54903-09-2Relevant articles and documents
Friedel-crafts acylation of 2(3H)-benzoxazolone: Investigation of the role of the catalyst and microwave activation
Liacha, Messaoud,Yous, Said,Poupaert, Jacques H.,Depreux, Patrick,Aichaoui, Hocine
, p. 1393 - 1397 (1999)
To study the scope and limitations of the use of complexed species of AlCl3 in Friedel-Crafts reactions, we investigated the acctylation and benzoylation of 2(3H)-benzoxazolone and 3-methyl-2(3H)-benzoxazolone varying the amide complexing agent. We replaced dimethylformamide by N-methylformamide, dimethylacetamide, pyrrolidone, N-methylpyrrolidone, tetramethylurea, and dimethylsulfoxide. However, there was no particular advantage of substituting dimethylformamide by another amide ligand. This can probably be ascribed to the fact that the complex formed between AlCl3 and the complexing agent becomes too stable. Alternatively, a route using polyphosphoric acid and microwave activation was explored. The major advantage of running the reaction in a microwave oven was that a good yield was reached in a rather short period of time.
Synthesis of some novel benzoxazolinonylcarboxamides as potential anti-inflammatory agents
Messaoud, Liacha,Wassila, Yahia,Khemissi, Seddiki,Yasmina, Adjeroud,Hanane, Chabane
, p. 331 - 333 (2014)
The synthesis of new 2(3H )-benzoxazolinonylcarboxamides starting from 2-amino-4,6-dimethylpyridine and 2(3H )-benzoxazolone which were designed as anti-inflammatory agents is described. These derivatives were synthesised from 2(3H )-(benzoxazolinon-6-yl)carboxylic acids, which were obtained by Friedel-Crafts acylation of 2(3H )-benzoxazolone derivatives with oxalyl chloride and acetylchloride in the presence of the AlCl3-DMF complex. The constitution of the products was supported by elemental analysis IR and 1H NMR spectral data.
Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)-benzoxazolones
Anil, Baris,Bilginer, Sinan,Demir, Yeliz,Gül?in, Ilhami,Koca, Mehmet
, p. 805 - 818 (2021/07/26)
In this study, a new series of Mannich bases, 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)-benzoxazolones (1a-g), were synthesized by the Mannich reaction. Inhibitory effects of the newly synthesized compounds towards carbonic anhydrases (CAs) and acetylcholinesterase (AChE) enzymes were evaluated to find out new potential drug candidate compounds. According to the inhibitory activity results, Ki values of the compounds 1 and 1a-g were in the range of 12.3 ± 1.2 to 154.0 ± 9.3 nM against hCA I, and they were in the range of 8.6 ± 1.9 to 41.0 ± 5.5 nM against hCA II. Ki values of acetazolamide (AZA) that was used as a reference compound were 84.4 ± 8.4 nM towards hCA I and 59.2 ± 4.8 nM towards hCA II. Ki values of the compounds 1 and 1a-g were in the range of 35.2 ± 2.0 to 158.9 ± 33.5 nM towards AChE. Ki value of Tacrine (TAC), the reference compound, was 68.6 ± 3.8 nM towards AChE. Furthermore, docking studies were done with the most potent compounds 1d, 1g, and 1f (in terms of hCA I, hCA II, and AChE inhibition effects, respectively) to determine the binding profiles of the series with these enzymes. Additionally, the prediction of ADME profiles of the compounds pointed out that the newly synthesized compounds had desirable physicochemical properties as lead compounds for further studies.
New halogenated chalcones with cytotoxic and carbonic anhydrase inhibitory properties: 6-(3-Halogenated phenyl-2-propen-1-oyl)-2(3H)-benzoxazolones
Bilginer, Sinan,Gul, Halise I.,Erdal, Feyza S.,Sakagami, Hiroshi,Gulcin, Ilhami
, (2020/04/23)
In this study, novel halogenated chalcones, 6-(3-halogenated phenyl-2-propen-1-one)-2(3H)-benzoxazolones (2a–n), were synthesized for the first time (except 2a), and their chemical structures were characterized by 1H nuclear magnetic resonance
Synthesis and cytotoxicity of new mannich bases of 6-[3-(3,4,5-trimetoxyphenyl)-2-propenoyl]-2(3h)-benzoxazolone
Gerova, Mariana S.,Ivanova, Yordanka B.,Momekov, Georgi Ts.,Petrov, Ognyan I.
