Synthesis and Cytokinin Activity of New Zeatin Derivatives

Haidoune, M.; Raynaud, Isabelle; O'Connor, Norval; Richomme, Pascal; Mornet, R.; Laloue, Michel

doi:10.1021/jf970752l

Cited by 17 publications

(3 citation statements)

References 26 publications

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“…Different authors explained the activity enhancing effect of halogen substitution differently, for example: the high electronegativity and small size of the halogens (Crocker et al 2007), the ability of organo-halogen compounds to form structural motifs via inter-molecular interactions (Emmerling et al 2007), decreased sensitivity of the compounds to CK oxidase (Clemenceau et al 1996;Haidoune et al 1998), and ability to form an hydrogen bond with electron donors of a CK receptor ) are proposed to be the contributing factors.…”

Section: The Effect Of An Halogen Substituentmentioning

confidence: 99%

Topolins: A panacea to plant tissue culture challenges?

Aremu

Bairu

Doležal

et al. 2011

Plant Cell Tiss Organ Cult

160

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Since the discovery of topolins as naturally occurring aromatic cytokinins (CKs), they have emerged as genuine alternatives to the long serving CKs such as benzyladenine, zeatin and kinetin in plant tissue culture (PTC). Globally, the past 15 years has witnessed a surge in the use of topolins and their derivatives in research laboratories. Topolins, especially the meta-topolin and its derivatives have been employed for culture initiation, protocol optimization and for counteracting various in vitro induced physiological disorders in many species. Evidence from various studies indicate the rising popularity and advantages (although not universal for all species) of topolins compared to other CKs. In this review, we assess the use of topolins in PTC with emphasis on their metabolism, structure-activity relations and effect on morphogenesis in vitro. In addition, the review provides a detailed list of species that have been used to study the effect of topolins in comparison with other CKs, the growth parameters affected and recommended concentrations are also provided.

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Section: The Effect Of An Halogen Substituentmentioning

confidence: 99%

Topolins: A panacea to plant tissue culture challenges?

Aremu

Bairu

Doležal

et al. 2011

Plant Cell Tiss Organ Cult

160

View full text Add to dashboard Cite

show abstract

“…Moreover, they are also significant building blocks in synthetic chemistry. [1][2][3] Therefore, developing concise and efficient strategies for the construction of versatile allylic amines has attracted great interest from academic and industrial communities. 4,5 Transition metal-catalyzed amination of allylic electrophiles, [6][7][8] rearrangement of allylic imidates, [9][10][11] and hydroamination of allenes [12][13][14] or dienes 15,16 have been well explored to efficiently provide substituted allylic amines, while prefunctionalized coupling partners are usually required through multistep synthesis.…”

Section: Introductionmentioning

confidence: 99%

Direct and modular access to allylic amines via nickel-catalyzed three-component coupling

Xu,

Chang,

Dong

et al. 2023

Org. Chem. Front.

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“…Moreover, they are also significant building blocks in synthetic chemistry. [1][2][3] Therefore, developing concise and efficient strategies for the construction of versatile allylic amines has attracted great interest from academic and industrial communities. 4,5 Transition metal-catalyzed amination of allylic electrophiles, [6][7][8] rearrangement of allylic imidates, [9][10][11] and hydroamination of allenes [12][13][14] or dienes [15][16][17] have been well explored to efficiently provide substituted allylic amines, while prefunctionalized coupling partners are usually required through multistep synthesis.…”

mentioning

confidence: 99%

Direct and Modular Access to Allylic Amines via Nickel-Catalyzed Three-Component Coupling

Xu,

Chang,

Dong

et al. 2023

Preprint

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The preparation of allylic amines by transition metal catalysis has played an important role in synthetic chemistry; however, the main employment of prefunctionalized coupling partners through multistep synthesis from available starting materials limits the scope and applications of allylic amines. In this context, we develop a Ni-catalyzed three-component coupling of commercially available aldehydes, amines and alkenes. Avoiding the isolation of imine inter-mediate, this direct and modular approach delivers a number of versatile allylic amines in high to excellent yields. Diverse aliphatic aldehydes are well tolerated in this reaction, largely reducing imine-enamine tautomerization and self-condensation, hydroamination and hydroacylation of alkenes, and alkenylation of aldehydes, showing high regio-, chemo- and stereoselectivity. The practical applicability of this method is also demonstrated by the late-stage diversi-fication of various natural products and drugs, as well as an array of product transformations. Preliminary asymmetric attempts provide enantio-enriched allylic amines in up to 48% ee by using chiral phosphoramidite ligand, offering the direction for further optimizations.

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Synthesis and Cytokinin Activity of New Zeatin Derivatives

Cited by 17 publications

References 26 publications

Topolins: A panacea to plant tissue culture challenges?

Topolins: A panacea to plant tissue culture challenges?

Direct and modular access to allylic amines via nickel-catalyzed three-component coupling

Direct and Modular Access to Allylic Amines via Nickel-Catalyzed Three-Component Coupling

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