108715-11-3Relevant articles and documents
Iodine-catalysed Bohlmann-Rahtz cyclodehydration reactions
Bagley, Mark C.,Glover, Christian,Chevis, Duncan
, p. 649 - 651 (2005)
The cyclodehydration of Bohlmann-Rahtz aminodienones is catalysed by iodine in ethanol at room temperature to give 2,3,6-trisubstituted pyridines in excellent yield, with total regiocontrol and without the need for chromatographic purification.
New N-halosuccinimide-mediated reactions for the synthesis of pyridines
Bagley, Mark C.,Glover, Christian,Merritt, Eleanor A.,Xiong, Xin
, p. 811 - 814 (2004)
5-Bromo-2,6-dialkylpyridine-4-carboxylates are generated in excellent yield by the Michael addition of enaminoesters and ethynyl ketones followed by bromocyclization using N-bromosuccinimide within 1 hour at 0°C. Treatment of the same aminopentadienone intermediates with N-iodosuccinimide facilitates a low temperature cyclodehydration under very mild conditions to give 2,3,6-trisubstituted pyridines with total regiocontrol.
Novel arylpyridine-based 1,3,4-oxadiazoles: Synthesis, antibacterial, and anti-inflammatory evaluation
Padejjar Vasantha, Sowmya,Poojary, Boja,Bistuvalli Chandrashekarappa, Revanasiddappa
, p. 638 - 650 (2019)
In view of developing novel bioactive compounds, a series of 2-(5-[2-methyl-6-arylpyridin-3-yl]-1,3,4-oxadiazol-2-ylthio)-1-arylethanones (6a–n) were designed and synthesized in good yield. Novel compounds were evaluated for their antibacterial and anti-i
A new one-step synthesis of pyridines under microwave-assisted conditions
Bagley, Mark C,Lunn, Rebecca,Xiong, Xin
, p. 8331 - 8334 (2002)
Tri- or tetrasubstituted pyridines are prepared by microwave irradiation of ethyl β-aminocrotonate and various alkynones in a single synthetic step and with total control of regiochemistry. This new one-pot Bohlmann-Rahtz procedure conducted at 170°C in a
A new mild method for the one-pot synthesis of pyridines
Xiong, Xin,Bagley, Mark C.,Chapaneri, Krishna
, p. 6121 - 6124 (2004)
Polysubstituted pyridines are prepared in good yield and with total regiocontrol by the one-pot reaction of an alkynone, 1,3-dicarbonyl compound and ammonium acetate in alcoholic solvents. This new three-component heteroannulation reaction proceeds under mild conditions in the absence of an additional acid catalyst and has been used in the synthesis of dimethyl sulfomycinamate, the acidic methanolysis degradation product of the sulfomycin family of thiopeptide antibiotics.
Design, synthesis and 2D QSAR study of novel pyridine and quinolone hydrazone derivatives as potential antimicrobial and antitubercular agents
Abdelrahman, Mohamed A.,Salama, Ismail,Gomaa, Mohamed S.,Elaasser, Mahmoud M.,Abdel-Aziz, Marwa M.,Soliman, Dalia H.
, p. 698 - 714 (2017)
The increased development of highly resistant bacterial strains and tuberculosis, constitute a serious public health threat, highlighting the urgent need of novel antibacterial agents. In this work, two novel series of nicotinic acid hydrazone derivatives (6a-r) and quinolone hydrazide derivatives (12a-l) were synthesized and evaluated as antimicrobial and antitubercular agents. The synthesized compounds were evaluated in vitro for their antibacterial, antifungal and antimycobacterial activities. Compounds 6f and 6p bearing the 3,4,5- (OCH3)3 and 2,5-(OCH3)2 benzylidene motifs were the most potent and as antibacterial, antifungal (MIC: 0.49–1.95 μg/mL) and (MIC: 0.49–0.98 μg/mL) respectively and antimycobacterial activity (MIC = 0.76 and 0.39 μg/mL) respectively. Besides, several derivatives, 6e, 6h, 6l-6o, 6q, 6r, 12a, 12b, 12e, 12h, 12k and 12l, exhibited significant antibacterial and antifungal activities with MIC values ranging from 1.95 to 7.81 μg/mL, they also displayed excellent to good activity against Mycobacterium tuberculosis with MIC range from 0.39 to 3.12 μg/mL. In addition, some of the most active compounds were tested for cytotoxic activities against human lung fibroblast normal cells (WI-38) and displayed low toxicity. Moreover, 2D-QSAR models to characterize the descriptors controlling the observed activities, were generated and validated.
