- A novel gold(I)-mediated intramolecular transamidation of benzoyl thiourea derivatives to form benzamides via dethiocyanation
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A novel gold(I)-mediated intramolecular transamidation of thiourea derivatives to yield benzamides via dethiocyanation have been achieved by the reaction of 3-(1,3-benzothiazol-2-yl)-1-(benzoyl)thiourea derivatives in the presence of gold(I) precursors. The compounds have been characterized using IR, NMR, GC-MS and microanalysis. The single crystal XRD of 3-(1,3-benzothiazol-2-yl)-1-(3-bromobenzoyl)thiourea (5), 3-(1,3-benzothiazol-2-yl)-1-(3-methoxybenzoyl)thiourea (6), N-(benzothiazol-2-yl)benzamide (10), N-(benzothiazol-2-yl)-3-chlorobenzamide (11), N-(benzothiazol-2-yl)-4-nitrobenzamide (12), N-(benzothiazol-2-yl)-3-bromobenzamide (14) have been discussed. The novel transformation is thought to proceed by a gold(I)-mediated intramolecular transamidation reaction which releases thiocyanate to yield the benzamide. Density functional theory calculations have been used to support the proposed mechanism for this transformation.
- Hosten, Eric C.,Lobb, Kevin,Odame, Felix,Tshentu, Zenixole R.,Woodcock, Guillaume
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- Copper promoted C-S and C-N cross-coupling Reactions:The synthesis of 2-(N-Aryolamino)benzothiazoles and 2-(N-Aryolamino)benzimidazoles
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The synthesis of 2-(N-aryolamino)benzothiazoles and 2-(N-aryolamino)benzimidazoles has been accomplished in the presence of copper catalyst. These reactions involve C-S and C-N cross-coupling reaction. All electron donating and withdrawing substituent's readily underwent the reaction to give target products in good to excellent yield. In addition, the reaction also gave target product in high yield with bulk scale.
- Shaik, Baji vali,Seelam, Mohan,Tamminana, Ramana,Kammela, Prasad Rao
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supporting information
p. 3865 - 3874
(2019/06/20)
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- Virtual screening identification and chemical optimization of substituted 2-arylbenzimidazoles as new non-zinc-binding MMP-2 inhibitors
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Matrix metalloproteinases (MMPs) are a large family of zinc-dependent endoproteases known to exert multiple regulatory roles in tumor progression and invasiveness. This encouraged over the years the approach of MMP, and particularly MMP-2, targeting for anticancer treatment. Early generations of MMP inhibitors, based on aspecific zinc binding groups (ZBGs) assembled on (pseudo)peptide scaffolds, have been discontinued due to the clinical emergence of toxicity and further drawbacks, giving the way to inhibitors with alternative zinc-chelator moieties or not binding the catalytic zinc ion. In the present paper, we continue the search for new non-zinc binding MMP-2 inhibitors: exploiting previously identified compounds, a virtual screening (VS) campaign was carried out and led to the identification of a new class of ligands. The structure-activity relationship (SAR) of the benzimidazole scaffold was explored by synthesis of several analogues whose inhibition activity was tested with enzyme inhibition assays. By performing the molecular simplification approach, we disclosed different sets of single-digit micromolar inhibitors of MMP-2, with up to a ten-fold increase in inhibitory activity and ameliorated selectivity towards off-target MMP-8, compared to selected lead compound. Molecular dynamics calculations conducted on complexes of MMP-2 with docked privileged structures confirmed that analyzed inhibitors avoid targeting the zinc ion and dip inside the S1′ pocket. Present results provide a further enrichment of our insights for the design of novel MMP-2 selective inhibitors.
- Agamennone, Mariangela,Caradonna, Alessia,Di Pizio, Antonella,Laghezza, Antonio,Loiodice, Fulvio,Luisi, Grazia,Piemontese, Luca,Tortorella, Paolo
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- Facile synthesis of N-acyl 2-aminobenzothiazoles by NHC-catalyzed direct oxidative amidation of aldehydes
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A mild, general, and high yielding synthesis of N-acyl 2-aminobenzothiazoles has been demonstrated by N-heterocyclic carbene (NHC)-organocatalyzed direct amidation of aldehydes with 2-aminobenzothiazoles proceeding via acyl azolium intermediates. The carbene generated from the triazolium salt under oxidative conditions was the key for the success of this reaction. The method was subsequently applied to the synthesis of various biologically important N-acyl 2-aminobenzothiazoles.
- Premaletha, Sethulekshmy,Ghosh, Arghya,Joseph, Sumi,Yetra, Santhivardhana Reddy,Biju, Akkattu T.
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supporting information
p. 1478 - 1481
(2017/02/05)
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- Access to Amide from Aldimine via Aerobic Oxidative Carbene Catalysis and LiCl as Cooperative Lewis Acid
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Herein, an efficient route to amides from aldimines via aza-Breslow intermediates through aerobic oxidative carbene catalysis with LiCl as a cooperative Lewis acid is described. Many of the obtained N-heteroarylamides feature biological activity. Ambient
- Wang, Guanjie,Fu, Zhenqian,Huang, Wei
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p. 3362 - 3365
(2017/07/13)
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- 2, 3-Butanediamide Epoxide Compound and Preparation Method and Use Thereof
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Provided are a compound of formula I which can be used as a drug against small RNA virus infections, and optical isomers, pharmaceutically acceptable salts, solvates or hydrates thereof. Also provided are the preparation method of the compound, the method for using the compound for treating bacterial infections and the use of the compound in the preparation of a drug for preventing and/or treating viral diseases caused by small RNA viruses.
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Paragraph 0196
(2016/05/19)
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- Synthesis of N-benzothiazol-2-yl-amides by a copper-catalyzed intramolecular cyclization process
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Employing N-(4,5-dihydrooxazol-2-yl)benzamide as novel and efficient ligand, the copper-catalyzed intramolecular cyclization of various substituted 1-acyl-3-(2-bromophenyl)thioureas could be successfully carried out under mild conditions. A variety of N-b
- Wang, Junke,Peng, Feng,Jiang, Ju-li,Lu, Zhi-jin,Wang, Le-yong,Bai, Junfeng,Pan, Yi
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p. 467 - 470
(2008/09/17)
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- Synthesis, Photolysis and Pyrolysis of 1-(2'-Benzothiazolyl)-5-aryltetrazoles
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Aroylaminobenzothiazoles (II), have been converted into 1-(2'-benzothiazolyl)-5-aryltetrazoles (IV) by treatment with PCl5 followed by azidolysis with sodium azide in aequeous acetone solution.Pyrolysis of IV in tetralin affords exclusively 2-aryl-s-triaz
- Kamala, K.,Rao, P. Jayaprasad,Reddy, K. Kondal
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p. 1194 - 1196
(2007/10/02)
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- Tautomerie von Heterocyclen, VIII. N-Acylsubstituierte Chlorformamidine als Heterocyclen- Bausteine
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N-(4-Nitrobenzoyl)-1-pyrrolidinecarbimidoyl chloride (1) reacts with bisnucleophilic reagents according to two possible pathways to differently structured heterocyclic compounds.In path A following the substitution of the chlorine atom ring closure from t
- Ried, Walter,Erle, Hanns-Eberhard
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p. 475 - 482
(2007/10/02)
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