- An overview on the progress and development on the palladium catalyzed direct cyanation
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Generation of the positive CN ion and the corresponding direct cyanation are both extremely important for cyanation of aromatic compounds. Hereby, we would like to report the simultaneous use of the new Pd nano-catalyst as well as the three types of the N-arylsulfonyl cyanamides (A, B and C) as potent reagents for the in situ generation of the positive CN ion for the direct cyanation of phenylboronic acids in acetonitrile at reflux conditions.
- Heydari, Somayyeh,Habibi, Davood,Reza Faraji, Ali,keypour, Hassan,Mahmoudabadi, Masoumeh
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- A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives
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A novel transition-metal-free cascade reaction to synthesize 4-quinolone derivatives has been demonstrated. Michael addition and Truce-Smiles rearrangement are included in this protocol, providing a broad scope of 4-quinolones in moderate-to-excellent yields. This work serves as an example of the use of sulfonamides through Truce-Smiles rearrangement to build heterocyclic compounds under mild conditions.
- Xie, Caixia,Yang, Di,Wang, Xinfeng,Ma, Chen
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p. 14937 - 14944
(2020/12/02)
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- Flexibility of small molecular CD4 mimics as HIV entry inhibitors
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CD4 mimics such as YIR-821 and its derivatives are small molecules which inhibit the interaction between the Phe43 cavity of HIV-1 gp120 with host CD4, an interaction that is involved in the entry of HIV to cells. Known CD4 mimics generally possess three
- Kobayakawa, Takuya,Ohashi, Nami,Hirota, Yuki,Takahashi, Kohei,Yamada, Yuko,Narumi, Tetsuo,Yoshimura, Kazuhisa,Matsushita, Shuzo,Harada, Shigeyoshi,Tamamura, Hirokazu
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supporting information
p. 5664 - 5671
(2018/10/24)
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- Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists
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To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HTS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial β-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure-activity relationships of these compounds were explored.
- Yrj?l?, Sari,Parkkari, Teija,Navia-Paldanius, Dina,Laitinen, Tuomo,Kaczor, Agnieszka A.,Kokkola, Tarja,Adusei-Mensah, Frank,Savinainen, Juha R.,Laitinen, Jarmo T.,Poso, Antti,Alexander, Amy,Penman, June,Stott, Lisa,Anskat, Marie,Irving, Andrew J.,Nevalainen, Tapio J.
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p. 119 - 132
(2015/11/24)
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- Novel Quinazoline Derivatives Bearing Various 4-Aniline Moieties as Potent EGFR Inhibitors with Enhanced Activity Against NSCLC Cell Lines
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A class of novel quinazoline derivatives bearing various C-4 aniline moieties was synthesized and biologically evaluated as potent epidermal growth factor receptor (EGFR) inhibitors for intervention of non-small-cell lung cancer (NSCLC). Most of these inhibitors are comparable to gefitinib in inhibiting these cancer cell lines, and several of them even displayed superior inhibitory activity. In particular, analogue 5b with an IC50 of 0.10 μm against the EGFR wild-type A431 cells and 5c with an IC50 of 0.001 μm against the gefitinib-sensitive HCC827 cells (EGFR del E746-A750) was identified as highly active EGFR inhibitors. It was also significant that the discovered analogue 2f, not only has high potency against the gefitinib-sensitive cells (IC50 = 0.031 μm), but also possesses remarkably improved activity against the gefitinib-resistant cells. In addition, the enzymatic assays and the Western blot analysis for evaluating the effects of the typical inhibitors indicated that these molecules strongly interfere with the EGFR target.
- Wang, Changyan,Sun, Yajun,Zhu, Xingqi,Wu, Bin,Wang, Qiao,Zhen, Yuhong,Shu, Xiaohong,Liu, Kexin,Zhou, Youwen,Ma, Xiaodong
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p. 635 - 643
(2016/03/19)
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- N-Acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides: Highly selective and efficient reagents for acylation of amines in water
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A variety of N-acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides (1a-e) were synthesized in one pot from 4-chloroaniline under solvent-free conditions and have been developed as chemoselective N-acylation reagents. Selective protection of primary amines in the presence of secondary amines, acylation of aliphatic amines in the presence of aryl amines, and monofunctionalization of primary-secondary diamines as well as selective N-acylation of amino alcohols using these reagents are described. All of the acylation reactions were carried out in water as a green solvent. High stability and easy preparation of these acylating reagents are other advantages of this method.
