21945-38-0Relevant articles and documents
Configurational and constitutional information storage: Multiple dynamics in systems based on pyridyl and acyl hydrazones
Chaur, Manuel N.,Collado, Daniel,Lehn, Jean-Marie
, p. 248 - 258 (2011)
The C=N group of hydrazones can undergo E/Z isomerization both photochemically and thermally, allowing the generation of a closed process that can be tuned by either of these two physical stimuli. On the other hand, hydrazine-exchange reactions enable a constitutional change in a given hydrazone. The two classes of processes: 1) configurational (physically stimulated) and 2) constitutional (chemically stimulated) give access to short-term and long-term information storage, respectively. Such transformations are reported herein for two hydrazones (bis-pyridyl hydrazone and 2-pyridinecarboxaldehyde phenylhydrazone) that undergo a closed, chemically or physically driven process, and, in addition, can be locked or unlocked at will by metal-ion coordination or removal. These features also extend to acyl hydrazones derived from 2-pyridinecarboxaldehyde. Similarly to the terpydine-like hydrazones, such acyl hydrazones can undergo both constitutional and configurational changes, as well as metal-ion coordination. All these types of hydrazones represent dynamic systems capable of acting as multiple state molecular devices, in which the presence of coordination sites furthermore allows the metal ion-controlled locking and unlocking of the interconversion of the different states.
Detection of a Metallo-intermediate and Geometrical Isomerizations in an Oxidative Cyclisation of a Heterocyclic Hydrazone with Mercury(II) Acetate
Butler, Richard N.,Johnston, Sean M.
, p. 376 - 377 (1981)
Oxidative cyclisation of the E-isomer of 2-pyridylcarbaldehyde 2-pyridylhydrazone with mercury(II) acetate involved an amino-N-mercurio intermediate with a Z-structure and an E -> Z -> E series of isomerizations.
A light-induced reversible phase separation and its coupling to a dynamic library of imines
Vantomme, Ghislaine,Hafezi, Nema,Lehn, Jean-Marie
, p. 1475 - 1483 (2014/03/21)
Irradiation of a 3:2 acetonitrile-water solution of the bis-pyridyl hydrazone 1 and calcium chloride causes a photo-induced phase separation, due to an increase in free calcium cations as a consequence of the photo-conversion of 1 from its E form to the Z
Synthesis and evaluation of analgesic, antiinflammatory and antiplatelet properties of new 2-pyridylarylhydrazone derivatives
Todeschini, Adriane R.,De Miranda, Ana Luisa P.,Da Silva, Kelly Christine M.,Parrini, Sergio C.,Barreiro, Eliezer J.
, p. 189 - 199 (2007/10/03)
This work describes recent results from our research program aiming at the synthesis and pharmacological evaluation of new compounds acting as antiinflammatory, analgesic and platelet antiaggregatory. In this paper the synthesis and the pharmacological profile as analgesic, antiinflammatory and anti-platelet of new functionalized 2-pyridylarylhydrazone derivatives 5a-r are discussed. This class of N-heterocyclic derivatives represents a new series of prototype candidates with analgesic and antiinflammatory properties possessing also an important anti-aggregating activity. The pharmacological results herein disclosed suggest that the anti-inflammatory and analgesic activities of these new pyridynehydrazone derivatives observed in the carrageenan pleurisy model and acetic acid writhing test, respectively, is probably due to an interference on the arachidonic acid (AA) metabolism. The most important antiinflammatory derivative 2-(2-formylfurane)pyridylhydrazone 5p presented a 79% inhibition of pleurisy at a dose of 80.1 μmol/kg. We also described the results concerning the mechanism of action of this series of N-heterocyclic derivatives in platelet aggregation which suggest a Ca2+ participation, probably by a complexation scavenger mechanism. Compound 2-(2-formylfurane)pyridylhydrazone 5p was able to complex Ca2+ in in vitro experiments at 100 μM concentration, indicating that this series of compounds can act as Ca2+ scavenger depending on the nature of the aryl moiety present at the imine subunit.
Stereoisomerization in Heterocyclic Hydrazones Derived from 2-Acylpyridines and their Oxidative Cyclization with Mercury(II) Acetate and Lead Tetra-acetate to Fused 1,2,4-Triazoles and 1,2,3-Triazolium Systems
Butler, Richard N.,Johnston, Sean M.
, p. 2109 - 2116 (2007/10/02)
Hydrazones prepared by coupling 2-acylpyridines with arylhydrazines were isolated predominantly as E-isomers when the acyl substituent R was small (H or Me).When R was a phenyl group significant yields of Z-isomers, containing an intramolecular hydrogen b
