- Utilization of N,N-dichloro-p-chlorobenzenesulfonamide
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The kinetic parameters of the reaction of N,N-dichloro-p-chlorobenzenesulfonamide with hydrochloric acid were determined, and the main parameters of the commercial process were estimated.
- Shiryaev
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Read Online
- Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups
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We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.
- Govindan, Karthick,Chen, Nian-Qi,Chuang, Yu-Wei,Lin, Wei-Yu
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supporting information
p. 9419 - 9424
(2021/11/30)
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- Synthesis, biological evaluation, and docking studies of novel pyrrolo[2,3-b]pyridine derivatives as both ectonucleotide pyrophosphatase/phosphodiesterase inhibitors and antiproliferative agents
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Ecto-nucleotide pyrophosphatases/phosphodiesterases (NPPs) together with nucleoside triphosphate diphosphohydrolases (NTPDases) and alkaline phosphatases (APs) are nucleotidases located at the surface of the cells. NPP1 and NPP3 are important members of NPP family that are known as druggable targets for a number of disorders such as impaired calcification, type 2 diabetes, and cancer. Sulfonylurea derivatives have been reported as antidiabetic and anticancer agents, therefore, we synthesized and investigated series of sulfonylurea derivatives 1a-m possessing pyrrolo[2,3-b]pyridine core as inhibitors of NPP1 and NPP3 isozymes that are over-expressed in cancer and diabetes. The enzymatic evaluation highlighted compound 1a as selective NPP1 inhibitor, however, 1c was observed as the most potent inhibitor of NPP1 with an IC50 value of 0.80 ± 0.04 μM. Compound 1l was found to be the most potent and moderately selective inhibitor of NPP3 (IC50 = 0.55 ± 0.01 μM). Furthermore, in vitro cytotoxicity assays of compounds 1a-m against MCF-7 and HT-29 cancer cell lines exhibited compound 1c (IC50 = 4.70 ± 0.67 μM), and 1h (IC50 = 1.58 ± 0.20 μM) as the most cytotoxic compounds against MCF-7 and HT-29 cancer cell lines, respectively. Both of the investigated compounds showed high degree of selectivity towards cancer cells than normal cells (WI-38). Molecular docking studies of selective and potent enzyme inhibitors revealed promising mode of interactions with important binding sites residues of both isozymes i.e., Thr256, His380, Lys255, Asn277 residues of NPP1 and His329, Thr205, and Leu239 residues of NPP3. In addition, the most potent antiproliferative agent, compound 1h, doesn't produce hypoglycemia as a side effect when injected to mice. This is an additional merit of the promising compound 1h.
- Ullah, Saif,El-Gamal, Mohammed I.,El-Gamal, Randa,Pelletier, Julie,Sévigny, Jean,Shehata, Mahmoud K.,Anbar, Hanan S.,Iqbal, Jamshed
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- Synthesis of magnetic chitosan supported metformin-Cu(II) complex as a recyclable catalyst for N-arylation of primary sulfonamides
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The application of chitosan, which has received much attention as a natural polymer and effective support, has many advantages such as biodegradability and biocompatibility. In this study, the immobilization of a copper complex on the magnetic chitosan bearing metformin ligand has been developed through immobilizing structurally defined metformin with long tail of (3-chloropropyl)trimethoxysilane (TMOS). The synthesized Fe3O4-chitosan@metformin-Cu(II) complex (Fe3O4-CS@Met-Cu(II)) was used as an effective, reusable and magnetic catalyst in the N-arylation of different derivatives of primary sulfonamides with arylboronic acids in ethanol. The primary sulfonamides were prepared from the reaction of sulfonyl chlorides with sodium cyanate in water under ultrasonic irradiation. Utilizing a wide variety of substrates in EtOH as a green solvent, high yields of the primary and secondary sulfonamides, easy work-up along with the excellent recovery and reusability of the catalyst, make this process a simple, economic and environmentally benign method. The synthesized Fe3O4-CS@Met-Cu(II) was characterized using various techniques such as XRD (X-ray diffraction), EDS (energy-dispersive X-ray spectroscopy), elemental mapping, TEM (transmission electron microscopy), FESEM (field emission scanning electron microscopy), VSM (vibrating sample magnetometer), ICP-MS (inductively coupled plasma mass spectroscopy), TGA (thermogravimetric analysis) and FT-IR (Fourier-transform infrared spectroscopy) analyses. The catalyst can be recycled and reused 5 times with no considerable loss of catalytic activity.
- Ahmadpoor, Fatemeh,Nasrollahzadeh, Mahmoud,Nezafat, Zahra,Pakzad, Khatereh
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- One-pot aerobic oxidative sulfonamidation of aromatic thiols with ammonia by a dual-functional β-MnO2 nanocatalyst
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High-surface-area β-MnO2 (β-MnO2-HS) nanoparticles could act as effective heterogeneous catalysts for the one-pot oxidative sulfonamidation of various aromatic and heteroaromatic thiols to the corresponding sulfonamides using molecular oxygen (O2) and ammonia (NH3) as respective oxygen and nitrogen sources, without the need for any additives.
- Hayashi, Eri,Yamaguchi, Yui,Kita, Yusuke,Kamata, Keigo,Hara, Michikazu
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supporting information
p. 2095 - 2098
(2020/02/26)
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- CARBOXYLIC ACID, ACYL SULFONAMIDE AND ACYL SULFAMIDE-DERIVATIZED BICYCLIC AZA-HETEROAROMATICS AS SELECTIVE MCL-1 INHIBITORS AND AS DUAL MCL-1/BCL-2 INHIBITORS
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Mcl-1 selective inhibitors, Bcl-2 selective inhibitors, and Mcl-1/Bcl-2 dual inhibitors and methods of using the same for the treatment of disease are disclosed.
