- 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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- 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
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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.
- Zhan, Xiao-Yu,Zhang, Hua,Dong, Yu,Yang, Jian,He, Shuai,Shi, Zhi-Chuan,Tang, Lei,Wang, Ji-Yu
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p. 6578 - 6592
(2020/07/17)
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- Synthesis method of 2,3-dihydrothiochromene-4-one and derivative thereof
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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.
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Paragraph 0007; 0026; 0028
(2020/02/14)
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- Synthesis and biological evaluation of novel pyrazoline derivatives containing indole skeleton as anti-cancer agents targeting topoisomerase II
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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.
- Dong, Jinjiao,Feng, Jiajia,Feng, Siran,Liu, Zhenming,Qiao, Xiaoqiang,Song, Yali,Yang, Kan
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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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supporting information
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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- SUBSTITUTED SULFONE-CONTAINING TRICYCLIC COMPOUNDS AND USES THEREOF
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The present invention relates to substituted sulfone-containing tricyclic compounds and analogues thereof which inhibit Bak-mediated apoptosis. The invention further relates to pharmaceutical compositions comprising a compound of the present invention and to methods of inhibiting a Bak-mediated apoptotic pathway and Bak-mediated apoptosis in a cell.
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Page/Page column 28; 29
(2014/05/24)
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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 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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- 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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- Dihydrobenzo(B)thiophenes and pharmaceutical compositions thereof useful as antifungals
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2-Alkyl-, 2-alkenyl- and 2-alkynyl-2,3-dihydro-2-(1H-azolyl(C1 -C2)alkyl)benzo[b]thiophenes especially 2-alkyl-, 2-alkenyl- and 2-alkynyl-2,3-dihydro-3-hydroxy-2-(1H-1-imidazolylmethyl)-4-,5-,6- and 7-halobenzo[b]thiophenes and related derivatives having antifungal activity are disclosed. Pharmaceutical compositions comprising compounds of the invention and their use in treating fungal infections in susceptible hosts such as humans are also disclosed.
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- 2,3-Dihydro-2-(imidazolylmethyl)benzo(b)thiophenes
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This invention relates to 2,3-dihydro-2-(imidazolylmethyl)benzo(b)thiophenes, to intermediates useful in their preparation, and to processes for preparing said intermediates. Also included in the invention are pharmaceutical compositions and the method of use of the compounds as antifungal agents.
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- MODERN FRIEDEL-CRAFTS CHEMISTRY. XI. CYCLIZATION OF ARYL HALOALKYL SULFONES, ARYLSULFONYLACYL CHLORIDES AND THEIR CORRESPONDING SULFIDES
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The sulfone group deactivation for cyclialkylation and cycliacylation reactions in the presence of Friedel-Crafts catalysts was demonstrated in a number of aryl chloroalkylsulfones (1-8) and arylsulfonylacyl chlorides (17a-22a), respectively.As expected, the corresponding arylchloroalkyl sulfides (9-16) and arylmercaptoacyl chlorides (13a-28a) underwent ring-closure reaction in most cases under the same conditions.The ease of cyclization was governed by the ring size, the stability of the attacking carbocation and the nucleophilicity of the aryl moiety.Also, the behaviour of benzyl sulfones (29, 31a, and 32a) and sulfides (33, 34a and 36a) was inconsistent.Noteworthy, the Friedel-Crafts cyclization reaction is thus considered an accessible method for the synthesis of compounds 37-41 and 45, 51.
- Abdel-Wahab, Aboel-Magd A.,El-Khawaga, Ahmed M.,El-Zohry, Maher F.,Khalaf, Ali A.
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- [1]Benzothiopyrano[4,3-c]pyrazoles as immunoregulatory agents
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1,2,3,4-Tetrahydrobenzothiopyrano[4,3-c]pyrazol-3-ones and 2,3-dihydro[1]benzothiopyrano[4,3-c]pyrazol-3-ones, of respective structure I and II, STR1 wherein n is an integer of value from 0 to 2; R is phenyl; phenyl monosubstituted with chloro, bromo, fluoro, methyl, methoxy, nitro or trifluoromethyl; or phenyl disubstituted with chloro; and X is hydrogen or chloro; are described. These novel compounds are immunoregulators which, through suppression of the immune response in mammals, are useful in inhibiting rejection of organ transplants, as well as in the therapy of auto-immune diseases.
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