39827-12-8Relevant articles and documents
Synthesis and pharmacological activity of benzo[b]thiophene-3-carboxylic acid derivatives
Shafiee,Hedayati,Salimi,Faghihi
, p. 198 - 202 (1983)
Several dialkylaminoethyl benzo[b]thiophene-3-carboxylates, N-(2-dialkylaminoethyl)benzo[b]thiophene-3-carboxamides, 2-dialkylaminoethyl benzo[b]thiophene-3-carbamates, and substituted ureas with benzo[b]thiophene moiety, were prepared and tested for local anesthetic, anticholinergic, and antihistaminic activities. Several of the compoundds showed significant activity.
Formal Lossen Rearrangement/Alkenylation or Annulation Cascade of Heterole Carboxamides with Alkynes Catalyzed by CpRhIII Complexes with Pendant Amides
Yamada, Takayuki,Shibata, Yu,Tanaka, Ken
, p. 16022 - 16031 (2019)
It has been established that a cyclopentadienyl (Cp) RhIII complex with two aryl groups and a pendant amide moiety catalyzes the formal Lossen rearrangement/alkenylation cascade of N-pivaloyl heterole carboxamides with internal alkynes, leading to alkenylheteroles. Interestingly, the use of sterically demanding internal alkynes afforded not the alkenylation but the [3+2] annulation products ([5,5]-fused heteroles). In these reactions, the pendant amide moiety of the CpRhIII complex may accelerate the formal Lossen rearrangement. The use of five-membered heteroles may deter reductive elimination to form strained [5,5]-fused heteroles; instead, protonation proceeds to give the alkenylation products. Bulky alkyne substituents accelerate the reductive elimination to allow the formation of the [5,5]-fused heteroles.
Development of a Library of Thiophene-Based Drug-Like Lego Molecules: Evaluation of Their Anion Binding, Transport Properties, and Cytotoxicity
Vieira, Paulo,Miranda, Margarida Q.,Marques, Igor,Carvalho, Sílvia,Chen, Li-Jun,Howe, Ethan N. W.,Zhen, Carl,Leung, Claudia Y.,Spooner, Michael J.,Morgado, Bárbara,da Cruz e Silva, Odete A. B.,Moiteiro, Cristina,Gale, Philip A.,Félix, Vítor
, p. 888 - 899 (2020)
The anion-binding and transport properties of an extensive library of thiophene-based molecules are reported. Seventeen bis-urea positional isomers, with different binding conformations and lipophilicities, have been synthesized by appending α- or β-thiophene or α-, β-, or γ-benzo[b]thiophene moieties to an ortho-phenylenediamine central core, yielding six subsets of positional isomers. Through 1H NMR, X-ray crystallography, molecular modelling, and anion efflux studies, it is demonstrated that the most active transporters adopt a pre-organized binding conformation capable of promoting the recognition of chloride, using urea and C?H binding groups in a cooperative fashion. Additional large unilamellar vesicle-based assays, carried out under electroneutral and electrogenic conditions, together with N-methyl-d-glucamine chloride assays, have indicated that anion efflux occurs mainly through an H+/Cl? symport mechanism. On the other hand, the most efficient anion transporter displays cytotoxicity against tumor cell lines, while having no effects on a cystic fibrosis cell line.
Binding and Transport Properties of a Benzo[b]thiophene-Based Mono-(thio)urea Library
Cachatra, Vasco,Carvalho, Sílvia,Chen, Li-Jun,Félix, Vítor,Gale, Philip A.,Goodfellow, Brian J.,Marques, Igor,Moiteiro, Cristina,Ryder, William G.
supporting information, (2022/02/02)
Using the chemical versatility of the benzo[b]thiophene motif, an extensive library of 24 (thio)urea receptors, with different binding properties and lipophilicities, was prepared and included α,α-, α,β-, β,β-, β,γ-, α,γ-, and γ,γ-benzo[b]thiophene positional isomers, as well as β- or γ-benzo[b]thiophene-based molecules decorated with aliphatic chains or aryl moieties with different fluorination degrees. 1H NMR titrations, X-ray crystallographic studies, and DFT calculations were used to study the chloride binding affinities between receptors and substrates. Experimental efflux studies suggested that the anion transmembrane transport activity is dependent on the receptors′ lipophilicity and hydrogen bonding ability. Moreover, LUV based assays indicated that anion efflux occurs mainly through an uniport mechanism. Further MD simulations showed that anion transport is highly dependent on the orientation and interactions of the receptors at the water/lipid interface.
Heterocyclic compound and preparation and application thereof
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Paragraph 0297-0299, (2020/07/24)
The invention relates to bromodomain inhibitors, and provides a compound represented by a general formula I, a pharmaceutically acceptable salt, an enantiomer, a diastereoisomer, an atropisomer, a racemate, a polymorph, a solvate or an isotope-labeled compound (including deuterium substitution) thereof, a preparation method thereof, a pharmaceutical composition containing the same, and applicationthereof in pharmacy.
