61341-26-2Relevant articles and documents
Mixed alkylthiophene-based heterocyclic polymers containing oxadiazole units via electrochemical polymerisation: Spectroscopic, electrochemical and spectroelectrochemical properties
Fisyuk, Alexander S.,Demadrille, Renaud,Querner, Claudia,Zagorska, Malgorzata,Bleuse, Joel,Pron, Adam
, p. 707 - 713 (2005)
Symmetric alkylthiophene-based mixed heterocyclic trimer and pentamer. containing central oxadiazole units, have been prepared. Because of the electron-withdrawing properties of oxadiazole, the trimer cannot be electropolymerised and undergoes an oxidative-type destruction at high potentials. In contrast, the pentamer readily polymerises, giving a short chain polymer. Both trimer and pentamer exhibit strong photoluminescence with a maximum at 399 nm (13% quantum yield) and 467 nm (46% quantum yield), respectively. The polymer resulting from the electropolymerisation of the pentamer is also luminescent with the maximum of the excitation band at 528 nm (33% quantum yield). The polymer can be oxidatively doped as demonstrated by cyclic voltammetry, showing a clear anodic peak at 0.62 V versus Ag/Ag + and its cathodic counterpart at 0.56 V, associated with the undoping process. The significantly higher potential of the oxidative doping of the prepared mixed heterocyclic polymer, as compared to the poly(alkylthiophene) homopolymer of similar molecular weight, is caused by the presence of the oxadiazole unit, which lowers the electron density in the π-electron system of the oligothiophene subunit and makes its oxidation more difficult. The spectroelectrochemical investigation of the polymer is consistent with its voltammetric behaviour, exhibiting doping-induced bleaching of the band originating from the π-π* transition and simultaneous growth of the bipolaron bands. The observed clear and reversible spectroelectrochemical behaviour makes the developed polymer a promising candidate for applications in electrochromic devices or electrochemical sensors. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
A Directed Metalation Approach to 2-Trialkylammoniomethyl-3-(trimethylsilylmethyl)-thiophene Iodides: Precursors to 2,3-Bis(methylene)-2,3-dihydrothiophene
Plant, Andrew,Chadwick, Derek J.
, p. 915 - 917 (1990)
Syntheses of precursors to 2,3-bis(methylene)-2,3-dihydrothiophene (2) are described.As key step, a lithiation reaction using secondary carboxamido functionality as directing group is used.
A streamlined synthesis of androstadiene C-17 ester derivatives
Gallou, Fabrice,Seeger-Weibel, Manuela,Lupp, Daniel
, p. 877 - 882 (2011)
The development of a fully telescoped synthesis of a derivative of androstadiene C-17 esters made from epoxyparamethasone was demonstrated. This streamlining allowed for the elimination of isolation and solvent change after each synthetic step. Thus it not only drastically reduced the solvent waste, but also minimized the potential exposure to highly active intermediates thereby increasing the overall yield. The intuitively obvious advantage inherent to lowering the number of solvents was illustrated by applying standard green metrics.
N-Heterocyclic Carbene Catalyzed Photoenolization/Diels–Alder Reaction of Acid Fluorides
Agrawal, Arush,G?tze, Jan P.,Golz, Paul,Hopkinson, Matthew N.,Mavroskoufis, Andreas,Rajes, Keerthana,Ru?, Vincent
supporting information, p. 3190 - 3194 (2020/01/24)
The combination of light activation and N-heterocyclic carbene (NHC) organocatalysis has enabled the use of acid fluorides as substrates in a UVA-light-mediated photochemical transformation previously observed only with aromatic aldehydes and ketones. Stoichiometric studies and TD-DFT calculations support a mechanism involving the photoactivation of an ortho-toluoyl azolium intermediate, which exhibits “ketone-like” photochemical reactivity under UVA irradiation. Using this photo-NHC catalysis approach, a novel photoenolization/Diels–Alder (PEDA) process was developed that leads to diverse isochroman-1-one derivatives.