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Paragraph 0230
(2020/12/19)
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- Palladium-Catalyzed ortho-Benzoylation of Sulfonamides through C?H Activation: Expedient Synthesis of Cyclic N-Sulfonyl Ketimines
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The ortho-carbonylation of sulfonylarenes by non-hazardous aryl aldehydes as a carbonyl precursor was reported. In this method, the sulfonamide group serves as a directing group for C?H activation in the presence of a Pd catalyst under ligand-free conditions. The scope of this strategy has been extended to the one-pot two-step synthesis of cyclic N-sulfonyl ketimines under mild reaction conditions. Our approach could be considered as an alternative by circumventing the use of highly reactive organolithium or Grignard reagents to access a wide range of biologically potent cyclic N-sulfonyl ketimines. (Figure presented.).
- Ojha, Subhadra,Panda, Niranjan
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p. 561 - 571
(2019/12/24)
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- Tetrahydropyridines via FeCl3-Catalyzed Carbonyl-Olefin Metathesis
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Herein we describe the application of Lewis-acid-catalyzed carbonyl-olefin metathesis toward the synthesis of substituted tetrahydropyridines from commercially available amino acids as chiral pool reagents. This strategy relies on FeCl3 as an inexpensive and environmentally benign catalyst and enables access to a variety of substituted tetrahydropyridines under mild reaction conditions. The reaction proceeds with complete stereoretention and is viable for a variety of natural and unnatural amino acids to provide the corresponding tetrahydropyridines in up to 99% yield.
- Gaviria, Mario A.,Groso, Emilia J.,Richardson, Alistair D.,Rykaczewski, Katie A.,Schindler, Corinna S.,Vonesh, Hannah L.,Zehnder, Troy E.
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supporting information
(2020/04/02)
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- New allyldithiocarbimate salts: Synthesis, structure and antifungal activity
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Fifteen new allyldithiocarbimates were prepared from different allylic bromides and various potassium dithiocarbimates, yielding (Z)-2-(methoxycarbonyl)-3-(X-nitrophenyl)allyl-(N-R-sulfonyl)dithiocarbimates (where X = 2, 3 and 4; R = phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl and 4-iodophenyl). These anions were isolated as tetraphenylphosphonium salts and characterized by HRMS, infrared, 1H and 13C NMR spectroscopies. Molecular electrostatic potentials were used to evaluate intermolecular interactions present in the new substances and to explain variations observed on their melting points. Single crystal X-ray diffraction experiments confirmed the Z stereochemistry of the allyldithiocarbimate anions. C–H?O, C–H?N, C–H?S and C–H?π intermolecular interactions in the solid state were studied by X-ray diffraction and Hirshfeld surface analyses. The new compounds inhibited the mycelial growth of various fungi species responsible for severe plant diseases. The allylithiocarbimates were especially active against Botrytis cinerea, with IC50 values as low as 20 μM, being more effective than the active principals of the commercial fungicides Ziram and Mancozeb.
- Albuini-Oliveira, Nathália M.,Alvarez, Natalia,Ellena, Javier,Guilardi, Silvana,Lima, Marcelo S.,Rubinger, Mayura M. M.,Souza, Rafael A. C.,Tavares, Eder C.,Vidigal, Antonio E. C.,Zacchi, Carlos H. C.,Zambolim, Laercio
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- Nickel(II)-Catalyzed Synthesis of Sulfinates from Aryl and Heteroaryl Boronic Acids and the Sulfur Dioxide Surrogate DABSO
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We report a redox-neutral Ni(II)-catalyzed sulfination of readily available aryl and heteroaryl boronic acids. Using the combination of commercially available, air-stable NiBr2·(glyme), a commercially available phenanthroline ligand, and DABSO, boronic acids are efficiently converted to the corresponding sulfinate salts, which can be further elaborated to valuable sulfonyl-containing groups, including sulfones, sulfonamides, sulfonyl fluorides, and sulfonate esters. The catalyst loading can be reduced to 2.5 mol ?% on a gram scale. This practically simple protocol tolerates an unprecedented range of pharmaceutically relevant and electron-poor (hetero)aryl boronic acids, allowing the direct synthesis of active pharmaceutical ingredients.
- Lo, Pui Kin Tony,Chen, Yiding,Willis, Michael C.
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p. 10668 - 10673
(2019/11/11)
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- Sulfonamide compound and synthesis method and application thereof
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The invention discloses a synthesis method of a sulfonamide compound represented in a formula (2). According to the method, diazonium salt is used as a reaction raw material, and under the action of an inorganic nitrogen reagent, an inorganic sulfur dioxide reagent, an additive and a phosphine reagent, the diazonium salt is reacted in a solvent at 60-100 DEG C to obtain various sulfonamide compounds. According to the method inorganic salt is used as a nitrogen atom source and a sulfur dioxide source under a metal-free catalytic condition to construct the sulfonamide compound through one step,thereby avoiding the conventional multi-step synthesis of sulfonamide by condensing unstable acid chloride and amine; and the developed sulfonamide synthesis method can be further applied to the synthesis of the arthritis drug celecoxib and the psychotropic drug sulpiride.
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Paragraph 0063-0065
(2019/04/02)
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- A Strategy for the Synthesis of Sulfonamides on DNA
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An efficient method is reported to synthesize sulfonamides on DNA from sulfinic acids or sodium sulfinates and amines in the presence of iodine under mild conditions. This method demonstrates a major expansion of scope of sulfonamide formation on DNA through the utilization of a novel sodium carbonate-sodium sulfinate bifunctional reagent class.
- Liu, Wei,Deng, Wei,Sun, Saisai,Yu, Chunyan,Su, Xubo,Wu, Aliang,Yuan, Youlang,Ma, Zhonglin,Li, Ke,Yang, Hongfang,Peng, Xuanjia,Dietrich, Justin
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supporting information
p. 9909 - 9913
(2019/12/24)
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- Design, synthesis and biological evaluation of novel phenylsulfonylurea derivatives as PI3K/mTOR dual inhibitors
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Five series of novel phenylsulfonylurea derivatives, 19a–d, 20a–d, 21a–d, 22a–d and 23a–d, bearing 4-phenylaminoquinoline scaffold were designed, synthesized and their IC50 values against four cancer cell lines (HepG-2, A549, PC-3 and MCF-7) were evaluated. Most compounds showed moderate cytotoxicity activity against the cancer cell lines. Structure–activity relationships (SARs) and pharmacological results indicated that introduction of 4-aminoquinoline scaffold and phenylsulfonylurea scaffold were beneficial for anti-tumor activity. Moreover, para-methoxyl substitution of 4-anilino moiety and para-halogen substitution of phenylsulfonylurea have different impacts on different series of compounds. Furthermore, the micromolecule group substitution in the 6-position of the quinoline ring have a slight impact on the cellular activity of the target compounds.
