- Electrochemical synthesis of sulfonamides from arenesulfonohydrazides or sodium p-methylbenzenesulfinate and amines
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An efficient electrochemical synthesis of sulfonamides (yields 56–98%) from arenesulfonohydrazides or sodium p-methylbenzenesulfinate and amines was performed in an undivided cell with graphite anode and iron cathode in MeCN–H2O medium using halides as redox mediators and supporting electrolytes.
- Terent'ev, Alexander O.,Mulina, Olga M.,Pirgach, Dmitry A.,Syroeshkin, Mikhail A.,Glinushkin, Alexey P.,Nikishin, Gennady I.
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- Cu-catalyzed aerobic oxidative synthesis of sulfonamides from sulfonyl hydrazides and amines
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An environmentally friendly route for sulfonamides has been developed. The oxidative coupling of sulfonyl hydrazides and amines was catalyzed by CuBr2 to produce various sulfonamides with the water and nitrogen gas as byproducts. Preliminary experiments revealed that the sulfonyl radical is likely to be involved in the reaction mechanism.
- Chung, Sohyun,Kim, Jinho
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Read Online
- Dynamic 1H NMR spectroscopic study of the ring inversion in N-sulfonyl morpholines - Studies on N-S interactions
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(Chemical Equation Presented) The effect of the exocyclic conjugation, via d-p orbital interaction and/or negative hyperconjugation (anomeric effect) of the N-S bond, on the inversion of the morpholine ring in some N-arylsulfonyl morpholines is studied by variable-temperature 1H NMR spectroscopy in different solvents. The observed free energy barriers are 9.2-10.3 kcal mol-1; the lower values were obtained with increasing conjugation (substituents of higher electron withdrawing power) along the series. The barrier to ring inversion of 1e was solvent independent. X-ray data of compounds 1b,d reveal the chair conformation of the six-membered ring, the flattened pyramidal orientation of the ring nitrogen atom, and the sulfonyl group in equatorial position with the plane containing the Caryl-S-N bond perpendicular to the plane of the benzene ring. In addition, the sulfonamide group prefers a conformation with the S-C bond antiperiplanar with respect to the nitrogen atom lone pair and the -CH2-N-CH2- moieties in staggered conformation with the S-O bonds of the SO2 group.
- Modarresi-Alam, Ali Reza,Amirazizi, Homeyra Alsadat,Bagheri, Hajar,Bijanzadeh, Hamid-Reza,Kleinpeter, Erich
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Read Online
- Antimicrobial action of arylsulfonamides bearing (aza)norbornane and related motifs: evaluation of new promising anti-MRSA agents
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Arylsulfonamides bearing (aza)norbornane and related motifs were evaluated for: (1) antimicrobial activity toward five key ESKAPE pathogenic bacteria, one Gram‐positive bacteria methicillin‐resistant Staphylococcus aureus (MRSA, ATCC 43300), four Gram‐neg
- Finiuk, Nataliya,Manko, Nazar,Obushak, Mykola,Palchykov, Vitalii,Pokhodylo, Nazariy,Stoika, Rostyslav
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p. 284 - 292
(2022/01/12)
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- Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid
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The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the ?NO2 radical is the active species.
- Baucom, Kyle D.,Brown, Derek B.,Caille, Seb,Murray, James I.,Quasdorf, Kyle,Silva Elipe, Maria V.
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supporting information
(2021/06/30)
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- AEROBIC OXIDATIVE SYNTHESIS OF SULFONAMIDE USING Cu CATALYST
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The present invention relates to a method for oxidative synthesis of sulfonamides using copper catalysts. , Oxygen (O) is used. 2 The oxidative synthesis of sulfonamides (1) comprises reacting a 2 th or sulfonyl hydrazide primary amine with a sulfonyl hydrazide (sulfonamide) with a copper catalyst on a solvent under the conditions in which the sulphonamide is fed. The oxidation coupling of the present invention showed extensive substrate ranges in an amine comprising a 2 primary amine, 1 primary amine and amine hydrochloride salt. It is worth notable that non-reactive aliphatic sulfonyl hydrazides in previously reported anaerobic systems can be used for the aerobic oxidation coupling of the present invention. The oxidation coupling of the present invention has been more effective on large scale.
