Synthesis, Anti‐Microbial, and Cytotoxic Activities Evaluation of Some New Pyrido[2,3‐<i>d</i>]Pyrimidines

Elsaedany, Samir Kamel; Zein, Mohamed A.-E.; AbedelRehim, Elsayed Mohmoud; Keshk, Reda Mohammed

doi:10.1002/jhet.2460

Cited by 20 publications

(7 citation statements)

References 26 publications

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“…Continuing our interest in preparing of new heterocyclic compounds and examining their various biological activities [ 1 – 6 ], this work was designed to prepare new derivatives of condensed and non-condensed five-membered rings with pyrimidine. Pyrimidine derivatives have aroused the interest of researchers in recent years, as they have demonstrated a wide variety of biological activities such as antibacterial [ 6 ], antiallergic, antihypertensive [ 7 ] and antitumor activity [ 5 , 8 ], along with their cardiopulmonary and bronchodilating effect [ 9 ]. It has been observed that the substitution of the benzene ring in pyrimidine derivatives with heterocyclic moieties such as pyrrole and thiophene shows some biological activities such as anti-proliferative and anti-inflammatory activities [ 10 – 12 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, screening as potential antitumor of new poly heterocyclic compounds based on pyrimidine-2-thiones

Abdelrehim

Soliman

2022

BMC Chemistry

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Background Continuing our interest in preparing of new heterocyclic compounds and examining their various biological activities, this work was designed to prepare new condensed and non-condensed heterocyclic compounds 9a-c, 10a-c, 11a-c, 13a-c and 14a-c were synthesized starting with pyrimidine-2-thiones 4a-c. Results Thiazolo[3,2-a]pyrimidines 9a-c were synthesized by S-alkylation of pyrimidine-2-thiones,4a-c, internal cyclization in alkaline medium with ammonia, condensation with benzaldehyde and finally reaction with hydroxylamine hydrochloride.[1,2,4]thiadiazolo[4,5-a]pyrimidines 11a-c were formed by heating of the 4a-c with benzoylcholride to afford 10a-c followed by reaction with sodium hypochlorite, ammonia and sodium hydroxide. Cyclocondensation of 4a-c with ethyl acetoacetate or formic acid yielded pyrazol-3-ones 13a-c or [1,2,4] triazolo[4,3-a]pyrimidines 14a-c, respectively Elements analysis, IR, 1H-NMR, 13C-NMR and mass spectra were used to validate the structures of newly synthesized heterocycles. Screening of the selected compounds 4a, 6a, 7a, 9a, 10a, 13a and 14a against colon carcinoma cell lines (HCT-116) and hepatocellular carcinoma cell lines (HepG-2). Conclusions Elements analysis, IR, 1H-NMR, 13C-NMR and mass spectra were used to validate the structures of newly synthesized heterocycles. Screening of the selected compounds 4a, 6a, 7a, 9a, 10a, 13a and 14a against colon carcinoma cell lines (HCT-116) and hepatocellular carcinoma cell lines (HepG-2) showed that compound 10a exhibited the most cytotoxic, while compounds 4a, 6a and 14a exhibited considerable cytotoxic activity.

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Section: Introductionmentioning

confidence: 99%

Synthesis, screening as potential antitumor of new poly heterocyclic compounds based on pyrimidine-2-thiones

Abdelrehim

Soliman

2022

BMC Chemistry

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“…Potential anticancer activity was observed by all the synthesized compounds. pyrimidine nucleus as a pharmacologically potential scaffold, including antitumor properties [36]. They also reported that organic molecule bearing fluorine [37] or trifluoromethyl [38] group at a strategic position leads to dramatic changes in the properties and activities of the molecule.…”

