Synthesis and in vitro antitumor evaluation of some new thiophenes and thieno[2,3-d]pyrimidine derivatives

Fouad, Mahasen M.; El‐Bendary, Eman R.; Suddеk, Ghada M.; Shehata, Ihsan A.; El‐Kerdawy, Mohamed M.

doi:10.1016/j.bioorg.2018.09.022

Cited by 71 publications

(34 citation statements)

References 40 publications

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“…As compounds containing thieno[2,3-d]pyrimidine motif have been reported to possess cytotoxicity against cancer cell lines [20,29,30,31], we evaluated the antiproliferative activity of thieno[2,3-d]pyrimidin-4(3H)-one compounds synthesized herein, against several human cancer cells, as well as human normal liver cells (HL-7702). The cancer cells used in the research include human non-small cell lung cancer cells A549, PC-9, human prostate cancer cell PC-3, and human breast cancer cell line MCF-7.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Novel Analogs of Thieno[2,3-d] Pyrimidin-4(3H)-ones as Selective Inhibitors of Cancer Cell Growth

et al. 2019

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New 2,3-disubstituted thieno[2,3-d]pyrimidin-4(3H)-ones were synthesized via a one-pot reaction from 2H-thieno[2,3-d] [1,3]oxazine-2,4(1H)-diones, aromatic aldehydes, and benzylamine or 4-hydroxylbezylamine. The obtained compounds were tested in vitro for cancer cell growth inhibition. Compound 19 can inhibit all four types of tested cancer cells, i.e., MCF-7, A549, PC-9, and PC-3 cells. Most of the compounds inhibited the proliferation of A549 and MCF-7 cells. Compound 15 exhibited the strongest anti-proliferative effect against A549 cell lines with IC50 values of 0.94 μM, and with no toxicity to normal human liver cells. Its potency was further proved by cell clone formation assay, Hoechst 33258 staining, and evaluation on the effects of apoptosis-related proteins.

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Section: Resultsmentioning

confidence: 99%

“…Recently reported representative compounds with the thieno[2,3- d ] pyrimidine motif as potent anti-cancer agents. [20,29,30,31]. …”

Section: Figures Scheme and Tablementioning

confidence: 99%

Synthesis of Novel Analogs of Thieno[2,3-d] Pyrimidin-4(3H)-ones as Selective Inhibitors of Cancer Cell Growth

et al. 2019

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“…The object was to combine the 1,2,4-triazole nucleus to the cinnamaldehyde since it is known that more e cacious antimicrobial substances can be discovered by adding two biologically effective components together into a single molecular structure [41,42]. Thereafter product Oxadiazole compound (12) was obtained as a result of ring closure reaction of hydrazide compound (5) with CS 2 in basic media. The NH and NH 2 peaks resulting from the hydrazide compound disappeared in both the FT-IR and 1 H NMR data of the oxadiazol derivative compound.…”

Section: Discussionmentioning

confidence: 99%

“…The World Health Organization's cancer agency warns that there will be 22 million new cases of cancer every year within the next two decades [4]. Hence, cancer treatment is the primary task of today's medical research [5]. Despite the invention of several chemotherapeutic agents, still treatment of cancer is a major challenge, because of multi-drug resistance, toxicity or poor bioavailability.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial, Antiproliferative Evaluation of Novel Quinolone and Conazole Analogues via Conventional and Microwave Techniques

Ceylan

Cebeci

Demirbaş

et al. 2021

Preprint

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1,2,4-Triazole-3-one (3), acquired from cinnemaldehyde was converted to the corresponding carbox(thio)amides via several steps (6a-c). Their reaction with sodium hydroxide gave the 1,2,4-triazole derivatives (7a-c). Compound 3 treatment with 2-bromo-1-(4-chlorophenyl) ethanone or 2-chloro-1-(2,4-dichlorophenyl)ethanone afforded the compounds 8a,b and by reducing these compounds reduction products were obtained (9a,b). The synthesis of (10a-e) was carried out by the reaction compounds 9a,b with different benzyl chlorides. Then oxadiazol derivative (12) was obtained by ring closure from hydrazide compound 5. Subsequently compounds 3, 7a-c and 12 were treated with various amines in the presence of formaldehyde to yield Mannich bases (11a-e, 14a-e, 13a,b). Microwave-assisted and conventional techniques were utilized for the syntheses. The structures of newly synthesized compounds were illuminated by spectroscopic methods. Their antimicrobial (MIC method), and anticancer activities (Abay’s method) were examined. Results showed that most of the compounds exhibited good antimicrobial activities. Especially compounds 14a-e which is a mannich base showed very good antitubercular activity against Mycobacterium smegmatis compared with Streptomycin standard drug. Also compounds 8a and 9b have been found to have strong antiproliferative effects on the HeLa cervical cancer cells and also these compounds did not have cytotoxic effect on normal cell.

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“…It is worth mentioning that compounds containing thienopyrimidine nucleus constitute a wide group of compounds that have accepted extensive consideration in the course of the most recent years owing to their potency as anticancer agents .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

Hassan

Husseiny

2019

Journal of Heterocyclic Chem

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In an attempt to establish novel candidate with promising anticancer activity, two derivatives of (benzo[d]thiazol‐2‐yl)thiophene backbone 1 and 14 were synthesized, and they further reacted with various chemical reagents to afford the corresponding substituted thiophene derivatives 6, 8, 10, 15, 17, and 20, thieno[3,2‐d]pyrimidine derivatives 2–5, 7, 9, 16, 21, 23, and 24, thieno[3,2‐b]pyridine derivatives 11–13, and thieno[3,2‐e][1,4]oxazepine derivative 18. Structures of prepared compounds were affirmed via spectral and elemental data. Among the obtained compounds, seven derivatives 2, 3, 4, 5, 11, 12, and 13 were chosen by National Cancer Institute, USA. Such compounds were screened for their antitumor activity versus 60 cancer cell lines in one‐dose (10 μmol) screening assay. The outcomes showed that all selected compounds exhibited moderate to high anticancer activity towards many cancer cell lines among which compounds 5 and 11 exerted potent antitumor activity against numerous malignant growth cell lines particularly Ovarian Cancer IGROV1.

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Synthesis and in vitro antitumor evaluation of some new thiophenes and thieno[2,3-d]pyrimidine derivatives

Cited by 71 publications

References 40 publications

Synthesis of Novel Analogs of Thieno[2,3-d] Pyrimidin-4(3H)-ones as Selective Inhibitors of Cancer Cell Growth

Synthesis of Novel Analogs of Thieno[2,3-d] Pyrimidin-4(3H)-ones as Selective Inhibitors of Cancer Cell Growth

Synthesis and Antimicrobial, Antiproliferative Evaluation of Novel Quinolone and Conazole Analogues via Conventional and Microwave Techniques

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

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