- Zhao, Bingbing,Lei, Fei,Wang, Caolin,Zhang, Binliang,Yang, Zunhua,Li, Wei,Zhu, Wufu,Xu, Shan
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- Metal-free construction of primary sulfonamides through three diverse salts
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In this report, the first metal-free construction of primary sulfonamides through a direct three-component reaction of sodium metabisulfite, sodium azide and aryldiazonium has been established. Readily available inorganic Na2S2O5 and NaN3 were applied as the sulfur dioxide surrogate and nitrogen source respectively. The widely used sulfonamide drugs Celecoxib and Sulpiride, which possess multiple heteroatoms and active hydrogen containing functional groups, are efficiently installed with -SO2NH2 groups at a late stage. Control experiments and kinetic studies demonstrated that aryl radicals, sulfonyl radicals and conjugated phosphine imine radicals are involved in this transformation.
- Wang, Ming,Fan, Qiaoling,Jiang, Xuefeng
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supporting information
p. 5469 - 5473
(2019/01/03)
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- Highly Chemoselective NH- and O-Transfer to Thiols Using Hypervalent Iodine Reagents: Synthesis of Sulfonimidates and Sulfonamides
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Aryl thiols can be selectively converted to sulfonimidates or sulfonamides with three new S-X connections being made selectively in one pot. Using hypervalent iodine reagents in the presence of ammonium carbamate, NH- and O-groups are transferred under mild and practical conditions. Reducing the loading of ammonium carbamate changed the product distribution, converting the sulfonimidate to the sulfonamide. Studies into the possible intermediate species are presented, suggesting that multiple pathways may be possible via sulfinate esters, or related intermediates, with each species forming the same products.
- Tota, Arianna,St John-Campbell, Sahra,Briggs, Edward L.,Estévez, Gala Ogalla,Afonso, Michelle,Degennaro, Leonardo,Luisi, Renzo,Bull, James A.
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supporting information
p. 2599 - 2602
(2018/05/22)
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- Implication of sulfonylurea derivatives as prospective inhibitors of human carbonic anhydrase II
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Selective carbonic anhydrase (CA) inhibitors have gained a lot of importance owing to the implication of specific isoforms of CA in certain diseases like glaucoma, leukemia, cystic fibrosis, and epilepsy. A novel class of sulfonylurea derivatives was synthesized from corresponding sulfonyl chlorides and amines. Compounds with different pendant moieties in the sulfonylurea derivatives show significant interactions with human carbonic anhydrase II (CAII). In vitro evaluation of the sulfonylurea derivatives revealed that three compounds possess admirable inhibitory activity against CAII. Compounds containing methyl (G2), isopropyl (G4) and o-tosyl (G5) groups displayed IC50 (109-137 μm) for CAII. Fluorescence binding and cytotoxicity studies revealed that these compounds are showing good binding affinity (18-34 μM) to CAII and non- toxic to human cells. Further, molecular docking studies of G2, G4 and G5 with CAII showed that these compounds fit nicely in the active site of CAII. Molecular dynamics simulation studies of these compounds complexed with CAII showed that essential interactions were maintained up to 50 ns of simulation. These results indicate the promising nature of the sulfonylurea scaffold towards CAII inhibition and opens scope of hit to-lead optimization for discovery of effective drugs against CAII-associated disorders.
- Idrees, Danish,Hadianawala, Murtuza,Mahapatra, Amarjyoti Das,Datta, Bhaskar,Roy, Sonam,Ahamad, Shahzaib,Khan, Parvez,Imtaiyaz Hassan, Md.
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p. 961 - 969
(2018/05/23)
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- The sulfonylurea-containing structure of the preparation and application of zola non-nepal derivatives (by machine translation)
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The invention discloses a sulfonylurea structure containing sorafenib derivative, its geometric isomer and pharmaceutically acceptable salt, hydrate, solvate or prodrug, and application thereof in preparation of drugs treating and/or preventing hyperplastic diseases, application in preparation of drugs treating and/or preventing cancers, and application in preparation of drugs treating and/or preventing lung cancer, liver cancer, gastric cancer, colon cancer and breast cancer.
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- THIAZOLIDINONE COMPOUNDS AND USE THEREOF
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A pharmaceutical composition containing a compound of Formula (I) for treating an opioid receptor-associated condition. Also disclosed is a method for treating an opioid receptor-associated condition using such a compound. Further disclosed are two sets of thiazolidinone compounds of formula (I): (i) compounds each having an enantiomeric excess greater than 90% and (ii) compounds each being substituted with deuterium.
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Paragraph 0054; 0401-0402; 0458-0459
(2017/09/21)
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- Glucose promoted facile reduction of azides to amines under aqueous alkaline conditions
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A quick and efficient method for the reduction of azides to amines in water using d-glucose and KOH as green reagents is reported. The protocol is simple, inexpensive, scalable, and can be applied to different aromatic, heteroaromatic and sulphonyl azides. A high level of chemoselectivity is observed for azide reduction in the presence of other reducible functionalities like cyano, nitro, ether, ketone, amide and acid. The reaction gets completed in a short time (5-20 minutes), and furnishes the amines in high yield (85-99%). Unlike conventional hydrogenations, this reduction protocol does not require any metal catalyst, elaborate experimental setup or use of high-pressure equipment.
