1080-44-0Relevant articles and documents
Design, synthesis and in vitro evaluation studies of sulfonyl-amino-acetamides as small molecule BACE-1 inhibitors
Jain, Priti,Wadhwa, Pankaj K.,Gunapati, Sinduri,Jadhav, Hemant R.
, p. 2567 - 2575 (2016)
The identification of a series of sulfonyl-amino-acetamides as BACE-1 (β-secretase) inhibitors for the treatment of Alzheimer's disease is reported. The derivatives were designed based on the docking simulation study, synthesized and assessed for BACE-1 inhibition in vitro. The designed ligands revealed desired binding interactions with the catalytic aspartate dyad and occupance of S1 and S2′ active site regions. These in silico results correlated well with in vitro activity. Out of 33 compounds synthesized, 12 compounds showed significant inhibition at 10 μM concentration. The most active compound 2.17S had IC50 of 7.90 μM against BACE-1, which was concomitant with results of in silico docking study.
New carboxamide derivatives bearing benzenesulphonamide as a selective COX-II inhibitor: Design, synthesis and structure-activity relationship
Ugwu, David Izuchukwu,Okoro, Uchechukwu Chris,Ahmad, Hilal
, (2017)
Sixteen new carboxamide derivatives bearing substituted benzenesulphonamide moiety (7a-p) were synthesized by boric acid mediated amidation of appropriate benzenesulphonamide with 2-amino-4-picoline and tested for anti-inflammatory activity. One compound 7c showed more potent anti-inflammatory activity than celecoxib at 3 h in carrageenan-induced rat paw edema bioassay. Compounds 7g and 7k also showed good anti-inflammatory activity comparable to celecoxib. Compound 7c appeared selectivity index (COX-2/COX-1) better than celecoxib. Compound 7k appeared selectivity index (COX-2/COX-1) a little higher than the half of celecoxib while compound 7g is non-selective for COX-2. The LD50 of compounds 7c, 7g and 7k were comparable to celecoxib.
Synthesis, crystal structure and antitumor activity of 1d coordination polymer of ca(ii) and na(i) with n-p-tolylsulfonyl-glycine
Tai, Xi-Shi,Li, Fa-Hui
, p. 4401 - 4403 (2013)
D coordination polymer formed by Ca(II) and Na(I) was synthesized by the reaction of calcium perchlorate, NaOH with N-p-tolylsulfonylglycine in the CH3CH2OH/H2O (v:v = 3:1). It was characterized by elemental analysis, IR and X-ray single crystal diffraction analysis. The crystal of the complex belongs to triclinic, space group P-1 with a = 0.95657(10) nm, b = 1.09171(11) nm, c = 1.8292(2) nm, a = 80.6790(10)°, b = 86.831(2)°, g = 89.957(2)°, V = 1.8821(3) nm3, Z = 2, Dc = 1.599 Mg m-3, μ = 0.507 mm-1, F(000) = 936 and final R1 = 0.0981, wR2 = 0.2262. The complex comprises a seven-coordinated Ca(II) center, with a O7 distorted pengonal coordination environment and a six-coordinated Na(I) center, with distorted octahedron environment. The molecules are connected by the oxygen atoms of carboxylates to form one dimensional chain structure. The antitumor activities against gastric cancer cells of free ligand and its Ca(II) complex were studied by MTT method.
Novel Phenoxazinones as potent agonist of PPAR-α: Design, synthesis, molecular docking and in vivo studies
Ugwu, David I.,Okoro, Uchechukwu C.,Mishra, Narendra K.,Okafor, Sunday N.