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Paragraph 0033-0037; 0039-0054; 0066-0069; 0157-0158
(2021/04/06)
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- Benzoylaniline compound and application of benzoylaniline compound in preparation of sensitizer of P.aeruginosa inhibitor
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The invention discloses a benzoylaniline compound. The benzoylaniline compound has a structural general formula shown in the specification. The invention also discloses application of the benzoylaniline compound in preparation of a sensitizer of a P.aeruginosa inhibitor or in preparation of a medicine for preventing or treating bacterial infection diseases caused by P.aeruginosa. The invention also discloses an application of niclosamide in preparation of a sensitizer of a P.aeruginosa inhibitor or in preparation of a medicine for preventing or treating bacterial infection diseases caused by P.aeruginosa. The benzoylaniline compound provided by the invention can be used as a medicine for treating and/or preventing bacterial infection diseases caused by P.aeruginosa.
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Paragraph 0194-0200
(2020/08/29)
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- Hydrogen-Bonding Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers over Ionic Liquid under Metal-Free Conditions
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O-heterocycles have wide applications, and their efficient and green synthesis is very interesting. Herein, we report hydrogen-bonding catalyzed ring-closing metathesis of aliphatic ethers to O-heterocycles over ionic liquid (IL) catalyst under metal- and solvent-free conditions. The IL 1-butylsulfonate-3-methylimidazolium trifluoromethanesulfonate ([SO3H-BMIm][OTf]) is discovered to show outstanding performance, better than the reported catalysts. An interface effect plays an important role in mediating the reaction rate due to the immiscibility between the products and the IL catalyst, and the products can be spontaneously separated. NMR analysis and DFT calculation suggest that a pair of cation and anion of [SO3H-BMIm][OTf] could form three strong H-bonds with an ether molecule, which catalyze the ether transformation via a cyclic oxonium intermediate. A series of O-heterocycles including tetrahydrofurans, tetrahydropyrans, morpholines and dioxane can be obtained from their corresponding ethers in excellent yields (e.g., >99 %). This work opens an efficient and metal-free way to produce O-heterocycles from aliphatic ethers.
- Wang, Huan,Zhao, Yanfei,Zhang, Fengtao,Wu, Yunyan,Li, Ruipeng,Xiang, Junfeng,Wang, Zhenpeng,Han, Buxing,Liu, Zhimin
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p. 11850 - 11855
(2020/05/16)
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- Novel method for preparing oxygen heterocyclic compound through ionic liquid catalysis
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The invention discloses a novel method for preparing an oxygen heterocyclic compound through ionic liquid catalysis. The ionic liquid catalytic system has the advantages of high efficiency, simplicity, mild reaction conditions, no metal participation, no by-product, simple separation and the like and can efficiently catalyze fatty diether metathesis cyclization to prepare an oxygen heterocyclic compound and has very high industrial application value.
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Paragraph 0103-0108
(2020/08/02)
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- Potassium tert-butoxide-mediated metal-free synthesis of sulfonamides from sodium sulfinates and N,N-disubstituted formamides
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By using formamides as amine sources, a novel and efficient KO-t-Bu mediated amination of sodium sulfinates has been developed. The reaction utilizes readily available starting materials under metal-free conditions, thus providing an alternative and attractive route to sulfonamides.
- Bao, Xiaodong,Rong, Xiaona,Liu, Zhiguo,Gu, Yugui,Liang, Guang,Xia, Qinqin
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supporting information
p. 2853 - 2858
(2018/06/25)
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- Iron-Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers
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Among all metathesis reactions known to date in organic chemistry, the metathesis of multiple bonds such as alkenes and alkynes has evolved into one of the most powerful methods to construct molecular complexity. In contrast, metathesis reactions involving single bonds are scarce and far less developed, particularly in the context of synthetically valuable ring-closing reactions. Herein, we report an iron-catalyzed ring-closing metathesis of aliphatic ethers for the synthesis of substituted tetrahydropyrans and tetrahydrofurans, as well as morpholines and polycyclic ethers. This transformation is enabled by a simple iron catalyst and likely proceeds via cyclic oxonium intermediates.
- Biberger, Tobias,Makai, Szabolcs,Lian, Zhong,Morandi, Bill
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supporting information
p. 6940 - 6944
(2018/05/14)
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- Synthesis of aromatic sulfonamides through a copper-catalyzed coupling of aryldiazonium tetrafluoroborates, DABCO·(SO2)2, and N-Chloroamines
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A copper-catalyzed aminosulfonylation of aryldiazonium tetrafluoroborates, DABCO·(SO2)2, and N-chloroamines is described. This coupling reaction provides an efficient and simple approach to a wide range of sulfonamides in moderate to good yields under mild conditions. Mechanistic investigation suggests that a radical process and transition-metal catalysis are merged in this tandem reaction.
