37028-85-6Relevant academic research and scientific papers
Synthesis and evaluation of novel S-benzyl- and S-alkylphthalimide- oxadiazole -benzenesulfonamide hybrids as inhibitors of dengue virus protease
Batool, Farwa,Hamdani, Syeda Shamila,Hameed, Shahid,Khan, Bilal Ahmad,Mughal, Ehsan Ullah,Saeed, Muhammad,Saleem, Hafiza Nosheen
, (2020/02/15)
Direct acting antiviral drugs (DAADs) are becoming therapeutics of choice for the treatment of viral infections. Successful development of anti HIV and HCV drugs by targeting the viral proteases has provided impetus for discovering newer DAADs. Dengue virus (DENV) protease, which is composed of two nonstructural proteins, NS2B and NS3pro, can be likewise exploited for discovering new anti-dengue therapeutics. In this study, we have linked together two pharmaceutically interesting motifs, namely 1,3,4-oxadiazole and benzenesulfonamide in two alternative series to develop novel S-benzylated and S-alkylphthalimidated hybrids. For the first series of hybrids, 4-aminobenzoic acid (1) was reacted with substituted benzenesulfonyl chlorides via its amino group, whereas the carboxylic acid side was elaborated to sulfonamido-1,3,4-oxadiazole-2-thiols (6a/b) in three steps. At this stage, the intermediates 6a/b were bifurcated to either S-alkylphthalimidated (8a-j) or S-benzylated (9a-c) hybrids by reacting with corresponding halides. For the alternative series of hybrids, the carboxylic acid group of probenecid (10) was similarly elaborated to sulfonamido-1,3,4-oxadiazole-2-thiols (13), and diverged to S-alkylphthalimidated (14a-f) and S-benzylated hybrids (15a-e). Bioactivity assays demonstrated that 8g and 8h are the most potent inhibitors among the synthesized analogs, exhibiting the IC50 values of 13.9 μM and 15.1 μM, respectively. Computational assessment predicted the binding of the inhibitors at an allosteric site developed in the open conformation of DENV2 NS2B/NS3pro. Taken together these findings point out that the synthesized hybrid inhibitors possess a great potential for further antiviral drug development.
Hydroxamic acid with benzenesulfonamide: An effective scaffold for the development of broad-spectrum metallo-β-lactamase inhibitors
Li, Jia-Qi,Chen, Cheng,Yao, Min,Sun, Le-Yun,Gao, Han,Chigan, Jiazhu,Yang, Ke-Wu
, (2020/11/11)
Given that β-lactam antibiotic resistance mediated by metallo-β-lactamases (MβLs) seriously threatens human health, we designed and synthesized nineteen hydroxamic acids with benzenesulfonamide, which exhibited broad-spectrum inhibition against four teste
Bio-potent sulfonamides
Dineshkumar, Selvakumar,Thirunarayanan, Ganesamoorthy
, p. 4386 - 4391 (2019/06/27)
Some 4-(substituted phenylsulfonamido)benzoic acids have been synthesized by fly-ash:H3PO3 nano catalyst catalyzed condensation of substituted benzenesulfonyl chlorides and 4-aminobenzoic acid in ultrasound irradiation conditions. The yields of the sulfonamides are more than 90%. The synthesized 4-(substituted phenylsulfonamido) benzoic acid derivatives were characterized by their physical constants, analytical and spectroscopic data. Antimicrobial activities of all sulfonamides were measured by Bauer-Kirby disc diffusion method.
Synthesis of N-arylsulfonamides through a Pd-catalyzed reduction coupling reaction of nitroarenes with sodium arylsulfinates
Yang, Bo,Lian, Chang,Yue, Guanglu,Liu, Danyang,Wei, Liyan,Ding, Yi,Zheng, Xiancai,Lu, Kui,Qiu, Di,Zhao, Xia
supporting information, p. 8150 - 8154 (2018/11/23)
A novel one-step direct reductive coupling reaction between nitroarenes and sodium arylsulfinates was realized in the presence of an inexpensive Pd/C catalyst. In this procedure, readily available nitroarenes are employed as the nitrogen sources, and sodium arylsulfinates serve as both coupling partners and reductants. The method features high efficiency by using cheap Pd/C with low catalyst loading and good functional group tolerance in the absence of any additional reductants or ligands. This facile and mild synthetic method enables the high efficiency synthesis of functionalized N-arylsulfonamides from readily available substrates.