, p. 511 - 516 (2020/04/17)
Background: Chemotherapy is one of the mainstays of cancer treatment, despite the serious side effects of the clinically available anticancer drugs. In recent years increasing attention has been directed towards novel agents with improved efficacy and sel
A Ratiometric Acoustogenic Probe for in Vivo Imaging of Endogenous Nitric Oxide
Reinhardt, Christopher J.,Zhou, Effie Y.,Jorgensen, Michael D.,Partipilo, Gina,Chan, Jefferson
, p. 1011 - 1018 (2018/02/07)
Photoacoustic (PA) imaging is an emerging imaging modality that utilizes optical excitation and acoustic detection to enable high resolution at centimeter depths. The development of activatable PA probes can expand the utility of this technology to allow for detection of specific stimuli within live-animal models. Herein, we report the design, development, and evaluation of a series of Acoustogenic Probe(s) for Nitric Oxide (APNO) for the ratiometric, analyte-specific detection of nitric oxide (NO) in vivo. The best probe in the series, APNO-5, rapidly responds to NO to form an N-nitroso product with a concomitant 91 nm hypsochromic shift. This property enables ratiometric PA imaging upon selective irradiation of APNO-5 and the corresponding product, tAPNO-5. Moreover, APNO-5 displays the requisite photophysical characteristics for in vivo PA imaging (e.g., high absorptivity, low quantum yield) as well as high biocompatibility, stability, and selectivity for NO over a variety of biologically relevant analytes. APNO-5 was successfully applied to the detection of endogenous NO in a murine lipopolysaccharide-induced inflammation model. Our studies show a 1.9-fold increase in PA signal at 680 nm and a 1.3-fold ratiometric turn-on relative to a saline control.
Carboline- and phenothiazine-derivated heterocycles as potent SIGMA-1 protein ligands
Donnier-Maréchal, Marion,Larchanché, Paul-Emmanuel,Le Broc, Delphine,Furman, Christophe,Carato, Pascal,Melnyk, Patricia
, p. 198 - 206 (2014/12/11)
Sigma 1 receptors are associated with neurodegenerative and psychiatric disorders. These receptors, via their chaperoning functions that counteract endoplasmic reticulum stress and block neurodegeneration, may serve as a target for a new generation of antidepressants or neuroprotective agents. The involvement of these receptors has also been observed in neuropathic pain and cancer. Only a few ligands, such as Igmesine and Anavex 2-73, have been involved in clinical trials. Thus the development of sigma 1 ligands is of interest to a new generation of drugs. Previous work in our lab underlined the potency of benzannulated bicyclic compounds as interesting ligands. Herein the work was extended to a series of novel tricyclic compounds. Carboline- and phenothiazine-derivated compounds were designed and synthesized. In vitro competition binding assays for sigma 1 and 2 receptors showed that most of them have high affinity for sigma 1 receptor (Ki = 2.5-18 nM), and selectivity toward sigma 2 receptor, without cytotoxic effects on SY5Y cells.
New heterocyclic chalcones. Part 6. Synthesis and cytotoxic activities of 5- or 6-(3-aryl- 2-propenoyl)-2(3H)-benzoxazolones
Ivanova, Yordanka B.,Momekov, Georgi T.,Petrov, Ognyan I.
, p. 23 - 28 (2013/05/22)
A number of chalcones bearing an oxazole cycle were synthesized by Claisen-Schmidt condensation of 5-acetyl-2(3 H )-benzoxazolone or 6-acetyl-2(3 H )-benzoxazolone and the appropriate aldehydes. The chalcones were evaluated for cytotoxic activity against several tumor cell lines - BV-173 (human B cell precursor leukemia), MCF-7 and MDA-MB-231 (human breast adenocarcinoma) using the MTT-dye reduction assay. The tested compounds exhibit concentration- dependent cytotoxic effects at micromolar concentrations. Exposure of the BV-173 tumor cell line to compound 3f results in strong monoand oligonucleosomal fragmentation of genomic DNA, as evidenced by a 'cell death detection' ELISA kit, which unambiguously indicates that the induction of apoptosis is implicated in the cytotoxic mode of action of the tested compound.
Synthesis, evaluation and docking studies on 3-alkoxy-4-methanesulfonamido acetophenone derivatives as non ulcerogenic anti-inflammatory agents
Bali, Alka,Ohri, Ruchika,Deb, Pran Kishore
experimental part, p. 397 - 405 (2012/04/10)
A series of 3-alkoxy-4-methanesulfonamido acetophenone derivatives were synthesized and evaluated for their anti-inflammatory activity in carrageenan-induced rat paw edema model. The synthesized compounds were also investigated for their gastric ulcerogenic potential. The compounds 4a, 4c and 4d showed comparable anti-inflammatory activity to rofecoxib and indomethacin, the standard drugs taken in both studies and were also non ulcerogenic at the test doses. In silico (docking studies) were done to investigate the hypothetical binding mode of the target compounds to the cyclooxygenase isoenzyme (COX-2). A binding model has been proposed based on the docking studies. Selected physicochemical properties were calculated for theoretical ADME profiling of the compounds and excellent compliance was shown with Lipinski's rules.
Design and synthesis of 3-acyl-2(3H)-benzoxazolone and 3-acyl-2(3H)- benzothiazolone derivatives
Guenadil, Faouzi,Aichaoui, Hocine,Kapanda, Coco N.,Lambert, Didier M.,McCurdy, Christopher R.,Poupaert, Jacques H.
experimental part, p. 67 - 80 (2011/09/20)
A simpler and efficient "green" method using solid sodium hydroxide in a solvent mixture of acetone/water was found to catalyze N-acylation of 2(3H)-benzoxazolones and 2(3H)-benzothiazolones for facile and rapid synthesis of N-acyl derivatives in excellent yields. This method was applied to the synthesis of a series of 132 compounds employing a variety of acyl chlorides. Graphical abstract: [Figure not available: see fulltext.]
