1576-35-8Relevant articles and documents
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.
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, 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.
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.
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.
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De Puy et al.
, p. 631 (1960)
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Biological evaluation of p-toluene sulphonylhydrazone as carbonic anhydrase IX inhibitors: An approach to fight hypoxia-induced tumors
Queen, Aarfa,Khan, Parvez,Idrees, Danish,Azam, Amir,Hassan, Md. Imtaiyaz
, p. 840 - 850 (2018)
To find potential inhibitors of human carbonic anhydrase IX (CAIX), we have successfully deigned, synthesized and characterized three p-toluene sulphonylhydrazone derivatives (1–3). Molecular docking studies provided the structural basis of CAIX inhibition and a deeper insight into the protein-ligand interactions. p-Toluene sulphonylhydrazone derivatives show a well organized conformational compatibility with the active site of CAIX. The protein-ligand complex was stabilized by several non-covalent interactions offered by residues present in the active site cavity. The actual binding affinity of synthesized compounds with CAIX was experimentally measured by fluorescence and isothermal titration calorimetry (ITC). Results of both fluorescence binding and ITC measurements show the binding affinity of p-Toluene sulphonylhydrazone derivatives to the CAIX in the μM range. CAIX enzyme inhibition assay showed the IC50 values in nM range. Though all the three compounds (1–3) showed a good binding with CAIX, compound 2 showed the best inhibition of CAIX activity. These compounds were non-toxic on normal cell lines (HEK-293) and significantly inhibit the proliferation of hypoxic cancer cells. All compounds induce apoptosis in the hypoxic cancer cells. These compounds may be further exploited as promising therapeutic agents to control the hypoxia-induced tumors.
Copper(I)/Bpy-Catalyzed C-2-H Benzylation of Quinazolin-4(3H)-ones with N-Tosylhydrazones
Li, Fei,Gu, Xiao-Juan,Zeng, Chang-E.,Li, Xia,Liu, Bo,Huang, Guo-Li
, p. 2923 - 2928 (2020)
A general and efficient copper-catalyzed C–H benzylation reaction of quinazolin-4(3H)-ones with N-tosylhydrazones is reported. The formation of new C(sp3)–C(sp2) bonds through cross-coupling occurs at the electron-poor C-2 position of quinazolin-4(3H)-one and represents an exceedingly practical method to afford 2-benzylated quinazolin-4(3H)-ones in moderate to good yields under mild reaction conditions. A possible reaction mechanism for this transformation was proposed. This catalytic transformation has the potential to be an important synthetic application for the late-stage functionalization of advanced synthetic intermediates.
Design of arylsulfonylhydrazones as potential fabh inhibitors: Synthesis, antimicrobial evaluation and molecular docking
Fernandes, Thais Batista,Segretti, Natanael Dante,Louren?o, Felipe Rebello,Candido, Thalita Marcílio,Baby, André Rolim,Barbosa, Euzébio Guimar?es,Parise-Filho, Roberto
, p. 474 - 484 (2021/03/26)
Background: Antimicrobial resistance is a persistent problem regarding infection treatment and calls for developing new antimicrobial agents. Inhibition of bacterial β-ketoacyl acyl carrier protein synthase III (FabH), which catalyzes the condensation reaction between a CoA-attached acetyl group and an ACP-attached malonyl group in bacteria is an interesting strategy to find new antibacterial agents. Objective: The aim of this work was to design and synthesize arylsulfonylhydrazones potentially FabH inhibitors and evaluate their antimicrobial activity. Methods: MIC50 values of sulfonylhydrazones against E. coli and S. aureus were determined. An-tioxidant activity was evaluated by DPPH (1-1’-diphenyl-2-picrylhydrazyl) assay and cytotoxicity against LL24 lung fibroblast cells was verified by MTT method. Principal component analysis (PCA) was performed in order to suggest a structure-activity relationship. Molecular docking allowed to propose sulfonylhydrazones interactions with FabH. Results: The most active compound showed activity against S. aureus and E. coli, with MIC50 = 0.21 and 0.44 μM, respectively. PCA studies correlated better activity to lipophilicity and molecular docking indicated that sulfonylhydrazone moiety is important to hydrogen-bond with FabH while methylcatechol ring performs π-π stacking interaction. The DPPH assay revealed that some sulfonylhydrazones derived from the methylcatechol series had antioxidant activity. None of the evaluated compounds was cytotoxic to human lung fibroblast cells, suggesting that the compounds might be considered safe at the tested concentration. Conclusion: Arylsufonylhydrazones is a promising scaffold to be explored for the design of new antimicrobial agents.
Electrochemical heterodifunctionalization of α-CF3alkenes to access α-trifluoromethyl-β-sulfonyl tertiary alcohols
Chen, Kai,Duan, Xin-Yu,Gao, Jie,Guan, Jian-Ping,Liu, Fang,Xiang, Hao-Yue,Xiao, Jun-An,Yang, Hua,Ye, Zhi-Peng
supporting information, p. 8969 - 8972 (2021/09/10)
An unprecedented electrochemical heterodifunctionalization of α-CF3alkenes with benzenesulfonyl hydrazides was accomplished in this work, wherein a β-sulfonyl and a α-hydroxyl group were simultaneously incorporated across the olefinic double bond in a single operation. Consequently, a series of potentially medicinally valuable and densely functionalized α-trifluoromethyl-β-sulfonyl tertiary alcohols were assembled under mild conditions. Electrochemically-driven oxidative 1,2-difunctionlization of electron-deficient alkenes well obviates the need for oxidizing reagents, thus rendering this protocol more eco-friendly.