- Chandna, Nisha,Kaur, Fatehjeet,Kumar, Shobhna,Jain, Nidhi
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supporting information
p. 4268 - 4271
(2017/09/29)
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- A general iodine-mediated synthesis of primary sulfonamides from thiols and aqueous ammonia
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A general and efficient methodology for preparing primary sulfonamides has been developed. In the presence of iodine as the catalyst and TBHP (70% in water) as the oxidant, a wide range of primary sulfonamides were prepared from the corresponding thiols and aqueous ammonia in moderate to good yields.
- Feng, Jian-Bo,Wu, Xiao-Feng
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supporting information
p. 6951 - 6954
(2016/07/30)
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- Electrochemical Oxidative Amination of Sodium Sulfinates: Synthesis of Sulfonamides Mediated by NH4I as a Redox Catalyst
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An efficient protocol for the synthesis of sulfonamides via the electrochemical oxidative amination of sodium sulfinates has been developed. The chemistry proceeds in a simple undivided cell employing a substoichiometric amount of NH4I that serves both as a redox catalyst and a supporting electrolyte; in this manner additional conducting salt is not required. A wide range of substrates, including aliphatic or aromatic secondary and primary amines, as well as aqueous ammonia, proved to be compatible with the protocol. Scale-up was possible, thereby demonstrating the practicality of the approach. The electrolytic process avoids the utilization of external oxidants or corrosive molecular iodine and therefore represents an environmentally benign means by which to achieve the transformation.
- Jiang, Yang-Ye,Wang, Qing-Qing,Liang, Sen,Hu, Li-Ming,Little, R. Daniel,Zeng, Cheng-Chu
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p. 4713 - 4719
(2016/07/06)
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- Natural Indian Natrolite zeolite-supported Cu nanoparticles: A new and reusable heterogeneous catalyst for N-arylation of sulfonamides with boronic acids in water under ligand-free conditions
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We report here on the preparation of primary sulfonamides and efficient, easily recoverable and reusable copper nanoparticles supported on natural Indian Natrolite zeolite as a catalyst for arylation of sulfonamides with arylboronic acids in water. The catalyst was characterized using the powder XRD, SEM, EDS and FT-IR spectroscopy. The significant advantages of this methodology are high yields, elimination of organic solvents, and simple work-up procedure. The catalyst was easily isolated from the reaction mixture and reused with no significant loss in its activity.
- Azarifar, Davood,Soleimanei, Fatemeh
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p. 12119 - 12126
(2014/03/21)
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- Cascade synthesis of 2-Amino-5-(4-methoxyphenyl)-4-phenyl-1,3-thiazole by Reaction of 4-Chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl] benzenesulfonamide with Thiourea
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4-Chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl] benzenesulfonamide reacted with thiourea on heating in DMF in the presence of sodium carbonate to give 5-(4-methoxyphenyl)-4-phenyl-1,3- thiazole-2-amine. A probable reaction scheme includes cyclization of the initial N-dichloroethyl amide to N-sulfonyl-2,3-diaryl-2-chloroaziridine which undergoes isomerization with opening of the three-membered ring to 1-arylsulfonylamino-2-chloro-2-(4- methoxyphenyl)-1-phenylethene. The subsequent heterocyclization in the reaction with thiourea is accompanied by aromatization via elimination of the arenesulfonamide fragment. Pleiades Publishing, Ltd., 2011.
- Rozentsveig,Serykh,Chernyshev,Rozentsveig,Levkovskaya,Krivdin
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experimental part
p. 572 - 576
(2011/07/30)
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- Superelectrophilic activation in superacid HF/SbF5 and synthesis of benzofused sultams
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(Figure Presented) The synthesis of benzofused sultams and/or fluorlnated sulfonamides, starting from N-allyllc sulfonamides, was performed In superacid HF/ SbF5, through superelectrophilic activation. A dramatic effect of superacid composition on the selectivity of the reaction was shown and applied to the synthesis of cyclic 4-aminobenzenesulfonamides.
- Liu, Fei,Martin-Mingot, Agnes,Jouannetaud, Marie-Paule,Zunino, Fabien,Thibaudeau, Sebastien
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supporting information; experimental part
p. 868 - 871
(2010/04/27)
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- Chemistry of diazocarbonyl compounds: XXVIII. Reaction of acyclic N-arylsulfonylacetamides with Rh(II)-carbenoids as a new synthetic route to alkyl acetimidoates
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A new procedure was proposed for the synthesis of alkyl acetimidoates via alkylation of the carbonyl group in N-arylsulfonylacetamides with Rh(II)-carbenoids. The procedure ensures preparation in good yield of acetimidoates having a polyfunctionalized O-alkyl group. The obtained alkyl acetimidoates in crystal exist as E isomers with respect to the C=N bond and as s-cis conformers relative to the C-OCHRR' bond. Alkyl N- arylsulfonylacetimidoates react with ammonia and hydrazine hydrate to give in good yield the corresponding carboximidamides(hydrazides) via replacement of the O-alkyl group. Unlike structurally related compounds having simple alkyl or aryl groups on the nitrogen atom, N-arylsulfonylacetimidoates readily undergo hydrolysis in the presence of moisture and traces of acids.
