Synthesis and Anti-tumor Activities of Novel [1,2,4]triazolo[1,5-a]pyrimidines

Zhao, Xianglin; Zhao, Yanfang; Guo, Shuchun; Song, Hwangjun; Wang, Ding; Gong, Ping

doi:10.3390/12051136

Cited by 65 publications

(42 citation statements)

References 15 publications

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“…Recently, 1,2,4-triazolo [1,5-a]pyrimidines have aroused increasing attention from the chemical and biological points of view due to their diverse pharmacological activities such as anti-inflammatory [5], antimalarial [6], antifungal effect [7], macrophage activation [8], antitumor potency [9][10][11][12], antimicrobial [13][14][15][16][20][21][22][23][24] and inhibition of KDR kinase [17]. They have proven to be promising anticancer [18] agents with dual mechanisms of tubulin polymerization promotion [9][10] as well as cyclin dependent kinases 2 inhibition [19].…”

Section: Introductionmentioning

confidence: 99%

An Efficient Solid Phase One Port Synthesis of Novel Triazolo[1,5-a]Pyrimidine Derivatives from 4-(4-Aminophenyl)Morpholin-3-One and Evaluation of their Antimicrobial Activity

Prajapati

Vilapara

Naliapara

2014

ILCPA

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A series of novel triazolo [1,5-a]pyrimidine derivatives was synthesized from 5-amino-1,2,4-triazole and biologically active morpholinone amine in excellent yield as promising class of antimicrobial agents. The antimicrobial activities were investigated against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Staphylococcus pyogen, Candida albicans, Aspergillusniger, Aspergillusclavatus and compared with standard drugs Ampicillin, Chloramphenicol, Norfloxacin and Griseofulvin. All the synthesized compounds were characterized by IR, 1 H NMR, 13 C and mass spectroscopy. The result of antimicrobial activity data revealed that compound 4f,4g and 4i were found more active against bacterial species and compound 4c, 4d, 4g, 4i and 4jwere found more active against fungal strain, while other compounds shows moderate to law activity against microbes.

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Section: Introductionmentioning

confidence: 99%

An Efficient Solid Phase One Port Synthesis of Novel Triazolo[1,5-a]Pyrimidine Derivatives from 4-(4-Aminophenyl)Morpholin-3-One and Evaluation of their Antimicrobial Activity

Prajapati

Vilapara

Naliapara

2014

ILCPA

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“…However, spectroscopic data and elemental analysis showed the formation of triazolopurine (6). Thus, we have shown that the use of cis-6-aminotriazole (2) Традиционно одним из наи-более распространенных способов превращения азинонов в аминоази-ны является хлордезоксигенирование гетероциклов с последующим ами-нированием хлорпроизводных [1,2]. Особенностью синтеза диаминоазинов таким методом является необходи-мость защиты уже имеющейся ами-ногруппы, например, а цильным фраг-ментом.…”

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6-Aminotriazolo[1,5-a]pyrimidines as precursors of 1,2,4-triazolo[5,1-b]purines

et al. 2015

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Triazolo[5,1-b]purines are rare structural analogues of natural nucleosides and nucleobases purine series. At the same time, prominent representatives of azolopurines exhibit a broad spectrum of antiviral effect, activity against of rheumatoid arthritis, psoriasis, Alzheimer's, Parkinson's and etc. Despite the practical value azolo[5,1-b]purines extremely sparingly represented in the chemical literature, due to the complexity of their synthesis. We suggest a convenient way to synthesize triazolopurines with aminotriazolo[1,5-a]pyrimidines (2) as available starting compounds obtained in good yield by reduction of nitro derivatives (1).

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“…On the other hand, the synthesis of triazolopyrimidine derivatives has attracted a great deal of attention in view of their potent biological and pharmacological activities, especially their antitumor properties [6][7][8][9][10][11][12][13][14][15][16]. This was exemplified by a series of triazolo [4,3-a]pyrimidin-6-sulfonamide derivatives I that demonstrated potent inhibitory effects on the growth of a wide range of cancer cell lines including leukemia and prostate and lung cancer at low dose levels [15].…”

Section: Introductionmentioning

confidence: 99%

Ethyl 7-Methyl-1-(4-nitrophenyl)-5-phenyl-3-(thiophen-2-yl)-1,5-dihydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate

Gomha

Muhammad

Edrees

2017

Molbank

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A novel compound, ethyl 7-methyl-1-(4-nitrophenyl)-5-phenyl-3-(thiophen-2-yl)-1,5-dihydro[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate (7) was synthesized by reaction of N-(4-nitrophenyl)thiophene-2-carbohydrazonoyl chloride (1) with ethyl 6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (2). The mechanism of the studied reaction is discussed and the assigned structure was confirmed by elemental analysis and spectral data. Moreover, the in vitro antitumor activities against human lung (A-549) and human hepatocellular carcinoma (HepG-2) cell lines were determined by the MTT method, and the results indicated a high potency compared with the employed standard antitumor drug (Cisplatin).

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Synthesis and Anti-tumor Activities of Novel [1,2,4]triazolo[1,5-a]pyrimidines

Cited by 65 publications

References 15 publications

An Efficient Solid Phase One Port Synthesis of Novel Triazolo[1,5-a]Pyrimidine Derivatives from 4-(4-Aminophenyl)Morpholin-3-One and Evaluation of their Antimicrobial Activity

An Efficient Solid Phase One Port Synthesis of Novel Triazolo[1,5-a]Pyrimidine Derivatives from 4-(4-Aminophenyl)Morpholin-3-One and Evaluation of their Antimicrobial Activity

6-Aminotriazolo[1,5-a]pyrimidines as precursors of 1,2,4-triazolo[5,1-b]purines

Ethyl 7-Methyl-1-(4-nitrophenyl)-5-phenyl-3-(thiophen-2-yl)-1,5-dihydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate

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