Synthesis and In Vitro Antitumor Activity of New Substituted Thiopyrimidine Acyclic Nucleosides and Their Thioglycoside Analogs

El‐Sayed, Wael A.; Rashad, Aymn E.; Awad, Samir M.; Ali, Mamdouh M.

doi:10.1080/15257770902946165

Cited by 47 publications

(29 citation statements)

References 37 publications

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“…Different nucleoside analogs incorporating substituents at the C-5 position in the heterocyclic base, especially in the 2-deoxyuridine type, were investigated to have interesting biological activities as antiviral and anticancer agents (Srinivasan et al, 20101;McGuian et al, 2000;Yoo et al, 2002;Hannah et al, 2000;Khan and Grinstaff, 1998). The above findings and our interest in glycosyl heterocycles synthesis with biological activity research field El-Sayed et al, 2009;Amr et al, 2006;ElSayed et al, 2016) promoted us to design and synthesize new pyrimidine and triazolopyrimidine glycosides with acetylated or free hydroxyl sugar moieties and acyclic analogs bearing ether or terminal hydroxyl studying their anticancer activity against a number of cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Docking Studies and Anticancer Activity of New Substituted Pyrimidine and Triazolopyrimidine Glycosides

2017

J App Pharm Sci

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New substituted pyrimidine and triazolopyrimidine derivatives were synthesized. The N 3 -glycosides of both heterocyclic systems and acyclic oxygenated alkyl derivatives were also prepared. The anticancer activity against human prostatic adenocarcinoma (PC3), human colorectal carcinoma (HCT116) and human breast adenocarcinoma (MCF7) cell lines in addition to their effect on human normal retinal pigmented epithelial cell line (RPE1) was studied. Furthermore, the docking studies revealed good binding affinities for compounds 7, 8, 10 and 12. The results showed the effect of N 3 -substitution in the pyrimidine ring on the activity of synthesized compounds.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Docking Studies and Anticancer Activity of New Substituted Pyrimidine and Triazolopyrimidine Glycosides

2017

J App Pharm Sci

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“…They have been recognized as important heterocyclic compounds due to their diverse biological activities such as Tie-2 kinase inhibitors [2], HIV-1 inhibitor [3], antimalarial [4] secretive adenosine A1 receptor antagonist [5], anticancer [6,7], analgesic [8], and cardiovascular [9] activities. Furthermore, it has been found that 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) have interesting multifaceted pharmacological profile as hepatitis B virus (HBV) replication inhibitors [10][11][12].…”

Section: Introductionmentioning

confidence: 99%

“…Condensation of the sodium salt of 3a-c with 2,3,4,6-tetra-O-acetyl-a-D-glucopyranosyl bromide (7) in dry DMF at 90 0 protons which are indicative of the b-configuration. Deacetylation of 8a-c in a mixture of methanol and ammonium hydroxide (25%) (1:1) at room temperature gave the free nucleosides 9a-c in 88-92% yields.…”

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confidence: 99%

Synthesis and antiviral activity of new substituted pyrimidine glycosides

Ramiz

El‐Sayed

Hagag

et al. 2011

Journal of Heterocyclic Chem

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A number of N-substituted pyrimidine glycosides were synthesized by coupling reaction of the pyrimidine base with acetobromosugars followed by deprotection. The synthesized compounds were tested for their antiviral activity against Hepatitis B Virus (HBV). Plaque reduction infectivity assay was used to determine virus count reduction as a result of treatment with tested compounds which showed moderate to high anti viral activities.

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“…5 The latest studies showed that nucleosides were important bioactive compounds related to anti-inflammatory, immunoregulation, antitumor and antivirus activities. [6][7][8][9] Clemastanin B, indigoticoside A, isolariciresinol and syringin are the major phenylpropanoids isolated from Radix Isatidis. [10][11][12] In our previous studies, 13 we found that clemastanin B and syringin had strong inhibitory effects on influenza FM1.…”

Section: Introductionmentioning

confidence: 99%

“…[6][7][8][9] Clemastanin B, indigoticoside A, isolariciresinol and syringin are the major phenylpropanoids isolated from Radix Isatidis. [10][11][12] In our previous studies, 13 we found that clemastanin B and syringin had strong inhibitory effects on influenza FM1.…”