- Selivanova,Nikolaev,Kostikov,Nikolaev,Siler,Schulze
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p. 1792 - 1799
(2007/10/03)
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- Kinetics and mechanism of oxidation of D-fructose and D-glucose by sodium salts of N-(chloro)-mono/di-substituted benzenesulfonamides in aqueous alkaline medium
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In an effort to introduce N-chloroarylsulfonamides of different oxidizing strengths, nine sodium salts of mono- and di-substituted N- chloroarylsulfonamides are employed as oxidants for studying the kinetics of oxidation of D-fructose and D-glucose in aqueous alkaline medium. The results are analyzed along with those by the sodium salts of N-chlorobenzenesulfonamide and N-chloro-4-methylbenzenesulfonamide. The reactions show first-order kinetics each in [oxidant], [Fru/Glu], and [OH-]. The rates slightly increase with increase in ionic strength of the medium. Further, the rate of oxidation of fructose is higher by 4 to 5 times than that of the glucose oxidation, by the same oxidant. Similarly, Ea values for glucose oxidations are higher by about 1.5 times the Ea values for fructose oxidations. The results have been explained by a plausible mechanism, and the related rate law deduced. The significant changes in the kinetics and thermodynamic data are observed with change of substituent in the benzene ring. It is because Cl + is the effective oxidizing species in the reactions of N-chloroarylsulfonamides. The oxidative strengths of the latter therefore depend on the ease with which Cl+ is released from them. The ease with which Cl+ is released from N-chloroarylsulfonamides depends on the electron density of the nitrogen atom of the sulfonamide group, which in turn depends on the nature of the substituent in the benzene ring. The following Hammett equations are valid for the oxidation of fructose and glucose, log kobs = -3.13 + 0.54 σ ρ and log kobs = -3.81 + 0.28 σ ρ, respectively. The enthalpies and entropies of activations for oxidations by all the N-chloroarylsulfonamides correlate well with isokinetic temperatures of 301 K and 299 K, for fructose and glucose oxidations, respectively. The effect of substitution in the oxidants on the Ea and log A for the oxidations is also considered.
- Gowda, B. Thimme,Damodara,Jyothi
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p. 572 - 582
(2007/10/03)
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- N-Acyl arylsulfonamides as novel, reversible inhibitors of human steroid sulfatase
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Steroid sulfatase (STS) is an attractive target for a range of oestrogen- and androgen-dependent diseases. In search of novel chemotypes of STS inhibitors, we had previously identified nortropinyl-arylsulfonylureas 1; however, while these compounds were good inhibitors of purified STS (lowest Ki = 76 nM), they showed only weak inhibition of STS activity in cells (lowest IC50 around 2 μM). Extended structure-activity relationship studies involving modification of the phenylacetyl side chain and replacement of the nortropine element by simpler scaffolds led to the discovery of N-acyl arylsulfonamides, more specifically N-(Boc-piperidine-4-carbonyl)- benzenesulfonamides, as STS inhibitors, some of which exhibit improved cellular potency (best IC50 = 270 nM).
- Lehr, Philipp,Billich, Andreas,Wolff, Barbara,Nussbaumer, Peter
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p. 1235 - 1238
(2007/10/03)
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- Excitatory amino acid receptor antagonists
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The present invention provides compounds of Formula I or Formula II, or the pharmaceutically acceptable salts or prodrugs thereof, pharmaceutical compositions comprising compounds or Formula I or Formula II, and methods for treating neurological disorders and neurodegenerative diseases, particularly migraine.
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- Unprecedented observation of sulfonamides in the transesterification of N-unsubstituted carbamates with sulfonyl chlorides
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Sulfonamides have been identified as by-products in the base-mediated transesterification of N-unsubstituted carbamates with sulfonyl chlorides to give the corresponding sulfonates. A proposed mechanism and the synthesis of hindered 2,6-disubstituted arylsulfonates via this method are also reported.
- Dauvergne, Jér?me,Wellington, Kevin,Chibale, Kelly
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- Thiylation of functionalized electrophiles with sulfur in basic reductive systems
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Functionalized electrophiles, specifically acetyl chloride, benzoyl chloride, chloroacetylchloride, benzenesulfonyl chloride, and N,N,4-trichlorobenzenesulfonamide, were brought into reaction with sulfur in the systems hydrazine hydrate-NaOH and sodium sulfide-water-ethanol. The efficiencies of these systems were compared. The reaction of chloroacetyl chloride with sulfur in the system hydrazine hydrate-base afforded new types of polymeric compounds, poly[(diacylhydrazine)polysulfides]. The reaction mechanisms were discussed.
- Deryagina,Russavskaya,Grabel'nykh
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p. 346 - 349
(2007/10/03)
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- Boron trichloride as an efficient and selective agent for deprotection of tert-butyl aryl sulfonamides
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A fast, mild and selective method for deprotection of tert-butyl aryl sulfonamides utilizing BCl3 as deprotection reagent has been developed. A variety of tert-butyl aryl sulfonamides used under these conditions gave the corresponding primary sulfonamides in high yields. The method does not cleave methoxy groups and prevents incorporation of tert-butyl groups onto electron-rich aromatic rings.
- Wan, Yiqian,Wu, Xiongyu,Kannan, Mahalingam A.,Alterman, Mathias
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p. 4523 - 4525
(2007/10/03)
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- A mild, efficient method for the synthesis of aromatic and aliphatic sulfonamides
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A two-step method was developed for the synthesis of aromatic and aliphatic sulfonamides from the corresponding sulfinates using bis(2,2,2-trichloroethyl)azodicarboxylate as the electrophilic nitrogen source. The intermediate sulfonylhydrazides were obtained in very good yields and were cleaved under reductive conditions to deliver the desired sulfonamides. A variety of substituents in the aromatic ring are well tolerated as well as heterocycles.
- Chan, Wing Yan,Berthelette, Carl
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p. 4537 - 4540
(2007/10/03)
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- Anisole alkylation with N-arenesulfonylimines of dichloro(phenyl)acetaldehyde and derivatives thereof
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N-[1-4-Methoxyphenyl-2-phenyl-2,2-dichloroethyl]arenesulfonamides are formed in reaction of N-(2-phenyl-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide and N-(2-phenyl-2,2-dichloroethylidene)-4-methylbenzenesulfonamide with anisole catalyzed by boron t
- Drozdova,Mirskova
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p. 819 - 821
(2007/10/03)
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- Synthesis of N-(2-benzene-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide and N-(2-benzene-2,2-dichloroethylidene)-4-methylbenzenesulfonamide
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In reaction of N,N-dichloro-4-chlorobenzene-and N,N-dichloro-4-methylbenzenesulfonamides with phenylacetylene were obtained in good yield N-(2-benzene-2,2-dichloroethylidene)arenesulfonamides. The latter undergo nucleophilic addition of water, ethanol, an
- Drozdova,Mirskova
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p. 284 - 287
(2007/10/03)
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- Hydrolysis of N-(2,2,2-trichloroethyl)arenesulfonamides
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The direction of alkaline hydrolysis of N-(2,2,2-trichloro-1-R-ethyl)arenesulfonamides depends on the R substituent in the α-position with respect to the nitrogen atom. Substituents R having an n-donor heteroatom X promote cleavage of the C-N and C-X bonds to release the corresponding sulfonamide. Alkaline hydrolysis of N-(1-aryl-2,2,2-trichloroethyl)arenesulfonamides occurs chemoselectively at the trichloromethyl group. This reaction can be regarded as a preparative route to N-arylsulfonyl-α-arylglycines.
