38426-10-7Relevant articles and documents
Synthesis, biological evaluation, and structure-activity relationships of new tubulin polymerization inhibitors based on 5-amino-1,2,4-triazole scaffold
Yang, Fang,Chen, Lin,Lai, Jin-Mei,Jian, Xie-Er,Lv, Dong-Xin,Yuan, Li-Li,Liu, Yu-Xia,Liang, Feng-Ting,Zheng, Xiao-Lan,Li, Xiong-Li,Wei, Li-Yuan,You, Wen-Wei,Zhao, Pei-Liang
, (2021/03/06)
Based on our previous research, thirty new 5-amino-1H-1,2,4-triazoles possessing 3,4,5-trimethoxyphenyl moiety were synthesized, and evaluated for antiproliferative activities. Among them, compounds IIa, IIIh, and IIIm demonstrated significant antiproliferative activities against a panel of tumor cell lines, and the promising compound IIIm dose-dependently caused G2/M phase arrest in HeLa cells. Furthermore, analogue IIa exhibited the most potent tubulin polymerization inhibitory activity with an IC50 value of 9.4 μM, and molecular modeling studies revealed that IIa formed stable interactions in the colchicine-binding site of tubulin, suggesting that 5-amino-1H-1,2,4-triazole scaffold has potential for further investigation to develop novel tubulin polymerization inhibitors with anticancer activity.
Novel selective ido1 inhibitors with isoxazolo[5,4-d]pyrimidin-4(5h)-one scaffold
?vajger, Urban,Bratkovi?, Toma?,Dol?ak, Ana,Gobec, Stanislav,Mlinari?, Larisa,Ogorevc, Eva,Sova, Matej
, (2021/04/02)
Indoleamine 2,3-dioxygenase 1 (IDO1) is a promising target in immunomodulation of several pathological conditions, especially cancers. Here we present the synthesis of a series of IDO1 inhibitors with the novel isoxazolo[5,4-d]pyrimidin-4(5H)-one scaffold. A focused library was prepared using a 6-or 7-step synthetic procedure to allow a systematic investigation of the structure-activity relationships of the described scaffold. Chemistry-driven modifications lead us to the discovery of our best-in-class inhibitors possessing p-trifluoromethyl (23), p-cyclohexyl (32), or p-methoxycarbonyl (20, 39) substituted aniline moieties with IC50 values in the low micromolar range. In addition to hIDO1, compounds were tested for their inhibition of indoleamine 2,3-dioxygenase 2 and tryptophan dioxygenase, and found to be selective for hIDO1. Our results thus demon-strate a successful study on IDO1-selective isoxazolo[5,4-d]pyrimidin-4(5H)-one inhibitors, defining promising chemical probes with a novel scaffold for further development of potent small-molecule immunomodulators.
Stereochemistry of Hexacoordinated Zn(II), Cu(II), Ni(II), and Co(II) Complexes with Iminodiacetamide Ligands
Pantalon Juraj, Natalija,Mileti?, Goran I.,Peri?, Berislav,Popovi?, Zora,Smre?ki, Neven,Vianello, Robert,Kirin, Sre?ko I.
supporting information, p. 16445 - 16457 (2019/12/11)
Metal complexes of iminodiacetamide (imda) ligands and metal ions Zn(II), Cu(II), Ni(II), and Co(II) were prepared using eight imda ligands (L1-L8) substituted with groups of different steric and electronic properties on the central amine N atom (H atom,
Discovery and optimization of 3,4,5-trimethoxyphenyl substituted triazolylthioacetamides as potent tubulin polymerization inhibitors
Yang, Fang,He, Cai-Ping,Diao, Peng-Cheng,Hong, Kwon Ho,Rao, Jin-Jun,Zhao, Pei-Liang
, p. 22 - 27 (2018/11/23)
Based on our previous research, three series of new triazolylthioacetamides possessing 3,4,5-trimethoxyphenyl moiety were synthesized, and evaluated for antiproliferative activities and inhibition of tubulin polymerization. The most promising compounds 8b and 8j demonstrated more significant antiproliferative activities against MCF-7, HeLa, and HT-29 cell lines than our lead compound 6. Moreover, analogues 8f, 8j, and 8o manifested more potent antiproliferative activities against HeLa cell line with IC50 values of 0.04, 0.05 and 0.16 μM, respectively, representing 100-, 82-, and 25-fold improvements of the activity compared to compound 6. Furthermore, the representative compound, 8j, was found to induce significant cell cycle arrest at the G2/M phase in HeLa cell lines via a concentration-dependent manner. Meanwhile, compound 8b exhibited the most potent tubulin polymerization inhibitory activity with an IC50 value of 5.9 μM, which was almost as active as that of CA-4 (IC50 = 4.2 μM). Additionally, molecular docking analysis suggested that 8b formed stable interactions in the colchicine-binding site of tubulin.
DIHYDROINDOLINONE DERIVATIVES
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Page/Page column 18, (2011/04/18)
Disclosed are dihydroindolone compounds which can modulate the activity of protein tyrosine kinases, a method for preparing the same, and pharmaceutical compositions comprising the same. Also disclosed are use of such compounds and pharmaceutical compositions thereof in the treatment and/or prophylaxis of protein tyrosine kinase associated diseases in an organism, particularly in the treatment and/or prophylaxis of tumors and fibroblast proliferation associated diseases.
α-Phenylsulfonyl-N-arylacetamides (α-phenylsulfonylacetanilides): 1H, 13C and 15N NMR spectral characterization
Kolehmainen, Erkki,Janota, Henryk,Gawinecki, Ryszard,Laihia, Katri,Kauppinen, Reijo
, p. 384 - 385 (2007/10/03)
1H and 13C NMR chemical shift assignments for 11 α-phenylsulfonylacetanilides and 15N NMR chemical shifts for four representative congeners are reported. The 1H and 13C chemical shift assignments are based on DQF COSY and PFG 1H, 13C HMQC/HMBC experiments. The 15N NMR chemical shifts were determined by PFG 1H, 15N HMBC experiments. The correlation analyses with Hammett-type substituent constants gave a significant result with δ(C-1) in the aniline ring. Copyright
