Synthesis andin vitro evaluation of the anticancer activity of novel fluorinated thiazolo[4, 5-d]pyrimidines

Fahmy, Hesham; Rostom, Sherif A. F.; Saudi, M. N. S.; Zjawiony, Jordan K.; Robins, David J.

doi:10.1002/ardp.200300734

Cited by 55 publications

(17 citation statements)

References 13 publications

(22 reference statements)

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“…In view of the aforementioned facts, and as a continuation of an on-going research program devoted to the synthesis and characterization of different heterocyclic ring systems endowed with potential chemotherapeutic activities [31][32][33][34][35][36][37][38][39][40][41][42][43], it was sought of interest to design and synthesize certain chalcones and some derived pyrazole, pyrimidine, and thiazolopyrimidine cyclized ring structures substituted basically with polymethoxy groups based on the fact that incorporation of alkoxy substituents would result in significant enhancement of several biological activities due to the magnification of compounds' lipophilicity [44][45][46]. The newly synthesized compounds were designed so as to comprise two polymethoxylated aryl rings attached to either a pyrazole ring substituted with formyl, acetyl or substituted aryl moieties, or a pyrimidine counterpart with different ketone, thione, and thioether functionalities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some Pyrazolines and Pyrimidines Derived from Polymethoxy Chalcones as Anticancer and Antimicrobial Agents

Rostom

Badr

Razik

et al. 2011

Archiv der Pharmazie

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The synthesis of a series of certain polymethoxy chalcones and some derived pyrazole, pyrimidine, and thiazolopyrimidine ring structures is reported. Eleven compounds 4, 6, 9, 11, 14-17, 22, 24, and 25 were selected by the National Cancer Institute (NCI) to be screened for their in-vitro anticancer activity, whereas all the synthesized compounds were evaluated for their in-vitro antimicrobial activity. Compounds 4, 6, and 11 were found to possess a significant broad spectrum antitumor potential against most of the tested subpanel tumor cell lines. The pyrazolines 4 and 6 displayed remarkable growth inhibitory activities (GI(50) MG-MID values of 2.10 and 1.38 µM, respectively), together with moderate cytostatic effects (TGI MG-MID values of 47.9 and 42.7 µM, respectively). Meanwhile, the pyrimidin-2-one 11 showed a noticeable overall tumor growth inhibitory activity, together with high cytostatic and cytotoxic efficacies (GI(50) , TGI and LC(50) MG-MID values of 3.39, 17.4, and 61.7 µM, respectively). On the other hand, compounds 3, 4, 13, 15, 19, 20, and 23 were found to be the most active antimicrobial members in this investigation with a broad spectrum of activity. Compound 23 was four times superior to ampicillin against Pseudomonas aeruginosa. The best antifungal activity was demonstrated by compounds 4, 5, and 11 which possessed almost half the activity of clotrimazole against Candida albicans. Collectively, the obtained biological results suggest that compound 4 could be considered as a possible dual antimicrobial-anticancer agent.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Some Pyrazolines and Pyrimidines Derived from Polymethoxy Chalcones as Anticancer and Antimicrobial Agents

Rostom

Badr

Razik

et al. 2011

Archiv der Pharmazie

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“…These designed thiazolo[4,5- d ]pyrimidine-2-ones are related to thiazolo[4,5- d ]pyrimidine-2-thiones that have been previously reported to be potent antitumor agents (Becan and Wagner, 2008). Thiazolo[4,5- d ]pyrimidine derivatives have been extensively studied as potential drug candidates and also have anticancer activity (Rida et al ., 1996; Fahmy et al ., 2002, 2003). Most of these compounds provided with anticancer activity possess an aromatic rings and electronegative substituent directly linked to the C-17 of the essential core (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and anticancer evaluation of novel 3,5-diaryl-thiazolo[4,5-d]pyrimidin-2-one derivatives

Becan

Wagner

2012

Med Chem Res

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The 2-oxo analogs of thiazolo[4,5-d]pyrimidine-2-thiones were prepared to study their cytotoxic activity. Five of the newly synthesized compounds were selected by the National Cancer Institute (Bethesda, MD, USA) for a primary in vitro antitumor assay. 7-Chloro-3,5-diphenyl-thiazolo[4,5-d]pyrimidin-2-one (5a) proved to be the most active one among the screened derivatives and was further evaluated in the full panel of 60 cell lines at five different concentrations. The structures of compounds were determined by IR, 1H-NMR, 13C-NMR, X-ray, and elemental analysis.

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“…Careful literature survey revealed that many substituted thiazoles and thiazolo [4,5-d] pyrimidines have been reported to possess anticancer [16][17][18][19][20], antiviral [21][22][23][24][25], and antimicrobial [26][27][28][29] activities. In addition, a family of 2-pyridinone derivatives has been found to be potent and selective non-nucleoside inhibitors of HIV-reverse transcriptase [30][31][32][33][34].…”

Section: Introductionmentioning

confidence: 99%

Cyanoacetic Acid Hydrazones of 3‐(and 4‐)Acetylpyridine and Some Derived Ring Systems as Potential Antitumor and Anti‐HCV Agents

El-Hawash

Wahab

El-Demellawy

2006

Archiv der Pharmazie

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Two new acetylpyridinehydrazones derived from cyanoacetic acid hydrazide have been synthesized namely: cyanoacetic acid (1-pyridin-3 or 4-yl-ethylidene) hydrazides (1a,b). and some derived ring systems: 2-imino or 2-oxo-2H-chromenes (2a,b and 3a,b), substituted 2-thioxo-2,3-dihydrothiazoles (4a-d), substituted 2-thioxo-2,3-dihydro-6H-thiazolo[4,5-d]pyrimidin-7-ones (5a-d), substituted dihydrothiazoles (7a,b), and substituted 2-oxo-1,2-dihydropyridines (8a-d and 9a,b). Fifteen compounds were evaluated for their anticancer activity using the USA-NCI in-vitro screening program. Among the tested compounds, 8d exhibited a high value of percent tumor growth inhibition at concentrations of 10(-5) to 10(-7) M in all cancer cell lines, while 8b exhibited a significant value of percent tumor growth inhibition at concentration <10(-8 )M against non-small cells lung HOP-92. In addition, nine compounds were investigated for their in-vitro effect on the replication of hepatitis-C virus (HCV) in HepG2 hepatocellular carcinoma cell line infected with the virus using the reverse transcription polymerase chain reaction technique. Six compounds were capable of inhibiting the replication of both the HCV RNA (+)- and (-)-strands at 5-100 microg/mL concentration range. The activity order was 7b > 1b = 3a > 4c > 7a > 5c.

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Synthesis andin vitro evaluation of the anticancer activity of novel fluorinated thiazolo[4, 5-d]pyrimidines

Cited by 55 publications

References 13 publications

Synthesis of Some Pyrazolines and Pyrimidines Derived from Polymethoxy Chalcones as Anticancer and Antimicrobial Agents

Synthesis of Some Pyrazolines and Pyrimidines Derived from Polymethoxy Chalcones as Anticancer and Antimicrobial Agents

Synthesis and anticancer evaluation of novel 3,5-diaryl-thiazolo[4,5-d]pyrimidin-2-one derivatives

Cyanoacetic Acid Hydrazones of 3‐(and 4‐)Acetylpyridine and Some Derived Ring Systems as Potential Antitumor and Anti‐HCV Agents

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