1576-35-8Relevant academic research and scientific papers
Facile synthesis of new N -sulfonamidyl-4-thiazolidinone derivatives and their biological evaluation
Subhedar, Dnyaneshwar D.,Shaikh, Mubarak H.,Kalam Khan, Firoz A.,Sangshetti, Jaiprakash N.,Khedkar, Vijay M.,Shingate, Bapurao B.
, p. 3047 - 3058 (2016)
The one-pot three-component syntheses of new N-sulfonamide-thiazolidin-4-one derivatives were carried out in excellent yield using [HDBU][HSO4] as an ionic liquid under solvent-free conditions. The newly synthesized compounds were screened against fungal strains and a number of compounds were seen to display excellent antifungal activity. In addition, the synthesized compounds were screened for their scavenging activity of the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and showed very good antioxidant activity. Finally, theoretical predictions derived from molecular docking studies against the potential target sterol 14α-demethylase (CYP51) helped establish a link between the observed biological activity and the binding affinity, thereby providing insights into the specific bonding and non-bonding interactions governing the activity.
Synthesis, Molecular Modeling, and Evaluation of Novel Sulfonylhydrazones as Acetylcholinesterase Inhibitors for Alzheimer's Disease
Fernandes, Thais B.,Cunha, Micael R.,Sakata, Renata P.,Candido, Thalita M.,Baby, André R.,Tavares, Maurício T.,Barbosa, Euzébio G.,Almeida, Wanda P.,Parise-Filho, Roberto
, (2017)
Alzheimer's disease (AD) is the most common type of dementia and related to the degeneration of hippocampal cholinergic neurons, which dramatically affects cognitive ability. Acetylcholinesterase (AChE) inhibitors are employed as drugs for AD therapy. Three series of sulfonylhydrazone compounds were designed, and their ability to inhibit AChE was evaluated. Fifteen compounds were synthesized and twelve of them had IC50 values of 0.64–51.09 μM. The preliminary structure–activity relationships indicated that the methylcatechol moiety and arylsulfonyl substituents generated better compounds than both the benzodioxole and alkylsulfonyl chains. Molecular dynamics studies of compound 6d showed that the interaction with the peripheral binding site of AChE was similar to donepezil, which may explain its low IC50 (0.64 μM). Furthermore, the drug-likeness of 6d suggests that the compound may have appropriate oral absorption and brain penetration. Compound 6d also presented antiradical activity and was not cytotoxic to LL24 cells, suggesting that this compound might be considered safe. Our findings indicate that arylsulfonylhydrazones may be a promising scaffold for the design of new drug candidates for the treatment of AD.
Green synthesis of novel pyrazolo-fused benzophenazines using H3PW12O40 as efficient and recyclable catalyst under microwave irradiation
Mohebat, Razieh,Dehgan, Parisa,Yazdani-Elah-Abadi, Afshin
, p. 1259 - 1265 (2018)
A high-yield, atom-efficient, and green protocol for the synthesis of novel pyrazolo-fused benzophenazines utilizing a multicomponent condensation reaction between 2-hydroxynaphthalene-1,4-dione, o-phenylenediamine, aromatic aldehydes, and 4-methylbenzenesulfonohydrazide in the presence of phosphotungstic acid (H3PW12O40) under microwave irradiation (MWI) in EtOH is reported. We provide a novel series of 1H-benzo[a]pyrazolo[3,4-c]phenazine derivatives interesting for biological screening tests. This protocol offers several advantages satisfying many principles of green chemistry, including atom economy, energy saving, clean reactions, inexpensive reagents, reusability of H3PW12O40, the absence of any tedious work-up or purification, and avoidance of hazardous or toxic reagents/catalysts/solvents.
Synthesis and potential anticonvulsant activity of new aryl sulfonyl semicarbazide derivatives
Nie, Yousong,Zhong, Min,Jiang, Zhiyuan,Sun, Jian,Gao, Yangguang,Ding, Fei,Li, Hang,Zhang, Yongmin,He, Xianran
, p. 1425 - 1432 (2016)
In the present study on the development of new anticonvulsants, twelve new aryl sulfonyl semicarbazide derivatives were synthesized and tested for anticonvulsant activity using maximal electroshock (MES), subcutaneous pentylenetetrazole screens. Their neurotoxicity was determined by the rotorod test. The most active compound 5i showed the MES-induced seizures with ED50 value of 7.3?mg/kg and TD50 value of 402.3?mg/kg after intraperitoneally injection to mice, which provided compound 5i with a protective index (TD50/ED50) of 55.1 in the MES test.
