- Synthesis of benzothiazonine by rhodium-catalyzed denitrogenative transannulation of 1-sulfonyl-1,2,3-triazole and thiochromone
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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.
- Duan, Shengguo,Jablasone, Saygbechi T.,Li, Chuan-Ying,Xu, Ze-Feng,Ye, Zihang
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supporting information
p. 5758 - 5761
(2021/07/12)
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- Cu(I)-Catalyzed Enantioselective Alkynylation of Thiochromones
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A highly efficient asymmetric synthesis of chiral thiochromanones is developed via Cu(I)/phosphoramidite catalyzed asymmetric alkynylation of thiochromones under mild reaction conditions. The catalyst system is tolerant of various thiochromone precursors and terminal alkynes. The established asymmetric transformation provides different enatiomeric-enriched thiochromanones with more molecular complexity and enables access to chiral thioflavanones, a subgroup of flavonoid by further functionalization.
- Chang, Xiaoyong,Lin, Zhenyang,Meng, Ling,Ngai, Ka Yan,Wang, Jun
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supporting information
p. 1155 - 1159
(2020/02/26)
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- Development of conjugate addition of lithium dialkylcuprates to thiochromones: Synthesis of 2-alkylthiochroman-4-ones and additional synthetic applications
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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.
- 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
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supporting information
(2018/08/21)
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- Cu-Catalyzed Conjugate Addition of Grignard Reagents to Thiochromones: An Enantioselective Pathway for Accessing 2-Alkylthiochromanones
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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.
- Luo, Shihui,Meng, Ling,Yang, Qingxiong,Wang, Jun
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supporting information
p. 2071 - 2075
(2018/09/18)
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- Design, synthesis, and biological evaluation of 4-chloro-2H-thiochromenes featuring nitrogen-containing side chains as potent antifungal agents
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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.
- Wang, Dan-Jiao,Hou, Zhuang,Xu, Hang,An, Ran,Su, Xin,Guo, Chun
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p. 3574 - 3578
(2018/10/15)
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- Microwave-assisted synthesis of novel bisspiropyrrolidine thiochromanone derivatives and antifungal activity
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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.
- Wu, Fan,Liang, Guo-Chao,Zhou, Guan,Liu, Quan-Jie,Zhang, Chao-Chao,Yu, Jiao-Jiao,Dong, Xiao-Hui,Song, Ya-Li
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p. 206 - 216
(2016/02/27)
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- Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones: A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones
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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.
- Meng, Ling,Jin, Ming Yu,Wang, Jun
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p. 4986 - 4989
(2016/10/14)
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- Ionic liquid catalyzed synthesis of 2-(indole-3-yl)-thiochroman-4-ones and their novel antifungal activities
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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.
- Song, Ya-Li,Wu, Fan,Zhang, Chao-Chao,Liang, Guo-Chao,Zhou, Guan,Yu, Jiao-Jiao
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supporting information
p. 259 - 261
(2015/04/13)
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- Facile one-pot synthesis of some novel thiazolylpyrazole derivatives with antifungal activity
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A series of novel 1-(4-phenylthiazol-2-yl)-1,4-dihydrothiochroman[ 4,3-c]pyrazole have been prepared by a three-component reaction of thiochromanone-3-carbaldehyde, phenacyl bromide, and thiosemicarbazide. The reaction was in one-pot and did not require any additional catalyst with moderate yields. This method provided several advantages such as environment friendliness and simple work-up procedure. The compounds were assayed for antifungal activity and some of the new compounds can be further utilized as lead compounds.
- Song, Ya-Li,Yang, Tao,Dong, Yun-Fang,Wu, Fan,Yang, Geng-Liang
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supporting information
p. 134 - 136
(2014/01/23)
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- Synthesis and antifungal activity of some thiazole derivatives
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A series of some thiazole derivatives were designed and synthesized. The structure of newly synthesized compounds was characterized by HRMS, 1H NMR and 13C NMR. The synthesized compounds were evaluated against ten species of fungi in vitro by agar cup plate and micro-titration methods, respectively. The results of antifungal screening reveal that among all the compounds screened three compounds showed moderate antifungal activity. The MIC value of 3 h against two fungal strains C. neoformans and C. albicas is 8 μg mL-1 respectively. The MIC value of 3i against two fungal strains C. neoformans and T. mentagrophytes is 8 μg mL-1 and 16 μg mL-1, respectively and 3a against T. mentagrophytes is 16 μg mL-1, the MIC of others are all beyond 32 μg mL-1.