- Ebrahimi, Sara,Saiadi, Safoura,Dakhilpour, Simin,Mirsattari, Seyed Nezamoddin,Massah, Ahmad Reza
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- Highly ortho-Selective Chlorination of Anilines Using a Secondary Ammonium Salt Organocatalyst
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An organocatalytic, highly facile, efficient, and regioselective ortho-chlorination of anilines is described. A secondary ammonium chloride salt has been employed as the catalyst and the reaction can be conducted at room temperature without protection from air and moisture. In addition, the reaction is readily scalable and the catalyst can be recycled and reused. This catalytic protocol has been applied to the efficient synthesis of a highly potent c-Met kinase inhibitor. Mechanistic studies revealed that unique structural features of the secondary ammonium chloride salt are important for both the catalysis and regioselectivity of the electrophilic ortho-chlorination.
- Xiong, Xiaodong,Yeung, Ying-Yeung
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supporting information
p. 16101 - 16105
(2016/12/26)
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- A highly efficient heterogeneous copper-catalyzed Chan-Lam coupling reaction of sulfonyl azides with arylboronic acids leading to: N -arylsulfonamides
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A heterogeneous Chan-Lam coupling reaction between sulfonyl azides and arylboronic acids was achieved in MeOH at room temperature in the presence of 10 mol% of an l-proline-functionalized MCM-41-immobilized copper(i) complex [MCM-41-l-proline-CuCl] under air, yielding a variety of N-arylsulfonamides in excellent yields. The new heterogeneous copper complex can be prepared from commercially readily available and inexpensive reagents, and recovered by simple filtration of the reaction solution and recycled at least 8 times without any decreases in activity.
- You, Chongren,Yao, Fang,Yan, Tao,Cai, Mingzhong
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p. 43605 - 43612
(2016/05/24)
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- 4-Amino-5-(arylaminomethyl)-2-(methylthio)furo[2,3-d]pyrimidines via Mitsunobu reaction of 4-amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d] pyrimidine with N-mesyl- and N-nosylarylamines
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An efficient method for the synthesis of 4-amino-5-(arylaminomethyl)-2- (methylthio)furo[2,3-d]pyrimidines via the Mitsunobu reaction of 4-amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine with N-mesyl- and N-nosylarylamines, and subsequent removal of the mesyl and nosyl groups, has been developed. The influence of substituents in the arylamine moiety on the Mitsunobu reaction was investigated. An unexpected nucleophilic substitution of a nitro group in the reaction of N-({4-amino-2-(methylsulfonyl)furo[2,3-d] pyrimidin-5-yl}methyl)-4-nitro-N-phenylbenzenesulfonamide with sodium methoxide was observed. Georg Thieme Verlag Stuttgart · New York.
- Masevicius, Viktoras,Petraityte, Grazina,Tumkevicius, Sigitas
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experimental part
p. 1329 - 1338
(2012/07/01)
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- Synthesis and biological evaluation of new sulfonamide derivatives as potential anti-Trypanosoma cruzi agents
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Chagas disease continues to be one of the main parasitic diseases in Latin America. Despite the fact that it was discovered more than 100 years ago, no suitable pharmacologic treatment is available. We report the synthesis of new sulfonamidoquinoline and sulfonamides derivatives that were evaluated in vitro against two strains of Trypanosoma cruzi (NINOA and INC-5). Structure-activity relationship analysis indicated that small aromatic and large aromatic substituents on 4-aminoquinaldine increased trypanocidal activity on INC-5 and NINOA strains, respectively. Additionally, results show the importance of the sulfonamide group as a scaffold for the development of new anti-T. cruzi agents. Seven sulfonamide derivatives showed better lytic activity than nifurtimox and beznidazole against both strains of T. cruzi. N- (biphenyl-4-yl-sulfonyl)- nicotinamide (P-012) was established as the leader of the series for the development of more effective agents.
- Bocanegra-Garcia, Virgilio,Villalobos-Rocha, Juan Carlos,Nogueda-Torres, Benjamín,Lemus-Hernandez, María Edith,Camargo-Ordo?ez, Argelia,Rosas-Garcia, Ninfa Maria,Rivera, Gildardo
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p. 1039 - 1044
(2013/01/15)
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- SOLUBLE EPOXIDE HYDROLASE INHIBITORS
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Disclosed are sulfonamide compounds and compositions that inhibit soluble epoxide hydrolase (sEH), methods for preparing the compounds and compositions, and methods for treating patients with such compounds and compositions. The compounds, compositions, and methods are useful for treating a variety of sEH mediated diseases, including hypertensive, cardiovascular, inflammatory, pulmonary, and diabetes-related diseases.
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Page/Page column 59
(2008/06/13)
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- Analgesic agents without gastric damage: Design and synthesis of structurally simple benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors
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In order to create novel analgesic agents without gastric disturbance, structurally simple cyclooxygenase-1 (COX-1) inhibitors with a benzenesulfonanilide skeleton were designed and synthesized. As a result, compounds 11f and 15a, which possess a p-amino group on the benzenesulfonyl moiety and p-chloro group on the anilino moiety, showed COX-1-selective inhibition. Moreover compound 11f, which is the most potent compound in this study showed more potent analgesic activity than that of aspirin at 30 mg/kg by po. The anti-inflammatory activity and gastric damage, however, were very weak or not detectably different from aspirin. Since the structure of our COX-1 inhibitors are very simple, they may be useful as lead compounds for superior COX-1 inhibitors as analgesic agents without gastric disturbance.
