- Utilization of transition metal fluoride-based solid support catalysts for the synthesis of sulfonamides: Carbonic anhydrase inhibitory activity and: In silico study
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The applications of solid support catalysts in catalyzing organic reactions are well-evident. In the present study, we explored a transition metal fluoride (FeF3) adsorbed on molecular sieves (4 ?) as a solid support catalyst for the preparation of sulfon
- Al-Rashida, Mariya,Ali, Deedar,Amjad, Sayyeda Tayyeba,Hameed, Abdul,Iftikhar, Shafia,Iqbal, Jamshed,Naseer, Muhammad Moazzam,Shafique, Zainab,Shah, Muhammad Raza,Sindhu, Tayyaba Allamgir
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p. 3165 - 3179
(2022/02/05)
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- Cyclometalated Ru(II)-isoquinoline complexes overcome cisplatin resistance of A549/DDP cells by downregulation of Nrf2 via Akt/GSK-3β/Fyn pathway
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Both ruthenium (Ru) and isoquinoline (IQ) compounds are regarded as potential anticancer drug candidates. Here, we report the synthesis and characterization of three novel cyclometalated Ru(II)-isoquinoline complexes: RuIQ-3, RuIQ-4, and RuIQ-5, and evalu
- Chen, Lanmei,Wang, Jie,Cai, Xianhong,Chen, Suxiang,Zhang, Jingjing,Li, Baojun,Chen, Weigang,Guo, Xinhua,Luo, Hui,Chen, Jincan
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- Efficient and Divergent Synthesis of Medium-Sized Lactams through Zinc-Catalyzed Oxidative Cyclization of Indoly Ynamides?
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An efficient zinc-catalyzed oxidative cyclization of readily available indoly ynamides has been developed, enabling rapid and practical access to a diverse array of valuable medium-sized lactams in mostly good to excellent yields with wide substrate scope. In addition, such an asymmetric synthesis has also been explored by employing the chiral substrate.
- Li, Hang-Hao,Ye, Si-Han,Chen, Yang-Bo,Luo, Wen-Feng,Qian, Peng-Cheng,Ye, Long-Wu
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supporting information
p. 263 - 268
(2020/02/05)
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- Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation
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A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.
- Henry, Martyn C.,Senn, Hans Martin,Sutherland, Andrew
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p. 346 - 364
(2019/01/08)
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- CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: An efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a] quinazolines
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A Cu(I)-catalyzed, intermolecular protocol for the synthesis of 2-amidoindoles and tetrahydroindolo[1,2-a]quinazolines in shorter time and high yields is reported. The key highlight of this disclosure is the formation of 2-amidoindole and tetrahydroindolo[1,2-a]quinazoline moieties directly from gem-dibromovinylanilides and sulfonamides in a one-pot fashion through the in situ formation of ynamides followed by a base-promoted intramolecular hydroamidation.
- Kiruthika, Selvarangam E.,Perumal, Paramasivan Thirumalai
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supporting information
p. 484 - 487
(2014/04/03)
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- Synthesis and cytotoxicity of novel N-sulfonyl-1,2,3,4- tetrahydroisoquinoline thiosemicarbazone derivatives
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The modified Pictet-Spengler reaction of phenylethylbenzene sulfonamide with a commercially available glyoxal to construct 1-benzoyl- and 1-acetyl-1,2,3,4-tetrahydroisoquinolines 9a-n has been reported. The reaction could be accomplished, regardless of th
- Pingaew, Ratchanok,Prachayasittikul, Supaluk,Ruchirawat, Somsak,Prachayasittikul, Virapong
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p. 267 - 277
(2013/03/13)
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- Electron-withdrawing substituted benzenesulfonamides against the predominant community-associated methicillin-resistant Staphylococcus aureus strain USA300
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A small focused chemical library constituted of sulfonamides was synthesized. These compounds were designed to lack the p-aminobenzene moiety typically found in sulfonamide antibiotics. Antimicrobial activities of these synthetic compounds were investigated against global predominant methicillin-resistant Staphylococcus aureus (MRSA) strain USA300 (SF8300) and control strains of Staphylococcus aureus (S. aureus) ATCC 25923 and ATCC 29213 using disk diffusion and microdilution assays. Based on susceptibility results, potent S. aureus and MRSA USA300 growth inhibitors such as N-[3,5- bis(trifluoromethyl)phenyl]-4-bromobenzenesulfonamide with minimum inhibitory concentration (MIC) as low as 5.6 μg/cm3 along with other effective sulfonamides were discovered. Structure-activity correlations revealed that these desamino-benzenesulfonamides required electron-withdrawing substituents to be effective inhibitors of bacterial pathogen growth. In addition, their ability to inhibit growth of S. aureus strains was retained even when bacterial folate synthetic intermediate, p-aminobenzoic acid (PABA), was supplemented, whereas PABA supplementation completely diminished the antibacterial activity of the known sulfa drug tested, sulfamethoxazole. The sulfa-resistant MRSA strain COL also showed great susceptibility to these desamino-benzenesulfonamides. These results imply a unique mechanism of growth inhibition by these potent desamino-benzenesulfonamides, different from the well-known folate pathway target of sulfonamide antibiotics.
