Next Article in Journal
Foreword to the Proceedings of the 12th National Symposium of Organic Chemistry "Dr. Eduardo Guerreiro", Los Cocos (Córdoba), Argentina, 14-17 November 1999
Previous Article in Journal
Platyconic Acid A, a Genuine Triterpenoid Saponin from the Roots of Platycodon grandiflorum
Article Menu

Export Article

Open AccessArticle
Molecules 2008, 13(11), 2880-2893; doi:10.3390/molecules13112880

Heterocycles [h]-Fused Onto 4-Oxoquinoline-3-Carboxylic Acid, Part VIII [1]. Convenient Synthesis and Antimicrobial Properties of Substituted Hexahydro[1,4]diazepino[2,3-h]quinoline-9-carboxylic acid and Its Tetrahydroquino[7,8-b]benzodiazepine Analog

1
Department of Pharmaceutical Sciences, Faculty of Pharmacy, The University of Jordan, Amman- 11942, Jordan
2
Department of Biopharmaceutics and Clinical Pharmacy, Faculty of Pharmacy, The University of Jordan, Amman-11942, Jordan
3
Department of Chemistry, Faculty of Science, The University of Jordan, Amman-11942, Jordan
*
Author to whom correspondence should be addressed.
Received: 23 October 2008 / Revised: 11 November 2008 / Accepted: 14 November 2008 / Published: 18 November 2008
View Full-Text   |   Download PDF [206 KB, uploaded 18 June 2014]   |  

Abstract

[1,4]Diazepino[2,3-h]quinolone carboxylic acid 3 and its benzo-homolog tetrahydroquino[7,8-b]benzodiazepine-3-carboxylic acid 5 were prepared via PPAcatalyzed thermal lactamization of the respective 8-amino-7-substituted-1,4-dihydroquinoline-3-carboxylic acid derivatives 8, 10. The latter compounds were obtained by reduction of their 8-nitro-7-substituted-1,4-dihydroquinoline-3-carboxylic acid precursors 7, 9 which, in turn, were prepared by reaction of 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydroquinoline-3-carboxylic acid (6) with each of β-alanine and anthranilic acid. All intermediates and target compounds were characterized using elemental analysis, NMR, IR and MS spectral data. The prepared targets and the intermediates have shown interesting antibacterial activity mainly against Gram positive strains. In particular, compound 8 showed good activity against S. aureus (MIC = 0.39 μg/mL) and B. subtilis (MIC = 0.78 μg/mL). Compounds 5a and 9 have also displayed good antifungal activity against C. albicans (MIC = 1.56 μg/mL and 0.78 μg/mL, respectively). None of the compounds tested showed any anticancer activity against solid breast cancer cell line MCF-7 cells or a human breast adenocarcinoma cell line. View Full-Text
Keywords: 7-Chloro-8-nitro-4-oxoquinoline-3-carboxylic acid; β-alanine; diazepino[2; 3- h]quinoline; 2-aminobenzoic acid; quino[7; 8-b]benzodiazepine; SN-Ar reaction; antibacterial activity 7-Chloro-8-nitro-4-oxoquinoline-3-carboxylic acid; β-alanine; diazepino[2; 3- h]quinoline; 2-aminobenzoic acid; quino[7; 8-b]benzodiazepine; SN-Ar reaction; antibacterial activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Al-Hiari, Y.M.; Abu-Dahab, R.; El-Abadelah, M.M. Heterocycles [h]-Fused Onto 4-Oxoquinoline-3-Carboxylic Acid, Part VIII [1]. Convenient Synthesis and Antimicrobial Properties of Substituted Hexahydro[1,4]diazepino[2,3-h]quinoline-9-carboxylic acid and Its Tetrahydroquino[7,8-b]benzodiazepine Analog. Molecules 2008, 13, 2880-2893.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top