- Zhang, Feng,Zheng, Danqing,Lai, Lifang,Cheng, Jiang,Sun, Jiangtao,Wu, Jie
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supporting information
p. 1167 - 1170
(2018/02/23)
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- A Route to O-Aminosulfonates and Sulfonamides through Insertion of Sulfur Dioxide and Hydrogen Atom Transfer
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A three-component reaction of aryldiazonium tetrafluoroborates, the 1,4-diazabicyclo[2.2.2]octane?bis(sulfur dioxide) adduct [DABCO?(SO2)2] and hydroxylamines under catalyst-free and additive-free conditions has been developed, providing aryl O-aminosulfonates in good yields. Sulfonamides could also be obtained via a one-pot process through the reaction of aryldiazonium tetrafluoroborates, DABCO?(SO2)2 and amines in the presence of N-hydroxybenzotriazole. A mechanism involving the insertion of sulfur dioxide and hydrogen atom transfer is proposed and supported by theoretical calculations. (Figure presented.).
- Liu, Tong,Zheng, Danqing,Li, Zhenhua,Wu, Jie
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supporting information
p. 2653 - 2659
(2017/08/16)
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- NH4I-Catalyzed Synthesis of Sulfonamides from Arylsufonylhydrazides and Amines
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A novel and efficient approach to sulfonamides has been developed. Using TBHP as the oxidant and NH4I (20 mol%) as the catalyst, arylsulfonyl hydrazides reacted with amines to provide sulfonamides in moderate to good yields. Possible reaction pathway for the formation of the products was also discussed in this paper. Sulfonimides were synthesized through the oxidation coupling of arylsufonylhydrazides and amines by TBHP/NH4I system in moderate to good yields.
- Yu, Hui,Zhang, Yonghao
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supporting information
p. 359 - 362
(2016/04/26)
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- Synthesis and biological evaluation of norcantharidin derivatives as protein phosphatase-1 inhibitors
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Cantharidin and norcantharidin display anticancer activity against a broad range of tumor cell lines. In this study, we have synthesized a series of norcantharidin derivatives and evaluated their cytotoxic effects on four human tumor cell lines together with the genetically normal human diploid fibroblast line WI-38. One of our compounds (1S,4R)-3-((4-(4-(4-fluorophenyl)piperazin-1-ylsulfonyl) phenyl)carbamoyl)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid (12) exhibited potent cytotoxic effects on the tumor cell lines A-549, HepG2, HeLa, and HCT-8, whereas it was less toxic to WI-38 cells than its parent compound, norcantharidin. In addition, this compound inhibited protein phosphatase-1 activity and microtubule formation in HeLa cells, and it also interacts with calf thymus DNA.
- Zhao, Jie,Guan, Xiao-Wen,Chen, Shi-Wu,Hui, Ling
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p. 363 - 366
(2015/02/19)
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- Iodine-catalyzed expeditious synthesis of sulfonamides from sulfonyl hydrazides and amines
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A new synthesis of sulfonamides has been developed via an iodine-catalyzed sulfonylation of amines with arylsulfonyl hydrazides. This metal-free strategy employs readily accessible and easy to handle starting materials, catalysts and oxidants, and can be easily conducted under mild conditions, providing a convenient access to a wide range of sulfonamides in moderate to excellent yields within a short reaction time.
- Yotphan, Sirilata,Sumunnee, Ladawan,Beukeaw, Danupat,Buathongjan, Chonchanok,Reutrakul, Vichai
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p. 590 - 597
(2016/01/12)
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- Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature
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A novel, practical and highly efficient method for the construction of a variety of sulfonamides mediated by I2 was demonstrated. The reaction proceeds readily at room temperature using a variety of sodium sulfinates and amines or ammonia in water in a metal-, base-, ligand-, or additive-free protocol. Primary, secondary and tertiary sulfonamides were obtained in good to excellent yields with a broad range of functional group tolerability. This journal is
- Yang, Kai,Ke, Miaolin,Lin, Yuanguang,Song, Qiuling
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p. 1395 - 1399
(2015/03/18)
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- CYCLOPROPYL AMIDE DERIVATIVES
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The present invention relates to certain cyclopropyl amide compounds, pharmaceutical compositions comprising such compounds, and methods of treating cancer, including leukemias and solid tumors, inflammatory diseases, osteoporosis, atherosclerosis, irritable bowel syndrome, and other diseases and medical conditions, with such compounds and pharmaceutical compositions. The present invention also relates to certain cyclopropyl amide compounds for use in inhibiting nicotinamide phosphoribosyltransferase ("NAMPT").