, (2018)
Background: The use of statin, a 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor for the treatment of dyslipidemia has been associated with dose limiting hepatoxicity, mytotoxicity and tolerability due to myalgias thereby necessitating the synthesis of new drug candidates for the treatment of lipid disorder. Methods: The reaction of appropriate benzenesulphonamide with substituted phenoxazinone in the presence of phenylboronic acid gave the targeted compounds. The molecular docking study were carried out using autodock tool against peroxisome proliferator activated receptor alpha. The in vivo lipid profile were assayed using conventional methods. The kidney and liver function test were carried out to assess the effect of the derivatives on the organs. The LD50 of the most active derivatives were determined using mice. Results: The targeted compounds were successfully synthesized in excellent yields and characterized using spectroscopic techniques. The results of the molecular docking experiment showed that they were good stimulant of peroxisome proliferator activated receptor alpha. Compound 9f showed activity at Ki of 2.8 nM and binding energy of 12.6 kcal/mol. All the compounds tested reduced triglyceride, total cholesterol, low density lipoprotein cholesterol and very low density lipoprotein cholesterol level in the mice model. Some of the reported compounds also increased high density lipoprotein cholesterol level in the mice. The compounds did not have appreciable effect on the kidney and liver of the mice used. The LD50 showed that the novel compounds have improved toxicity profile. Conclusion: The synthesis of fifteen new derivatives of carboxamides bearing phenoxazinone and sulphonamide were successful. The compounds possessed comparable activity to gemfibrozil. The reported compounds had better toxicity profile than gemfibrozil and could serve as a replacement for the statins and fibrate class of lipid agents.
Synthesis, characterization, and biological activity of five new mixed-ligand palladium(II) complexes with ethylenediamine and 4-toluenesulfonyl-L-amino acid dianion
Zhang, Jinchao,Ma, Lili,Zhang, Fangfang,Zhang, Zhilei,Li, Luwei,Wang, Shuxiang
, p. 239 - 250 (2012)
Five new palladium(II) complexes with 4-toluenesulfonyl-L-amino acid dianion and en, [Pd(en)(TsserNO)] (1), [Pd(en)(TsglyNO)] (2), [Pd(en)(TsalaNO)]·1.5H2O (3), [Pd(en)(TsleuNO)]·H 2O (4), and [Pd(en)(TspheNO)]·2H2O (5), have been synthesized and characterized by elemental analysis, IR, UV, 1H NMR, and mass spectrometry. Crystal structure of 1 has been determined by X-ray diffraction analysis. The cytotoxicity was tested by MTT and SRB assays. The results indicate 1-5 exert cytotoxic effects against HL-60, Bel-7402, BGC-823, and KB cell lines and 5 displays the best cytotoxicity. The structure-activity relationships suggest that both amino acid and N-containing ligands have important effects on cytotoxicity. Copyright
Synthesis, characterization, and cytotoxicity of mixed-ligand complexes of platinum(II) with 2,2′-bipyridine and 4-toluenesulfonyl-L-amino acid dianion
Zhang, Jin Chao,Li, Luwei,Ma, Lili,Zhang, Fangfang,Wang, Shuxiang
, p. 1695 - 1706 (2011)
Five new platinum(II) complexes (1-5) with 4-toluenesulfonyl-L-amino acid dianion and 2,2′-bipyridine (bipy) have been synthesized and characterized by elemental analysis, IR, UV, 1H-NMR, 13C-NMR, and mass spectra. The crystal structure of 1 has been determined by X-ray diffraction analysis. Cytotoxicity was tested by 3-(4,5-dimethylthiazol-2-yl)-2,5- diphenyltetrazolium bromide (MTT) and sulforhodamine B (SRB) assays. The results indicate that 1-5 exert cytotoxic effects with selectivity against tested carcinoma cell lines; 5 displays better cytotoxicity against BGC-823, Bel-7402, and KB cell lines, while 1 has better cytotoxicity against KB cell line. The 4-toluenesulfonyl- L-amino acid dianions have important effects on cytotoxicity; when 4-toluenesulfonyl-L-amino acid dianions are 4-toluenesulfonyl-L-glycine and 4-toluenesulfonyl-L-phenylalanine, the complexes show better cytotoxicity.
