14442-25-2Relevant academic research and scientific papers
Design and synthesis of novel anti-inflammatory/anti-ulcer hybrid molecules with antioxidant activity
Balaini, Ajitesh,Bali, Alka,Chaudhari, Bhim Bahadur
, p. 994 - 1006 (2021/11/30)
Background: NSAIDs are the most widely prescribed medications worldwide for their anti-inflammatory, antipyretic, and analgesic effects. However, their chronic use can lead to several adverse drug events including GI toxicity. The selective COX-2 inhibitors developed as gastro-sparing NSAIDs also suffer from serious adverse effects which limit their efficacy. Objective: Local generation of reactive oxygen species is implicated in NSAID-mediated gastric ul-ceration and their combination with H2 antagonists like famotidine reduces the risk of ulcers. The objective of this work was to design and synthesize novel methanesulphonamido isoxazole derivatives by hybridizing the structural features of NSAIDs with those of antiulcer drugs (ranitidine, fa-motidine, etc.) to utilize a dual combination of anti-inflammatory activity and reducing (antioxidant) potential. Methods: The designing process utilized three dimensional similarity studies and utilized an isoxa-zole core having a potential for anti-inflammatory as well as radical scavenging antioxidant activity. The compounds were assayed for their anti-inflammatory activity in established in vivo models. The in vitro antioxidant activity was assessed in potassium ferricyanide reducing power (PFRAP) assay employing ascorbic acid as the standard drug. Results: Compounds 5, 6, 9 and 10 showed anti-inflammatory activity comparable to the standard drugs and were also found to be non-ulcerogenic at the test doses. Compounds 6-10 exhibited good antioxidant effect in the concentration range of 1.0-50.0 μmol/ml. The test compounds were also found to comply with the Lipinski rule suggesting good oral absorption. Conclusion: A new series of isoxazole based compounds is being reported with good anti-inflammatory activity coupled with antioxidant potential as gastro-sparing anti-inflammatory agents.
Catalyst control in positional-selective C-H alkenylation of isoxazoles and a ruthenium-mediated assembly of trisubstituted pyrroles
Kumar, Pravin,Kapur, Manmohan
, p. 2134 - 2138 (2019/03/26)
High levels of catalyst control are demonstrated in determining the positional selectivity in C-H alkenylation of isoxazoles. A cationic rhodium-mediated, strong-directing group promotes C(sp2)-H activation at the proximal aryl ring whereas, the palladium-mediated electrophilic metallation leads to the C(sp2)-H activation at the distal position of the directing group. Synthetic elaboration of this C-H alkenylation product via ruthenium and copper co-catalysis leads to an efficient method for the assembly of densely substituted pyrroles.
Heterocycle-heterocycle strategies: (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1 H-indoles, and quinolin-4(1 H)-ones
Coffman, Keith C.,Palazzo, Teresa A.,Hartley, Timothy P.,Fettinger, James C.,Tantillo, Dean J.,Kurth, Mark J.
supporting information, p. 2062 - 2065 (2013/06/05)
Reductive heterocycle-heterocycle (heterocycle → heterocycle; H-H) transformations that give 4-aminoquinolines, 3-acylindoles, and quinolin-4(1H)-ones from 2-nitrophenyl substituted isoxazoles are reported. When this methodology is applied to 3,5-, 4,5-,
Synthesis of novel isoxazole-benzoquinone hybrids via 1,3-dipolar cycloaddition reaction as key step
Ravi Kumar,Behera, Manoranjan,Raghavulu,Jaya Shree,Yennam, Satyanarayana
scheme or table, p. 4108 - 4113 (2012/08/28)
An efficient method for the preparation of novel 2-(5-arylisoxazol-3-yl) cyclohexa-2,5-diene-1,4-dione hybrids via 1,3-dipolar cycloaddition followed by an oxidation reaction using ceric ammonium nitrate (CAN) has been described. Using this method, various aryl as well as alkyl substituted isoxazole-benzoquinone hybrids were synthesized in high yields.
On the Oximation of Diaryl-β-diketones
Bandiera, T.,Gruenanger, P.,Albini, F. Marinone
, p. 1423 - 1428 (2007/10/02)
The reaction of asymmetrically substituted β-diketones with hydroxylamine to give 3,5-diarylisoxazoles has been re-investigated, and has been found to occur with a low degree of site-selectivity unless steric effects are operating.The isoxazole that has t
Synthesis of Simple Quinoline Alkaloids. A Novel Quinazoline Synthesis
Thomsen, Ib,Torssell, Kurt B. G.
, p. 309 - 313 (2007/10/02)
2-Alkyl (aryl), 4-amino-substituted quinolines are prepared in two steps by cycloaddition of 2-nitrobenzaldoximes with acetylenes and subsequent reductive cleavage of the intermediate isoxazole in acetic acid.Diazotization of the 4-aminoquinolines gives t