Synthesis, biological activities and molecular docking simulation of hydrazone scaffolds of carvacrol, thymol and eugenol
Rajput, Jamatsing D.,Bagul, Suresh D.,Bendre, Ratnamala S.
, p. 6601 - 6616 (2017)
In present work, we report the synthesis of 12 new hydrazones and sulfonyl hydrazones linkage containing carvacrol, thymol and eugenol derivatives by simple condensation reactions. Synthesized derivatives have been characterized by 1H NMR, 13C NMR, LC–MS, and X-ray single crystallography techniques, and these derivatives were screened for anticancer testing by using sulforhodamine B assay and anti-oxidant testing by using DPPH assay. Docking studies of all the derivatives against the active site of human heme oxygenase-1 indicated that interaction with the maximum site of the amino acid residue of human heme oxygenase-1 was crucial for anti-oxidant activity. The results show that all derivatives possess interesting biological activities.
Synthesis, molecular structure, photoluminescence, multiple interaction, chemical reactivity and first hyperpolarizability analysis of ethyl 2-cyano-3-{5-(4-methylbenzenesulfonyl)-hydrazonomethyl]-1H-pyrrol-2-yl} -acrylate: Experimental and quantum chemical approaches
Singh,Rawat, Poonam,Kumar, Amit
, p. 140 - 149 (2014)
A detailed spectroscopic, molecular structure, photoluminescence, multiple interaction, chemical reactivity and first hyperpolarizability analysis of a newly synthesized ethyl 2-cyano-3-{5-[(4-methylbenzenesulfonyl)-hydrazonomethyl] -1H-pyrrol-2-yl}-acrylate (ECMHPA) has been carried out. TD-DFT is used to find various electronic excitations and their nature within molecule. The emission spectra show photoluminescence behavior of title molecule in yellow region. The red shift in both the proton donor (pyrrole NH) and proton acceptor (SO) group designates the presence of intermolecular hydrogen bonding N1H2a?O49 and N46H47a?O4. The binding energy of dimer formation has been calculated to be 12.12 kcal/mol after basis set superposition error (BSSE) correction. The global electrophilicity index (ω = 5.44 eV) shows that ECMHPA is a strong electrophile. First hyperpolarizability (β0) of ECMHPA has been computed to evaluate non-linear optical (NLO) response of the investigated molecule.
Copper-Catalyzed Radical Cascade Cyclization to Access 3-Sulfonated Indenones with the AIE Phenomenon
Sun, Kai,Chen, Xiao-Lan,Li, Shi-Jun,Wei, Dong-Hui,Liu, Xiao-Ceng,Zhang, Yin-Li,Liu, Yan,Fan, Lu-Lu,Qu, Ling-Bo,Yu, Bing,Li, Kai,Sun, Yuan-Qiang,Zhao, Yu-Fen
, p. 14419 - 14430 (2018)
An efficient copper-catalyzed radical cascade cyclization strategy was developed, by which a wide variety of 3-sulfonyl substituted indenones were prepared in one pot via reaction of 2-alkynylbenzonitriles with sulfonyl hydrazides in the presence of TBHP and CuI under mild reaction conditions. Much more importantly, the 3-sulfonyl indenones, synthesized through our newly developed copper-catalyzed radical cascade cyclization strategy, were found to own typical aggregation-induced emission (AIE) properties, showing orange to red emission with large Stokes shift (more than 135 nm). In addition, such newly found AIEgens could be successfully used in live cell imaging, exhibiting excellent biocompatibility and application potential.