Design and synthesis of heteroaromatic-based benzenesulfonamide derivatives as potent inhibitors of H5N1 influenza A virus
Yu, Yongshi,Tazeem,Xu, Zhichao,Du, Liaoqi,Jin, Mengyu,Dong, Chune,Zhou, Hai-Bing,Wu, Shuwen
, p. 89 - 100 (2019/01/30)
Influenza A virus is an enveloped negative single-stranded RNA virus that causes febrile respiratory infection and represents a clinically challenging threat to human health and even lives worldwide. Even more alarming is the emergence of highly pathogenic avian influenza (HPAI) strains such as H5N1, which possess much higher mortality rate (60%) than seasonal influenza strains in human infection. In this study, a novel series of heteroaromatic-based benzenesulfonamide derivatives were identified as M2 proton channel inhibitors. A systematic investigation of the structure-activity relationships and a molecular docking study demonstrated that the sulfonamide moiety and 2,5-dimethyl-substituted thiophene as the core structure played significant roles in the anti-influenza activity. Among the derivatives, compound 11k exhibited excellent antiviral activity against H5N1 virus with an EC50 value of 0.47 μM and selectivity index of 119.9, which are comparable to those of the reference drug amantadine.
Benzene sulfonamide compound and application of compound in preparing anti-influenza A virus drug
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Paragraph 0027; 0031, (2018/07/06)
The invention discloses a benzene sulfonamide compound and an application of the compound in preparing an anti-influenza A virus drug and belongs to the technical field of pharmaceuticals. A structural formula of the benzene sulfonamide compound is shown as formula (I) as shown in the specification, and the benzene sulfonamide compound is prepared by preparing a corresponding furoyl chloride compound, a thiophenecarbonyl chloride compound and a benzothiophene formyl chloride compound from a furoic acid compound, a thiophenic acid compound or a thionaphthencarboxylic acid compound under the backflow conditions of thionyl chloride and methylbenzene, further performing amination reaction to form a corresponding furoylamide compound, a thiophenecarboxamide compound and a benzothiophene formamide compound, reducing to a corresponding furylmethylamine compound, a thienylmethylamine compound and a benzothiophene methylamine compound under the condition of lithium aluminium hydride, and performing sulfonylation reaction under the conditions of taking triethylamine as an acid-binding agent and dichloromethane as a solvent. The benzene sulfonamide compound can effectively inhibit activity ofan influenza A virus, is low in cytotoxicity and can be used for preparing the anti-influenza A virus drug.
Dehydrative Nazarov-type electrocyclizations of alkenyl (hetero)aryl carbinols via calcium catalysis: Access to cyclopenta[b]thiophenes and indene derivatives
Martin, M. Cynthia,Sandridge, Matthew J.,Williams, Corey W.,Francis, Zola A.,France, Stefan
, p. 4093 - 4108 (2017/06/29)
A general approach to the understudied cyclopenta[b]thiophenes is reported. The products were directly generated from calcium-catalyzed, dehydrative, Nazarov-type electrocyclizations of alkenyl thienyl carbinols in up to 82% yield. The thienyl carbinols demonstrated good tolerance for aryl and heteroaryl substituents on the alkene. Aryl carbinols were also amenable to the calcium-catalyzed conditions and afforded indene derivatives in good yields. In most cases, the reaction was selective for the thermodynamic alkene isomer; however, substituent effects played a role in determining product outcomes. Mechanistically, the calcium catalyst initiated formation of alkenyl (hetero)aryl carbinyl cations which subsequently underwent a 4π electrocyclization and elimination that is reminiscent of the Nazarov reaction. This transformation is significant for two main reasons: 1) it represents one of the only examples of catalysis for dehydrative, Nazarov-type electrocyclizations in which thiophene was compatible; 2) it allowed for the direct formation of cyclopenta[b]thiophenes while circumventing the need for cyclopenta[b]thiophenones as precursors.
Synthesis and preliminary biological evaluation of new heterocyclic carboxamide models
Sweidan, Kamal,Engelmann, J?rn,Rayyan, Walid Abu,Sabbah, Dima,Zarga, Musa Abu,Al-Qirim, Tariq,Al-Hiari, Yusuf,Sheikha, Ghassan Abu,Shattat, Ghassan
, p. 417 - 429 (2015/06/22)
The heterocyclic system is a promising core nucleus in many bioactive compounds. This work describes our effort to synthesize and characterize a set of new biphenyl, benzofuran and benzothiophene carboxamide derivatives. Our biological studies showed that
Dual role of Rh(III) catalyst enables regioselective halogenation of (electron-rich) heterocycles
Schr?der, Nils,Lied, Fabian,Glorius, Frank
supporting information, p. 1448 - 1451 (2015/02/19)
The Rh(III)-catalyzed selective bromination and iodination of electron-rich heterocycles is reported. Kinetic investigations show that Rh plays a dual role in the bromination, catalyzing the directed halogenation and preventing the inherent halogenation of these substrates. As a result, this method gives highly selective access to valuable halogenated heterocycles with regiochemistry complementary to those obtained using uncatalyzed approaches, which rely on the inherent reactivity of these classes of substrates. Furans, thiophenes, benzothiophenes, pyrazoles, quinolones, and chromones can be applied.
