- The discrete role of chlorine substitutions in the conformation and supra-molecular architecture of aryl-sulfonamides
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Two aryl-sulfonamide derivatives, N-(4-acetyl-phen-yl)benzene-sulfonamide, C14H13NO3S, and N-(4-acetyl-phen-yl)-2,5-di- chloro-benzene-sulfonamide, C14H11Cl2NO 3S, differing by t
- Fernandes, William B.,Aragao, Angelo Q.,Martins, Felipe T.,Noda-Perez, Caridad,Lariucci, Carlito,Napolitano, Hamilton B.
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Read Online
- Synthesis, biological evaluation and molecular docking of new sulfonamide-based indolinone derivatives as multitargeted kinase inhibitors against leukemia
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Series of novel sulfonamide-based 3-indolinones 3a-m and 4a-f were designed, synthesized and then their cytotoxic activity was evaluated against a panel of sixty cancer cell lines. This screening indicated that 4-(2-(5-fluoro-2-oxoindolin-3-ylidene)acetyl)phenyl benzenesulfonate (4f) possessed promising cytotoxicity against CCRF-CEM and SR leukemia cell lines with IC50 values 6.84 and 2.97 μM, respectively. Further investigation of the leukemic cytotoxicity of compound 4f was carried out by performing PDGFRα, VEGFR2, Aurora A/B and FLT3 enzyme assays and CCRF-CEM and SR cell cycle analysis. These investigations showed that compound 4f exhibited pronounced dual inhibition of both kinases PDGFRα and Aurora A with potency of 24.15 and 11.83 nM, respectively. The in vitro results were supported by molecular docking studies in order to explore its binding affinity and its key amino acids interactions. This work represents compound 4f as a promising anticancer agent against leukemia.
- El-Hussieny, Marwa,El-Sayed, Naglaa F.,Fouad, Marwa A.,Ewies, Ewies F.
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- Sequential C-S and S-N Coupling Approach to Sulfonamides
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A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.
- Chen, Kai,Chen, Wei,Han, Bing,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
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supporting information
p. 1841 - 1845
(2020/03/04)
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- Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound
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The invention belongs to the field of organic synthesis, and specifically discloses a method for coupling a nitroaromatic compound and a boric acid compound to synthesize a sulfonamide compound. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound comprises the steps that in an organic solvent, pyrosulfite is used as a source of SO2,and heating is carried out for a coupling reaction, and then after the post-treatment, the sulfonamide compound is obtained. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound is simple in operation, does not require nitrogen protection, and can be carried out under air. The nitroaromatic compound and the boric acid compound are abundant in source, relatively low in price, high in reaction yield, wide in applicability of a substrate and free in metal residual. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound can be used for synthesizing a series of sulfonamide compounds, and the synthesized compounds have wide application value in the fields of pesticidesand medicines.
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Paragraph 0072-0076
(2019/11/12)
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- Synthesis of N-arylsulfonamides through a Pd-catalyzed reduction coupling reaction of nitroarenes with sodium arylsulfinates
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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.
- Yang, Bo,Lian, Chang,Yue, Guanglu,Liu, Danyang,Wei, Liyan,Ding, Yi,Zheng, Xiancai,Lu, Kui,Qiu, Di,Zhao, Xia
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supporting information
p. 8150 - 8154
(2018/11/23)
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- Method for ultrasound-assisted synthesis of N-arylsulfonamide
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The invention discloses a method for ultrasound-assisted synthesis of N-arylsulfonamide. N-arylsulfonamide compound is synthesized by series reaction of nitro reduction/sulfonyl chloride reduction/sulfonamidation with taking aromatic nitro compounds, sulfonyl chloride and iron powder as raw materials under ultrasonic stirring conditions. Water is used as a reaction medium and a hydrogen source inthe reaction. The method has the advantages of cheap and easily obtained raw materials, simple and mild reaction conditions, environmental friendliness, saving energy, high reaction selectivity and high yield, excellent compatibility of substrate functional groups and high application value.