- Rozentsveig,Levkovskaya,Mirskova,Kashik
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p. 1760 - 1764
(2007/10/03)
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- S-aminosulfeniminopenicillins: Multimode β-lactamase inhibitors and template structures for penicillin-based β-lactamase substrates as prodrugs
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A series of novel penicillins, bearing an S-aminosulfenimine (R'(R'')NSN=) side chain at the 6-position, have been prepared by direct reaction of a penicillin ester with sulfur diimides. A set of these structures, with the thiazolidine-ring sulfur in the sulfide oxidation state, exhibited a pattern of reactivity not previously encountered in penicillin chemistry, viz., cleavage of the β-lactam ring resulted in a rapid intramolecular displacement of the S-amino moiety as R'(R'')NH. This was found to be the exclusive reaction occurring consequent on cleavage of the β-lactam ring. The mechanism of this process was delineated in a detailed study in basic methanol. That a similar reactivity pattern held for a penicillin salt in aqueous solution was also verified. Thus the salt 5bm (R' = CH3, R'' = p-CH3C6H4SO2) behaved as a moderate substrate for β- lactamase type I from Bacillus cereus (k(cat)/K(m) = 6.26 x 105 M-1 min- 1). On enzyme-catalyzed hydrolysis of this compound, displacement of N- methyl-p-toluenesulfonamide (R'(R'')NH) was directly observed (1H NMR) and found to occur faster than displacement of this group from (intact) 5bm in aqueous buffer, by a factor of at least 600. These findings identified the potential of the s-aminosulfeniminopenicillin structure type to be developed as β-lactamase substrates for use as site-specific-release prodrugs. A degree of enzyme inhibition was also observed with this set of thiazolidine- ring-sulfide structures with the most potent inhibitor having the most nucleofugic S-amino moiety p-ClC6H4SO2N(CH3), indicating that displacement of this group, at the enzyme active site, played a role in their mode of inhibition. Structures with the thiazolidine-ring sulfur in the sulfone oxidation state were considerably more potent as inhibitors, with the structure 5a2 being the most active. As this compound bore the least nucleofugic S-amino moiety C2H5OC(O)NH, it indicated that the mode of inhibition of the sulfones was distinct from that of the thiazolidine-ring sulfides; it is probable that the sulfones reacted in a manner similar to that shown by sulbactam viz., rapid scission of the thiazolidine-sulfone ring after cleavage of the β-lactam ring. Synergy of action was observed with 5a2 at high concentration (78 μg/mL) against Escherichia coli when combined 1:1 with penicillin G; no synergy was observed at low concentration (4 μg/mL) when combined with pipericillin, indicating poor permeation characteristics.
- Smyth, Timothy P.,O'Donnell, Michael E.,O'Connor, Michael J.,St Ledger, James O.
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p. 7600 - 7618
(2007/10/03)
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- Reaction of Trimeric Dimethyltin Sulfide with Sodium 4,N-Dichlorobenzenesulfamidate
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Reaction of the trimeric cyclic dimethyltin sulfide (Me2SnS)3 with sodium 4,N-dichlorobenzenesulfamidate (Khloramin-KhB) at a 1:2 molar ratio in anhydrous methanol first results in clevage of the six-membered ring with Khloramin-KhB and release of one of the three sulfur atoms in the form of S0 (oxidative degradation). The second stage involves oxidative imination of one of the two remaining sulfur atoms in the resulting acyclic compound with a second Khloramin-KhB molecule to give organotin sufimide, including a -Me2SnS(=NSO2C6H4Cl 4)SnMe2- functional fragment. Hydrolysis of this sulfimide gives 4-chlorobenzenesulfamide and the sulfite HO-Me2Sn-O-S(=O)-O-SnMe2-OH.
- Shcherbakov,Basova
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p. 1049 - 1053
(2007/10/03)
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- Reaction of N,N-dichloroarenesulfonamides with propargyl alcohol
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The reaction of N,N-dichloroarenesulfonamides with propargyl alcohol gives 3-hydroxy-2,2-dichloro-1,1-di(N-arenesulfonamido)propanes and N-(3-hydroxy-2,2-dichloropropylidene)arenesulfonamides. The latter were obtained due to the transformation of intermediate products, N-chloro-N-(3-hydroxy-2-chloro1-propenyl)arenesulfonamides, by the 1,3-migration of the halogen atom. The addition of arenesulfonamides formed in the reaction to N-(3-hydroxy-2,2-dichloropropylidene)arenesulfonamides results in the formation of 3-hydroxy-2,2-dichloro-1,1-di(N-arenesulfonamido)propanes.
- Drozdova,Kozyreva,Mirskova
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p. 243 - 245
(2007/10/03)
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- Effects of medium and substituents on dissociation of 4,4′-disubstituted bis(benzenesulfon)imides
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Ten 4,4′-disubstituted bis(arenesulfon)imides of the general formula XC6H4SO2NHSO2C6H 4X have been synthesized and their structures confirmed by their 1H NMR spectra. Elemental analyses are presented for the compounds not yet described. The dissociation constants of these model substances have been measured potentiometrically in pyridine, dimethylformamide, methanol, ethanol, propylene carbonate, acetone, acetonitrile, 1,2-dichloroethane and tetramethylene sulfone. The pKHA values obtained have been correlated with three sets of the Hammett substituent constants and the results have been used to discuss the solvent and substituent effects on the dissociation of the compounds studied. Sulfonimides with electron-acceptor substituents behave as rather strong acids in some solvents (pyridine, dimethylformamide, methanol and ethanol), whereas normal substituent dependences are found in other solvents. The experimental data have also been interpreted with the help of the statistical methods based on latent variables. From the calculations it follows that only the first principal component, which correlates well with the substituent constant sets adopted, is statistically significant in describing the substituent effect on the acid-base process studied.