Chiral Br?nsted Acid Catalyzed Enantioselective Dehydrative Nazarov-Type Electrocyclization of Aryl and 2-Thienyl Vinyl Alcohols
Jin, Jianwen,Zhao, Yichao,Gouranourimi, Ali,Ariafard, Alireza,Hong Chan, Philip Wai
, p. 5834 - 5841 (2018)
An efficient chiral Br?nsted acid-catalyzed enantioselective dehydrative Nazarov-type electrocyclization (DNE) of electron-rich aryl- and 2-thienyl-β-amino-2-en-1-ols is described. The 4π conrotatory electrocyclization reaction affords access to a wide variety of the corresponding 1H-indenes and 4H-cyclopenta[b]thiophenes in excellent yields of up to 99% and enantiomeric excess (ee) values of up to 99%. Experimental and computational studies based on a proposed intimate contact ion-pair species that is further assisted by hydrogen bonding between the amino group of the substrate cation and chiral catalyst anion provide insight into the observed product enantioselectivities.
Synthesis, characterization, and cytotoxicity of complexes of palladium(II) with 1,4-diaminobutane/1,3-diaminopropane and 4-toluenesulfonyl-L-amino acid dianion
Ma, Lili,Zhang, Jinchao,Zhang, Fangfang,Chen, Chao,Li, Luwei,Wang, Shuxiang,Li, Shenghui
, p. 3160 - 3173 (2012)
Eight new palladium(II) complexes with 4-toluenesulfonyl-L-amino acid dianion and 1,4-dab/1,3-dap, [Pd(1,4-dab)(TsglyNO)]H2O (1), [Pd(1,4-dab)(TsvalNO)] (2), [Pd(1,4-dab)(TsleuNO)] (3), [Pd(1,4-dab)(TsileNO)] (4), [Pd(1,4-dab)(TsserNO)]0.5H2O (5), [Pd(1,4-dab)(TspheNO)]0. 5H2O (6), [Pd(1,4-dab)(TsthrNO)]H2O (7), and [Pd(1,3-dap)(TsserNO)] (8), have been synthesized and characterized by elemental analysis, IR, UV, 1H NMR, and mass spectrometry. Crystal structure of 8 has been determined by X-ray diffraction. The cytotoxicities were tested by MTT assay. The results indicate the complexes exert cytotoxic effects against HL-60 and Bel-7402. The structure-activity relationship suggests that both amino acids and N-containing ligands have important effects on cytotoxicity, but the IC50 values do not show definite correlation with variation of these ligands.
β-cyclodextrin-catalyzed monosulfonylation of amines and amino acids in water
Sridhar,Srinivas,Kumar, V. Pavan,Narender,Rao, K. Rama
, p. 1873 - 1876 (2007)
A mild and efficient procedure has been developed for the first time under biomimetic conditions for the monosulfonylation of various amines and amino acids catalyzed by β-cyclodextrin in water at room temperature to afford the corresponding sulfonamides in high yields.
Inducing Endoplasmic Reticulum Stress to Expose Immunogens: A DNA Tetrahedron Nanoregulator for Enhanced Immunotherapy
Li, Yanhua,Zhang, Xia,Wan, Xiuyan,Liu, Xiaohan,Pan, Wei,Li, Na,Tang, Bo
, (2020)
Immunogenic cell death (ICD) is an important modulation type for stimulating anticancer immune responses and amplifying immunotherapy efficacy. When ICD occurs, endoplasmic reticulum (ER) stress plays a vital role for exposing immunogens. Herein, a functionalized DNA tetrahedron nanoregulator to specifically trigger ER stress for enhancing cancer immunotherapy is designed. The nanoregulator can target ER organelles by binding to the sulfonamide receptor of cancer cells. Then glucose depletion and reactive oxygen species generation cause a strong ER stress response to induce ICD to expose tumor immunogens. Thereafter, the dendritic cell (DC) maturation is promoted, and T cell proliferation and infiltration are stimulated to advance cancer immunotherapy. Combined with immune checkpoint inhibitor (α-PD-1), the ER stress triggered nanoregulator exhibits significant suppression for breast cancer and melanoma.
