45438-73-1Relevant articles and documents
Identification of intermediates in the reaction of 2-thenyl halides with magnesium
Egorov,Kuznetsova,Anisimov
, p. 1544 - 1547 (2000)
The reaction of 2-thenyl chloride with magnesium was shown by the ESR method to proceed via the intermediate formation of radicals and radical ion pairs, whereas similar reactions of 2-thenyl bromide and iodide occur through the formation of free radicals only.
Direct Vicinal Difunctionalization of Thiophenes Enabled by the Palladium/Norbornene Cooperative Catalysis
Li, Renhe,Zhou, Yun,Xu, Xiaolong,Dong, Guangbin
, p. 18958 - 18963 (2019)
Herein we report a direct vicinal difunctionalization of thiophenes via the palladium/norbornene (Pd/NBE) cooperative catalysis. A series of mono- and disubstituted thiophenes can be difunctionalized site-selectively and regioselectively at the C4 and C5 positions in good yields, enabled by an arsine ligand and a unique amide-based NBE. The synthetic utility has been shown in derivatizations of complex bioactive compounds and an open-flask gram-scale preparation. Preliminary results have been obtained in the difunctionalization of furans and a direct C4-selective arylation of 2-substituted thiophenes.
Optimization of interactions in crystal packing revealed by crystal structures [ethyl 2-(formylamino)-3-thien-2-yl-2-(thien-2-ylmethyl)propanoate and ethyl 3-(5-bromothien-2-yl)-2-[(5-bromothien-2-yl)methyl]-2-(formylamino) propanoate]
Damodharan, Lakshminarasimhan,Pattabhi, Vasantha,Behera, Manoranjan,Kotha, Sambasivarao
, p. 101 - 106 (2004)
The title compounds, C15H14NO3S 2 (I) and C15H15Br2NO 3S2 (II), are derivatives of Aib (α-aminoisobutyric acid) with thiophene rings substituted at the Cα position. The Cα substitution causes the backbone to assume an extended conformation in the crystal structure. N-H and C-H donors share the thiophene ring π system for X-H?π interactions. The packings of the molecules are stabilized by intermolecular N-H?O, C-H?O, C-H?π and C-H?Br hydrogen bonds. Br?O interactions and a weak dihydrogen bond have also been observed in the crystal structure of II. The packing adopted by II has maximized the number of interactions that are possible.
From Stoichiometric Reagents to Catalytic Partners: Selenonium Salts as Alkylating Agents for Nucleophilic Displacement Reactions in Water
Martins, Nayara Silva,ángel, Alix Y. Bastidas,Anghinoni, Jo?o M.,Lenard?o, Eder J.,Barcellos, Thiago,Alberto, Eduardo E.
supporting information, p. 87 - 93 (2021/11/03)
The ability of chalcogenium salts to transfer an electrophilic moiety to a given nucleophile is well known. However, up to date, these reagents have been used in stoichiometric quantities, producing a substantial amount of waste as byproducts of the reaction. In this report, we disclose further investigation of selenonium salts as S-adenosyl-L-methionine (SAM) surrogates for the alkylation of nucleophiles in aqueous solutions. Most importantly, we were able to convert the stoichiometric process to a catalytic system employing as little as 10 mol % of selenides to accelerate the reaction between benzyl bromide and other alkylating agents with sodium cyanide in water. Probe experiments including 77Se NMR and HRMS of the reaction mixture have unequivocally shown the presence of the selenonium salt in the reaction mixture. (Figure presented.).
Synthesis and pharmacological characterisation of arctigenin analogues as antagonists of AMPA and kainate receptors
Butts, Craig P.,Collingridge, Graham L.,Jane, David E.,Mallah, Shahida,Molnár, Elek,Re?nik, Lisa-Maria,Thatcher, Robert J.,Willis, Christine L.
supporting information, p. 9154 - 9162 (2021/11/16)
(-)-Arctigenin and a series of new analogues have been synthesised and then tested for their potential as AMPA and kainate receptor antagonists of human homomeric GluA1 and GluK2 receptors expressed in HEK293 cells using a Ca2+ influx assay. In general, these compounds showed antagonist activity at both receptors with greater activity evident at AMPARs. Schild analysis indicates that a spirocyclic analogue 6c acts as a non-competitive antagonist. Molecular docking studies in which 6c was docked into the X-ray crystal structure of the GluA2 tetramer suggest that (-)-arctigenin and its analogues bind in the transmembrane domain in a similar manner to the known AMPA receptor non-competitive antagonists GYKI53655 and the antiepileptic drug perampanel. The arctigenin derivatives described herein may serve as novel leads for the development of drugs for the treatment of epilepsy. This journal is
[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization
Alam, Md Nirshad,Dash, Soumya Ranjan,Mukherjee, Anirban,Pandole, Satish,Marelli, Udaya Kiran,Vanka, Kumar,Maity, Pradip
supporting information, p. 890 - 895 (2021/02/01)
A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.
