- A catalyst-free method for the synthesis of 1,4,2-dithiazoles from isothiocyanates and hydroxylamine triflic acid salts
-
A catalyst-free method for the preparation of 1,4,2-dithiazoles is developed by reactions of isothiocyanates with hydroxylamine triflic acid salts. This reaction achieves C-S, C-N, and S-N bond formation, and a range of products are obtained in moderate to good yields. The obvious feature is using shelf-stable hydroxylamine triflic acid salts as a N source to synthesize heterocycles under mild conditions.
- An, Zhenyu,Liu, Yafeng,Ren, Yi,Wang, Ting,Yan, Rulong
-
supporting information
p. 6206 - 6209
(2021/07/28)
-
- The novel copper(I) π,σ-complexes with 1-(aryl)-5-(allylthio)-1H-tetrazoles: Synthesis, structure characterization, DFT-calculation and third-order nonlinear optics
-
The present work is directed toward preparation, structure and optical property characterization of tetrazole-containing Cu(I) compounds. By means of the alternating-current electrochemical technique copper(I) π,σ-compounds with 1-(4-methylphenyl)- (Matht), 1-(3-chloro-4-methylphenyl)- (Chmatht) and 1-[2-(trifluoromethyl)phenyl]- (Tfmatht) 5-(allylthio)-1H-tetrazoles were obtained in a single crystal form and structurally characterized by X-ray diffraction and Raman spectroscopy. Matht and Chmatht ligands, being attached to the Cu(I) through S-allylic C = C-bond and two tetrazole N-atoms, form stable centrosymmetric dimers [Cu2(Matht)2(H2O)2](BF4)2 and [Cu2(Chmatht)2(СlO4)2]. The presence of an electron acceptor trifluoromethyl group promotes formation of the monomeric [Cu(Tfmatht)2]BF4 and [Cu(Tfmatht)(NH2SO3)(MeOH)] compounds. The compounds were investigated by means of Raman spectroscopy, third-order nonlinear optics and DFT calculations.
- Slyvka, Yurii,Goreshnik, Evgeny,Veryasov, Gleb,Morozov, Dmitry,Fedorchuk, Andrii A.,Pokhodylo, Nazariy,Kityk, Iwan,Mys’kiv, Marian
-
p. 1049 - 1063
(2019/03/07)
-
- Synthesis and biological evaluation of terminal functionalized thiourea-containing dipeptides as antitumor agents
-
A series of antitumor agents based on terminal functionalized dipeptide derivatives containing the thiourea moiety were synthesized and evaluated for antiproliferative activity using a panel of cancer cell lines, and the effects and mechanism of apoptosis induction were determined. These compounds exhibited significant selectivity to different cancer cell lines with IC50 values at micromolar concentrations. In particular, compound I-11 appeared to be the most potent compound, with an IC50 = 4.85 ± 1.44 μM against the NCI-H460 cell line, at least partly, by the induction of apoptosis. Mechanistically, compound I-11 induced the activation of caspase-12 and CHOP, which triggered apoptotic signalling via the ROS-dependent endoplasmic reticulum pathway and arrested the cell cycle at the S phase. Thus, we concluded that dipeptide derivatives containing the thiourea moiety terminally functionalized by electron-withdrawing substituents may be potential antitumor agents for further investigation.
- Huang, Ri-Zhen,Zhang, Bin,Huang, Xiao-Chao,Liang, Gui-Bin,Qin, Jian-Mei,Pan, Ying-Ming,Liao, Zhi-Xin,Wang, Heng-Shan
-
p. 8866 - 8878
(2017/02/10)
-
- Double three bromo 1,3-di-pyridine salt-based propane and its preparation method, method of use, recovery method and application
-
The invention discloses a double tribromo 1,3-bipyridine onium salt dimethylmethane, and a preparation method, an application method, a recovery method and application thereof. The preparation method comprises the following steps: dissolving 1,3-bipyridine onium salt dimethylmethane by using water, and then adding potassium bromide; adding potassium peroxymonosulfate sulfate compound brine solution to prepare a clear solution after dissolving potassium bromide, and then stirring and reacting at -10 to 0 DEG C until solid is separated out; separating out solid, so as to obtain the double tribromo 1,3-bipyridine onium salt dimethylmethane. The product can be used for preparing isothiocyanate, aromatic thiourea or acetanilide. The preparation method disclosed by the invention is mild in condition, and simple to operate the reaction process, and raw materials are easily available. The double tribromo 1,3-bipyridine onium salt dimethylmethane not only can be used as a brominating reagent, but also can be used as organic synthesis intermediates, meanwhile, the reaction efficiency is improved, and the double tribromo 1,3-bipyridine onium salt dimethylmethane is convenient to recover and can be recycled.