- Yang, Geng-Liang,Song, Ya-Li,Liu, Xiao-Ming,Yang, Ning
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p. 1849 - 1852
(2013/05/08)
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- Synthesis and antifungal activity of some novel (E)-2, 3-dihydro-3- [(phenylamino) methylene]-4H-1-benzothiopyran-4-ones
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A series of novel (E)-2,3-dihydro-3-[(phenylamino)methylene]-4H-1- benzothiopyran-4-ones has been synthesized by using 2,3-dihydro-4H-1- benzothiopyran-4-ones as the starting material. The structures of the new compounds are characterized by UV-vis, IR, HRMS, 1H NMR, and 13C NMR. 2D NMR spectroscopic studies revealed that at room temperature, these compounds rather exist in the keto-enamine than in the Schiff base form. The synthesized compounds were evaluated against two species of fungi in vitro by agar double dilution method. The results of antifungal screening revealed that the MIC value of (E)-8-chloro-2,3-dihydro-3-[(4- nitrophenylamino)methylene]-4H-1-benzothiopyran-4-one (4j) against Candida albicans is 32 μg·ml-1 while the control Fluconazole is 64 μg?ml-1.
- Liu, Xiao-Ming,Yang, Geng-Liang,Song, Ya-Li,Liu, Jie-Jie,Yang, Wang,Zhang, Dong-Nuan
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p. 228 - 234
(2013/07/26)
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- Synthesis and pharmacological evaluation of novel bisindolylalkanes analogues
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In an effort to develop potent anti-cancer chemopreventive agents that act on topoisomerase II, a novel series of bisindolylalkanes analogues such as 3,3′-(thiochroman-4,4-diyl)bis(1H-indole) are synthesized. Structures of all compounds are elucidated by 1H NMR, 13C NMR and HRMS. Anti-proliferative activities for all of these compounds are investigated by the method of MTT assay on 7 human cancer lines. Most of them showed antitumor activities in vitro, the half maximal inhibitory concentration (IC50) value is 7.798 μg/mL of 3a against MCF7. Compound 3a showed comparable topoisomerase II inhibitory activity to etoposide (VP-16) at 100 μM concentration. The rest of the compounds also showed varying degree topoisomerase II inhibitory activity.
- Song, Ya-Li,Dong, Yun-Fang,Yang, Tao,Zhang, Chao-Chao,Su, Li-Min,Huang, Xin,Zhang, Dong-Nuan,Yang, Geng-Liang,Liu, Yu-Xin
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p. 7624 - 7627
(2014/01/06)
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- Design and synthesis of α,β-epoxyketones as new anticancer agents
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As epoxy functional group has high anticancer activity, α,β-epoxyketones were designed and synthesized as new anticancer agents, and their structures were confirmed by UV, 1H NMR, IR, MS technigeces and elemental analysis. Their in vitro anticancer activities were evaluated by MTT method and the results showed that the compound 4c exhibited good activity with IC50 of 17.8, 22.0 and 24.1 μg/mL against A-549, Hela and HepG2 cells, respectively. The dose of LD50 of the mice by intragastric administration was 1864.4 mg/kg. Therefore, the α,β-epoxyketones could potentially provide as new anticancer agents. A series of α,β-epoxyketones were synthesized in a four steps reaction and tested for their anticancer activities.
