13735-12-1Relevant articles and documents
Synthesis of benzothiazonine by rhodium-catalyzed denitrogenative transannulation of 1-sulfonyl-1,2,3-triazole and thiochromone
Duan, Shengguo,Jablasone, Saygbechi T.,Li, Chuan-Ying,Xu, Ze-Feng,Ye, Zihang
, p. 5758 - 5761 (2021/07/12)
A facile synthesis of multi-functionalized benzothiazonine was achieved by the rhodium-catalyzed denitrogenative annulation of 1-sulfonyl-1,2,3-triazole and thiochromone. In view of the excellent atom economy, broad substrate scope and easy availability of starting materials, the protocol provided an efficient strategy for the construction of mediumN,S-heterocycles.
Synthesis method of 2,3-dihydrothiochromene-4-one and derivative thereof
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, (2020/02/14)
The invention discloses a synthesis method of 2,3-dihydrothiochromene-4-one and a derivative thereof. The synthesis method is characterized in that a substituted and unsubstituted aromatic thiophenolcompound is used as a raw material, and reacts with acrylic acid to generate corresponding aromatic thiopropionic acid, and cyclizing is performed under the action of concentrated sulfuric acid to obtain the corresponding 2,3-dihydrothiochromene-4-one and the derivative thereof. According to the invention, the raw materials use acrylic acid and concentrated sulfuric acid, so that the raw materialsare easy to obtain, the cost is low, and the feeding is easy; and the post-treatment only needs acidification, extraction, washing and solvent evaporation, so that the method is simple in post-treatment, high in yield, low in cost and suitable for industrial production.
Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- And α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol
Zhan, Xiao-Yu,Zhang, Hua,Dong, Yu,Yang, Jian,He, Shuai,Shi, Zhi-Chuan,Tang, Lei,Wang, Ji-Yu
, p. 6578 - 6592 (2020/07/17)
The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies revealed that hexafluoro-2-propanol also served as a hydrogen source in the process.
Synthesis and biological evaluation of novel pyrazoline derivatives containing indole skeleton as anti-cancer agents targeting topoisomerase II
Dong, Jinjiao,Feng, Jiajia,Feng, Siran,Liu, Zhenming,Qiao, Xiaoqiang,Song, Yali,Yang, Kan
, (2020/06/03)
In order to develop potent anticaner agents, a novel series of 3-(1H-indol-3-yl)-2,3,3a,4-tetrahydrothiochromeno[4,3-c]pyrazole derivatives were synthesized. Structures of all compounds were confirmed. MTT assay has been employed to study antiproliferative activity of these compounds with four human cancer cell lines (MGC-803, Hela, MCF-7 and Bel-7404) and a normal cell line L929. Most of these compounds showed potential anticancer activity and low cytotoxicity on normal cell in vitro. 7d and 7f showed the best anticancer activity, whose IC50 value is 15.43 μM and 20.54 μM towards MGC-803, respectively. Most of them exhibited topoisomerase II selective inhibitory. Cleavage reaction assay and DNA unwinding assay showed that 7f was a nonintercalative Topo II catalytic inhibitor, which was consistent with the docking results. Laser scanning confocal microscopy system tracks the location of representative compounds 7d and 7f which can be abundantly entering the nucleus. In particular, the most potent compounds 7d and 7f were shown to be able to induce G2/M cell cycle arrest and apoptosis in MGC-803 cells.
Development of conjugate addition of lithium dialkylcuprates to thiochromones: Synthesis of 2-alkylthiochroman-4-ones and additional synthetic applications
Bass, Shekinah A.,Parker, Dynasty M.,Bellinger, Tania J.,Eaton, Aireal S.,Dibble, Angelica S.,Koroma, Kaata L.,Sekyi, Sylvia A.,Pollard, David A.,Guo, Fenghai
, (2018/08/21)
Lithium dialkylcuprates undergo conjugate addition to thiochromones to afford 2-alkylthiochroman-4-ones in good yields. This approach provide an efficient and general synthetic approach to privileged sulfur-containing structural motifs and valuable precursors for many pharmaceuticals, starting from common substrates-thiochromones. Good yields of 2-alkyl-substituted thiochroman-4-ones are attained with lithium dialkylcuprates, lithium alkylcyanocuprates or substoichiometric amount of copper salts. The use of commercially available inexpensive alkyllithium reagents will expedite the synthesis of a large library of 2-alkyl substituted thiochroman-4-ones for additional synthetic applications.
Cu-Catalyzed Conjugate Addition of Grignard Reagents to Thiochromones: An Enantioselective Pathway for Accessing 2-Alkylthiochromanones
Luo, Shihui,Meng, Ling,Yang, Qingxiong,Wang, Jun
, p. 2071 - 2075 (2018/09/18)
The enantioselective incorporation of alkyl groups in thiochromones was realized for the first time by a Cu/(R, S)-PPF-P t Bu 2 -catalyzed conjugate addition of Grignard reagents to thiochromones. With this method, a series of 2-methylthiochromanones were obtained in good yields (up to 96% yield) with moderate-to-good ee values (up to 87% ee). The established method expedites the synthesis of a large library of chiral thiochromanones for further synthetic applications and biological studies.