- -
-
Paragraph 0075; 0076; 0160; 0161
(2016/10/07)
-
- Design, synthesis, X-ray crystallographic analysis, and biological evaluation of thiazole derivatives as potent and selective inhibitors of human dihydroorotate dehydrogenase
-
Human dihydroorotate dehydrogenase (HsDHODH) is a flavin-dependent mitochondrial enzyme that has been certified as a potential therapeutic target for the treatment of rheumatoid arthritis and other autoimmune diseases. On the basis of lead compound 4, which was previously identified as potential HsDHODH inhibitor, a novel series of thiazole derivatives were designed and synthesized. The X-ray complex structures of the promising analogues 12 and 33 confirmed that these inhibitors bind at the putative ubiquinone binding tunnel and guided us to explore more potent inhibitors, such as compounds 44, 46, and 47 which showed double digit nanomolar activities of 26, 18, and 29 nM, respectively. Moreover, 44 presented considerable anti-inflammation effect in vivo and significantly alleviated foot swelling in a dose-dependent manner, which disclosed that thiazole-scaffold analogues can be developed into the drug candidates for the treatment of rheumatoid arthritis by suppressing the bioactivity of HsDHODH.
- Zhu, Junsheng,Han, Le,Diao, Yanyan,Ren, Xiaoli,Xu, Minghao,Xu, Liuxin,Li, Shiliang,Li, Qiang,Dong, Dong,Huang, Jin,Liu, Xiaofeng,Zhao, Zhenjiang,Wang, Rui,Zhu, Lili,Xu, Yufang,Qian, Xuhong,Li, Honglin
-
p. 1123 - 1139
(2015/03/04)
-
- Design, synthesis and in vitro evaluation of novel ursolic acid derivatives as potential anticancer agents
-
A series of novel ursolic acid (UA) derivatives modified at the C-3 and the C-28 positions were designed and synthesized in an attempt to develop potential antitumor agents. The in vitro cytotoxicity were evaluated against five cancer cell lines (MGC-803, HCT-116, T24, HepG2 and A549 cell lines) and a normal cell (HL-7702) by MTT assay. The screening results indicated that some of these target compounds displayed moderate to high levels of antiproliferative activities compared with ursolic acid and 5-fluorouracil (5-FU), and exhibited much lower cytotoxicity than 5-FU, indicating that the targeted compounds had selective and significant effect on the cell lines. The induction of apoptosis and affects on the cell cycle distribution of compound 6r were investigated by acridine orange/ethidium bromide staining, Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining and flow cytometry, which revealed that the antitumor activity of 6r was possibly achieved through the induction of cell apoptosis by G1 cell-cycle arrest. Western blot and qRT-PCR (quantitative real-time PCR) experiments demonstrated that compound 6r may induce apoptosis through both of intrinsic and extrinsic apoptosis pathway.
- Hua, Shi-Xian,Huang, Ri-Zhen,Ye, Man-Yi,Pan, Ying-Ming,Yao, Gui-Yang,Zhang, Ye,Wang, Heng-Shan
-
p. 435 - 452
(2015/04/14)
-
- Synthesis and pesticidal properties of thio and seleno analogs of some common urea herbicides
-
Thio and seleno analogs of fenuron, isoproturon, chlorotoluron, metoxuron, monuron, and diuron were synthesized from the corresponding aryl amines. Their reaction with thiophosgene leads to isothiocyanates. Aryl amines were also converted (via isocyanides) to isoselenocyanates. The reaction of both isothio- and isoselenocyanates with dimethylamine affords the corresponding thio and seleno analogs of the above-mentioned urea herbicides. Herbicidal activity of the synthesized compounds was slightly lower than the activity of the parent urea herbicides. The thio and seleno analogs as well as the parent ureas showed good fungicidal activity at a concentration of 200 ppm against selected fungi.
- Zakrzewski, Jerzy,Krawczyk, Maria
-
experimental part
p. 1880 - 1903
(2010/02/28)
-
- Discovery of dual inhibitors targeting both HIV-1 capsid and human cyclophilin A to inhibit the assembly and uncoating of the viral capsid
-
HIV-1 assembly and disassembly (uncoating) processes are critical for the HIV-1 replication. HIV-1 capsid (CA) and human cyclophilin A (CypA) play essential roles in these processes. We designed and synthesized a series of thiourea compounds as HIV-1 assembly and disassembly dual inhibitors targeting both HIV-1 CA protein and human CypA. The SIV-induced syncytium antiviral evaluation indicated that all of the inhibitors displayed antiviral activities in SIV-infected CEM cells at the concentration of 0.6-15.8 μM for 50% of maximum effective rate. Their abilities to bind CA and CypA were determined by ultraviolet spectroscopic analysis, fluorescence binding affinity and PPIase inhibition assay. Assembly studies in vitro demonstrated that the compounds could potently disrupt CA assembly with a dose-dependent manner. All of these molecules could bind CypA with binding affinities (Kd values) of 51.0-512.8 μM. Fifteen of the CypA binding compounds showed potent PPIase inhibitory activities (IC50 values 1 μM) while they could not bind either to HIV-1 Protease or to HIV-1 Integrase in the enzyme assays. These results suggested that 15 compounds could block HIV-1 replication by inhibiting the PPIase activity of CypA to interfere with capsid disassembly and disrupting CA assembly.
- Li, Jiebo,Tan, Zhiwu,Tang, Shixing,Hewlett, Indira,Pang, Ruifang,He, Meizi,He, Shanshan,Tian, Baohe,Chen, Kan,Yang, Ming
-
scheme or table
p. 3177 - 3188
(2009/09/05)
-