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Paragraph 0143; 0144; 0145
(2018/11/27)
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- Discovery and structure-activity relationship of novel 4-hydroxy-thiazolidine-2-thione derivatives as tumor cell specific pyruvate kinase M2 activators
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Pyruvate kinase M2 isoform (PKM2) is a crucial protein responsible for aerobic glycolysis of cancer cells. Activation of PKM2 may alter aberrant metabolism in cancer cells. In this study, we discovered a 4-hydroxy-thiazolidine-2-thione compound 2 as a novel PKM2 activator from a random screening of an in-house compound library. Then a series of novel 4-hydroxy-thiazolidine-2-thione derivatives were designed and synthesized for screening as potent PKM2 activators. Among these, some compounds showed higher PKM2 activation activity than lead compound 2 and also exhibited significant anti-proliferative activities on human cancer cell lines at nanomolar concentration. The compound 5w was identified as the most potent antitumor agent, which showed excellent anti-proliferative effects with IC50 values from 0.46 μM to 0.81 μM against H1299, HCT116, Hela and PC3 cell lines. 5w also showed less cytotoxicity in non-tumor cell line HELF compared with cancer cells. In addition, Preliminary pharmacological studies revealed that 5w arrests the cell cycle at the G2/M phase in HCT116 cell line. The best PKM2 activation by compound 5t was rationalized through docking studies.
- Li, Ridong,Ning, Xianling,Zhou, Shuo,Lin, Zhiqiang,Wu, Xingyu,Chen, Hong,Bai, Xinyu,Wang, Xin,Ge, Zemei,Li, Runtao,Yin, Yuxin
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- Purine-ring-containing benzene sulfonamide chalcone derivative and preparation and application methods thereof
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The invention discloses a purine-ring-containing benzene sulfonamide chalcone derivative and preparation and application methods thereof. The purine-ring-containing benzene sulfonamide chalcone derivative has a formula (I) shown as below, in which R1 is 4-oxymethyl, 4-tert-butyl, 4-methyl, 4-flouride, 4-bromide, 2-methyl, 2-fluoride, 2-chloride, 2-bromide and hydrogen atom and R2 is methyl, ethyland benzyl. The purine-ring-containing benzene sulfonamide chalcone derivative can inhibit tobacco mosaic virus, cucumber mosaic virus, potato Y virus and southern rice black-streaked dwarf virus.
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Paragraph 0039
(2019/01/05)
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- HETEROCYCLIC COMPOUNDS USEFUL AS IDO AND/OR TDO MODULATORS
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Present invention relates to novel heterocyclic compounds as indoleamine 2,3- dioxygenase (IDO) and/or tryptophan 2,3-dioxygenase (TDO) modulators. Compounds of the present invention inhibit tryptophan degradation by modulating IDO and/or TDO. Formula (I) The invention further relates to the process of their preparation, pharmaceutical composition and their use in modulating the activity of indoleamine 2,3-dioxygenase (IDO) and/or tryptophan 2,3- dioxygenase (TDO). The compounds of the invention can be used alone or in combination for the treatment of conditions that benefits from the inhibition of tryptophan degradation.
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Page/Page column 58; 59
(2017/09/15)
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- Functional induction of P-glycoprotein efflux pump by phenyl benzenesulfonamides: Synthesis and biological evaluation of T0901317 analogs
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N-(2,2,2-Trifluoroethyl)-N-[4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]-benzenesulfonamide (T0901317, 6) is a potent activator of pregnane-X-receptor (PXR), which is a nuclear receptor controlling P-gp expression. Herein, we aimed to inv
- Padala, Anil K.,Wani, Abubakar,Vishwakarma, Ram A.,Kumar, Ajay,Bharate, Sandip B.
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p. 744 - 755
(2016/08/08)
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- Cascade Michael-Aldol reaction: Efficient annulation of sulfonamide chalcones into novel cyclohexenones under solvent-free conditions
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A simple, convenient and efficient synthesis of novel sulfonamide cyclohexenones from differently substituted sulfonamide chalcones has been developed. Syntheses of cyclohexenones have been achieved via cascade Michael-Aldol reaction under solvent free condition. This process features mild and solvent-free synthesis of the titled compounds with high yields (18 examples, up to 95% yield). The synthesized scaffold is a promising intermediate for the further transformation into various heterocyclic compounds.
- Agrawal, Nikita R.,Bahekar, Sandeep P.,Agrawal, Abhijeet R.,Sarode, Prashant B.,Chandak, Hemant S.
