4-Hydroxy-2-quinolones. 168. Synthesis, chemical and antitubercular properties of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid pyrazin-2-ylamides
1-R-4-Hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid pyrazin-2-ylamides have been synthesized as potential antitubercular agents. In contrast to pyrimidin-2-ylamides the compounds prepared are brominated by molecular bromine in glacial acetic acid at position 6 of the quinolone ring rather tha...
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| Published in | Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 45; no. 9; pp. 1058 - 1068 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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01.09.2009
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| Abstract | 1-R-4-Hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid pyrazin-2-ylamides have been synthesized as potential antitubercular agents. In contrast to pyrimidin-2-ylamides the compounds prepared are brominated by molecular bromine in glacial acetic acid at position 6 of the quinolone ring rather than in the amide part of the molecule. The 1-N-allyl derivative behaves similarly but undergoes halocyclization to give 2-bromomethyl-5-oxo-1,2-dihydro-5H-oxazolo[3,2-a]quinoline-4-carboxylic acid pyrazin-2-ylamide. A comparative analysis of the antimycobacterial properties of the synthesized compounds and their isomeric pyrimidin-2-ylamides has been carried out. |
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| AbstractList | 1-R-4-Hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid pyrazin-2-ylamides have been synthesized as potential antitubercular agents. In contrast to pyrimidin-2-ylamides the compounds prepared are brominated by molecular bromine in glacial acetic acid at position 6 of the quinolone ring rather than in the amide part of the molecule. The 1-N-allyl derivative behaves similarly but undergoes halocyclization to give 2-bromomethyl-5-oxo-1,2-dihydro-5H-oxazolo[3,2-a] quinoline-4-carboxylic acid pyrazin-2-ylamide. A comparative analysis of the antimycobacterial properties of the synthesized compounds and their isomeric pyrimidin-2-ylamides has been carried out. 1-R-4-Hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid pyrazin-2-ylamides have been synthesized as potential antitubercular agents. In contrast to pyrimidin-2-ylamides the compounds prepared are brominated by molecular bromine in glacial acetic acid at position 6 of the quinolone ring rather than in the amide part of the molecule. The 1-N-allyl derivative behaves similarly but undergoes halocyclization to give 2-bromomethyl-5-oxo-1,2-dihydro-5H-oxazolo[3,2- a ]quinoline-4-carboxylic acid pyrazin-2-ylamide. A comparative analysis of the antimycobacterial properties of the synthesized compounds and their isomeric pyrimidin-2-ylamides has been carried out. |
| Author | Slobodzian, S. V Ukrainets, I. V Grinevich, L. A Tkach, A. A Bevz, O. V |
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| Cites_doi | 10.1016/j.bmcl.2007.11.049 10.1128/AAC.46.4.977-981.2002 10.1021/jm020310n 10.1128/AAC.01494-06 10.1007/s10593-009-0367-7 10.1128/AAC.01369-06 10.1128/AAC.01458-06 10.1002/ardp.200700119 10.1007/s10593-009-0297-4 10.1107/S1600536808013378 10.1128/AAC.00356-07 10.3390/11040242 10.2174/157340607780620635 10.1002/9783527616091 |
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| Keywords | X-ray structural analysis antitubercular activity 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides 2-aminopyrazine bromination VITRO ANTIMYCOBACTERIAL T-705 IN-VIVO ACTIVITIES DERIVATIVES PYRAZINE |
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| PublicationTitle | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
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| SubjectTerms | 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides 2-aminopyrazine antitubercular activity bromination Chemistry Chemistry and Materials Science Chemistry, Organic Organic Chemistry Pharmacy Physical Sciences Science & Technology X-ray structural analysis |
| Title | 4-Hydroxy-2-quinolones. 168. Synthesis, chemical and antitubercular properties of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid pyrazin-2-ylamides |
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