Synthesis, characterization and biological evaluation of some novel sulfonylthiosemicarbazides
?enkarde?, Sevil,Han, ?hsan,Han?er, Hakan,Abbak, Mürüvvet,?evik, ?zge,Güniz Kü?ükgüzel
, p. 1164 - 1170 (2019)
A series of thiosemicarbazides were synthesized and structurally characterized by spectroscopic techniques (NMR, FT-IR) besides elemental analysis. These compounds were evaluated for their cytotoxicity against human breast cancer cell line MCF7 and prostate cancer cell line PC3 and nonmalignant fibroblast L929 cell line by MTT assay. Among the compounds, N-[2-(4-chlorophenyl)ethyl]-2-[(4-methylphenyl)sulfonyl]hydrazinecarbothioamide (3d) and 2-[(4-methylphenyl)sulfonyl]-N-[4-(trifluoromethoxy)phenyl]hydrazinecarbothioamide (3f) were found to display significant cytotoxicity with IC50 of 13.87 μM (against PC3 cell line) and 1.47 μM (against MCF7 cell line), respectively. These compounds were non-cytotoxic to normal cell line with IC50>100 μM. Western blotting studies demonstrated that compound 3f induced apoptosis and caused cell death in the MCF7 and PC3 cell lines via an increase in Bax protein expression and a slight decrease in Bcl-2 protein expression. The gene expression ratio Bax/Bcl-2 showed the induction of mitochondrial apoptosis in cancer cell lines. All of synthesized compounds have also been tested for antioxidant activity and all compounds achieved strong inhibition of the DPPH radical. These findings showed that compound 3f, displays potential to be further explored in the development of new anticancer agents.
Design, synthesis, biological evaluation and in silico studies of certain aryl sulfonyl hydrazones conjugated with 1,3-diaryl pyrazoles as potent metallo-β-lactamase inhibitors
Shaaban, Marwa M.,Ragab, Hanan M.,Akaji, Kenichi,McGeary, Ross P.,Bekhit, Alaa-Eldin A.,Hussein, Waleed M.,Kurz, Julia L.,Elwakil, Bassma H.,Bekhit, Salma A.,Ibrahim, Tamer M.,Mahran, Mona A.,Bekhit, Adnan A.
, (2020)
Based on a structure-guided approach, aryl sulfonyl hydrazones conjugated with 1,3-diaryl pyrazoles were designed to target metallo-β-lactamases (MBLs), using Klebsiella pneumoniae NDM-1 as a model. The in vitro MBLs inhibition showed remarkable inhibition constant for most of the designed compounds at a low micromolar range (1.5–16.4 μM) against NDM-1, IMP-1 and AIM-1 MBLs. Furthermore, all compounds showed promising antibacterial activity against (K+, K1-K9) resistant clinical isolates of K. pneumoniae and were able to re-sensitize resistant K. pneumoniae (K5) strain towards meropenem and cefalexin. Besides, in vivo toxicity testing exhibited that the most active compound was non-toxic and well tolerated by the experimental animals orally up to 350 mg/kg and up to 125 mg/kg parenterally. The docking experiments on NDM-1 and IMP-1 rationalized the observed in vitro MBLs inhibition activity. Generally, this work presents a fruitful matrix to extend the chemical space for MBLs inhibition. This aids in tackling drug-resistance issues in antibacterial treatment.
A highly selective and sensitive dual-channel chemosensor for cyanide based on sulfahydrazone derivative
Leng, Yan-Li,Zhang, Jian-Hui,Li, Qiao,Zhang, You-Ming,Lin, Qi,Yao, Hong,Wei, Tai-Bao
, p. 1318 - 1323 (2016)
A colorimetric and fluorescent cyanide probe bearing naphthol and sulfahydrazone groups has been designed and synthesized. This structurally simple probe displays a rapid response and high selectivity for cyanide in DMSO/EtOH (v/v = 2:8) solution. The addition of CN? to the sensor p-toluenesulfonyl-2-hydroxy-1-naphthylhydrazone (L3) induced a remarkable color change from pale-yellow to yellow, and green fluorescence changed to yellow. The 1H NMR titration and DFT calculations suggested that the selective sensing process is based on a nucleophilic addition reaction of cyanide to imine. Test strips based on sensor L3 were fabricated, which could act as a convenient and efficient test kit to detect CN? for “in-the-field” measurements.