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p. 227 - 245
(2016/07/06)
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- Novel 5-Hydroxy, 5-Substituted Benzenesulfonamide Pyrimidine-2,4,6-Triones Attenuate Lipopolysaccharide-Induced Acute Lung Injury via Inhibition of the Gelatinases, MMP-2 and MMP-9
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(Table presented.). A novel series of ten 5-hydroxy, 5-substituted benzene sulfonamide pyrimidine-2,4,6-triones were synthesized and their structures ascertained using 1H-NMR, 13C-NMR, mass and elemental analysis. These compounds wer
- He, Wei,Jiang, Jie,Yu, Ze-Qian,Zhou, Jia-Hua
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p. 251 - 257
(2016/08/26)
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- Metal-free direct construction of sulfonamides via iodine- mediated coupling reaction of sodium sulfinates and amines at room temperature
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A simple, practical, and metal-free protocol has been developed for the synthesis of sulfonamides from sodium sulfinates and various amines through an iodine-mediated SN bond formation reaction at room temperature. This green reaction is cost-effective, operationally straightforward, and especially proceeds under very mild conditions to afford the target products in good to excellent yields (up to 98%).
- Wei, Wei,Liu, Chunli,Yang, Daoshan,Wen, Jiangwei,You, Jinmao,Wang, Hua
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supporting information
p. 987 - 992
(2015/03/30)
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- Synthesis, anticancer and radiosensitizing evaluation of some novel sulfonamide derivatives
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In this study, novel series of sulfonamide derivatives were synthesized starting from 2-cyanoacetyl)hydrazono)ethyl)phenyl)benzenesulfonamide 4a and 2-cyanoacetyl)hydrazono)ethyl)phenyl)-4-methylbenzenesulfonamide 4b. Different biologically active moietie
- Ghorab, Mostafa M.,Ragab, Fatma A.,Heiba, Helmy I.,El-Gazzar, Marwa G.,Zahran, Sally S.
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p. 682 - 692
(2015/01/30)
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- Synthesis, anti-inflammatory and antioxidant activity of ring-a-monosubstituted chalcone derivatives
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A library of ring-A-monosubstituted chalcone derivatives (4a-4i, 5a and 5b) was designed and synthesised. The structures as well as the identities of these compounds were established on the basis of spectral (1H NMR, 13C NMR, FT-IR and Mass) and elemental (C, H, N) analyses. All the derivatives were evaluated for their anti-inflammatory and antioxidant activities in vitro using the inhibition of protein denaturation and 2,2-diphenyl-1-picrylhydrazyl radical scavenging assays, respectively. The results indicated a promising anti-inflammatory activity for most of the synthesised compounds with many derivatives showing activities similar to or greater than that of the standard. The sulphonamide-substituted chalcones 4h, 4i, 5a and 5b were found to be the most active derivatives across the concentration range tested. However, all the derivatives exhibited rather mild antioxidant activity compared to the ascorbic acid standard. Interestingly, it was observed that the unsubstituted parent chalcone was one of the optimal compounds with only the trifluoromethyl analogue 4a showing better activity as an antioxidant. The two regioisomeric aminochalcones and 4′-cyanochalcone 4b also seemed to possess decent antioxidant potential.
- Iqbal, Hiba,Prabhakar, Visakh,Sangith, Atul,Chandrika, Baby,Balasubramanian, Ranganathan
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p. 4383 - 4394
(2015/04/22)
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- Inhibitory evaluation of sulfonamide chalcones on β-secretase and acylcholinesterase
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The action of β-secretase (BACE1) is strongly correlated with the onset of Alzheimer's disease (AD). Aminochalcone derivatives were examined for their ability to inhibit BACE1. Parent aminochalcones showed two digit micromolar IC50s against BACE1. Potency
- Kang, Jae Eun,Cho, Jung Keun,Curtis-Long, Marcus J.,Ryu, Hyung Won,Kim, Jin Hyo,Kim, Hye Jin,Yuk, Heung Joo,Kim, Dae Wook,Park, Ki Hun
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p. 140 - 153
(2013/04/23)
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- Copper-catalyzed N-arylation of sulfonamides with aryl bromides under mild conditions
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This Letter describes a copper catalyzed sulfonamide coupling reaction with aryl bromides to form N-aryl sulfonamides under mild conditions, including the first examples of Cu-catalyzed sulfonamide coupling at room temperature. The reaction protocol tolerates a broad range of substrates including a variety of primary and secondary sulfonamides and challenging heteroaryl bromides such as 2-bromothiazole.