Synthetic process of tiaprofenic acid
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Paragraph 0044; 0045, (2018/04/01)
The invention relates to a synthetic process of tiaprofenic acid. The synthetic process comprises the following steps: adopting 2-thiotolene as a starting raw material, enabling 2-thiotolene to reactwith trimethylsilyl cyanide to synthesize 2-thiopheneacetonitrile by virtue of bromation, then enabling the 2-thiopheneacetonitrile to react with dimethyl carbonate to be methylated, hydrolyzing cyanogroups, and finally performing F-K reaction with benzoyl chloride, and preparing tiaprofenic acid. The synthetic process has the advantages that the conventional safe raw materials low in price are used for substituting the rare expensive and dangerous raw materials, so that the severe pollution problem is avoided, and the production cost is greatly decreased; and in addition, the process route adopted by the invention is simple, the reaction period is short, the reaction condition is stable, the yield is high and can reach more than 90 percent, the produce obtained after the reaction is highin purity, and the purity can reach more than 99 percent, so that the synthetic process is suitable for the industrialized production.
MLKL INHIBITORS
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Paragraph 0718-0719, (2018/09/26)
Purine derivatives that inhibit cellular necroptosis and/or human MLKL, pharmaceutical compositions thereof, and methods of treating an MLKL-mediated disorder with an effective amount of the compound or composition. Said MLKL-mediated disorder is pathology associated necroptosis, including ischemia-reperfusion damage, neurodegeneration, and inflammatory diseases such as acute pancreatitis, multiple sclerosis, inflammatory bowel disease, and allergic colitis.
Aromatic heterocycle and alkyl side chain disubstituted benzenesulfonamide compound and application thereof to preparation of medicine for resisting influenza A virus
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Paragraph 0037; 0038; 0039; 0040, (2018/07/07)
The invention discloses an aromatic heterocycle and alkyl side chain disubstituted benzenesulfonamide compound and application thereof to the preparation of a medicine for resisting influenza A virusand belongs to the technical field of medicine. The structure of the benzenesulfonamide compound is shown as a formula (I); a preparation method of the benzenesulfonamide compound comprises the following steps: generating a 3-((thiophene-2-ylmethyl)amino)propionitrile derivative with R1 and R2 substituent groups by a bromomethyl compound with the R1 substituent group and a methylamine compound with the R2 substituent group under the condition of sodium hydride and N,N-dimethylformamide; carrying out sulfonylation reaction on the 3-((thiophene-2-ylmethyl)amino)propionitrile derivative under thecondition of taking triethylamine as an acid binding agent and dichloromethane as a solvent, so as to generate the aromatic heterocycle and alkyl side chain disubstituted benzenesulfonamide compound.The benzenesulfonamide compound disclosed by the invention can be used for effectively inhibiting the replication of the influenza A virus, has small toxicity in cells and can be used for preparing the medicine for resisting the influenza A virus. (The formula (I) is shown in the description.).
Synthesis and structure-activity relationship study of arylsulfonamides as novel potent H5N1 inhibitors
Yu, Yongshi,Tang, Qi,Xu, Zhichao,Li, Siliang,Jin, Mengyu,Zhao, Zixuan,Dong, Chune,Wu, Shuwen,Zhou, Hai-Bing
, p. 206 - 216 (2018/10/15)
H5N1 virus, one subtype of highly pathogenic influenza A virus in human infection, has recently received attention due to its unpredictable and high mortality. In this study, a series of arylsulfonamide derivatives were identified as improved H5N1 inhibitors for the influenza treatment by systematic structure-activity relationship investigation. Among them, the most potent H5N1 inhibitor 3h exhibited excellent antiviral activity against H5N1 virus with EC50 value of 0.006 μM and selectivity index 33543.3. Moreover, the molecular docking of 3h with M2 proton channel protein provides practical way for understanding the inhibition of H5N1 with this kind of compounds.
