3344-19-2Relevant articles and documents
Structure and spectroscopic characteristics of 4-tert-butylphenoxyacetylhydrazones of arylaldehydes
Podyachev,Litvinov,Shagidullin,Buzykin,Bauer,Osyanina,Avvakumova,Sudakova,Habicher,Konovalov
, p. 250 - 261 (2007)
By reaction of 4-tert-butylphenoxyacetylhydrazide with aromatic aldehydes and acetone a new series of 4-tert-butylphenoxyacetylhydrazones was synthesized. The structural peculiarities of the investigated molecules have been determined by means of X-ray analysis and IR spectroscopy. The diagnostically important IR spectral criteria required for the conformational analysis of acethylhydrazones have been considered. It was established that the 4-tert-butylphenoxyacetylhydrazide in condensed phase exists only as a ZN-C(O)-conformer. Its derivatives exist as EN-C(O) and ZN-C(O)-forms. As a rule, the prevalence of ZN-C(O)-form has been observed in CCl4 solutions. The structure of investigated compounds is also determined by a system of inter- and intramolecular hydrogen bonds. The energy of hydrogen bonds was estimated.
Synthesis and larvicidal activity of 1,3,4-oxadiazole derivatives containing a 3-chloropyridin-2-yl-1H-pyrazole scaffold
Wang, Yanyan,Lu, Xiumian,Shi, Jun,Xu, Jiahong,Wang, Fenghua,Yang, Xiao,Yu, Gang,Liu, Zhiqian,Li, Chuanhui,Dai, Ali,Zhao, Yonghui,Wu, Jian
, p. 611 - 623 (2018/01/17)
Abstract: A new series of 1,3,4-oxadiazole derivatives with a 3-chloropyridin-2-yl-1H-pyrazole moiety was designed, synthesized, and characterized. The results of bioassay against Helicoverpa armigera and Plutella xylostella indicated that some of the synthesized compounds showed remarkable larvicidal activity. In particular, the LC50 values of the most active compounds against P. xylostella were 46.5, 23.9, and 13.9?mg/dm3, and against Helicoverpa armigera were 88.3 and 69.5?mg/dm3, the latter being slightly better than commercial chlorpyrifos (LC50 103.77?mg/dm3). Preliminary SAR was also discussed. Graphical abstract: [Figure not available: see fulltext.].
Methyl 3-(3-(4-(2,4,4-Trimethylpentan-2-yl)phenoxy)-propanamido)benzoate as a Novel and Dual Malate Dehydrogenase (MDH) 1/2 Inhibitor Targeting Cancer Metabolism
Naik, Ravi,Ban, Hyun Seung,Jang, Kyusic,Kim, Inhyub,Xu, Xuezhen,Harmalkar, Dipesh,Shin, Seong-Ah,Kim, Minkyoung,Kim, Bo-Kyung,Park, Jaehyung,Ku, Bonsu,Oh, Sujin,Won, Misun,Lee, Kyeong
, p. 8631 - 8646 (2017/11/03)
Previously, we reported a hypoxia-inducible factor (HIF)-1 inhibitor LW6 containing an (aryloxyacetylamino)benzoic acid moiety inhibits malate dehydrogenase 2 (MDH2) using a chemical biology approach. Structure-activity relationship studies on a series of (aryloxyacetylamino)benzoic acids identified selective MDH1, MDH2, and dual inhibitors, which were used to study the relationship between MDH enzyme activity and HIF-1 inhibition. We hypothesized that dual inhibition of MDH1 and MDH2 might be a powerful approach to target cancer metabolism and selected methyl-3-(3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanamido)-benzoate (16c) as the most potent dual inhibitor. Kinetic studies revealed that compound 16c competitively inhibited MDH1 and MDH2. Compound 16c inhibited mitochondrial respiration and hypoxia-induced HIF-1α accumulation. In xenograft assays using HCT116 cells, compound 16c demonstrated significant in vivo antitumor efficacy. This finding provides concrete evidence that inhibition of both MDH1 and MDH2 may provide a valuable platform for developing novel therapeutics that target cancer metabolism and tumor growth.