- Wang, Xiang,Guram, Anil,Ronk, Michael,Milne, Jacqueline E.,Tedrow, Jason S.,Faul, Margaret M.
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supporting information; experimental part
p. 7 - 10
(2012/01/06)
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- Copper-catalysed N-arylation of arylsulfonamides with aryl bromides and aryl iodides using KF/Al2O3
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An efficient synthesis of N-arylsulfonamides with a variety of aryl bromides, aryl iodides and heteroaryl bromides using KF/Al2O 3 as a suitable base, CuI as an inexpensive catalyst and N,N′dimethylethylenediamine (N,N′-DMEDA) as an effective ligand is described. Indian Academy of Sciences.
- Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Mohadjerani, Maryam,Alikarami, Mohammad
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experimental part
p. 143 - 148
(2010/11/16)
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- Evaluation of anti-pigmentary effect of synthetic sulfonylamino chalcone
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The 4′-(p-toluenesulfonylamino)-4-hydroxychalcone (TSAHC), which bears inhibitory chemotypes for both α-glucosidase and tyrosinase, was evaluated for tyrosinase activity and depigmenting ability relative to compounds designed to only target tyrosianse act
- Seo, Woo Duck,Ryu, Young Bae,Curtis-Long, Marcus J.,Lee, Chan Woo,Ryu, Hyung Won,Jang, Ki Chang,Park, Ki Hun
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scheme or table
p. 2010 - 2017
(2010/07/04)
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- Chemoselective regulation of TREK2 channel: Activation by sulfonate chalcones and inhibition by sulfonamide chalcones
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Although it has not been extensively studied, a significant volume of literature suggests that TREK2 will probably turn out to be an important channel in charge of tuning neuronal transmitter and hormone levels. Thus, pharmacological tools which can manip
- Kim, Eun-Jin,Ryu, Hyung Won,Curtis-Long, Marcus J.,Han, Jaehee,Kim, Jun Young,Cho, Jung Keun,Kang, Dawon,Park, Ki Hun
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supporting information; experimental part
p. 4237 - 4239
(2010/08/22)
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- Solvent hydrogen bonding and structural effects on nucleophilic aromatic substitution reactions. Part-2: Reaction of benzenesulphonyl chloride with anilines in propan-2-ol/2-methylpropan-2-ol mixtures
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Substitution reactions of fourteen para- and meta-substituted anilines with benzenesulphonyl chloride in different mole fractions of propan-2-ol in 2-methylpropan-2-ol have been investigated conductometrically. The second order rate constants correlates satisfactorily with pKa values of the anilines and also with the Hammett's substituent constant. The para-substituted anilines shows a satisfactory correlation with Charton's LDR equation. The results of these correlations indicate the formation of an electron deficient transition state. The rate data correlate satisfactorily with macroscopic solvent parameters such as relative permittivity, εr and polarity, ETN. Multiple correlation analysis of the rate data via Kamlet-Taft's solvatochromic parameters reveals that the solvent dipolarityfpolarizability plays a dominant role in governing the reactivity.
- Bhuvaneshwari,Elango
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experimental part
p. 233 - 241
(2010/04/05)
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- α-Mercaptoketone based histone deacetylase inhibitors
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In an effort to discover novel non-hydroxamic acid histone deacetylase (HDAC) inhibitors, a novel α-mercaptoketone was identified in a high-throughput screen. Lead optimization of the screening hit, led to a number of potent HDAC inhibitors. In particular, α-mercaptoketone 19y (KD5150) exhibited nanomolar in vitro activity and inhibition of tumor growth in vivo.
- Wash, Paul L.,Hoffman, Timothy Z.,Wiley, Brandon M.,Bonnefous, Celine,Smith, Nicholas D.,Sertic, Michael S.,Lawrence, Charles M.,Symons, Kent T.,Nguyen, Phan-Manh,Lustig, Kevin D.,Guo, Xin,Annable, Tami,Noble, Stewart A.,Hager, Jeffrey H.,Hassig, Christian A.,Malecha, James W.
