21198-79-8Relevant articles and documents
Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues
Filipovi?, Nenad R.,Elshaflu, Hana,Grubi?i?, Sonja,Jovanovi?, Ljiljana S.,Rodi?, Marko,Novakovi?, Irena,Male?evi?, Aleksandar,Djordjevi?, Ivana S.,Li, Haidong,?oji?, Ne?o,Marinkovi?, Aleksandar,Todorovi?, Tamara R.
, p. 2910 - 2924 (2017)
The first Co(iii) complexes with (1,3-selenazol-2-yl)hydrazones as an unexplored class of ligands were prepared and characterized by NMR spectroscopy and X-ray diffraction analysis. The novel ligands act as NNN tridentate chelators forming octahedral Co(iii) complexes. The impact of structural changes on ligands' periphery as well as that of isosteric replacement of sulphur with selenium on the electrochemical and electronic absorption features of complexes are explored. To support the experimental data, density functional theory (DFT) calculations were also conducted. Theoretical NMR chemical shifts, the relative energies and natural bond orbital (NBO) analysis are calculated within the DFT approach, while the singlet excited state energies and HOMO-LUMO energy gap were calculated with time-dependent density functional theory (TD-DFT). The electrophilic f- and nucleophilic f+ Fukui functions are well adapted to find the electrophile and nucleophile centres in the molecules. Both (1,3-selenazol-2-yl)- and (1,3-thiazol-2-yl)hydrazone Co(iii) complexes showed potent antimicrobial and antioxidant activity. A significant difference among them was a smaller cytotoxicity of selenium compounds.
The balance between hydrogen bonds, halogen bonds, and chalcogen bonds in the crystal structures of a series of 1,3,4-chalcogenadiazoles
Aaker?y, Christer B.,Averkiev, Boris B.,De Silva, Viraj,Sinha, Abhijeet S.
, (2021/07/25)
In order to explore how specific atom-to-atom replacements change the electrostatic potentials on 1,3,4-chalcogenadiazole derivatives, and to deliberately alter the balance between inter-molecular interactions, four target molecules were synthesized and characterized. DFT calculations indicated that the atom-to-atom substitution of Br with I, and S with Se enhanced the σ-hole potentials, thus increasing the structure directing ability of halogen bonds and chalcogen bonds as compared to intermolecular hydrogen bonding. The delicate balance between these intermolecular forces was further underlined by the formation of two polymorphs of 5-(4-iodophenyl)-1,3,4-thiadiazol-2-amine; Form I displayed all three interactions while Form II only showed hydrogen and chalcogen bonding. The results emphasize that the deliberate alterations of the electrostatic potential on polarizable atoms can cause specific and deliberate changes to the main synthons and subsequent assemblies in the structures of this family of compounds.
Macrocyclic glutaminase GLS1 inhibitor or pharmaceutically acceptable salt thereof and preparation method and application thereof
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Paragraph 0157; 0159-0161, (2020/08/02)
The invention relates to the field of biological medicine, in particular to a series of macrocyclic glutaminase inhibitors, a synthesis method and medical application thereof, and particularly relatesto prevention or treatment of glutaminase related diseases. Meanwhile, the inventor performs a series of in-vitro anti-tumor activity evaluation on the synthesized compounds, and particularly, most of the compounds have good inhibitory activity on cancer cells.
Novel 1,3,4-Selenadiazole-Containing Kidney-Type Glutaminase Inhibitors Showed Improved Cellular Uptake and Antitumor Activity
Chen, Zhao,Li, Di,Xu, Ning,Fang, Jinzhang,Yu, Yan,Hou, Wei,Ruan, Haoqiang,Zhu, Panpan,Ma, Renchao,Lu, Shiying,Cao, Danhui,Wu, Rui,Ni, Mowei,Zhang, Wei,Su, Weike,Ruan, Benfang Helen
supporting information, p. 589 - 603 (2019/01/10)
Kidney-type glutaminase [KGA/isoenzyme glutaminase C (GAC)] is becoming an important tumor metabolism target in cancer chemotherapy. Its allosteric inhibitor, CB839, showed early promise in cancer therapeutics but limited efficacy in in vivo cancer models. To improve the in vivo activity, we explored a bioisostere replacement of the sulfur atom in bis-2-(5-phenylacetamido-1,2,4-thiadiazol)ethyl sulfide and CB839 analogues with selenium using a novel synthesis of the selenadiazole moiety from carboxylic acids or nitriles. The resulting selenadiazole compounds showed enhanced KGA inhibition, more potent induction of reactive oxygen species, improved inhibition of cancer cells, and higher cellular and tumor accumulation than the corresponding sulfur-containing molecules. However, both CB839 and its selenium analogues show incomplete inhibition of the tested cancer cells, and a partial reduction in tumor size was observed in both the glutamine-dependent HCT116 and aggressive H22 liver cancer xenograft models. Despite this, tumor tissue damage and prolonged survival were observed in animals treated with the selenium analogue of CB839.
