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

Date

2020-04-01

Author

Khan, Rehan
Doğan, Özdemir
Guven, Kiymet

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

101
views

0
downloads

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 phosphoric 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.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/36529

Journal

ORGANIC COMMUNICATIONS

DOI

https://doi.org/10.25135/acg.oc.77.20.03.1594

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Asymmetric synthesis of norbornene based 1,4-amino alcohol derivatives and applications in asymmetric transformations Sünbül, Murat; Tanyeli, Cihangir; Department of Chemistry (2005) The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene backbone was performed starting with simple and cheap anhydride 30. Quinine-mediated desymmetrization of anhydride 30 with methanol resulted in (2S,3R)-(-)-cis-hemiester 31 (98% e.e.). Chemoselective amination with HMPTA and NH4OH followed by LAH reduction afforded (2S,3R)-(+)-36 and (2S,3R)-(-)-37, respectively. The amidoester (2S,3R)-(-)-32 was transformed into chiral ligand (2S,3R)-(-)-35 with Grignard reaction followed by LAH reduction. T...
Asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohol derivatives and applications in various asymmetric transformation reactions Odabaş, Serhat; Tanyeli, Cihangir; Department of Chemistry (2007) The asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohols and their applications in asymmetric borane reduction and enantioselective diethylzinc addition to benzaldehyde reactions were performed starting from meso-anhydride 51 that is the cycloadduct of cyclopentadiene and maleic anhydride. The desymmetrization of meso-anhydride 51 was achieved by using quinine or quinidine with very high enantiomeric excess value (up to 98% ee) and with high chemical yield. The quinine-mediated desymmetrizati...
Asymmetric synthesis of norbornene based 1,4-Aminoalcohol derivatives and applications in asymmetric diethylzinc reactions Erdem, Mine; Tanyeli, Cihangir; Department of Chemistry (2007) The asymmetric synthesis of chiral norbornene based 1,4-aminoalcohols and their applications in asymmetric diethylzinc addition reactions was perfomed starting from meso-anhydride 50. The desymmetrization of this meso-anhydride 50 was done by the usage of quinine or quinidine cinchona alkaloids with very high enantiomeric excess values (up to 98% ee) and chemical yields. The Quinidine-mediated desymmetrization of meso-anhydride 50 with methanol gave (2R,3S)-(+)-cis-monoester 51. The amination of this result...
Novel studies on the chemoenzymatic synthesis of polychlorinated bicyclic systems and the synthesis of C2 and C3 symmetric chiral ligands Türkmen, Yunus Emre; Tanyeli, Cihangir; Department of Chemistry (2006) Optically active polychlorinated bicyclic systems are important starting materials for the synthesis of complex target molecules. In the first part of the study, the syntheses of several racemic and meso hexachloronorbornene derivatives were executed successfully, starting from hexachlorocyclopentadiene. The enantio-enriched acetoxymethyl derivative (-)-2 and the hemiester (-)-6 were synthesized in high e.e. values by using several hydrolase type enzymes. The absolute configuration of (-)-2 was determined b...
Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes Dengiz, Çağatay; GUTIERREZ, Gregory D.; SWAGER, Timothy M. (American Chemical Society (ACS), 2017-07-21) The synthesis of a set of naphthazarin-containing polycyclic conjugated hydrocarbons is described herein. Sequential Diels-Alder reactions on a tautomerized naphthazarin core were employed to access the final conjugated systems. Complete conjugation across the backbone can be achieved through complexation with BF2, as observed by (HNMR)-H-1 analysis and UV/vis spectroscopy. Precise synthetic control over the degree of oxidation of naphthazarin quinone Diels-Alder adduct 10 is additionally demonstrated and e...

Citation Formats

R. Khan, Ö. Doğan, and K. Guven, “N-Substituted aziridine-2-phosphonic acids and their antibacterial activities,” ORGANIC COMMUNICATIONS, pp. 51–56, 2020, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/36529.