Design, synthesis, and biological evaluation of 4-chloro-2H-thiochromenes featuring nitrogen-containing side chains as potent antifungal agents
Wang, Dan-Jiao,Hou, Zhuang,Xu, Hang,An, Ran,Su, Xin,Guo, Chun
, p. 3574 - 3578 (2018/10/15)
A series of 4-chloro-2H-thiochromenes featuring nitrogen-containing side chains were designed, synthesized and tested in vitro for their antifungal activities. The results of preliminary antifungal tests showed that most target compounds exhibited good inhibitory activities against Candida albicans, Cryptococcus neoformans, Candida tropicalis. Notably, compounds 10e and 10y showed most potent activity in vitro against a variety of fungal pathogens with low MICs. Meanwhile, low cytotoxicity on mammalian cells has been observed for compounds 10e and 10y in the tested concentrations by the MTT assay. Therefore, the 4-chloro-2H-thiochromenes with nitrogen-containing groups provide new lead structures in the search for novel antifungal agents.
Microwave-assisted synthesis of novel bisspiropyrrolidine thiochromanone derivatives and antifungal activity
Wu, Fan,Liang, Guo-Chao,Zhou, Guan,Liu, Quan-Jie,Zhang, Chao-Chao,Yu, Jiao-Jiao,Dong, Xiao-Hui,Song, Ya-Li
, p. 206 - 216 (2016/02/27)
Background: Multicomponent Reactions are being widely used in the synthesis of heterocyclic compounds. Spiroheterocyclic compounds also have various physiological activities such as anti-tumor and antifungal, and they are important in drug discovery. In order to find novel spiroheterocyclic compounds having potential antifungal activity, we found a fast and efficient approach to the synthesis of novel 4′-phenyldispiro[indoline-3,2′-pyrrolidine-3′,3″-thiochromane]-2,4″-dione, and the antifungal activity of the novel spiroheterocyclic compounds were tested. Methods: A variety of different substituents of 3-arylidene-thiochroman-4-one (1mmol) with isatin (1mmol) and different substituted amino acids (sarcosine, proline, leucine, glycine, phenylglycine, alanine, phenylalanine, glutamic acid or arginine, 1mmol) were mixed in [Bmim]Cl (2mL) and then gave microwave irradiation. After the reaction have finished, the reaction system was added in 10mL water, and a lot of white precipitation was obtained and filtrated. The pure objects were recrystallization by mixture of ethanol and water. The antifungal activity was determined by consecutive double dilution method. Results: Microwave irradiation dramatically decreases reaction time from hours to minutes for this multicomponent reaction, and the yields were also slightly increased. Neutral and acidic amino acids can successfully occur 1, 3-dipolar cycloaddition reactions but basic amino acids such as arginine can not. The solvent - [Bmim]Cl can be recycled to reuse after treatment. Compounds 6c and 6d have good inhibition than fluconazole for the two invasive fungi (C.n. and M.r.) and some compounds show moderate inhibition activities for tested fungi. Conclusion: A microwave-enhanced, fast, and efficient three-component reaction in [Bmim]Cl for generation of series novel 4′-phenyldispiro[indoline-3,2′-pyrrolidine-3′,3″-thiochromane]-2,4″-dione compounds has been developed. Among these compounds, several show better anti-invasive fungal activity than fluconazole and some show moderate inhibiton activity.
Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones: A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones
Meng, Ling,Jin, Ming Yu,Wang, Jun
, p. 4986 - 4989 (2016/10/14)
A highly efficient asymmetric synthesis of chiral thioflavanones is developed via conjugate addition of arylzinc reagents to thiochromones using Rh(COD)Cl2/(R)-3,4,5-MeO-MeOBIPHEP catalyst. This method overcomes catalyst poisoning and substrate inertness and affords a series of chiral thioflavanones (2-arylthiochroman-4-ones) in good yields (up to 91% yield) with excellent ee values (up to 97% ee). The established asymmetric synthesis paves the way for further pharmaceutical studies.
Ionic liquid catalyzed synthesis of 2-(indole-3-yl)-thiochroman-4-ones and their novel antifungal activities
Song, Ya-Li,Wu, Fan,Zhang, Chao-Chao,Liang, Guo-Chao,Zhou, Guan,Yu, Jiao-Jiao
, p. 259 - 261 (2015/04/13)
2-(Indole-3-yl)-thiochroman-4-ones were synthesized via ionic liquid and tested for in vitro antifungal activity. The contribution of ionic liquid to Michael addition reaction is significant. Structures of all compounds are elucidated by 1H NMR, 13C NMR and HRMS. Most of these compounds showed better antifungal activity than fluconazole. The results suggest that 2-(indole-3-yl)-thiochroman-4-ones would be efficient antifungal agents.
