26496-36-6Relevant articles and documents
Novel chelators based on adamantane-derived semicarbazones and hydrazones that target multiple hallmarks of Alzheimer's disease
Palanimuthu, Duraippandi,Wu, Zhixuan,Jansson, Patric J.,Braidy, Nady,Bernhardt, Paul V.,Richardson, Des R.,Kalinowski, Danuta S.
, p. 7190 - 7205 (2018)
Alzheimer's disease (AD) is characterized by multiple pathological hallmarks, including β-amyloid aggregation, oxidative stress, and metal dys-homeostasis. In the absence of treatments addressing its multi-factorial pathology, we designed novel multi-functional adamantane-based semicarbazones and hydrazones (1-12) targeting AD hallmarks. Of these, 2-pyridinecarboxaldehyde (N-adamantan-1-yl)benzoyl-4-amidohydrazone (10) was identified as the lead compound, which demonstrated: (1) pronounced iron chelation efficacy; (2) attenuation of CuII-mediated β-amyloid aggregation; (3) low cytotoxicity; (4) inhibition of oxidative stress; and (5) favorable characteristics for effective blood-brain barrier permeation. Structure-activity relationships revealed that pyridine-derived hydrazones represent a promising pharmacophore for future design strategies due to their ability to bind critical FeII pools. Collectively, the unique multi-functional activity of these agents provides a novel therapeutic strategy for AD treatment.
Highly Regioselective Carbamoylation of Electron-Deficient Nitrogen Heteroarenes with Hydrazinecarboxamides
He, Zeng-Yang,Huang, Chao-Fan,Tian, Shi-Kai
supporting information, p. 4850 - 4853 (2017/09/23)
The use of hydrazinecarboxamides as a new class of carbamoylating agents has been established through the dehydrazinative Minisci reaction of electron-deficient nitrogen heteroarenes. A wide range of electron-deficient nitrogen heteroarenes, including isoquinoline, quinoline, pyridine, phenanthridine, quinoxaline, and phthalazine, underwent copper/acid-catalyzed oxidative carbamoylation with hydrazinecarboxamide hydrochlorides to afford structurally diverse nitrogen-heteroaryl carboxamides as single regioisomers in moderate to excellent yields. The functional group tolerance was substantially demonstrated in the direct carbamoylation of quinine obviating multistep sequences involving protecting groups and prefunctionalization of the heterocycle.
Adamantane derivatives, part III*: Synthesis of some aminoadamantanes as novel antitumor aqents
El-Sherbeny,Youssef,Mahran
, p. 195 - 209 (2007/10/03)
New series of 1-(1-adamantyl)semicarbazide 3a, 1-(1-adamantyl)-4-(4-substituted phenyl)semicarbazides 3b-e, 1-(1-adamantyl)-3-(substituted aminosulfonyl)ureas 5a-g, 1-(1-adamantyl)-4-(1-adamantylamino-methylene)-semicarbazide 7, 1-(1-adamantyl)-4-(1-adama
