35511-21-8Relevant articles and documents
Structural Modifications of the Antiinflammatory Oxicam Scaffold and Preparation of Anticancer Organometallic Compounds
Ashraf, Adnan,Aman, Farhana,Movassaghi, Sanam,Zafar, Ayesha,Kubanik, Mario,Siddiqui, Waseeq Ahmad,Reynisson, Jóhannes,S?hnel, Tilo,Jamieson, Stephen M. F.,Hanif, Muhammad,Hartinger, Christian G.
, p. 361 - 374 (2019)
Nonsteroidal antiinflammatory drugs (NSAIDs) have chemopreventive effects in several cancer types, and the oxicam-based NSAIDs meloxicam and piroxicam exhibit potential to treat cancer. We prepared a series of novel oxicams and coordinated them to RuII(cym)Cl and OsII(cym)Cl moieties (η6-p-cymene = cym). The oxicam ligands acted either as monodentate N-donors or bidentate N,O-chelators, depending upon the ligand structure as well as reaction conditions such as the pH value and solvent used in the reaction. The cytotoxic activity of the complexes toward carcinoma cells was investigated. The isoxazolyl motif-containing ligand 1 and its complexes with RuII(cym)Cl 1a and the Os analogue 1b proved to have anticancer activity with IC50 values in a range similar to that observed for the RuIII investigational drug IT-139, and in general the Os compounds were equally or even slightly more potent than the Ru derivatives. Since meloxicam is known as a selective inhibitor of COX-2, molecular docking studies were carried out to understand the possible interactions of the compounds with COX-2, where the organic ligands gave higher scores than their organometallic counterparts.
Antioxidant potential of new methyl-4-hydroxy-2h-1,2-benzothiazine-3- carboxylate-1,1-dioxide derivatives
Arshad, Muhammad Nadeem,Khan, Islam Ullah,Zia-Ur-Rehman, Muhammad,Shafiq, Muhammad
experimental part, p. 2801 - 2805 (2012/02/02)
An easy synthesis of a series of N-alkyl-1,2-benzothiazine-1,1-dioxide derivatives from commercially available saccharine is reported in order to explore their antioxidant potential. The newly synthesized compounds were characterized by spectroscopic techniques (FT-IR, NMR, MS) and single crystal X-ray diffraction analyses. All the synthesized compounds were screened for their DPPH and FRAP analyses to determine their antioxidant activity.
Effect of structural modification of enol-carboxamide-type nonsteroidal antiinflammatory drugs on COX-2/COX-1 selectivity
Lazer, Edward S.,Miao, Clara K.,Cywin, Charles L.,Sorcek, Ronald,Wong, Hin-Chor,Meng, Zhaoxing,Potocki, Ian,Hoermann, MaryAnn,Snow, Roger J.,Tschantz, Matt A.,Kelly, Terence A.,McNeil, Daniel W.,Coutts, Simon J.,Churchill, Laurie,Graham, Anne G.,David, Eva,Grob, Peter M.,Engel, Wolfhard,Meier, Hans,Trummlitz, Günter
, p. 980 - 989 (2007/10/03)
Meloxicam (5), an NSAID in the enol-carboxamide class, was developed on the basis of its antiinflammatory activity and relative safety in animal models. In subsequent screening in microsomal assays using human COX-1 and COX-2, we discovered that it possessed a selectivity profile for COX-2 superior to piroxicam and other marketed NSAIDs. We therefore embarked on a study of enol-carboxamide type compounds to determine if COX-2 selectivity and potency could be dramatically improved by structural modification. Substitution at the 6- and 7-positions of the 4-oxo-1,2-benzothiazine-3- carboxamide, alteration of the N-methyl substituent, and amide modification were all examined. In addition we explored several related systems including the isomeric 3-oxo-1,2-benzothiazine-4-carboxamides, thienothiazines, indolothiazines, benzothienothiazines, naphthothiazines, and 1,3- and 1,4- dioxoisoquinolines. While a few examples were found with greater potency in the COX-2 assay, no compound tested had a better COX-2/COX-1 selectivity profile than that of 5.
