Molecules 2008, 13(11), 2880-2893; doi:10.3390/molecules13112880
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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; in revised form: 11 November 2008 / Accepted: 14 November 2008 / Published: 18 November 2008
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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.
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

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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.

AMA Style

Al-Hiari YM, Abu-Dahab R, El-Abadelah MM. 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(11):2880-2893.

Chicago/Turabian Style

Al-Hiari, Yusuf M.; Abu-Dahab, Rana; El-Abadelah, Mustafa M. 2008. "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 13, no. 11: 2880-2893.

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