Preparation method of thieno[2,3-c]pyridine-7(6h)-ketone
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Paragraph 0034-0035, (2019/04/27)
The invention discloses a preparation method of thieno[2,3-c]pyridine-7(6h)-ketone, belonging to a thienopyridine compound. According to the technical key points, the preparation method comprises thefollowing operation steps of: adding 3-methylthiophene-2-formamide to tetrahydrofuran, then adding DMF-DMA, completely reacting after carrying out heating reflux for 2 to 3 hours, boiling off the tetrahydrofuran and the DMF-DMA under reduced pressured to obtain an oily matter; then adding the oily matter to the tetrahydrofuran, adding alkali in batches, carrying out heating reflux for 1.5-3 hourstill completely reacting, boiling off the tetrahydrofuran, adding 400 to 500ml of water and stirring for 1-2 hours, filtering and drying to obtain the thieno[2,3-c]pyridine-7(6h)-ketone. The preparation method has the beneficial effects that raw materials have relatively low price, the operation steps are simple, and the safety performance in the preparation process is improved.
Combined Acylselenourea-Diselenide Structures: New Potent and Selective Antitumoral Agents as Autophagy Activators
Garnica, Pablo,Encío, Ignacio,Plano, Daniel,Palop, Juan A.,Sanmartín, Carmen
supporting information, p. 306 - 311 (2018/04/20)
A series of 16 new diselenide-acylselenourea conjugates have been designed following the fragment-based drug strategy. Compound in vitro cytotoxic potential was evaluated against six human cancer cell lines and two nonmalignant derived cell lines with the aim of determining their potency and selectivity. Nine derivatives exhibited GI50 values under 10 μM in at least four cancer cell lines. A clear gap situated phenyl substitution over heterocyclic moieties in terms of selectivity. Among carbocyclic compounds, derivatives 2 and 7 significantly inhibited cell growth of breast adenocarcinoma cells with GI50 values of 1.30 and 0.15 nM, respectively, with selectivity indexes 12 and 121 times higher than those obtained for doxorubicin. Preliminary mechanistic studies indicated that compounds 2 and 7 induce cell cycle arrest and autophagy-dependent cell death evidenced by the blockage of cell death with pretreatment with wortmannin or chloroquine and confirmed by the upregulation of the markers Beclin1 and LC3B in MCF-7 cells.
Pd(II)-Catalyzed Arylation and Intramolecular Amidation of γ-C(sp3)-H Bonds: En Route to Arylheteroarylmethane and Pyrrolidone Ring Annulated Furan/Thiophene Scaffolds
Parella, Ramarao,Babu, Srinivasarao Arulananda
, p. 7123 - 7150 (2017/07/26)
We report the Pd(II)-catalyzed, bidentate directing group (BDG)-assisted arylation and successive arylation/intramolecular amidation of γ-C(sp3)-H bonds. The Pd(II)-catalyzed BDG-assisted C-H activation and functionalization of the β-C(sp3)-H bonds of carboxylic acids are well documented, but only a few reports are available that deal with the BDG-directed functionalization of the γ-C(sp3)-H bonds. Various 3-methylthiophene/furan-2-carboxamides (1a-e) were derived from their corresponding carboxylic acids and bidentate directing groups. These compounds were then used as substrates to investigate the arylation and successive arylation/intramolecular amidation of the γ-C(sp3)-H bonds. The γ-C(sp3)-H arylation arose from the Pd(II)-catalyzed reactions of these compounds with aryl iodides with reaction periods of 4-24 h (except a few reactions which required 36 or 48 h). Notably, these reactions led to the construction of various unsymmetrical diarylmethane scaffolds, such as thiophene/furan-based arylheteroarylmethanes (3-6). Prolonging the reaction period to 48-70 h led to successive γ-C(sp3)-H arylation/intramolecular amidation and the construction of both C-C and C-N bonds. Accordingly, these reactions led to the construction of new classes of pyrrolidone-ring annulated thiophene/furan-based heterocyclic scaffolds (e.g., 4,5-dihydro-6H-thieno[2,3-c]pyrrol-6-ones (8), 4,5-dihydro-6H-furo[2,3-c]pyrrol-6-ones (10), and 1-phenyl-1,2-dihydro-3H-benzo[4,5]thieno[2,3-c]pyrrol-3-ones (12)), and notably, compounds 8, 10, and 12 resemble the skeletons of 3-phenylisoindolin-1-ones.