- Zheng, Xiaoxia,Oda, Hiroyuki,Takamatsu, Kayo,Sugimoto, Yukio,Tai, Akihiro,Akaho, Eiichi,Ali, Hamed Ismail,Oshiki, Toshiyuki,Kakuta, Hiroki,Sasaki, Kenji
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p. 1014 - 1021
(2007/10/03)
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- Effect of para substitution on dissociation of N-phenylbenzenesulfonamides
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The reaction of substituted anilines and benzenesulfonyl chlorides has been used to prepare 49 substituted N-phenylbenzenesulfonamides of general formula 4-X-C6H4SO2NHC6H4-Y- 4′. Their purity was checked by elemental analysis. The substituents X and Y include H, CH3, CH3O, Cl, Br, CN, and NO2. The dissociation constants of all compounds were determined by potentiometric titration in methanol, acetonitrile, N,N-dimethylformamide, and pyridine. The obtained dissociation constants, pKHA, were correlated with various sets of substituent constants. It was found that the effects of substituents X and Y on the dissociation are best described by using the Hammett equation with σp constants and the Yukawa-Tsuno equation with σp- and σp constants, respectively. This result confirms the direct conjugation of Y substituent with the reaction centre. The explained variability using the additive model was above 96% in all the solvents used. The data also provided information about the transmission effect of the SO2 group. The average dissociation constants were further processed by the latent variables methods, principal components and conjugated deviations analyses.
- Mansfeld, Martin,Parik, Patrik,Ludwig, Miroslav
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p. 1479 - 1490
(2007/10/03)
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- BISARYLSULFONAMIDE COMPOUNDS AND THEIR USE IN CANCER THERAPY
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The present invention relates to the use of bisarylsulfonamide compounds of formula (I) wherein W is a CI-5 branched or unbranched alkyl group or a C2-5alkenyl group; nis0or1; R1 is H, a C, 1-8 branched or unb
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- Bimolecular nucleophilic displacement at tertiary carbon centers: Aminolyses of 2-cyano-2-propyl and 1-cyanocyclooctyl arenesulfonates
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Kinetic studies were carried out on the reactions of anilines with 2-cyano-2-propyl and 1-cyanocyclooctyl arenesulfonates in acetonitrile at 50·0°C. The second-order rate constants for the former are in general greater than those for the latter but the rates of the two become comparable for a strong nucleofuge. The cross-interaction constants, ρXZ (and βXZ), are considerably smaller (ca -0·04) than those for the primary (ca 0·33) and secondary (ca 0·12) compounds. The negative sign and small magnitude are consistent with a dissociative SN2 mechanism with a loose transition state structure. The ab initio MO theoretical results for Cl- + RCl?ClR + Cl- at the MP2 level (MP2/6-31 + G*//MP2/6-31 + G*) confirm the looseness of the transition state for the tertiary (R) alkyl compounds. The average r*(Cl...Cl) value is 4·88 ± 0·03 A, which is larger than those for the reactions at primary (4·68± 0·02 A) and secondary (4·80 ± 0·02 A) carbon centers. Thus a looser transition state with a smaller magnitude of ρXZ for the tertiary carbon centers has a larger theoretical r*(Cl-Cl) value.
- Oh, Hyuck Keun,Kwon, Young Bong,Chung, Dong Soo,Lee, Ikchoon
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p. 683 - 688
(2007/10/03)
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- VARIATION OF TRANSITION STATE IN REACTIONS OF BENZENSULFONYL CHLORIDES WITH ANILINES IN MeOH-MeCN SOLVENTS
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Kinetic studies of nucleophilic substitution reactions of substituted benzenesulfonyl chlorides with anilines were conducted at 35 deg C in a range of methanol-acetonitril solvent mixtures.Results showed that (i) the magnitudes of ρN and β associated with a change of substituent in the nucleophile are large and indicate a relatively advanced bond-formation in the transition state, (ii) maximum size of ρN, ρS and β at the solvent composition of the maximum ionizing power, together with a positive cross-interaction coefficient, suggest SN2 transition state of a "synchronous push-pull" type, and (iii) the potential energy surface model is unstable to predict the transition state variation to a more product-like transition state, where bond formation is much more progressed and bond-breaking is slightly more advanced, upon changing the solvent to a more ionizing one enhancing leaving ability.In this respect the quantum mechanical model is superior to the potential energy surface model.
- Lee, Ikchoon,Koo, In Sun
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p. 1803 - 1808
(2007/10/02)
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