Straightforward and Sustainable Synthesis of Sulfonamides in Water under Mild Conditions
Eid, Nadim,Karamé, Iyad,Andrioletti, Bruno
supporting information, p. 5016 - 5022 (2018/09/14)
Ideally, a sustainable chemical synthesis should involve the use of non-toxic solvents and reactants, easy separations and purification by energy-efficient processes. In this context, reconsidering the synthesis of widely used drugs is especially timely and should allow important benefits to be obtained in terms of environmental impact. Sulfonamides are pertinent as their synthesis generally requires the use of toxic and/or hard-to-remove solvents such as dichloromethane, DMF and DMSO. In addition, toxic and highly reactive sulfur-containing sources such as sulfonyl chloride are often involved and coupled with amines. Moreover, the latter may exhibit some toxicity and are generally difficult to purify. Herein, we disclose the unprecedented and sustainable synthesis of sulfonamides by using sodium sulfinate as a commercial and stable sulfur source and nitroarenes as the nitrogen-containing reactant. In addition, under the optimized conditions only water is used as a “green” solvent and the products are collected by simple filtration.
Copper-catalyzed cross-coupling of chloramine salts and arylboronic acids in water: A green and practical route to N-arylsulfonamides
Ouyang, Banlai,Zheng, Yanxia,Liu, Yi,Liu, Fei,Yao, Juying,Peng, Yiyuan
, p. 3694 - 3698 (2018/09/14)
A green and practical method for the synthesis of N-arylsulfonamides from chloramine salts and arylboronic acids is herein developed. The reaction proceeds readily in the presence of 5 mol% of CuI and 2.5 equiv. K2CO3 in water at room temperature, generating a variety of N-arylsulfonamides in moderate to good yields with good functional group tolerance.
Iron-catalyzed N -arylsulfonamide formation through directly using nitroarenes as nitrogen sources
Zhang, Weixi,Xie, Junyao,Rao, Bin,Luo, Meiming
, p. 3504 - 3511 (2015/04/14)
One-step, catalytic synthesis of N-arylsulfonamides via the construction of N-S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N-S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.
A convenient and benign synthesis of sulphonamides in PEG-400
Das, Pranab Jyoti,Sarmah, Bhaskar
, p. 189 - 191 (2015/02/19)
A simple and convenient method is reported for the synthesis of a series of sulphonamides in PEG-400 using potassium carbonate as the base. The reaction is carried out in a heterogeneous medium and consequently product recovery is simple. The desired products with a variety of aromatic amines could be synthesized in a short reaction time in good yield. The PEG could be recovered for reuse.
Development and validation of a docking-based virtual screening platform for the identification of new lactate dehydrogenase inhibitors
Granchi, Carlotta,Capecchi, Alice,Del Frate, Gianluca,Martinelli, Adriano,Macchia, Marco,Minutolo, Filippo,Tuccinardi, Tiziano
, p. 8772 - 8790 (2015/09/01)
The human muscle isoform of lactate dehydrogenase (hLDH5) is one of the key enzymes of the glycolytic process. It is overexpressed in metastatic cancer cells and is linked to the vitality of tumors in hypoxic conditions. With the aim of identifying new hLDH5 inhibitors, a fully automated docking-based virtual screening platform was developed by considering different protein conformations and the consensus docking strategy. In order to verify the reliability of the reported platform, a small database of about 10,000 compounds was filtered by using this method, and the top-ranked compounds were tested for their hLDH5 inhibition activity. Enzymatic assays revealed that, among the ten selected compounds, two proved to efficiently inhibit enzyme activity with IC50 values in the micromolar range. These results demonstrate the validity of the methodologies we followed, encouraging the application of larger virtual screening studies and further refinements of the platform. Furthermore, the two active compounds herein described may be considered as interesting leads for the development of new and more efficient LDH inhibitors.
Copper-catalyzed mild nitration of protected anilines
Hernando, Elier,Castillo, Rafael R.,Rodríguez, Nuria,G?mez Arrayás, Ram?n,Carretero, Juan C.
supporting information, p. 13854 - 13859 (2016/02/18)
A practical copper-catalyzed direct nitration of protected anilines, by using one equivalent of nitric acid as the nitrating agent, has been developed. This procedure features mild reaction conditions, wide structural scope (with regard to both N-protecting group and arene substitution), and high functional-group tolerance. Dinitration with two equivalents of nitric acid is also feasible. Practical and reliable: A Cu-catalyzed selective nitration of para- and ortho-substituted aniline derivatives by using one equivalent of HNO3 has been developed that produces water as the only stoichiometric byproduct (see scheme; PG=protecting group). This method is compatible with strongly electron-deficient substrates, enabling dinitration (by using 2.0 equiv of HNO3). This method allows for a rapid access to relevant nitrogen-containing heterocyclic architectures.
