- Synthesis of azabicyclo[3.1.0]amine analogues of anacardic acid as potent antibacterial agents
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Azabicyclo[3.1.0]amine analogues of anacardic acid (16a, 16b, 18a, 18b, 19 and 19b) were synthesized from anacardic acid and tested for their antibacterial activity against Gram positive and Gram negative bacteria. Most of the compounds are having potency at par with ampicillin and inferior with other standard drugs.
- Vempati, Ravi Kumar,Reddy,Alapati, Srinivasa Rao,Dubey
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p. 986 - 994
(2013/06/26)
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- Synthesis of an amino moiety in trovafloxacin by using an in-expensive amidine base, N, N-diethylacetamidine
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The simple and in-expensive amidine base, N.N-diethylacetamidine, has been prepared and utilized in the construction of bicyclic hetero compound, 4 and employed for further reduction of amidic carbonyl groups of 4 by using NaBH 4I2-THF condition which is an efficient and commercially viable method to prepare 5 towards the synthesis of amino moiety I, in Trovafloxacin 2 an antibacterial agent.
- Madhusudhan,Balraju,Rajesh,Narayana, B. Venkata,Reddy
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experimental part
p. 569 - 573
(2009/12/06)
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- Discovery of conformationally rigid 3-azabicyclo[3.1.0]hexane-derived dipeptidyl peptidase-IV inhibitors
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The induction of conformationally restricted N-(aryl or heteroaryl)-3-azabicyclo[3.1.0]hexane derivatives at P2 region of compounds of 2-cyanopyrrolidine class was explored to develop novel DPP-IV inhibitors. The synthesis, structure-activity r
- Sattigeri, Jitendra A.,Andappan, Murugaiah M.S.,Kishore, Kaushal,Thangathirupathy, Srinivasan,Sundaram, Sinduja,Singh, Shuchita,Sharma, Suchitra,Davis, Joseph A.,Chugh, Anita,Bansal, Vinay S.
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scheme or table
p. 4087 - 4091
(2009/04/10)
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- Mechanisms of trovafloxacin hepatotoxicity: Studies of a model cyclopropylamine-containing system
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The mechanism for the hepatotoxicity of trovafloxacin remains unresolved. Trovafloxacin contains a cyclopropylamine moiety which has a potential to be oxidized to reactive intermediate(s) although other putative elements may exist. In this study, a drug model of trovafloxacin containing the cyclopropylamine substructure was synthesized. Chemical oxidation of the drug model by K3Fe(CN)6 and NaClO revealed that both oxidants oxidize this drug model to a reactive α,β-unsaturated aldehyde, 11. The structure of 11 was fully elucidated by LC/MS/MS and NMR analysis. These results suggested that P450s with heme-iron center and myeloperoxidase generating hypochlorous acid in the presence of chloride ion are capable of bioactivating the cyclopropylamine moiety of trovafloxacin. This deleterious metabolism may lead to eventual hepatotoxicity.
- Sun, Qin,Zhu, Ran,Foss Jr., Frank W.,Macdonald, Timothy L.
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p. 6682 - 6686
(2008/03/14)
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- SUBSTITUTED AZABICYCLO HEXANE DERIVATIVES AS MUSCARINIC RECEPTOR ANTAGONISTS
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The present invention relates to a radio telephony network (1) supporting at least one link of a radio channel (6) for a packet data transmission service. The radio telephony network (1) comprises a plurality of network controllers (RNC). Each network con
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- Synthesis of trovafloxacin using various (1α,5α,6α)-3-azabicyclo[3.1.0]hexane derivatives
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Trovafloxacin, a novel broad spectrum antibacterial, contains the unusual (1α,5α,6α)-3-azabicyclo[3.1.0]hexane ring system. The prototype of the industrial synthesis of this ring system and possible mechanistic pathways to exclusive formation of the exo or 6α-nitro derivative 4 are described, which leads to the key 6a-nitro-3-azabicyclo[3.1.0]hexane intermediate 10. The synthesis of 6a-amino-3-azabicyclo[3.1.0]hexane 16 and useful protected cxo 6-amino derivatives 15 and 17 follows from 10. These can be coupled with the 7-chloronaphthyridone 18 to yield protected trovafloxacin compounds 20-22 in good yield. The ethyl ester of trovafloxacin 21 can also be accessed from the product of coupling 19, derived from 18 and the exo 6-nitro-3-azabicyclo[3.1.0]hexane compound 12. Removal of protecting groups from 20-22 with methanesulfonic acid yields trovafloxacin mesylate from which trovafloxacin zwitterion 1 can be liberated with base treatment. Zwitterion l can also be prepared directly from 16 tosylate salt and naphthyridone-2-carboxylic acid 26. The Royal Society of Chemistry 2000.
- Norris, Timothy,Braish, Tamim F.,Butters, Michael,DeVries, Keith M.,Hawkins, Joel M.,Massett, Stephen S.,Rose, Peter R.,Santafianos, Dinos,Sklavounos, Constantine
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p. 1615 - 1622
(2007/10/03)
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- Process for preparing quinolone and naphthyridone carboxylic acids
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Antibacterial quinolone carboxylic acids and naphthyridone carboxylic acids, having an external amino group attached to their 7-substituent are prepared without the use, and subsequent removal, of blocking groups on the external amino group. In a preferre
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- Intermediates in the synthesis of quinoline antibiotics
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This invention relates to compounds of the formulae STR1 wherein R and X are defined as below. These compounds are useful as intermediates in the syntheses of azabicyclo quinoline carboxylic acids having antibacterial activity.
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- Preparation of intermediates in the synthesis of quinoline antibiotics
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This invention relates to novel processes for preparing compounds of the formulae STR1 wherein R and X defined as below. Compounds of the formulae VII are useful as intermediates in the syntheses of azabicyclo quinoline carboxylic acids having antibacteri
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