One-pot synthesis of pyridines or pyrimidines by tandem oxidation-heteroannulation of propargylic alcohols
Bagley, Mark C.,Hughes, David D.,Sabo, Halima M.,Taylor, Paul H.,Xiong, Xin
, p. 1443 - 1446 (2003)
Pyridines and pyrimidines are prepared in a single step from propargylic alcohols by in situ oxidation with o-iodoxybenzoic acid or manganese dioxide and reaction with enamines or amidines, respectively, under either thermal or microwave-assisted conditions in a new one-pot tandem oxidation-heteroannulation procedure. The reaction of a β-ketoester, propargylic alcohol and ammonium acetate, with in situ oxidation, constitutes a highly facile three-component reaction for the synthesis of pyridines that accomplishes four distinct synthetic operations in one-pot, good yield and with total regiocontrol.
Synthesis, anti-inflammatory activity and in silico studies of some novel morpholine based carboxamides
Honavar, Premanand M.,Kumar, Vasantha,Nikhil,Kumar, Naveen,Sreenivasa,Vishwanatha,Poojary, Boja,Holla, B. Shivarama
, p. 901 - 906 (2020/03/24)
Two series of carboxamides were synthesized from 3-fluoro-4-morpholinoaniline and different substituted aromatic/heterocyclic carboxylic acids. All the compounds were characterized by IR, 1H NMR, 13C NMR and mass spectral data. The n
Substituted aryl pyridine compounds and use thereof
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Paragraph 0389; 0390, (2016/10/07)
The invention discloses substituted aryl pyridine compounds with the structure represented by general formula I shown in the description. All substituent groups in the formula I are defined as in the description. The compounds of general formula I have br
Protective effect of novel substituted nicotine hydrazide analogues against hypoxic brain injury in neonatal rats via inhibition of caspase
Deng, Chang-Bo,Li, Juan,Li, Lu-Yi,Sun, Feng-Jie
supporting information, p. 3195 - 3201 (2016/06/13)
In hypoxic-ischemic injury of the brain of neonates, the level of caspase-3 was found to be aberrantly activated. Its overexpression leads to the alteration of cytoskeleton protein fodrin and loss of DNA repair enzyme which ultimately results in neurological impairment and disability. Concerning this, the present study was intended to develop novel nicotine hydrazide analogues as caspase inhibitors via efficient synthetic route. These compounds were subsequently tested for inhibitory activity against caspase-3 and -7 where they exhibit highly potent activity against caspase-3 revealing compound 5k as most potent inhibitor (IC50 = 19.4 ± 2.5 μM). In Western blot analysis, 5k considerably inhibits the overexpression of caspase-3. The aryl nicotinate of compound 5k, as indicated by molecular docking was found to engage His121 and critical enzyme thiols, i.e., Cys163 of caspase-3 for its potent activity. Moreover, histopathological examination of brain tissues and hippocampus neurons showed that compound 5k considerably improves the brain injury and exert neuroprotective effects in hypoxic-ischemic (HI). In brain homogenate, 5k significantly improves the activity of MDA, SOD, GSH-Px, CAT and T-AOC to exert its beneficial effect against oxidative stress induced by HI injury.
