Highly regioselective 1,3-dipolar cycloaddition of 3′-O-propargyl guanosine with nitrile oxide: An efficient method for the synthesis of guanosine containing isoxazole moiety

Shanmugasundaram, Muthian; Senthilvelan, Annamalai; Kore, Anilkumar R.

doi:10.1016/j.tetlet.2020.152464

Cited by 8 publications

(4 citation statements)

References 25 publications

(19 reference statements)

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“…After completion of the reaction TLC: (EtOAc:Hexane) (3:7)], water was added to the above reaction mixture, and the crude obtained was filtered. The crude was purified by column chromatography to yield pure thiouracil tethered isoxazole derivatives ( 6a – l ) ( Scheme 1 ) [ 42 ].…”

Section: Methodsmentioning

confidence: 99%

Electrochemical Synthesis of New Isoxazoles and Triazoles Tethered with Thiouracil Base as Inhibitors of Histone Deacetylases in Human Breast Cancer Cells

Vishwanath

Ravish

et al. 2023

Molecules

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Histone deacetylases (HDACs) are an attractive drug target for the treatment of human breast cancer (BC), and therefore, HDAC inhibitors (HDACis) are being used in preclinical and clinical studies. The need to understand the scope of the mode of action of HDACis, as well as the report of the co-crystal structure of HDAC6/SS-208 at the catalytic site, provoked us to develop an isoxazole-based lead structure called 4-(2-(((1-(3,4-dichlorophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio) pyrimidin-4-yl) morpholine (5h) and 1-(2-(((3-(p-tolyl) isoxazol-5-yl)methyl)thio) pyrimidin-4-yl) piperidin-4-one (6l) that targets HDACs in human BC cells. We found that the compound 5h or 6l could inhibit the proliferation of BC cells with an IC50 value of 8.754 and 11.71 µM, respectively. Our detailed in silico analysis showed that 5h or 6l compounds could target HDAC in MCF-7 cells. In conclusion, we identified a new structure bearing triazole, isoxazole, and thiouracil moiety, which could target HDAC in MCF-7 cells and serve as a base to make new drugs against cancer.

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Section: Methodsmentioning

confidence: 99%

Electrochemical Synthesis of New Isoxazoles and Triazoles Tethered with Thiouracil Base as Inhibitors of Histone Deacetylases in Human Breast Cancer Cells

Vishwanath

Ravish

et al. 2023

Molecules

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“…1,3‐dipolar cycloaddition of 3'‐O‐propargyl guanosine carried out by nitrile oxides, exhibits the preparation of guanosine encompassing isoxazole moiety in good amounts has been reported [25]. The reaction between the benzaldehyde oxime 1 and N‐chlorosuccinimide 2 with dimethyl formamide as a solvent, which further react with 3'‐O‐propargyl guanosine and triethylamine as a basic agent exhibited guanosine having isoxazole molecule with a decent amount.…”

Section: Synthetic Methods Of Isoxazole and Their Derivativesmentioning

confidence: 99%

“…Yazdani et al [29] first explored the potential of a 1,3-dipolar cycloaddition reaction that produces asymmetric dendrimer formation. It begins with the propargylation of pentaerythritol 1 with potassium hydroxide in S C H E M E 2 Preparation of 3, 5-disubstituted isoxazole derivatives [25] S C H E M E 3 Preparation of innovative acridone having isoxazoles [26] dry DMF and propargyl bromide 2 (Scheme 7), and the tetrapropargylated core 3 with the bromonitrile oxide precursor in THF at 45 C. It was monitored by the 1,3-bipolar cycloaddition reaction for 3 h, NaHCO 3 was used as the base and ZnCl 2 was used as the catalyst. 5,5 0 -(((2,2-bis(([3-bromoisoxazol-5-yl] methoxy)-methyl)propane-1,3-diyl)bis(oxy))-bis-(methylene))-bis(3-bromoisoxazole) 4 was obtained with an isolation yield of 44% (Scheme 7).…”

Section: 3 Cycloaddition Reaction Routementioning

confidence: 99%

A review of recent synthetic strategies and biological activities of isoxazole

Pandhurnekar¹,

Pandhurnekar

Mungole³

et al. 2022

Journal of Heterocyclic Chem

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Among different heterocyclic compounds, isoxazole and their analogues are very important classes of heterocyclic compounds as they display an extensive range of biological actions. This makes such scaffolds very important structures in the field of medicinal chemistry. From an extensive literature assessment, isoxazole is clinically proven to be very effective as an anti‐bacterial, anti‐fungal, anti‐inflammatory, anti‐cancer, anti‐tubercular, and anti‐neoplastic agent. The different derivatives of isoxazole which exhibits adjustment in their structure have shown a high degree of variety in their medicinal properties which makes evident them as very beneficial in the progress of novel bioactive drugs which show enhanced effectiveness along with minor harmfulness. Structural aspects of isoxazole having aromaticity with weaker nitrogen‐oxygen bonding provide a potential site for the ring cleavage. Thus, this isoxazole ring system allows easier modifications of substituents in their ring structure which consequently make isoxazole very useful intermediates in various synthetic routes of bioactive compounds. Hence, the synthesis and evaluation of isoxazole‐containing molecules with wider therapeutic consequences are always the topic of interest for chemists. Hence, in light of this comprehensive research on isoxazole, it is thought worthwhile to review various pathways for the synthesis of isoxazole analogues and having a broad spectrum of bioactive actions.

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“…Despite their significance, the majority of the methods that have been documented encounter challenges such as suboptimal efficacy, restricted range of applicable substrates, and intricate procedures. Moreover, the functionalization of oximes via C(sp 2 )–H bond activation has been rarely reported, particularly through electrochemical means. Therefore, the development of practical, efficient, and green approaches that consist of aerobic oxidation to construct oximes is still in demand.…”

mentioning

confidence: 99%

Electrochemical-Induced C–N Bond Formation: A New Method to Synthesis (Z)-Quinazolinone Oximes Using Primary Amines and Quinazolin-4(3H)-one

Zong,

Zhang,

et al. 2024

Org. Lett.

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sı Supporting InformationThe Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.4c00107.Experimental details and data, including NMR for all new compounds, and crystallographic data for 3aa (CCDC 2259037) (PDF)Accession CodesCCDC 2259037 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk

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Highly regioselective 1,3-dipolar cycloaddition of 3′-O-propargyl guanosine with nitrile oxide: An efficient method for the synthesis of guanosine containing isoxazole moiety

Abstract: Graphical abstract

Cited by 8 publications

References 25 publications

Electrochemical Synthesis of New Isoxazoles and Triazoles Tethered with Thiouracil Base as Inhibitors of Histone Deacetylases in Human Breast Cancer Cells

Electrochemical Synthesis of New Isoxazoles and Triazoles Tethered with Thiouracil Base as Inhibitors of Histone Deacetylases in Human Breast Cancer Cells

A review of recent synthetic strategies and biological activities of isoxazole

Electrochemical-Induced C–N Bond Formation: A New Method to Synthesis (Z)-Quinazolinone Oximes Using Primary Amines and Quinazolin-4(3H)-one

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