KaydedilenlerDerginizi ekleyin

Dergiler / Organic Communications / 2020 / Cilt: 13 - Sayı: 2

N-Substituted aziridine-2-phosphonic acids and their antibacterial activities

Rehan KHAN
Özdemir DOĞAN
Kıymet GÜVEN
Sayfa
51–56
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)

In general, all the compounds showed moderate antibacterial activity.

📌 3 Maddede Bu Makale

🎯
Amaç & Hipotez:N-substituted aziridine diethyl phosphonates were synthesized easily in two steps starting from vinyl phosphonate or acetyl phosphonate.
📊
Temel Bulgular & Veri:The corresponding phosphonic acid lithium salt was desalted by the use of Amberlite IRC-50H+ acting as an efficient and recyclable weakly acidic cation exchange promoter.
💡
Sonuç & Katkı:In general, all the compounds showed moderate antibacterial activity.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Alan Parametreleri

Özet

N-substituted aziridine diethyl phosphonates were synthesized easily in two steps starting from vinyl phosphonate or acetyl phosphonate. The controlled mono hydrolysis without opening the aziridine ring under mild reaction conditions was achieved by alkaline solution of LiOH. The corresponding phosphonic acid lithium salt was desalted by the use of Amberlite IRC-50H+ acting as an efficient and recyclable weakly acidic cation exchange promoter. Antimicrobial activity of the synthesized compounds was tested against E. coli ATCC 25922, Staphylococcus aureus (MRSA), Klebsiella pneumoniae NRLL B-4420, Acetobacter baumanii (wild type), Pseudomonas aeroginosa (ATCC 27853) and Enterobacter aerogenes NRLL B-3567. In general, all the compounds showed moderate antibacterial activity.

🔖

Bu Makaleye Atıf Yap

KHAN, R., DOĞAN, Ö., GÜVEN, K. (2020). N-Substituted aziridine-2-phosphonic acids and their antibacterial activities. Organic Communications, Cilt: 13 - Sayı: 2, 51–56. https://ajindex.com/articles/288456

📄 Tam Metin PDF Okuyucu

📄

PDF görüntüleyici hazırlanıyor...

Kaynakça (15)

  1. Naydenova, E. D.; Todorov, P T.; Troev, K. D. Recent synthesis of aminophosphonic acids as potential biological importance. Amino Acids 2010, 38, 23–30
  2. Horsman, G. P.; Zechel, D. L. Phosphonate biochemistry. Chem. Rev. 2017, 117, 5704−5783
  3. Rabinowitz, R. Synthesis of monoesters of phosphonic acids. J. Am. Chem. Soc., 1960, 82, 4564–4567
  4. Huang, J.; Chen, R. An overview of recent advances on the synthesis and biological activity of α- aminophosphonic acid derivatives. Heteroatom Chem. 2000, 11, 480-492
  5. Failla, S.; Finocchiaro, P.; Consiglio, G. A. Syntheses, characterization, stereochemistry and complexing properties of acyclic and macrocyclic compounds possessing α-amino or α-hydroxyphosphonate units. Heteroatom Chem. 2000, 11, 493-504
  6. Zefirov, N. S.; Matveeva, E. D. Catalytic Kabachnik-Fields reaction: new horizons for old reaction. Arkivoc 2008, (i), 1-17
  7. Tarik E. A. Synthetic methods of cyclic α-aminophosphonic acids and their esters. Arkivoc 2014, (i), 21-91
  8. Christensen, B. G.; Beattie, T. R. Ger. Offen. 2011092, 1970; Chem. Abstr. 1971, 74, 42491
  9. Davis, F. A.; Wu, Y. Z.; Yan, H.; Kavirayani, R. P.; McCoull, W. 2H-Azirine 3-phosphonates: A new class of chiral iminodienophiles. asymmetric synthesis of quaternary piperidine phosphonates. Org. Lett. 2002, 4, 655-658
  10. Davis, F. A.; McCoull, W.; Titus, D. D. Asymmetric synthesis of α-methylphosphophenylalanine derivatives using sulfinimine-derived enantiopure aziridine-2-phosphona. Org. Lett. 1999, 1, 1053-1055
  11. Davis, F. A.; Wu, Y.; Yan, H.; McCoull, W.; Prasad, K. R. Asymmetric synthesis of aziridine 2-phosphonates from enantiopure sulfinimines (N-sulfinyl imines). Synthesis of α-amino phosphonates. J. Org. Chem. 2003, 68, 2410-2419
  12. Zygmunt, J. Aziridine-2-phosphonic acid, the valuable synthon for synthesis of 1-amino-2-functionalized ethanephosphonic acids. Tetrahedron 1985, 41, 4979-4982
  13. Khan, R.; Ulusan, S.; Banerjee, S.; Dogan, Ö. Synthesis, characterization and evaluation of cytotoxic activities of novel aziridinyl phosphonic acid derivatives. Chem. Biodiversity 2019, 16, e1900375
  14. Doğan, Ö.; Babiz, H.; Gözen, A. G.; Budak, S. Synthesis of 2-aziridinyl phosphonates by modified GabrielCromwell reaction and their antibacterial activities. Eur. J. Med. Chem. 2011, 46, 2485-2489
  15. Stanković, S.; D'hooghe M.; Catak, S.; Eum H.; Waroquier, M.; Speybroeck, V. V.; De Kimpe, N.; Ha, H. J. Regioselectivity in the ring opening of non-acti