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Paragraph 0234
(2014/05/24)
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- 1,2-Benzisothiazol-3-one derivatives as a novel class of small-molecule caspase-3 inhibitors
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A novel series of 1,2-benzisothiazol-3-one derivatives was synthesized and their biological activities were evaluated for inhibiting caspase-3 and -7 activities, in which some of them showed low nanomolar potency against caspase-3 in vitro and significant protection against apoptosis in a camptothecin-induced Jurkat T cells system. Among the tested compounds, compound 5i exhibited the most potent caspase-3 inhibitory activity (IC50 = 1.15 nM). The molecular docking predicted the interactions and binding modes of the synthesized inhibitor in the caspase-3 active site.
- Wu, Lixin,Lu, Meiqi,Yan, Zhihui,Tang, Xiaobin,Sun, Bo,Liu, Wei,Zhou, Honggang,Yang, Cheng
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p. 2416 - 2426
(2014/05/06)
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- NOVEL TETRAHYDROQUINOLINE DERIVATIVES
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The present invention relates to a compound of formula (I) or a pharmaceutically acceptable salt or ester thereof, wherein R1 to R8, A1 to A3 have the are as described herein and compositions including the compounds.
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Page/Page column 23
(2012/07/31)
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- NOVEL TETRAHYDROQUINOLINE DERIVATIVES
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A compound of formula (I) or a pharmaceutically acceptable salt or ester thereof, wherein R1 to R8, A1 to A3 have the significance given in claim 1, can be used as AMPK modulators for treating obesity, hyperglycemia or type 2 diabetes.
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Page/Page column 61-62
(2012/08/08)
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- 2, 4 -DIAMINOPYRIMIDINE DERIVATIVES AS PROTEIN KINASE INHIBITORS
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The present invention relates to novel pyrimide derivatives of formula (I): that are useful as kinase inhibitors. More particularly, the present invention relates to novel pyrimidine compounds, methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment of proliferative disorders.
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Page/Page column 140-141
(2012/05/20)
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- Exploration of secondary and tertiary pharmacophores in unsymmetrical N,N′-diaryl urea inhibitors of soluble epoxide hydrolase
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The impact of various secondary and tertiary pharmacophores on in vitro potency of soluble epoxide hydrolase (sEH) inhibitors based on the unsymmetrical urea scaffold 1 is discussed. N,N′-Diaryl urea inhibitors of soluble epoxide hydrolase exhibit subtle variations in inhibitory potency depending on the secondary pharmacophore but tolerate considerable structural variation in the second linker/tertiary pharmacophore fragment.
- Anandan, Sampath-Kumar,Gless, Richard D.
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scheme or table
p. 2740 - 2744
(2010/07/15)
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- Preparation of arylsulfonyl chlorides by chlorosulfonylation of in situ generated diazonium salts using a continuous flow reactor
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A new flow procedure for the preparation of arylsulfonyl chlorides from aniline starting materials is described. The reaction conditions are mild, requiring no added acid and are amenable to continuous flow processing, in a safe, easily scalable and less labour intensive way than the corresponding batch method.
- Malet-Sanz, Laia,Madrzak, Julia,Ley, Steven V.,Baxendale, Ian R.
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experimental part
p. 5324 - 5332
(2011/01/12)
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- TRIAZINES AND THEIR USE AS INHIBITORS OF METALLOPROTEINASES
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The present invention relates to compounds or pharmaceutically acceptable salts thereof, to processes for their preparation, to pharmaceutical compositions containing them, and to the use of such compounds in therapeutical use. In particular, the compound
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Page/Page column 21; 23
(2008/12/05)
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- A new method for the preparation of nitrogen-containing cyclic compounds from p-nitrobenzenesulfonamide and alkyl bis(diphenylphosphinite)s by oxidation-reduction condensation using 1-azidoadamantane
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A new and efficient method was established for the preparation of nitrogen-containing cyclic compounds from p-nitro-benzenesulfonamide, bisphosphinites, and 1-azidoadamantane in good yields under neutral conditions. Copyright
- Mukaiyama, Teruaki,Kuroda, Kiichi,Aoki, Hidenori
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p. 1644 - 1645
(2007/10/03)
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- Neuropeptide Y antagonists
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The compound is a neuropeptide Y antagonist and is effective in treating feeding disorders, cardiovascular diseases and other physiological disorders.
