Synthesis of 2-aziridinyl phosphonates by modified Gabriel-Cromwell reaction and their antibacterial activities

Date

2011-06-01

Author

Doğan, Özdemir
Gözen, Ayşe Gül

Metadata

Show full item record

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

Item Usage Stats

245
views

0
downloads

A set of new aziridinyl phosphonates (4a-g) were synthesized by using the Gabriel-Cromwell reaction and its modified version developed in this study and their structures confirmed by HRMS, IR. and NMR spectra. All the compounds were screened for their antibacterial activity. They all showed comparable moderate to good growth inhibitory activity in reference to ampicillin and streptomycin. (C) 2011 Elsevier Masson SAS. All rights reserved.

Subject Keywords

Organic Chemistry, Pharmacology, Drug Discovery, General Medicine

URI

https://hdl.handle.net/11511/35076

Journal

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

DOI

https://doi.org/10.1016/j.ejmech.2011.03.037

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis of new derivatives of boehmeriasin A and their biological evaluation in liver cancer Guzelcan, Ece Akhan; Baxendale, Ian R.; Atalay, Rengül; Baumann, Marcus (Elsevier BV, 2019-03-15) Two series of boehmeriasin A analogs have been synthesized in short and high yielding processes providing derivatives differing either in the alkaloid's pentacyclic scaffold or its peripheral substitution pattern. These series have enabled, for the first time, comparative studies into key biological properties revealing a new lead compound with exceptionally high activity against liver cancer cell lines in the picomolar range for both well (Huh7, Hep3B and HepG2) and poorly (Mahlavu, FOCUS and SNU475) diffe...
Synthesis of chiral acetoxy lactones via the Baeyer-Villiger oxidation of cyclic aromatic acetoxy ketones Demir, Ayhan Sıtkı; Aybey, Asuman (Elsevier BV, 2008-12-01) The alpha-acetoxylation of indanones and tetralones by using Mn(OAc)(3) followed by the enzyme catalyzed kinetic resolution of acetoxy ketones furnished both of the enantiomers of alpha-acetoxy ketones in good chemical and optical yields. The Baeyer-Villiger oxidation of alpha-acetoxy ketones with m-CPBA, CF(3)SO(3)H, and CH(2)O(2), at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords ph...
Synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from 2-(2-bromoallyl)-1,3-dicarbonyl compounds Demir, Ayhan Sıtkı; Akhmedov, IM; Sesenoglu, O (Elsevier BV, 2002-12-02) 2-(2-Bromoallyl)-1,3-dicarbonyl compounds are converted into beta-enamino, beta-hydrazino esters and ketones, followed by base-promoted cyclization, leading to the formation of the corresponding 1,2,3,5-tetrasubstituted pyrroles. 1,2,4- and 1,2,3,4-Substituted pyrroles are also isolated as minor products. Starting from the 2-(2-bromoallyl)-cyclohexane-1,3-dione the corresponding tetrahydro indolone is prepared in good yield.
Synthesis of various camphor-based chiral pyridine derivatives Tanyeli, Cihangir; Isik, M (Elsevier BV, 2004-07-19) (+)-beta-Hydroxymethylenecamphor 1 and enamines 2a-e were transformed into chiral camphor-based pyridine derivatives 3a-e via a tandem condensation reaction in good yields.
Enzyme catalyzed hydroxymethylation of aromatic aldehydes with formaldehyde. Synthesis of hydroxyacetophenones and (S)-benzoins Demir, Ayhan Sıtkı; Ayhan, P; Igdir, AC; Duygu, AN (Elsevier BV, 2004-07-26) Benzaldehyde lyase from the Pseudomonas Fluorescens catalyzed reaction of aromatic aldehydes with formaldehyde providing 2-hydroxy-1-arylethan-1-one in high yields via an acyloin linkage. Kinetic resolution of rac-benzoins with formaldehyde providing (S)-benzoins and 2-hydroxy-1-arylethan-1-one via C-C bond cleavage and a bond formation reaction.

Citation Formats

Ö. Doğan and A. G. Gözen, “Synthesis of 2-aziridinyl phosphonates by modified Gabriel-Cromwell reaction and their antibacterial activities,” EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, pp. 2485–2489, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/35076.