- Design, synthesis and biological evaluation of benz-fused five-membered heterocyclic compounds as tubulin polymerization inhibitors with anticancer activities
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A series of benz-fused five-membered heterocyclic compounds were designed and synthesized as novel tubulin inhibitors targeting the colchicine binding site. Among them, compound 4d displayed the highest antiproliferative activity against four cancer cell lines with an IC50 value of 4.9?μM in B16-F10 cells. Compound 4d effectively inhibited tubulin polymerization in vitro (IC50 of 13.1?μM). Further, 4d induced cell cycle arrest in G2/M phase. Finally, 4d inhibited the migration of cancer cells in a dose-dependent manner. In summary, these results suggest that compound 4d represents a new class of tubulin inhibitors deserving further investigation.
- Komuraiah, Buduma,Ren, Yichang,Xue, Mingming,Cheng, Binbin,Liu, Jin,Liu, Yao,Chen, Jianjun
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- Rh-Catalyzed Asymmetric Hydrogenation of Unsaturated Medium-Ring NH Lactams: Highly Enantioselective Synthesis of N-Unprotected 2,3-Dihydro-1,5-benzothiazepinones
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A straightforward method to prepare 1,5-benzothiazepines was reported. Catalyzed by a Rh/Zhaophos complex, unsaturated cyclic NH lactams with a medium-size ring were hydrogenated smoothly, giving remarkably high enantioselectivities. The sulfur atom in the substrates did not bring an inhibition which was observed with commercially available bisphosphine ligands. This method was successfully applied in the scale-up synthesis of (R)-(-)-thiazesim.
- Yin, Congcong,Yang, Tao,Pan, Yingmin,Wen, Jialin,Zhang, Xumu
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- Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization
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3-CF3S substituted thioflavones and benzothiophenes were achieved via the reactions of AgSCF3 with methylthiolated alkynones and alkynylthioanisoles, respectively, promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process was involved, which includes addition of CF3S radical to triple bond and cyclization with SMe moiety.
- Wang, Lu,Wang, Huaiyu,Meng, Weidong,Xu, Xiu-Hua,Huang, Yangen
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supporting information
p. 389 - 392
(2020/03/04)
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- Benzothiazolyl ureas are low micromolar and uncompetitive inhibitors of 17Β-HSD10 with implications to Alzheimer’s disease treatment
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Human 17β-hydroxysteroid dehydrogenase type 10 is a multifunctional protein involved in many enzymatic and structural processes within mitochondria. This enzyme was suggested to be involved in several neurological diseases, e.g., mental retardation, Parkinson’s disease, or Alzheimer’s disease, in which it was shown to interact with the amyloid-beta peptide. We prepared approximately 60 new compounds based on a benzothiazolyl scaffold and evaluated their inhibitory ability and mechanism of action. The most potent inhibitors contained 3-chloro and 4-hydroxy substitution on the phenyl ring moiety, a small substituent at position 6 on the benzothiazole moiety, and the two moieties were connected via a urea linker (4at, 4bb, and 4bg). These compounds exhibited IC50 values of 1–2 μM and showed an uncompetitive mechanism of action with respect to the substrate, acetoacetyl-CoA. These uncompetitive benzothiazolyl inhibitors of 17β-hydroxysteroid dehydrogenase type 10 are promising compounds for potential drugs for neurodegenerative diseases that warrant further research and development.
