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
[1,4]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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2008-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/13/11/2880/ |
| _version_ | 1811299956491812864 |
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| author | Yusuf M. Al-Hiari Rana Abu-Dahab Mustafa M. El-Abadelah |
| author_facet | Yusuf M. Al-Hiari Rana Abu-Dahab Mustafa M. El-Abadelah |
| author_sort | Yusuf M. Al-Hiari |
| collection | DOAJ |
| description | [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. |
| first_indexed | 2024-04-13T06:43:18Z |
| format | Article |
| id | doaj.art-ddb694af54c149be95053c22ca4b8a45 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T06:43:18Z |
| publishDate | 2008-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-ddb694af54c149be95053c22ca4b8a452022-12-22T02:57:40ZengMDPI AGMolecules1420-30492008-11-0113112880289310.3390/molecules13112880Heterocycles [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 AnalogYusuf M. Al-HiariRana Abu-DahabMustafa M. El-Abadelah[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.http://www.mdpi.com/1420-3049/13/11/2880/7-Chloro-8-nitro-4-oxoquinoline-3-carboxylic acidβ-alaninediazepino[23- h]quinoline2-aminobenzoic acidquino[78-b]benzodiazepineSN-Ar reactionantibacterial activity |
| spellingShingle | Yusuf M. Al-Hiari Rana Abu-Dahab Mustafa M. El-Abadelah 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 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 |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | 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 |
| url | http://www.mdpi.com/1420-3049/13/11/2880/ |
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