Section: Ethyl 2-cyanoacetate As Precursormentioning

confidence: 99%

Synthesis and Anticancer Perspective of Pyridopyrimidine Scaffold - An Overview

Shetty

Shastry

2021

JPRI

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The core pyridopyrimidines are gaining interest in organic and heterocyclic chemistry in recent days, as this scaffold acts as a building block because of its wide range of biological and pharmacological applications like anticancer, antimicrobial, fungicidal, antiviral, CNS, antibacterial, and anti-inflammatory properties. This review mainly emphasizes the evolution in anticancer properties of pyridopyrimidines since 2008 especially the method of synthesis and anticancer activity of synthesized compounds with reporting of active anticancer scaffolds. Important starting materials which are widely used for the synthesis are 2-thioxopyrimidine, ethyl 2-cyanoacetate, 2-amino-3-cyano-4-trifluoromethyl-6-phenyl-pyridine, 2-amino-4,6-disubstituted nicotinonitrile, 2-chloro-3-pyridine carboxylic acid, in which 2-thioxopyrimidine is found to be mostly employed in the synthesis. Pyridopyrimidines which are synthesized from different starting materials, in which the more active compounds are reported here which may help in further discovery/ development of novel molecules.

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“… 1 , 2 Also, [1,2,4]triazole derivatives have been reported as antimicrobial, insecticidal, fungicidal, antidepressant, hypnotic, anti-inflammatory, antihypertensive, and plant growth regulator. 3 − 8 On the other hand, 1,3,4-oxadiazole has become an essential building unit for the creation of new drugs where a literature survey showed that a slight systemic change in 1,3,4-oxadiazole moiety structure could lead to qualitative as well as quantitative changes in 1,3,4-oxadiazole derivative activity, which convinced us to start synthesizing different new 1,3,4-oxadiazole derivatives in order to increase their activity and lower their toxicity. Over the last 2 decades, the synthesis of novel 1,3,4-oxadiazole derivatives and the investigation into their chemical properties and biological behavior have increased.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Screening of New [1,3,4]Oxadiazole, [1,2,4]Triazole, and [1,2,4]Triazolo[4,3-b][1,2,4]triazole Derivatives as Potential Antitumor Agents on the Colon Carcinoma Cell Line (HCT-116)

Abdelrehim

2021

ACS Omega

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New derivatives of [1,3,4]oxadiazole-2-thione and triazole-3-thione were synthesized through the cyclocondensation of dicarbonyl ester 2 with phenyl hydrazine followed by hydrazinolysis to give the corresponding hydrazide, which reacted with carbon disulfide or ammonium thiocyanate to afford [1,3,4]oxadiazole 5 or triazole-3-thione 7, respectively. Hydrazinolysis of compound 5 gave [1,2,4]triazole-3-thiol 9 which was treated with different aromatic aldehydes to obtain 10a−c. Mannich bases 11a−c were obtained from the reaction of Schiff bases 10a−c with morpholine and formaldehyde. Moreover, treatment of triazole-3thione 7 with hydrazine was followed by cyclocondensation with diethyl oxalate, chloroacetic acid, or formic acid to give the corresponding [1,2,4]triazine-3,4-dione 14, [1,2,4]triazin-4-one 15, or [1,2,4]triazolo [4,3-b][1,2,4] triazole 16, respectively. Screening of some chosen synthesized compounds against the human colon carcinoma cancer cell lines showed that the compound [1,2,4]triazole-3-thiol 9 exhibiting cytotoxic activity was roughly equivalent to standard Vinblastine, while compounds 4, 7, 10, 11a, 14, and 16 exhibited moderate cytotoxic activity.

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Synthesis, Anti‐Microbial, and Cytotoxic Activities Evaluation of Some New Pyrido[2,3‐d]Pyrimidines

Cited by 20 publications

References 26 publications

Synthesis, screening as potential antitumor of new poly heterocyclic compounds based on pyrimidine-2-thiones

Synthesis, screening as potential antitumor of new poly heterocyclic compounds based on pyrimidine-2-thiones

Synthesis and Anticancer Perspective of Pyridopyrimidine Scaffold - An Overview

Synthesis and Screening of New [1,3,4]Oxadiazole, [1,2,4]Triazole, and [1,2,4]Triazolo[4,3-b][1,2,4]triazole Derivatives as Potential Antitumor Agents on the Colon Carcinoma Cell Line (HCT-116)

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