Cytokinin activity of disubstituted aminopurines in Amaranthus

Garcı́a-Raso, Ángel; Cabot, Catalina; Fiol, Juan J.; Spíchal, Lukáš; Nisler, Jaroslav; Tasada, Andrés; Luna, Joana Maria; Albertí, Francisca M.; Sibole, John V.

doi:10.1016/j.jplph.2009.03.012

Cited by 13 publications

(10 citation statements)

References 26 publications

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“…Ligand L was prepared following a reported method as described elsewhere . Crystals suitable for X‐ray crystallography were obtained by recrystallization from EtOH.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis, X‐ray characterization and density functional theory studies of N⁶‐benzyl‐N⁶‐methyladenine–M(II) complexes (M = Zn, Cd): The prominent role of π–π, C–H···π and anion–π interactions

Pons

Ibáñez

Buades

et al. 2019

Applied Organom Chemis

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We report the synthesis and X-ray characterization of the N 6 -benzyl-N 6methyladenine ligand (L) and three metal complexes, namely [Zn(HL) Cl 3 ]·H 2 O (1), [Cd(HL) 2 Cl 4 ] (2) and [H 2 L] 2 [Cd 3 (μ-L) 2 (μ-Cl) 4 Cl 6 ]·3H 2 O (3). Complex 1 consists of the 7H-adenine tautomer protonated at N3 and coordinated to a tetrahedral Zn(II) metal centre through N9. The octahedral Cd(II) in complex 2 is N 9 -coordinated to two N 6 -benzyl-N 6 -methyladeninium ligands (7H-tautomer protonated at N3) that occupy apical positions and four chlorido ligands form the basal plane. Compound 3 corresponds to a trinuclear Cd(II) complex, where the central Cd atom is six-coordinated to two bridging μ-L and four bridging μ-Cl ligands. The other two Cd atoms are six-coordinated to three terminal chlorido ligands, to two bridging μ-Cl ligands and to the bridging μ-L through N3. Essentially, the coordination patterns, degree of protonation and tautomeric forms of the nucleobase dominate the solid-state architectures of 1-3. Additionally, the hydrogen-bonding interactions produced by the endocyclic N atoms and NH groups stabilize high-dimensional-order supramolecular assemblies. Moreover, energetically strong anion-π and lone pair (lp)-π interactions are important in constructing the final solid-state architectures in 1-3. We have studied the non-covalent interactions energetically using density functional theory calculations and rationalized the interactions using molecular electrostatic potential surfaces and Bader's theory of atoms in molecules. We have particularly analysed cooperative lp-π and anion-π interactions in 1 and π + -π + interactions in 3.

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“…Ligand L was prepared following a reported method as described elsewhere . Crystals suitable for X‐ray crystallography were obtained by recrystallization from EtOH.…”

Section: Methodsmentioning

confidence: 99%

“…N 6 ‐substituted adenines are particularly interesting substrates due to their possible cytokinin (CK) activity . Natural CKs are adenine molecules substituted with a side chain at the N 6 ‐position and are involved in many aspects of plant growth, leaf senescence and cell division .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X‐ray characterization and density functional theory studies of N⁶‐benzyl‐N⁶‐methyladenine–M(II) complexes (M = Zn, Cd): The prominent role of π–π, C–H···π and anion–π interactions

Pons

Ibáñez

Buades

et al. 2019

Applied Organom Chemis

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“…It has proved to be a very convenient method for testing series of compounds (see, for example ref. [49]). The cytokinin activity of HBAP, HCy5ade and HCy6ade ligands is shown in Fig.…”

Section: Cytokinin Activitymentioning

confidence: 99%

Structural insights on the molecular recognition patterns between N6-substituted adenines and N-(aryl-methyl)iminodiacetate copper(II) chelates

Domínguez‐Martín

Garcı́a-Raso

Cabot

et al. 2013

Journal of Inorganic Biochemistry

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“…[24,25] Natural cytokinins (CK) are modified adenine molecules with a side chain at the N 6 -position that are involved in most aspects of plant growth and development and exhibit interesting biological properties. [26,27] Moreover, CK-metal complexes (with Zn II , Cu II , Fe II , Pt II , among others) show significant cytotoxic activity.…”