- Aitken, Laura,Benek, Ondrej,Chribek, Matej,Dolezal, Rafael,Gunn-Moore, Frank,Hrabinova, Martina,Hroch, Lukas,Jun, Daniel,Kralova, Vendula,Kuca, Kamil,Lycka, Antonin,Musilek, Kamil,Prchal, Lukas,Schmidt, Monika,Vinklarova, Lucie,Zemanova, Lucie
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- Catalytic Enantioselective Synthesis of Protecting-Group-Free 1,5-Benzothiazepines
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A one-pot enantioselective route to N-unprotected 2,3-dihydro-1,5-benzothiazepinones, by an organocatalyzed sulfa-Michael reaction of readily available α,β-unsaturated N-acyl pyrazoles with 2-aminothiophenols followed by silica-gel-catalyzed lactamization
- Meninno, Sara,Volpe, Chiara,Lattanzi, Alessandra
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supporting information
p. 4547 - 4550
(2017/04/13)
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- Selective reduction of nitroaromatic compounds on silver nanoparticles by visible light
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For the first time, we report experimentally and theoretically that nitroaromatic compounds, 2,4-dinitrobenzenethiol and 4-chloro-2- nitrobenzenethiol, on silver sols can be selectively reduced to 2-amino-4-nitrobenzenethiol and 2-amino-4-chlorobenzenethiol simply by irradiating with a visible light in ambient conditions, and the selective photoreduction is a very facile process. The results of quantum chemical calculations are in good agreement with our experimental data. Copyright
- Xia, Lixin,Hu, Xinhu,Sun, Mengtao,Li, Jushi,Yang, Donghui,Wang, Xiaofang,Xu, Hongxing
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p. 1024 - 1028
(2012/10/29)
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- Benzothiazole cyclobutyl amine derivatives
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Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions comprising the histamine-3 receptor ligands, methods for using such compounds and compositions, and a process for preparing compounds within the scope of formula (I).
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Page/Page column 47
(2008/06/13)
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- Identification of a novel series of tetrahydrodibenzazocines as inhibitors of 17β-hydroxysteroid dehydrogenase type 3
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A novel series of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3) inhibitors has been identified. These inhibitors, based on a dibenzazocine core, exhibited picomolar to low nanomolar inhibition of 17β-HSD3 in cell-free enzymatic as well as in cell-based transcriptional reporter assays.
- Fink, Brian E.,Gavai, Ashvinikumar V.,Tokarski, John S.,Goyal, Bindu,Misra, Raj,Xiao, Hai-Yun,Kimball, S. David,Han, Wen-Ching,Norris, Derek,Spires, Thomas E.,You, Dan,Gottardis, Marco M.,Lorenzi, Matthew V.,Vite, Gregory D.
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p. 1532 - 1536
(2007/10/03)
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- 2-(Anilinomethyl)imidazolines as α1 adrenergic receptor agonists: The discovery of α10 subtype selective 2′-alkylsulfonyl-substituted analogues
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A series of 2′-alkylthio-2-(anilinomethyl)imidazolines were prepared to examine the effect of the alkyl group size, sulfur oxidation state, and phenyl ring substitution on ligand binding and agonism of α-adrenergic receptor subtypes α1a, α1b, α1d, α2a, and α2c. Binding at all receptor subtypes decreased for compounds in the sulfone oxidation state as compared to their sulfide analogues. While sulfides were generally potent, nonselective agonists, sulfones exhibited α1a subtype selectivity in a cell-based functional assay. Sulfone (32) was 250-7000-fold selective for α1a vs all other subtypes.
- Hodson, Stephen J.,Bishop, Michael J.,Speake, Jason D.,Navas III, Frank,Garrison, Deanna T.,Bigham, Eric C.,Saussy Jr., David L.,Liacos, James A.,Irving, Paul E.,Jeffrey Gobel,Sherman, Bryan W.
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p. 2229 - 2239
(2007/10/03)
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- Process for the preparation of O-aminothiophenols
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Preparation and isolation in substance of ortho-aminothiphenols by the reduction of ortho-chloronitrobenzenes with hydrogensulfides or sulfides, subsequent neutralization in the presence of sulfites, hydrogensulfites or disulfites, separation and following purification of the crude products. The ortho-aminothiophenols are obtained in very good yields and with a high degree of purity. Oxydation to the disulfide compound is avoided by the processes of the invention.
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- Synthesis and pharmacologic properties of 2 chloro and 2 trifluoromethyl 5a,6,7,8,9,10,10a,11 octahydrobenzo[b]cyclohepta[e][1,4]thiazine derivatives. II
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Dialkylaminoalkyl derivatives of 2 chloro and 2 trifluoromethyl 5α,6,7,8,9,10,10α,11 octahydrobenzo [b]cyclohepta [e] [1,4]thiazine were synthesized and their activities on central nervous system, and in vitro on smooth muscle, were tested. They have little antiserotonin or antihistamine activity but their effects on the CNS are considerable.
- Cardellini,Claudi,Gulini,et al.
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p. 513 - 518
(2007/10/05)
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