- Phetsang, Wanida,Chaturongakul, Soraya,Jiarpinitnun, Chutima
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p. 461 - 471
(2013/07/26)
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- Synthesis, cytotoxicity and QSAR study of N-tosyl-1,2,3,4- tetrahydroisoquinoline derivatives
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1-Substituted-N-tosyl-1,2,3,4-tetrahydroisoquinoline analogs (4a-4l) were synthesized using the modified Pictet-Spengler reaction and evaluated for cytotoxicity. All tetrahydroisoquinolines displayed cytotoxicity against MOLT-3 cell lines, except for p-me
- Pingaew, Ratchanok,Worachartcheewan, Apilak,Nantasenamat, Chanin,Prachayasittikul, Supaluk,Ruchirawat, Somsak,Prachayasittikul, Virapong
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p. 1066 - 1077
(2013/09/24)
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- Design, synthesis and antimalarial activity of benzene and isoquinoline sulfonamide derivatives
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A new series of benzene and isoquinoline sulfonamide derivatives were synthesized by nucleophilic displacement reaction on benzene and isoquinoline sulfonyl chlorides by substituted amines (primary and secondary). The title compounds were evaluated for an
- Kumar Parai, Maloy,Panda, Gautam,Srivastava, Kumkum,Kumar Puri, Sunil
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p. 776 - 781
(2008/09/18)
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- Asymmetric synthesis of 1-vinyltetrahydroisoquinoline through Pd-catalyzed intramolecular allylic amination
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Asymmetric synthesis of 6,7-dimethoxy-1-vinyltetrahydroisoquinolines through Pd-catalyzed intramolecular allylic amination of 3-(amidoethylphenyl)prop-2-enyl carbonates was studied, using a library of fine-tunable monodentate phosphoramidite ligands. Unde
- Shi, Ce,Ojima, Iwao
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p. 8563 - 8570
(2008/02/08)
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- Development of a novel ionic support and its application in the ionic liquid phase assisted synthesis of a potent antithrombotic
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The synthesis of ionic support 1 and its application in the preparation of a set of amides and sulfonamides is described. The potential of 1 is further exemplified by its use in a one-pot multistep ionic liquid phase assisted synthesis of tirofiban analogue 2.
- De Kort, Martin,Tuin, Adriaan W.,Kuiper, Suzanne,Overkleeft, Hermen S.,Van Der Marel, Gijs A.,Buijsman, Rogier C.
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p. 2171 - 2175
(2007/10/03)
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- Pictet-Spengler condensation of N-sulfonyl-β-phenethylamines with α- chloro-α-phenylselenoesters. New synthesis of 1,2,3,4- tetrahydroisoquinoline-1-carboxylates
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The reaction of N-sulfonyl-β-phenethylamines with α-chloro-a- phenylseleno acetate/propionate esters under Lewis acid promotion gives moderate to good yields of the corresponding 1,2,3, 4- tetrahydroisoquinoline-1-carboxylates. Varying degrees of diastereoselection were obtained using chiral sulfonamides and/or esters. Employing this strategy, the achievement of a new total synthesis of Calycotomine is reported.
- Silveira, Claudio C.,Bernardi, Carmem R.,Braga, Antonio L.,Kaufman, Teodoro S.
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p. 4969 - 4972
(2007/10/03)
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- THALLIUM IN ORGANIC SYNTHESIS. 67. INTRAMOLECULAR CAPTURE OF AROMATIC RADICAL CATIONS BY AN N-TOSYL GROUP
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Radical cations, generated by oxidation of electron-rich arenes by thallium(III) tris(trifluoroacetate), undergo rapid intramolecular capture by an N-tosyl group.
- McKillop, Alexander,Davies, Huw M. L.,Taylor, Edward C.
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p. 267 - 282
(2007/10/02)
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