Section: (Dmso-κs)hl] (M = Rumentioning

confidence: 99%

“…6 -Alkyladenines (AdeC x ) and Their Hydrochlorides H-(AdeC x )Cl: N 6 -alkyladenines (AdeC x ) were easily prepared in good yield by a procedure previously described from 6-chloropurine and the corresponding alkylamine under reflux in BuOH/Et 3 N. [23,24,47] Dissolution of all these compounds in HCl (2 m) yielded the corresponding hydrochloride salts. , 0.19 mmol), dissolved in distilled water or methanol (3 mL), was added, and the solution was kept at 40°C without stirring for 3-4 d (see below).…”

Section: Synthesis Of Nmentioning

confidence: 99%

New Chlorido(dimethyl sulfoxide)iridium(III) Complexes with N⁶‐Substituted Adenines – Kinetic N(7) versus Thermodynamic N(9) Coordinated Adenine Isomers

et al. 2010

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New chlorido(dimethyl sulfoxide)iridium(III) complexes with N 6 -substituted adenine derivatives: [Ir III Cl 4 (DMSO-κS){H-AdeC x -κN(7)}]·nH 2 O [x = 3, n = 3 for 1; x = 4, n = 0.5 and 3 for 2a and 2b, respectively; x = 5, n = 0 for 3; x = 10, n = 0.33 for 4] and [Ir III Cl 4 (DMSO-κS){H-AdeC x -κN(9)}] [x = 3 for 5; x = 4 for 6, x = 5 for 7; x = 10 for 8] have been synthesized and characterized by spectroscopic techniques and by singlecrystal X-ray diffraction studies (1, 2b and 5). In all cases, iridium shows octahedral geometry and is coordinated to four chlorido ligands and one S atom from dimethyl sulfoxide (DMSO-κS). The coordination sphere of the metal is com-

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Cytokinin activity of disubstituted aminopurines in Amaranthus

Cited by 13 publications

References 26 publications

Synthesis, X‐ray characterization and density functional theory studies of N⁶‐benzyl‐N⁶‐methyladenine–M(II) complexes (M = Zn, Cd): The prominent role of π–π, C–H···π and anion–π interactions

Synthesis, X‐ray characterization and density functional theory studies of N⁶‐benzyl‐N⁶‐methyladenine–M(II) complexes (M = Zn, Cd): The prominent role of π–π, C–H···π and anion–π interactions

Structural insights on the molecular recognition patterns between N6-substituted adenines and N-(aryl-methyl)iminodiacetate copper(II) chelates

New Chlorido(dimethyl sulfoxide)iridium(III) Complexes with N⁶‐Substituted Adenines – Kinetic N(7) versus Thermodynamic N(9) Coordinated Adenine Isomers

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Cytokinin activity of disubstituted aminopurines in Amaranthus

Cited by 13 publications

References 26 publications

Synthesis, X‐ray characterization and density functional theory studies of N6‐benzyl‐N6‐methyladenine–M(II) complexes (M = Zn, Cd): The prominent role of π–π, C–H···π and anion–π interactions

Synthesis, X‐ray characterization and density functional theory studies of N6‐benzyl‐N6‐methyladenine–M(II) complexes (M = Zn, Cd): The prominent role of π–π, C–H···π and anion–π interactions

Structural insights on the molecular recognition patterns between N6-substituted adenines and N-(aryl-methyl)iminodiacetate copper(II) chelates

New Chlorido(dimethyl sulfoxide)iridium(III) Complexes with N6‐Substituted Adenines – Kinetic N(7) versus Thermodynamic N(9) Coordinated Adenine Isomers

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Synthesis, X‐ray characterization and density functional theory studies of N⁶‐benzyl‐N⁶‐methyladenine–M(II) complexes (M = Zn, Cd): The prominent role of π–π, C–H···π and anion–π interactions

Synthesis, X‐ray characterization and density functional theory studies of N⁶‐benzyl‐N⁶‐methyladenine–M(II) complexes (M = Zn, Cd): The prominent role of π–π, C–H···π and anion–π interactions

New Chlorido(dimethyl sulfoxide)iridium(III) Complexes with N⁶‐Substituted Adenines – Kinetic N(7) versus Thermodynamic N(9) Coordinated Adenine Isomers