- Pure organic room-temperature phosphorescent material based on thiochromanone derivative as well as preparation method and application of pure organic room-temperature phosphorescent material
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The embodiment of the invention discloses a pure organic room-temperature phosphorescent material based on a thiochromanone derivative as well as a preparation method and application of the pure organic room-temperature phosphorescent material. The organi
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Paragraph 0040; 0044; 0047-0048
(2021/04/21)
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- 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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- 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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- Synthesis and anti cervical cancer activity of novel 5H-thiochromeno [4,3-d]pyrimidines
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A series of novel 5H-Thiochromeno[4,3-d]pyrimidine derivatives were synthesized, purified and characterized by different spectroscopy techniques such as1H NMR,13C NMR, Mass and Elemental Analysis. The new compounds were evaluated for their anti-cervical cancer activity on Human Cervical Cell Line HeLa. They were found to be potent anti-cervical cancer agents with GI50 values less than 10 μg/mL with respect to positive control drug Adriamycin.
- Naliapara, Yogesh,Pandya, Dhananjay
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p. 294 - 302
(2020/04/21)
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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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- Hydrazone derivatives enhance antileishmanial activity of thiochroman-4-ones
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Cutaneous leishmaniasis (CL) is a neglected tropical disease, which causes severe skin lesions. Due to the lack of effective vaccines, and toxicity or reduced effectiveness of available drugs in addition to complex and prolonged treatments, there is an urgent need to develop alternatives for the treatment for CL with different mechanisms of action. In our effort to search for new promising hits against Leishmania parasites we prepared 18 acyl hydrazone derivatives of thiochroman-4-ones. Compounds were evaluated for their in vitro antileishmanial activity against the intracellular amastigote form of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Our results show that derivatization of the thiochroman-4-ones with acyl hydrazones significantly enhances the antileishmanial activity. Among the compounds tested semicarbazone and thiosemicarbazone derivatives of thioflavanone 19 and 20 displayed the highest antileishmanial activities, with EC50 values of 5.4 and 5.1 μM and low cytotoxicities (100.2 and 50.1 μM respectively), resulting in higher indexes of selectivity (IS).
- Vargas, Esteban,Echeverri, Fernando,Upegui, Yulieth A.,Robledo, Sara M.,Qui?ones, Wiston
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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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supporting information
p. 3574 - 3578
(2018/10/15)
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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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- Synthesis and evaluation of thiochroman-4-one derivatives as potential leishmanicidal agents
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The S-containing heterocyclic compounds benzothiopyrans or thiochromones stand out as having promising biological activities due to their structural relationship with chromones (benzopyrans), which are widely known as privileged scaffolds in medicinal chemistry. In this work, we report the synthesis of 35 thiochromone derivatives and the in vitro antileishmanial and cytotoxic activities. Compounds were tested against intracellular amastigotes of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Compounds bearing a vinyl sulfone moiety, 4h, 4i, 4j, 4k, 4l and 4m, displayed the highest antileishmanial activity, with EC50 values lower than 10 μM and an index of selectivity over 100 for compounds 4j and 4l. When the double bond or the sulfone moiety was removed, the activity decreased. Our results show that thiochromones bearing a vinyl sulfone moiety are endowed with high antileishmanial activity and low cytotoxicity.
- Vargas, Esteban,Echeverri, Fernando,Vélez, Iván D.,Robledo, Sara M.,Qui?ones, Wiston
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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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- 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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- Synthesis and antitumor activities of a new series of 4,5-dihydro-1H- thiochromeno[4,3-d]pyrimidine derivatives
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A new series of 4,5-dihydro-1H-thiochromeno[4,3-d ]pyrimidine derivatives have been designed and synthesized. The antitumor activities of the target compounds have been evaluated in vitro against two human cancer cell lines including A549 (human alveolar adenocarcinoma cell) and H460 (human lung cancer) by MTT assay. Most of the target compounds exhibited significant antitumor activities against A549 and H460 cancer cell lines. The most potent compound 4-(benzo[d][1,3]dioxol-5-yl)-8,9-difluoro-2-(4-methylpiperazin-1-yl)-4, 5-dihydro-1H-thiochromeno[4,3-d]pyrimidine (CH05) (IC50 = 0.44 μM, 3.07 μM) was 2.0 and 8.4 times more active than gefitinib (IC50 = 0.89 μM, 16.81 μM) against A549 and H460 cell lines, respectively.
- Guo, Dexiang,Liu, Yajing,Li, Ting,Wang, Nan,Zhai, Xin,Hu, Chun,Gong, Ping
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experimental part
p. 347 - 351
(2012/08/08)
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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 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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- Substituted heterocycle fused gamma-carbolines
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The present invention is directed to methods of treating addictive behavior and sleep disorders by administering compounds represented by structural Formula (I) or pharmaceutically acceptable salt forms thereof, wherein R1, R5, R6a, R6b, R7, R8, R9, X, b, k, m, and n, and the dashed lines are described herein. The compounds used in the method of treatment of this invention are serotonin agonists and antagonists and are useful in the control or prevention of central nervous system disorders including addictive behavior and sleep disorders.
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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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