- Ludwig, Miroslav,Stverka, Pavel
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p. 1205 - 1214
(2007/10/03)
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- Photodegradation and in vitro phototoxicity of the antidiabetic drug chlorpropamide
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Methanolic solutions of the phototoxic antidiabetic drug chlorpropamide (CAS 94-20-2, 1) are photolabile towards UVB light under aerobic conditions. Irradiation of 1 produces the formation of the stable compounds p-chlorobenzenesulfonamide (2), N-(p-chlorophenylsulfonyl)formamide (3) and the dimer 4. A radical intermediate was evidenced by thiobarbituric acid that was used as a radical sonde, as well as by the dimerization of cysteine. The compound 1 showed moderate lytic activity upon the photohemolysis in vitro test on human erythrocytes which was increased with the addition of traces of its aggregate excipient. Inhibition of this process on addition of reduced glutathione (GSH), superoxide dismutase (SOD) or ascorbic acid suggests the involvement of radicals and superoxide ion in the photohemolysis process. The absence of inhibition with 1,4-diazabicyclo[2.2.2]octane (DABCO) and sodium azide (NaN3), and the lack of formation of singlet oxygen during the photolysis (confirmed with 2,5-dimethylfuran) rule out the possibility of participation of 1O2 in this process. Glutathione depletion was also observed. No photohemolysis was detected in the presence of the isolated photoproduct.
- Vargas,Matskevitch,Sarabia
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p. 1079 - 1081
(2007/10/02)
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- A Novel One-Pot Conversion of Methyl Sulfones to Sulfonamides
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A one-pot synthesis of sulfonamides from methyl sulfones has been developed.Treatment of methyl sulfones with base and trialkylboranes gave the corresponding rearranged sulfinic acid salts which were converted to sulfonamides during oxidative-amination workup.
- Huang, Horng-Chih,Reinhard, Emily J.,Reitz, David B.
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p. 7201 - 7204
(2007/10/02)
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- Reactions of 1-Arenesulfonyl-4-nitroimidazoles with Aniline in Aqueous Methanol Solution
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Several 1-arenesulfonyl-4-nitroimidazoles were obtained and reacted with aniline in methanol-water medium at 65-70 deg C to yield mixtures of 1-arenesulfonylamide, 1-arenesulfonylanilide, 4-nitro-1-phenylimidazole and 4(5)-nitroimidazole in varied proportions depending on the arenesulfonyl group. - Key words: 1-arenesulfonyl-4-nitroimidazoles, nucleophilic substitution, imidazole ring transformation
- Suwinski, Jerzy,Salwinska, Ewa
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p. 5741 - 5752
(2007/10/02)
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- Sulfonamides and uses
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Sulfonamides of formula I, in which the symbols R1 -R6, X, Y and n have the significance given in the description and which are in part novel compounds, and salts thereof, which can be used as active ingredients for the manufacture of medicaments for the treatment of circulatory disorders, especially hypertension, ischemia, vasospasms and angina pectoris, are described.
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- SUBSTITUTED SULPHONAMIDES, PHARMACEUTICALS THEREOF AND METHODS OF USING THEM
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The present invention concerns compounds of the formula: STR1 where R 1 is an alkyl or alkenyl radical containing up to 6 carbon atoms, a cycloalkyl radical containing 3 to 7 carbon atoms, an aralkyl, aralkenyl or aryl radical in which the aryl radical or moiety can be substituted one or more times by halogen, C 1-C 6-alkyl, C 1-C 6-alkoxy, hydroxyl, trifluoromethyl, cyano, nitro, amino, C. sub.1-C 6-alkylamino, C. sub.2-C 12-dialkylamino, C 1-C. sub.6-acylamino, C 1-C 16-acyl, C 1-C 6-alkylsulphenyl,-sulphinyl or-sulphonyl or by azido, R 2 is hydrogen atom or a C 1-C 6-alkyl, aralkyl, aralkenyl or acyl radical, A and B are saturated or unsaturated alkylene chains containing up to 10 carbon atoms which can be substituted one or more times by C. sub.1-C. sub.3-alkyl radicals, the sum of carbon atoms in chains A and B being at least 4 and at most 11, Q is an oxygen or sulphur atom, a sulphonyl or sulphinyl group or an amino group--N(R 2)--, R 2 having the same meaning as above, and Y is a free carboxylic acid group or a carboxylic acid ester, carboxylic acid amide, hydroxymethyl or tetrazolyl radical; the pharmacologically acceptable salts thereof and the optically active and E-Z isomers thereof, as well as mixtures thereof. These compounds are useful as they have an antagonistic action towards thromboxane A 2 as well as against prostaglandin endoperoxide. They inhibit the aggregation of blood platelets and prevent the constriction of the smooth musculature as well as bronchoconstriction.
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- Mild and Efficient Synthesis of Aromatic Sulfonamides by in situ Preparation of the Corresponding Sulfonyl Isothiocyanates
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A new reaction between chlorosulfonyl isocyanate (1) and trialkylstannyl-substituted arenes 2a-k, 7, 9 is described.It provides the aromatic sulfonyl isocyanates 3 or their derivatives, the sulfonamides 4a-j, the sulfonylcarbamates 5a-b, or sulfonylureas 6, respectively.The trialkylstannyl group as an efficient leaving group allows mild reaction conditions to be applied and unusual substitution patterns to be obtained, normally not accessible by electrophilic aromatic substitutions.Thus, sulfonamidation can be achieved in meta position to a trifluoromethyl group. Key words: Electrophilic aromatic substitution; sulfodestannalytion; isocyanates, sulfonyl, aromatic; sulfonyl compounds; trialkylarylstannanes, application of
- Arnswald, Martin,Neumann, Wilhelm P.