- Ma, Zhengyue,Zhang, Xinghua,Wang, Shikui,He, Yang,Yang, Gengliang,Li, Beilei,Yang, Junjie,Lu, Yuejuan,Sun, Jiewei
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scheme or table
p. 757 - 764
(2011/11/12)
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- Synthesis and in vitro anti-hepatitis B virus activity of 6H-[1]benzothiopyrano[4,3-b]quinolin-9-ols
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A series of novel 6H-[1]benzothiopyrano[4,3-b]quinoline derivatives were prepared and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in human hepatoblastoma-derived liver Hep-G2 cells. Compounds 10g, 10h, 10j, 10l and 10o were found to be potent anti-HBV compounds with IC50 values less than 50 μM. The most promising compound was 10l, with an IC50 value of 14.7 μM and a SI value of 12.4. This is the first report of the anti-HBV effects of 6H-[1]benzothiopyrano[4,3-b] quinolin-9-ols. Crown Copyright
- Jia, Wei,Liu, Yajing,Li, Wei,Liu, Yan,Zhang, Dajun,Zhang, Peng,Gong, Ping
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experimental part
p. 4569 - 4574
(2009/10/17)
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- A structure-taste study of arylsulfonyl(cyclo)alkanecarboxylic acids
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A number of sweeteners contain a sulfonyl group. In our current search for new glucophores several new compounds containing such group were obtained. A series of novel 1-phenylsulfonylcyklohexanecarboxylic acids and 2-arylsulfonylalkanecarboxylic acids was obtained and evaluated for their sweet taste quality. It has been found that methyl substituents are of the key importance for the activity of these compounds.
- Lysiak, Violetta,Ratajczak, Aleksander,Mencel, Agnieszka,Jarzembek, Krystyna,Polanski, Jaroslaw
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p. 671 - 675
(2007/10/03)
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- Nickel chloride hexahydrate: A novel reagent for Michael addition on α,β-unsaturated acids - A facile one-step route to 3-arylmercaptopropionic acids from thiophenols and α,β-unsaturated acids
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Michael additions have been successfully carried out in presence of a base, but when an α,β00-unsaturated acid is a substrate, it would be most unlikely for a carboxylate ion bearing α,β-unsaturated site to undergo a Michael addition. This problem has been circumvented in the present paper by carrying out a nickel chloride hexahydrate mediated Michael addition of thiophenols 1a-k on acrylic acid and on cinnamic acid to give 3-aryl mercaptopropionic acids 3a-k in excellent yield.
- Gogia, Santosh,Sirohi, Reenu,Gupta, Suman,Kishore,Joshi
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p. 1008 - 1011
(2007/10/03)
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- A new set of nickelacyclic carboxylates ( nickelalactones ) containing pyridine as supporting ligand: Synthesis, structures and application in C-C- and C-S- linkage reactions
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Nickelacycles of the type [(py)2Ni(CH2 COO)](1a), [(py) 2Ni(C(Et) C(Et)=COO)] (2a), and [(py)Ni (CH2)-CH2-COO)] (3a) were synthesized and structurally investigated by NMR, IR spectroscopy and in case of 1a and 2a by X-ray diffraction analysis. In 1a and 2a the Ni(II) ion has square-planar geometry, in contrast to the η3 allyl compound [(bipy)Ni(CH2)-CH2-COO)] (3b), in which nickel center adopts square-pyramidal geometry. 1a reacts with di(2-pyridyl)dimethylsilane (Me2(2-py)2Si) under exchange of the pyridine ligands to give 1c. 1a-3a and their bipy derivatives react with di-p-tolyldisulfide to form β-thioesters upon workup. Furthermore, reaction of 2-bromopropiophenone with nickelacycles of the type 2 results in the formation of 3,4-diethyl-6-hydroxy-5-methyl-6-phenyl-5,6-dihydro-2H-pyrane-2-one in good yields (64-75%). These reactions offer attractive new preparative routes for functionalized organic compounds.
- Langer, Jens,Fischer, Reinald,G?rls, Helmar,Walther, Dirk
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p. 2952 - 2962
(2007/10/03)
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- Nickel chloride catalyzed arylation of 3-mercaptopropionic acid: A facile one step route to 3-aryl mercaptopropionic acids from unactivated aryl halides and arenes
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Nickel chloride catalyzed arylation of 3-mercaptopropionic acid by (i) unactivated aryl halides (path a) and (ii) diphenyliodonium bromide (path b) gave 3-aryl mercaptopropionic acid (3) in good yield.
- Gogia, Santosh,Sirohi, Reenu,Gupta, Suman,Kishore,Joshi
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p. 515 - 517
(2007/10/03)
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- A rapid and efficient synthesis of thiochroman-4-ones under microwave irradiation
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Thiochroman-4-ones were synthesised by the cyclization of β-arylthiopropionic acids which were prepared by the condensation of the arylthiols with chloropropionic acid under microwave irriadiation within 4min.
- Li, Ji-Tai,Li, Hong-Ya,Li, Hui-Zhang,Xiao, Li-Wei
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p. 394 - 395
(2007/10/03)
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