Dergiler / Organic Communications / 2021 / Cilt: 14 - Sayı: 4

Design, synthesis and antimicrobial screening of some new thienopyrimidines

Sayfa
334–345
DOI
—
🏛️Bu makalenin bibliyografik verileri ve tam metin bağlantısı DergiPark üzerinden sağlanmıştır.
DergiPark Kaydı ↗
✨

Yapay Zeka Hızlı Bakış & Çıkarımlar

AI Insight
⚡ TL;DR(1 Cümlede Hızlı Çıkarım)

Furthermore, the synthesized compounds were tested for their antimicrobial activity against different strains of bacteria and fungi, and the results obtained showed good to moderate activity with almost all the strains

📌 3 Maddede Bu Makale

🎯
Amaç & Hipotez:Heterocyclic compounds play an important role in our life due to their biological importance in the struggle of microorganisms.
📊
Temel Bulgular & Veri:Herein, a series of novel hybrid compounds of thienopyrimidine with triazine and pyrimidine scaffolds were synthesized starting from difunctionalized compound 5-amino-4-phenyl-2-(p-tolylamino)thieno[2,3- d]pyrimidine-6-carbonitrile (1).
💡
Sonuç & Katkı:Furthermore, the synthesized compounds were tested for their antimicrobial activity against different strains of bacteria and fungi, and the results obtained showed good to moderate activity with almost all the strains
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Alan Parametreleri

Özet

Heterocyclic compounds play an important role in our life due to their biological importance in the struggle of microorganisms. Herein, a series of novel hybrid compounds of thienopyrimidine with triazine and pyrimidine scaffolds were synthesized starting from difunctionalized compound 5-amino-4-phenyl-2-(p-tolylamino)thieno[2,3- d]pyrimidine-6-carbonitrile (1). Moreover, the diazotization of compound 1 with sodium nitrite in an acidic medium gave the chloro-triazine compound 2 which was subjected to the nucleophilic substitution of chlorine atom with different nucleophiles delivered compounds 3a-5c. Furthermore, the reaction of compound 1 with carbon disulfide led to the formation of dithione derivative 6 which was alkylated with ethyl chloroacetate to give compound 7, on the other hand, the reaction of compound 1 with phenyl isothiocyanate produced 4-imino-3,9-diphenyl-7-(p-tolylamino)-3,4- dihydropyrimido[4',5':4,5]thieno [2,3-d]pyrimidine-2(1H)-thione (8), while acylation of the amino group in compound 1 with acetic anhydride gave compound 9. All synthesized compounds were characterized by elemental and spectral analysis techniques (IR, 1H NMR, 13C NMR, Mass spectroscopy). Furthermore, the synthesized compounds were tested for their antimicrobial activity against different strains of bacteria and fungi, and the results obtained showed good to moderate activity with almost all the strains

🔖

Bu Makaleye Atıf Yap

TOLBA, M. S., SAYED, M., DEAN, A. M. K. E., HASSANİEN, R., RAHEEM, S. A. A. A., AHMED, M. (2021). Design, synthesis and antimicrobial screening of some new thienopyrimidines. Organic Communications, Cilt: 14 - Sayı: 4, 334–345. https://ajindex.com/articles/419572

Kaynakça (12)

  1. Parveen, H.; Alatawi, R.A.S.; El Sayed, N.H.; Hasan, S.; Mukhtar, S.; Khan, A.U. Synthesis, characterization and biological evaluation of some novel nitrogen and sulphur containing organometallic heterocycles. Arab. J. Chem. 2017, 10, 1098–1106
  2. Mermer, A.; Keles, T.; Sirin, Y. Recent studies of nitrogen containing heterocyclic compounds as novel antiviral agents: A review. Bioorg. Chem. 2021, 114, 105076
  3. Jang, H.J.; Kim, S.M.; Rho, M.C.; Lee, S.W.; Song, Y.H. Synthesis of thienopyrimidine derivatives as inhibitors of STAT3 activation induced by IL-6. J. Microbiol. Biotechnol. 2019, 29, 856–862
  4. Abdel-Megid, M.; Elmahdy, K.M.; Elkazak, A.M.; Seada, M.H.; Mohamed, O.F. Chemistry of thienopyrimidines and their biological applications. J. Pharm. Appl. Chem. 2016, 2, 103–127
  5. Ali, E.M.H.; Abdel-Maksoud, M.S.; Oh, C.H. Thieno[2,3-d]pyrimidine as a promising scaffold in medicinal chemistry: Recent advances. Bioorg. Med. Chem. 2019, 27, 1159–1194
  6. Rashad, A.E.; Shamroukh, A.H.; Abdel-Megeid, R.E.; Mostafa, A.; El-Shesheny, R.; Kandeil, A.; Ali, M.A.; Banert, K. Synthesis and screening of some novel fused thiophene and thienopyrimidine derivatives for antiavian influenza virus (H5N1) activity. Eur. J. Med. Chem. 2010, 45, 5251–5257
  7. Ibrahim, Y.A.; Elwahy, A.H.M.; Kadry, A.M. Thienopyrimidines: Synthesis, reactions, and biological activity. Adv. Heterocycl. Chem. 1996, 65, 235–281
  8. Zhuang, J.; Ma, S. Recent Development of pyrimidine-containing antimicrobial agents. ChemMedChem 2020, 15, 1875–1886
  9. El-Dash, Y.; Elzayat, E.; Abdou, A.M.; Hassan, R.A. Novel thienopyrimidine-aminothiazole hybrids: Design, synthesis, antimicrobial screening, anticancer activity, effects on cell cycle profile, caspase-3 mediated apoptosis and VEGFR-2 inhibition. Bioorg. Chem. 2021, 114, 105137
  10. El-Sayed, W.A.; Ali, O.M.; Zyada, R.A.F.; Mohamed, A.A.; Abdel-Rahman, A.A.H. Synthesis and antimicrobial activity of new substituted thienopyrimidines, their tetrazolyl and sugar derivatives. Acta Pol. Pharm. - Drug Res. 2012, 69, 439–447
  11. Barrows, R.D.; Hammill, J.T.; Tran, M.C.; Falade, M.O.; Rice, A.L.; Davis, C.W.; Emge, T.J.; Rablen, P.R.; Kiplin Guy, R.; Knapp, S. Evaluation of 1,1-cyclopropylidene as a thioether isostere in the 4-thiothienopyrimidine (TTP) series of antimalarials. Bioor. Med. Chem. 2020, 28, 115758
  12. Gonzàlez Cabrera, D.; Douelle, F.; Le Manach, C.; Han, Z.; Paquet, T.; Taylor, D.; Njoroge, M.; Lawrence, N.; Wiesner, L.; W