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scheme or table
p. 6482 - 6485
(2009/10/01)
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- Crystal structure of the PXR-T1317 complex provides a scaffold to examine the potential for receptor antagonism
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The human pregnane X receptor (PXR) recognizes a range of structurally and chemically distinct ligands and plays a key role in regulating the expression of protective gene products involved in the metabolism and excretion of potentially harmful compounds. The identification and development of PXR antagonists is desirable as a potential way to control the up-regulation of drug metabolism pathways during the therapeutic treatment of disease. We present the 2.8 A resolution crystal structure of the PXR ligand binding domain (LBD) in complex with T0901317 (T1317), which is also an agonist of another member of the orphan class of the nuclear receptor superfamily, the liver X receptor (LXR). In spite of differences in the size and shape of the receptors' ligand binding pockets, key interactions with this ligand are conserved between human PXR and human LXR. Based on the PXR-T1317 structure, analogues of T1317 were generated with the goal of designing an PXR antagonist effective via the receptor's ligand binding pocket. We find that selectivity in activating PXR versus LXR was achieved; such compounds may be useful in addressing neurodegenerative diseases like Niemann-Pick C. We were not successful, however, in producing a PXR antagonist. Based on these observations, we conclude that the generation of PXR antagonists targeted to the ligand binding pocket may be difficult due to the promiscuity and structural conformability of this xenobiotic sensor.
- Xue, Yu,Chao, Esther,Zuercher, William J.,Willson, Timothy M.,Collins, Jon L.,Redinbo, Matthew R.
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p. 2156 - 2166
(2008/02/01)
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- Solvent hydrogen bonding and structural effects on nucleophilic substitution reactions: Part 3. Reaction of benzenesulfonyl chloride with anilines in benzene/ propan-2-ol mixtures
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Substitution reactions of 13 para- and meta-substituted anilines with benzene-sulfonyl chloride in varying mole fractions of benzene in propan-2-ol have been investigated conductometrically, The second-order rate constants correlate well with pKa values of anilines and with the Hammett's equation. The negative Hammett reaction constant indicates the formation of an electron-deficient transition state. The rate data correlate satisfactorily with macroscopic solvent parameters such as relative permittivity, εr, and polarity, ETN. Correlation of rate data with Kamlet-Taft solvatochromic parameters (α, β, π*) suggests that both the specific and nonspecific solute-solvent interactions influence the reactivity.
- Bhuvaneshwari,Elango
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p. 657 - 663
(2008/09/17)
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- Solvent hydrogen bonding and structural effects on nucleophilic substitution reactions. Part-1: Reaction of benzenesulphonyl chloride with anilines in benzene/2-methylpropan-2-ol-mixtures
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Substitution reactions of eleven para- and meta-substitutcd anilines with benzencsulphonyl chloride in different mole fractions of benzene in 2-methylpropan-2-ol have been investigated conductometrically. The second order rate constants don't correlate either with pK values of the anilines or with the Hammett's and its modified equations. The para-substituted anilines shows a satisfactory correlation with Charton's LDR equation and the results indicate the formation of an electron deficient transition state. The rate data correlate satisfactorily with macroscopic solvent parameters such as relative permittivity, εr, and polarity, ETN. Multiple correlation analysis of the rate data via Kamlet-Taft's solvatochromic parameters reveals that the solvent hydrogen bond donor property plays a dominant role in governing the reactivity.
- Bhuvaneshwari,Elango
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experimental part
p. 1227 - 1233
(2009/12/31)
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- Copper-catalyzed cross-coupling of sulfonamides with aryl iodides and bromides facilitated by amino acid ligands
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A highly general, convenient, and inexpensive catalyst system was developed for the N-arylation of sulfonamides with aryl iodides or bromides by using 5-20 mol % of CuI as catalyst, 20 mol % of N-methylglycine (for aryl iodides) or N,N-dimethylglycine (for aryl bromides) as ligand, and K3PO 4 as base.
- Deng, Wei,Liu, Lei,Zhang, Chen,Liu, Min,Guo, Qing-Xiang
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p. 7295 - 7298
(2007/10/03)
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- Synthesis and antimicrobial activity of some new cyanopyridines, isoxazoles, pyrazoles, and pyrimidines bearing sulfonamide moiety
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Reaction of p-aminoacetophenone 1 with p-substituted benzenesulfonyl chloride 2a,b in pyridine afforded p-acetyl derivatives 3a,b, which was then condensed with araldehydes to yield the corresponding chalcones 4a-f. On condensation of latter chalcones wit
- Moustafa, Osama S.,Ahmad, Ragaa A.
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p. 475 - 484
(2007/10/03)
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