotecan and capecitabine has been synthesized and evaluated in vitro . 23 Biological studies confirmed its anti-tumour activity and explored the potential molecular mechanism of action: cell cycle arrest and DNA damage.…”

Section: Introductionmentioning

confidence: 99%

The conjugates of 5′-deoxy-5-fluorocytidine and hydroxycinnamic acids – synthesis, anti-pancreatic cancer activity and molecular docking studies

Cybulski,

Zaremba-Czogalla,

Trzaskowski

et al. 2024

RSC Adv.

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Synthesis and biological activity evaluation of cytidine-5′-deoxy-5-fluoro-N-[(alkoxy/aryloxy)] carbonyl-cyclic 2′,3′-carbonates

Cited by 15 publications

References 11 publications

Identification of human presequence protease (hPreP) agonists for the treatment of Alzheimer's disease

Identification of human presequence protease (hPreP) agonists for the treatment of Alzheimer's disease

Heteroaryl-Ethylenes as New Lead Compounds in the Fight against High Priority Bacterial Strains

The conjugates of 5′-deoxy-5-fluorocytidine and hydroxycinnamic acids – synthesis, anti-pancreatic cancer activity and molecular docking studies

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