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p. 1997 - 2000
(2007/10/02)
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- REAKTIONEN VON THIOXOHETEROCYCLEN MIT N-CHLORAMIDEN III. 2- ODER 4-THIOPYRIDONE OHNE SUBSTITUENTEN AM STICKSTOFF UND NATRIUM-N-CHLORBENZOLSULFONAMIDE
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2- and 4-pyridinethiones (A) react with sodium N-chlorobenzenesulfonamides (1) in alcoholic solvents to N-(pyridylthio)benzenesulfonamides (C), sodium N,N'-bis(phenylsulfonyl)-S-pyridylsulfodiimidates (D) and S-alkoxy-N-phenylsulfonyl-S-pyridylsulfimides (E).Constitution proofs for the new compounds D, E are reactions and 1H-, 13C-, 15N-nmr data.
- Boberg, Friedrich,Bruchmann, Bernd,Garming, Alfons,Nink, Gunter
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p. 313 - 326
(2007/10/02)
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- REGIOSELECTIVITY OF ADDITION OF N-HALOGENOAMIDES TO 1,3-ALKENYNES
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The addition of N,N-dihalogenoamides to conjugated alkenynes is a regioselective homolytic process and begins with attack by the amidyl radical at the terminal ethylene atom of the vinylacetylene system.The order of addition of the N,N-dihalogenosulfonamides does not depend on the nature of the halogen atom or on the experimental conditions.
- Labeish, N. N.,Porfir'eva, Yu. I.,Petrov, A. A.
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p. 1461 - 1467
(2007/10/02)
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- NUCLEAR MAGNETIC RESONANCE AND X-RAY DIFFRACTION STUDIES ON SOME SUBSTITUTED BENZENESULPHONAMIDES
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Solid-state 13C c.p.-m.a.s. and solution 13C, 15N, and 17O n.m.r. spectra were measured for toluene-p-sulphonamide, N-methyltoluene-p-sulphonamide, NN-dimethyltoluene-p-sulphonamide, p-chlorobenzenesulphonamide, and NN-simethyl-p-chlorobenzenesulphonamide.The 13C c.p.-m.a.s. n.m.r. resonance lines of the carbon atoms bonded to nitrogen show characteristic line broadening with sligthly asymmetric doublet petterns.Some differences are evident in the 13C shielding of the carbon atoms between the solid-state and solution-state spectra.In the solution spectra the 15N and 17O chemical shifts increase in conformity with the polarity order of the amides.The n.m.r. relaxation times of the methyl groups of the compounds were measured as well.The crystal structures of N-methyltoluene-p-sulphonamide and NN-dimethyltoluene-p-sulphonamide were determined by single-crystal X-ray diffraction technique and refined to final R values of 0.056 and 0.044, respectively.Except for some baely significant differences, the bond lengths and angles are similar in the two compounds.The most striking difference is the value of the C-C-S-N torsion angle.
- Haekkinen, Anna-Marija,Ruostesuo, Pirko,Kivekaes, Raikko
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p. 815 - 820
(2007/10/02)
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- Iodide Reduction of Sulfilimines. 3. Evidence of a Minor Role for Catalysis by Hydrogen Bonding in the Decomposition of Sulfurane Intermediates
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The iodide reduction of N-(substituted benzoyl or benzenesulfonyl)-S,S-dimethylsulfilimine ylides (aqueous solution, 25 deg C, μ = 1.0 with KCl) is first order with respect to iodide concentration in the pH range 0.5-5; the order with respect to the proton is slightly > 1.0.The solvent deuterium isotope effect for the reduction of N-(4-chlorobenzoyl)-S,S-dimethylsulfilimine ylide is kH/kD = 0.6.Electron-withdrawing groups in the leaving group accelerate the rate of the reaction and give βl.g. value of -0.67.General acid catalysis is observed in the reduction reaction with Broensted α values of 0.15 and 0.29 for 4-methoxybenzamide and 4-chlorobenzenesulfonamide leaving groups, respectively.The value of βl.g. increases with decreasing strength of the catalyzing acid and the term pxy = (δβl.g./δpKaHA) = (δα/δpKal.g.) ca. +0.05.The solvent deuterium isotope effect on the general catalyzed reduction reaction is small (kBH/kBD = 1.32) and independent of acid strength.For the solvent-catalyzed reaction, it is suggested that the rate-limiting step involves diffusion apart of the amide anion-iodosulfonium cation pair.It is concluded, however, that the observed general catalysis does not arise from hydrogen bonding effects in a preassociation-type mechanism, but rather it involves proton transfer that is concerted with S-N bond cleavage.
- Young, Paul R.,Huang, H. C.
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p. 1810 - 1813
(2007/10/02)
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- THERMAL Z,E-ISOMERIZATION OF IMINES. VI. N-ARYLSULFONYLIMINES OF ACETONE AND 2,6-DI-tert-BUTYL-1,4-BENZOQUINONE
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The thermal topomerization of acetone N-arylsulfonylimines and 2,6-di-tert-butyl-1,4-benzoquinone N-arylsulfonyl-4-monoimines was studied by the dynamic PMR method.The inversion mechanism of the topomerization of the N-arylsulfonylimines was established on the basis of an investigation into the electronic and steric effects of substituents at the sulfur atom on the sizes of the barriers to topomerization.The effect of nN-3dS and nN-?c-s* interactions and the induction effect of the arylsulfonyl group on the sizes of the barriers to inversion at the nitrogen atom are considered.The reduction of the barriers to inversion in the N-arylsulfonylimines with increase in the electron-withdrawing characteristics of the para substituents in the aryl ring is largely determined by the increase in the nN-3dS interaction.
- Prosyanik, A.V.,Kol'tsov, N.Yu.,Romanchenko, V.A.,Belov, V.V.,Burmistrov, K.S.,Loban', S.V.
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p. 335 - 342
(2007/10/02)
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