Ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate

Suwito, Hery; Kurnyawaty, Noorma; Haq, Kautsar Ul; Abdulloh, Abdulloh; Indriani, Indriani

doi:10.3390/m998

Cited by 3 publications

(5 citation statements)

References 12 publications

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“…Firstly, the synthesis of the title compound was conducted by a one step multicomponent Biginelli reaction between 4 -bromoacetophenone, 5-aminotetrazole, and 2,4-dimethoxybenzaldehyde in ethanol as solvent, using pTsOH as catalyst [12]. However, we did not get the product.…”

Section: Resultsmentioning

confidence: 99%

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5-(4-Bromophenyl)-7-(2,4-dimethoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine

Haq

Liawati

Abdulloh

et al. 2018

Molbank

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Section: Resultsmentioning

confidence: 99%

“…First is cyclization of a substrate possessing pyrimdine ring, such as ring closure in azidopyrimidine [9]. The second is cyclocondensation of a substrate possessing tetrazole ring, like a cyclocondensation reaction between chalcone [10] with 5-aminotetrazole or using a multicomponent reaction (Biginelli reaction) [5,11,12].…”

Section: Introductionmentioning

confidence: 99%

5-(4-Bromophenyl)-7-(2,4-dimethoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine

Haq

Liawati

Abdulloh

et al. 2018

Molbank

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“…The motivation behind designing such a skeleton is because the presence of a morpholinophenyl group in an organic molecule induces certain biological activities. 108 Suwito and co-workers then extended this method to the facile and regioselective synthesis of a series of dihydrotetrazolopyrimidine compounds 8 using the same domino reaction between 5-aminotetrazole (1), ethyl acetoacetate (7), and various aromatic aldehydes 2 under refluxing conditions with ethanol as the solvent and 4-toluenesulfonic acid (pTSA) as a Brønsted acid (Scheme 15). The prepared compounds exhibited moderate to strong antiproliferative activity on HeLa cancer cell lines.…”

Section: Review Synthesismentioning

confidence: 99%

“…The motivation behind designing such a skeleton is because the presence of a morpholinophenyl group in an organic molecule induces certain biological activities. 108…”

Section: Tetrazolopyrimidine Compoundsmentioning

confidence: 99%

Recent Advances in the Multicomponent Synthesis of Heterocycles Using 5-Aminotetrazole

Javahershenas,

Makarem,

Mei

et al. 2024

Synthesis

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The unique reactivity and beneficial features of the 5-aminotetrazole synthon (1H-tetrazol-5-amine) have made it a versatile and effective building block in the synthesis of heterocyclic compounds. In addition, several drugs containing this scaffold with a wide array of biological properties have been already introduced. Heterocyclic structures are the backbone of many biologically active and industrially important compounds. 5-Aminotetrazole is one of the favored synthons used in the preparation of heterocycle-bearing compounds, especially in multicomponent synthesis. This review highlights a comprehensive overview of the emerging applications of 5-aminotetrazole as a key component in the synthesis of heterocyclic frameworks through multicomponent reactions, reported between 2017 and July 2023.1 Introduction2 5-Aminotetrazole3 Tetrazolopyrimidine Compounds4 Spiro Compounds5 Miscellaneous6 Conclusion

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“…Turunan senyawa pirimidin golongan dihidrotetrazolopirimidin yaitu senyawa etil 5metil-7-(4-morfolinofenil)-4,7dihidrotetrazolo [1,5a] pirimidin-6-karboksilat (MDP) telah berhasil disintesis menggunakan Reaksi Biginelli (Suwito et al, 2018). Senyawa MDP merupakan senyawa baru yang diprediksi memiliki berbagai potensi aktivitas farmakologi yang berperan dalam bidang kesehatan.…”

Section: Pendahuluanunclassified

Studi in Silico Potensi Aktivitas Farmakologi Senyawa Golongan Dihidrotetrazolopirimidin

Kurnyawaty

Suwito

Kusumattaqiin

2021

JCHEM

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Senyawa golongan dihidrotetrazolopirimidin dapat disintesis menggunakan Reaksi Biginelli. Senyawa etil 5-metil-7-(4-morfolinofenil)-4,7-dihidrotetrazolo[1,5a] pirimidin-6-karboksilat (MDP) merupakan senyawa organik baru terdiri atas cincin dihidrotetrazolopirimidin dengan gugus samping morfolinofenil. Penelitian sebelumnya menyebutkan bahwa senyawa pirimidin dan turunannya memiliki berbagai macam aktivitas farmakologi. Pada penelitian ini, senyawa MDP dianalisis menggunakan studi in silico untuk mengetahui potensi yang dimiliki sebagai agen terapi untuk mengatasi masalah kesehatan. Hasil analisis menunjukkan bahwa senyawa MDP berpotensi sebagai antimalaria, antikanker, dan antihiperurisemia dilihat dari binding energy yang bernilai negatif atau rendah. Interaksi senyawa MDP dengan reseptor yang bernilai paling negatif pada saat berinteraksi dengan protein XOD dibandingkan dengan nilai binding energy MDP dengan Kinesin Eg5 dan PfDHODH. Sehingga dapat disimpulkan bahwa senyawa MDP paling potensial jika digunakan sebagai antihiperurisemia dengan nilai binding energy sebesar -8,33 kkal/mol dengan konstanta inhibisi 0,79 µM. Kata kunci: antihiperurisemia, antikanker, antimalaria, dihidrotetrazolopirimidin, in silico Dihydrotetrazolopyrimidine derivatives can be synthezed using the Biginelli Reaction. Ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5a]pyrimidine-6-carboxylate (MDP) is a new organic compound consisting of a dihydrotetrazolopyrimidine ring with morpholinophenyl moiety. Previous studies showed that pyrimidine compounds and their derivatives exhibited various pharmacological activities. In this study, MDP compound was analyzed using in silico studies to determine its potential to be used as therapeutic agent to overcome health problems. The results of the analysis showed that the MDP compound has potential activity as an antimalarial, anticancer, and antihyperuricemia, based on negative or low binding energy. The interaction of MDP compound with XOD protein showed the lowest binding energy compared to Kinesin Eg5 and PfDHODH. Based on the docking experiments performed, it can be concluded that MDP compound showed the most potential to be used as an antihyperuricemia with binding energy of -8.33 kcal/mol and inhibition concentration of 0,79 µM. Keywords: anticancer, antihyperuricemia, antimalarial, dihydrotetrazolopyrimidine, in silico

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Ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate

Cited by 3 publications

References 12 publications

5-(4-Bromophenyl)-7-(2,4-dimethoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine

5-(4-Bromophenyl)-7-(2,4-dimethoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine

Recent Advances in the Multicomponent Synthesis of Heterocycles Using 5-Aminotetrazole

Studi in Silico Potensi Aktivitas Farmakologi Senyawa Golongan Dihidrotetrazolopirimidin

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