- Quinone imines with a fused azine ring: I. Synthesis and hydrochlorination of 5-(p-tolylsulfonylimino)quinolin-8-one
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5-(p-Tolylsulfonylimino)quinolin-8-one was synthesized, and its reaction with hydrogen chloride was studied. The reaction leads to formation of 7-chloro-8-hydroxy-5-(p-tolylsulfonylamino)quinoline hydrochloride.
- Belov,Nichvoloda
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- Palladium catalyzed transformation and antimicrobial screening of novel angular azaphenothiazines
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Base mediated condensation reaction between 2-amino-5-bromopyrazine-3[4H]-thione and 7-chloro-5,8-quinolinequinone under anhydrous condition gave 9-bromo-1,8,11-triaza-5H-benzo[a]phenothiazin-5-one. Palladium catalyzed cross-coupling reaction between 9-bromo-1,8,11-triaza-5H-benzo[a]phenothiazin-5-one and four arylated halogeno compounds utilizing Heck-Mizoroki protocol furnished 6-substituted derivatives of the angular tetracyclic heterocycle. Structures were assigned based on spectroscopic and elemental analytical data. Antimicrobial screening of these compounds showed they were biologically active.
- Godwin-Nwakwasi,Okoro,Ijeomah,Agbo,Ezeokonkwo
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p. 742 - 748
(2017/02/10)
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- Substituted oxines inhibit endothelial cell proliferation and angiogenesis
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Two substituted oxines, nitroxoline (5) and 5-chloroquinolin-8-yl phenylcarbamate (22), were identified as hits in a high-throughput screen aimed at finding new anti-angiogenic agents. In a previous study, we have elucidated the molecular mechanism of antiproliferative activity of nitroxoline in endothelial cells, which comprises of a dual inhibition of type 2 human methionine aminopeptidase (MetAP2) and sirtuin 1 (SIRT1). Structure-activity relationship study (SAR) of nitroxoline offered many surprises where minor modifications yielded oxine derivatives with increased potency against human umbilical vein endothelial cells (HUVEC), but with entirely different as yet unknown mechanisms. For example, 5-nitrosoquinolin-8-ol (33) inhibited HUVEC growth with sub-micromolar IC50, but did not affect MetAP2 or MetAP1, and it only showed weak inhibition against SIRT1. Other sub-micromolar inhibitors were derivatives of 5-aminoquinolin-8-ol (34) and 8-sulfonamidoquinoline (32). A sulfamate derivative of nitroxoline (48) was found to be more potent than nitroxoline with the retention of activities against MetAP2 and SIRT1. The bioactivity of the second hit, micromolar HUVEC and MetAP2 inhibitor carbamate 22 was improved further with an SAR study culminating in carbamate 24 which is a nanomolar inhibitor of HUVEC and MetAP2. The Royal Society of Chemistry 2012.
- Bhat, Shridhar,Shim, Joong Sup,Zhang, Feiran,Chong, Curtis Robert,Liu, Jun O.
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supporting information; experimental part
p. 2979 - 2992
(2012/05/07)
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- 6,7-Disubstituted -5,8-quinolinedione derivatives as an antifungal agent
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Novel 6,7-disubstituted-5,8-quinolinedione derivatives of general formula (I) or the process for the preparation thereof, wherein R1is C1-C20alkylmercapto or phenylamino substituted by up to 3 groups selected from halogen, aceto; R2is halogen, thiocyano or C1-C20alkylmercapto, are useful as an antifungal agent.
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Page column 5
(2008/06/13)
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