18782-63-3Relevant academic research and scientific papers
Discovery of 6,7-dihydro-3H-pyrano[4,3-c]isoxazol-3-ones as a new class of pathogen specific anti-leptospiral agents
Ilangovan, Andivelu,Sakthivel, Palaniappan,Sivasankari, Karikalacholan,Mercy, Charles Solomon Akino,Natarajaseenivasan, Kalimuthusamy
, p. 29 - 40 (2017)
A simple and efficient method for the synthesis of a series of 6,7-dihydro-3H-pyrano[4,3-c]isoxazol-3-one derivatives starting from 5-carboalkoxy-2,3-dihydropyranone (5-CDHPs) has been developed. Pyranoisoxazolones 10a-j, dihydronaphthopyran-4-one (DHNPs) class of natural product 12b and 12c and its analogues 12a and 13a-c were preliminarily screened against pathogenic leptospiral serovar Autumnalis strain N2 at various concentrations. Six pyranoisoxazolones, 10b, 10d, 10f, 10g, 10i and 10j which displayed very good anti-leptospiral activity was taken for secondary screening against twelve strains of pathogenic and one non-pathogenic leptospiral serovars. While all the compounds displayed significant anti-leptospiral activity against the pathogenic serovars at MIC of 62.5–500?μg/mL. Compounds 10d, 10g and 10j did not show any significant effect on non-pathogenic serovar. Inhibition of leptospires at a significant level by pyranoisoxazolone 10g was confirmed using RT-qPCR assay. In?vivo treatment of BALB/c mice with compound 10g revealed that, it has 95% survivability against the pathogenic strain Canicola and also showed inhibition of renal colonization of leptospires. Compound 10g was found to show cytotoxicity against THP-1?cells only at higher concentration (≥75?μg/mL). Effective binding of compound 10g with leptospiral outer membrane protein LipL32 observed via in silico molecular docking provided a suitable explanation for pathogen specificity of compound 10g. Antibiotics acting against leptospirosis in human are very few. The results obtained from in?vitro, in?vivo and in silico study reveals that 6,7-dihydro-3H-pyrano[4,3-c]isoxazol-3-ones class of compounds are lead molecules for further development as pathogen specific anti-leptospiral agents.
Simple access to 5-carboalkoxy-2,3-dihydro-4H-pyran-4-ones via domino acylative electrocyclization: The first three step total synthesis of the dihydronaphthopyran-4-one class of natural products
Ilangovan, Andivelu,Sakthivel, Palaniappan
, p. 55150 - 55161 (2015/01/16)
Intermolecular domino C-acylation/6π-oxaelectrocyclization between β-ketoesters and α,β-unsaturated acid chlorides took place readily in the presence of CaCl2 to afford a variety of polysubstituted 5-carboalkoxy-2,3-dihydro-4H-pyran-4-ones, in good yields. The products were successfully exploited as precursors, for a simple and efficient construction of a naphthalene fused pyran-4-one ring system. This intramolecular Friedel-Crafts acylative aromatization approach was useful for the synthesis of the phytogrowth inhibiting dihydronaphthopyranone class of natural products.
A New General Synthesis of 2,2-Dialkyl-2,3-dihydro-4H-pyran-4-ones and Their Application for the in situ Preparation of Electron-Rich Dienes in Carbonyl-Alkyne Exchange Reactions with Acetylenes
Obrecht, Daniel
, p. 27 - 46 (2007/10/02)
The substituted 2,2-dialkyl-2,3-dihydro-4H-pyran-4-ones of type II and III have been prepared by acid-catalyzed cyclization of the corresponding substituted acetylenic ketones I in good to excellent yields (Scheme 1).These 2,2-dialkyl-2,3-dihydro-4H-pyran
A NOVEL SYNTHETIC METHOD OF DIHYDRO-4-PYRONE DERIVATIVES AND ITS APPLICATION TO THE SYNTHESES OF ar-ATLANTONE AND (+/-)-ar-TURMERONE
Sakai, Takashi,Miyata, Kazuyoshi,Ishikawa, Mutsumi,Takeda, Akira
, p. 4727 - 4730 (2007/10/02)
Reaction of 1,3-dihalo-3-methyl-2-butanone with t-butyl acetoacetate (NaH) gave t-butyl 3,4-dihydro-2,2,6-trimethyl-4-oxo-2H-pyran-5-carboxylate via the Favorskii-type rearrangement.Michael addition of 4-methylphenyllithium (CuI) followed by ring cleavage