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Page column 37
(2010/02/05)
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- Structure-based design of lipophilic quinazoline inhibitors of thymidylate synthase
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To develop novel lipophilic thymidylate synthase (TS) inhibitors, the X- ray structure of Escherichia coli TS in ternary complex with FdUMP and the inhibitor 10-propargyl-5,8-dideazafolic acid (CB3717) was used as a basis for structure-based design. A total of 31 novel lipophilic TS inhibitors, lacking a glutamate residue, were synthesized; 26 of them had in common a N-((3,4- dihydro-2-methyl-6-quinazolinyl)methyl)-N-prop-2-ynylaniline structure in which the aniline was appropriately substituted with simple lipophilic substituents either in position 3 or 4, or in both. Compounds were tested for their inhibition of E. coli TS and human TS and also for their inhibition of the growth in tissue culture of a murine leukemia, a human leukemia, and a thymidine kinase-deficient human adenocarcinoma. The crystal structures of five inhibitors complexed with E. coli TS were determined. Five main conclusions are drawn from this study. (i) A 3-substituent such as CF3, iodo, or ethynyl enhances binding by up to 1 order of magnitude and in the case of CF3 was proven to fill a nearby pocket in the enzyme. (ii) A simple strongly electron-withdrawing substituent such as NO2 or CF3SO2 in the 4- position enhances binding by 2 orders of magnitude; it is hypothesized that the transannular dipole so induced interacts favorably with the protein. (iii) Attempts to combine the enhancements of i and ii in the same molecule were generally unsuccessful. (iv) A 4-C6H5SO2 substituent provided both electron withdrawal and a van der Waal's interaction of the phenyl group with a hydrophobic surface at the mouth of the active site. The inhibition (K(is) = 12 nM) of human TS by this compound, 7n, showed that C6H5SO2 provided virtually as much binding affinity as the CO-glutamate which it had replaced. (v) The series of compounds were poorly water soluble, and also the potent TS inhibition shown by several of them did not translate into good cytotoxicity. Compounds with large cyclic groups linked to position 4 by an SO or SO; group did, however, have IC50's in the range 1-5 μM. Of these, 4-(N-((3,4- dihydro-2-methyl-6-quinazolinyl)methyl)-N-prop-2-ynylamino)phenyl phenyl sulfone, 7n, had IC50's of about 1 μM and was chosen for further elaboration.
- Jones, Terence R.,Varney, Michael D.,Webber, Stephen E.,Lewis, Kathleen K.,Marzoni, Gifford P.,Palmer, Cindy L.,Kathardekar, Vinit,Welsh, Katharine M.,Webber, Stephanie,Matthews, David A.,Appelt, Krzysztof,Smith, Ward W.,Janson, Cheryl A.,Villafranca,Bacquet, Russell J.,Howland, Eleanor F.,Booth, Carol L. J.,Herrmann, Steven M.,Ward, Robert W.,White, Jennifer,Moomaw, Ellen W.,Bartlett, Charlotte A.,Morse, Cathy A.
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p. 904 - 917
(2007/10/03)
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- Steric and electronic effects on the partitioning of a persulfinyl intermediate along the physical quenching and chemical reaction channels
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The rate constants, k(T), k(r), and k(Q), corresponding to the substrate induced total removal, chemical removal, and physical removal of singlet oxygen, respectively, have been measured for a series of sulfenamides. The structural effects on the partitioning of the persulfinamide intermediate along the chemical and physical deactivation pathways is discussed.
- Clennan, Edward L.,Greer, Alexander
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p. 6093 - 6096
(2007/10/03)
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- Reactions of benzenesulfonohydrazides and benzenesulfonamides with hydrogen chloride or hydrogen bromide in acetic acid
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Benzenesulfonohydrazides capable of yielding a sulfinic acid intermediate by virtue of a basic nitrogen atom in the second position of the hydrazide moiety produced thiosulfonates when treated with 1 N hydrogen chloride in acetic acid and produced disulfides when treated with 1 N hydrogen bromide in the same solvent. In two cases, a crystalline mixture of p-nitrophenyl p-nitrobenzenethiosulfonate and bis(p-nitrophenyl) disulfide was isolated from the hydrogen chloride reactions. No reaction product was obtained from either the hydrogen chloride or hydrogen bromide reaction with benzenesulfonohydrazides that were unable to form a sulfinic acid intermediate. Reduction of benzenesulfonamides to disulfides appeared to be possible only with hydrogen bromide in acetic acid. No thiosulfonate was isolated from the treatments of benzenesulfonamides with 1 N hydrogen chloride in acetic acid. p-Nitrophenyl p-nitrobenzenethiosulfonate and p-bromophenyl p-bromobenzenethiosulfonate exhibited some antimicrobial activities against Gram-positive bacteria. The latter compound also showed analgesic properties in the phenylquinone test.
- Yung,Forrest,Manzer,Gilroy
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p. 1009 - 1012
(2007/10/06)
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