Design, synthesis and activity evaluation study of novel substituted N-sulfonyl homoserine lactone derivatives as bacterial quorum sensing inhibitors
Sun, Qi,Zhao, Mingming,Liang, Jingwei,Xiao, Junhai,Meng, Fanhao
, p. 3345 - 3353 (2017/11/16)
A novel series of N-sulfonyl homoserine lactone derivatives 7a–7m has been designed, synthesized, and evaluated for quorum sensing inhibitory activities through the violacein inhibition in Chromobacterium violaceum CV026. Compound 7e displayed the high level of inhibitory activity among all the compounds synthesized. Studies of structure-activity relationship indicated that compounds with thiophene group in side chain showed better activity than those substituted by furan, pyrrole, pyridyl, and phenethyl group. Thiophene substituted compounds which connected electron withdrawing group exhibited better inhibitory activity relate to those connected electron donating group. Further analysis indicated that compound bearing an electron withdrawing substituent at the position 2 of their thiophene ring exhibited superior activity against violacein production to those bearing the substituent at the position 3 and 4. Compound 7e in particular, with IC50 value of 6.19 μM, were identified as promising lead compounds for further development.
Iron-Catalyzed, Fluoroamide-Directed C-H Fluorination
Groendyke, Brian J.,Abusalim, Deyaa I.,Cook, Silas P.
supporting information, p. 12771 - 12774 (2016/10/13)
This communication describes a mild, amide-directed fluorination of benzylic, allylic, and unactivated C-H bonds mediated by iron. Upon exposure to a catalytic amount of iron(II) triflate (Fe(OTf)2), N-fluoro-2-methylbenzamides undergo chemoselective fluorine transfer to provide the corresponding fluorides in high yield. The reaction demonstrates broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic and computational experiments suggest that the reaction proceeds through short-lived radical intermediates with F-transfer mediated directly by iron.
Synthesis, antileishmanial and antitrypanosomal activities of N-substituted tetrahydro-β-carbolines
Manda, Sudhakar,Khan, Shabana I.,Jain, Surendra K.,Mohammed, Shabber,Tekwani, Babu L.,Khan, Ikhlas A.,Vishwakarma, Ram A.,Bharate, Sandip B.
supporting information, p. 3247 - 3250 (2014/07/22)
A series of N-substituted tetrahydro-β-carbolines were synthesized and screened for antileishmanial activity through an in vitro assay that involves promastigotes and axenic amastigotes of Leishmania donovani, the causative agent for visceral leishmaniasis. The thiophen-2-yl analogs 9b and 11f and naphthyl analog 11h were found to show significant activity against promastigotes with IC50 values of 12.7, 9.1 and 22.1 μM, respectively. Analogs 9b and 11h were also effective against axenic amastigotes with IC50 values of 62.8 and 87.6 μM, respectively. The antileishmanial activity of analogs was then tested in human macrophage cell line infected with L. donovani amastigotes and 2-naphthyl linked analog 11h was found to be effective with IC50 value of 28.3 μM. Several analogs also displayed antitrypanosomal activity against Trypanosoma brucei, the causative agent for human African trypanosomiasis. Compounds 11e, 11f and 11h were more effective than others with IC50 values of 1.0, 8.9 and 10.2 μM, respectively. All synthesized analogs were not cytotoxic towards mammalian cell lines including Vero (monkey kidney fibroblasts), HEPG2 (human hepatoma cells), LLC-PK1 (pig kidney epithelial cells) and THP-1 (human macrophages).