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confidence: 99%

Simultaneous Quantification of Three Chemical Types Bioactive Compounds in Radix Isatidis and Its Relevant Pharmaceutical Dosage Forms by HPLC-DAD

Xiao¹,

Li²,

Chen³

et al. 2016

J. Braz. Chem. Soc.

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A simple and rapid high performance liquid chromatography coupled with diode array detector (HPLC-DAD) method was developed for simultaneous quantification of three chemical types of bioactive compounds including an alkaloid (epigoitrin), six nucleosides (uracil, cytidine, hypoxanthine, uridine, guanosine and adenosine), and four phenylpropanoids (syringin, clemastanin B, indigoticoside A and isolariciresinol) in Radix Isatidis and its relevant pharmaceutical dosage forms. The developed method was successfully applied to analyze 32 batches of samples with good linearity (R 2 , 0.9966-0.9999), precisions (relative standard deviation (RSD), 0.24-4.61%), repeatability (RSD, 0.39-4.93%), stability (RSD, 1.18-4.29%) and recovery (range, 95.4-104.6%) of the eleven compounds. The limits of detection (LOD) and limits of quantification (LOQ) of the method ranged 0.0383-0.1744 and 0.1550-0.5467 μg mL -1 , respectively. The results indicated that the newly established HPLC-DAD method was sensitive, precise, accurate and reproducible. It could be applied to the quality control of Radix Isatidis and its relevant pharmaceutical dosage forms. Keywords: Radix Isatidis, HPLC-DAD, alkaloid, phenylpropanoid, nucleosides IntroductionThe well-known traditional Chinese medicine Radix Isatidis (common name: Banlangen) is the dried root of the plant Isatis indigotica Fort. It belongs to the Cruciferae family and widely distributed in the north and central of China.1,2 Radix Isatidis are one of the most frequently used traditional Chinese medicine for treatment of influenza, bacterial infection, fever and epidemic hepatitis.3 Because of the unique pharmacological activities, Radix Isatidis has been developed into various dosage forms such as granules, tablets, capsules and altapharmas.Chemical studies showed that Radix Isatidis contains various compounds such as alkaloids, phenylpropanoids, nucleosides and organic acids. 4 Epigoitrin as an alkaloid was used as a marker compound of Radix Isatidis in the 2015 edition of the Chinese Pharmacopoeia. Uracil, cytidine, hypoxanthine, uridine, guanosine and adenosine are the main nucleosides in Radix Isatidis. 5The latest studies showed that nucleosides were important bioactive compounds related to anti-inflammatory, immunoregulation, antitumor and antivirus activities. [6][7][8][9] Clemastanin B, indigoticoside A, isolariciresinol and syringin are the major phenylpropanoids isolated from Radix Isatidis. [10][11][12] In our previous studies, 13 we found that clemastanin B and syringin had strong inhibitory effects on influenza FM1. Clemastanin B was found to inhibit different subtypes of human (H1N1, including swineorigin H1N1; H3N2 and influenza B) and avian influenza viruses (H6N2, H7N3, H9N2) at different magnitudes of activity.14 From the latest studies, indigoticoside A could inhibit herpes simplex virus (HSV) and influenza A virus. 15Qualitative and quantitative analysis of major bioactive compounds are very important for the quality control of Radix Isatidis. It is well known that traditi...

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Synthesis and In Vitro Antitumor Activity of New Substituted Thiopyrimidine Acyclic Nucleosides and Their Thioglycoside Analogs

Cited by 47 publications

References 37 publications

Synthesis, Docking Studies and Anticancer Activity of New Substituted Pyrimidine and Triazolopyrimidine Glycosides

Synthesis, Docking Studies and Anticancer Activity of New Substituted Pyrimidine and Triazolopyrimidine Glycosides

Synthesis and antiviral activity of new substituted pyrimidine glycosides

Simultaneous Quantification of Three Chemical Types Bioactive Compounds in Radix Isatidis and Its Relevant Pharmaceutical Dosage Forms by HPLC-DAD

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