60481-02-9Relevant academic research and scientific papers
Expedient discovery for novel antifungal leads targeting succinate dehydrogenase: Pyrazole-4-formylhydrazide derivatives bearing a diphenyl ether fragment
Chen, Min,Li, Guohua,Lu, Aimin,Qiu, Lingling,Wang, An,Wang, Xiaobin,Xue, Wei,Yang, Chunlong
, p. 14426 - 14437 (2020/12/22)
The pyrazole-4-carboxamide scaffold containing a flexible amide chain has emerged as the molecular skeleton of highly efficient agricultural fungicides targeting succinate dehydrogenase (SDH). Based on the above vital structural features of succinate dehydrogenase inhibitors (SDHI), three types of novel pyrazole-4-formylhydrazine derivatives bearing a diphenyl ether moiety were rationally conceived under the guidance of a virtual docking comparison between bioactive molecules and SDH. Consistent with the virtual verification results of a molecular docking comparison, the in vitro antifungal bioassays indicated that the skeleton structure of title compounds should be optimized as an N′-(4-phenoxyphenyl)-1H-pyrazole-4-carbohydrazide scaffold. Strikingly, N′-(4-phenoxyphenyl)-1H-pyrazole-4-carbohydrazide derivatives 11o against Rhizoctonia solani, 11m against Fusarium graminearum, and 11g against Botrytis cinerea exhibited excellent antifungal effects, with corresponding EC50 values of 0.14, 0.27, and 0.52 μg/mL, which were obviously better than carbendazim against R. solani (0.34 μg/mL) and F. graminearum (0.57 μg/mL) as well as penthiopyrad against B. cinerea (0.83 μg/mL). The relative studies on an in vivo bioassay against R. solani, bioactive evaluation against SDH, and molecular docking were further explored to ascertain the practical value of compound 11o as a potential fungicide targeting SDH. The present work provided a non-negligible complement for the structural optimization of antifungal leads targeting SDH.
Synthesis of Aryl Hydrazines via CuI/BMPO Catalyzed Cross-Coupling of Aryl Halides with Hydrazine Hydrate in Water
Kumar, Siripuram Vijay,Ma, Dawei
supporting information, p. 1003 - 1006 (2018/09/20)
The N,N’-bis(2,6-dimethylphenyl)oxalamide was discovered as a powerful ligand for Cu-catalyzed cross-coupling of aryl halides with hydrazine hydrate, leading to the formation of a variety of aryl hydrazines at 80 oC in water under the assistance of K3PO4 and 4 mol% cetyltrimethylammonium bromide from aryl bromides and aryl iodides. Good to excellent yields were observed in most cases.
A class of 1, 5 - diphenyl pyrazole - 3 - carboxylic acid compound and use thereof
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Paragraph 0065; 0067, (2017/10/31)
The invention provides a 1, 5-diphenyl pyrazol-3-carboxylic acid compound and application thereof. The compound has a structure as shown in general formula I, wherein R1 is selected from -H, halogen, saturated alkyl of C1-C6, or -X1-R4; R2 is selected from H, halogen, saturated alkyl of C1-C6, or -X2-R5; R3 is selected from H, -NH2 or -NH-CO-Ph-(o, m, p)R6; R6 is selected from H, halogen, saturated alkyl of C1-C6, or -O-R7; X1 and X2 are respectively selected from O or S independently; R4, R5 and R7 are respectively selected from H, saturated alkyl of C1-C6, benzyl or phenyl substituted by saturated alkyl of C1-C6 independently. The compound provided by the invention simulates BH3-only and p53TAD protein alpha-helix at the same time, competitively binds and antagonize Mcl-1, Bcl-2 and MDM2 protein, and specifically causes tumor cell apoptosis, thereby realizing application as an anticancer compound. (general formula I).
Bcl-2/MDM2 Dual Inhibitors Based on Universal Pyramid-Like α-Helical Mimetics
Wang, Ziqian,Song, Ting,Feng, Yingang,Guo, Zongwei,Fan, Yudan,Xu, Wenjie,Liu, Lu,Wang, Anhui,Zhang, Zhichao
supporting information, p. 3152 - 3162 (2016/05/19)
No α-helical mimetic that exhibits Bcl-2/MDM2 dual inhibition has been rationally designed due to the different helicities of the α-helixes at their binding interfaces. Herein, we extracted a one-turn α-helix-mimicking ortho-triarene unit from o-phenylene foldamers. Linking benzamide substrates with a rotatable C-N bond, we constructed a novel semirigid pyramid-like scaffold that could support its two-turn α-helix mimicry without aromatic stacking interactions and could adopt the different dihedral angles of the key residues of p53 and BH3-only peptides. On the basis of this universal scaffold, a series of substituent groups were installed to capture the key residues of both p53TAD and BimBH3 and balance the differences of the bulks between them. Identified by FP, ITC, and NMR spectroscopy, a compound 6e (zq-1) that directly binds to Mcl-1, Bcl-2, and MDM2 with balanced submicromolar affinities was obtained. Cell-based experiments demonstrated its antitumor ability through Bcl-2/MDM2 dual inhibition simultaneously.
Analysis of the discriminative inhibition of mammalian digestive lipases by 3-phenyl substituted 1,3,4-oxadiazol-2(3H)-ones
Point, Vanessa,Pavan Kumar,Marc, Sylvain,Delorme, Vincent,Parsiegla, Goetz,Amara, Sawsan,Carrière, Frédéric,Buono, Gérard,Fotiadu, Frédéric,Canaan, Stéphane,Leclaire, Julien,Cavalier, Jean-Fran?ois
, p. 452 - 463 (2013/02/23)
We report here the reactivity and selectivity of three 5-Methoxy-N-3-Phenyl substituted-1,3,4-Oxadiazol-2(3H)-ones (MPOX, as well as meta and para-PhenoxyPhenyl derivatives, i.e. MmPPOX and MpPPOX) with respect to the inhibition of mammalian digestive lip
