Simple syntheses of the polyamine alkaloid tenuilobine and analogues using selectively N-tritylated polyamines and dicarboxylic acids as bridging elements

Vassis, Stratos; Govaris, Ioannis; Voyagi, Katerina; Mamos, Petros; Papaioannou, Dionissios

doi:10.1016/s0040-4039(02)00338-6

Cited by 9 publications

(4 citation statements)

References 25 publications

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“…154 Recently, the same group have used reduction of amides as a versatile way to prepare various N-alkylated spermidine derivatives in solution 155 and also linear as well as cyclic polyamines have been synthesized using selective N-tritylation of polyamines. 156,157 B. Structure-Activity Relationship Studies…”

Section: A Novel Synthetic Methodsmentioning

confidence: 99%

AMPA receptor ligands: Synthetic and pharmacological studies of polyamines and polyamine toxins

Strømgaard

Mellor

2004

Medicinal Research Reviews

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Alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) receptors (AMPAR), subtype of the ionotropic glutamate receptors (IGRs), mediate fast synaptic transmission in the central nervous system (CNS), and are involved in many neurological disorders, as well as being a key player in the formation of memory. Hence, ligands affecting AMPARs are highly important for the study of the structure and function of this receptor, and in this regard polyamine-based ligands, particularly polyamine toxins, are unique as they selectively block Ca2+ -permeable AMPARs. Indeed, endogenous intracellular polyamines are known to modulate the function of these receptors in vivo. In this study, recent developments in the medicinal chemistry of polyamine-based ligands are given, particularly focusing on the use of solid-phase synthesis (SPS) as a tool for the facile generation of libraries of polyamine toxin analogues. Moreover, the recent development of highly potent and very selective AMPAR ligands is described. Additionally, we provide a detailed account on the mechanism and site of action of AMPAR blockade by polyamine-based ligands, including examples of how these ligands are used as tools to study AMPAR, and a comparison with their action on other ionotropic receptors.

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Section: A Novel Synthetic Methodsmentioning

confidence: 99%

AMPA receptor ligands: Synthetic and pharmacological studies of polyamines and polyamine toxins

Strømgaard

Mellor

2004

Medicinal Research Reviews

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“…5b). The precursors to compounds 5 and 6 [42-44] and to the compound 7 [45] were obtained according to reported procedures.…”

Section: Methodsmentioning

confidence: 99%

Effect of polyamines and synthetic polyamine-analogues on the expression of antizyme (AtoC) and its regulatory genes

et al. 2007

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BackgroundIn bacteria, the biosynthesis of polyamines is modulated at the level of transcription as well as post-translationally. Antizyme (Az) has long been identified as a non-competitive protein inhibitor of polyamine biosynthesis in E. coli. Az was also revealed to be the product of the atoC gene. AtoC is the response regulator of the AtoS-AtoC two-component system and it functions as the positive transcriptional regulator of the atoDAEB operon genes, encoding enzymes involved in short chain fatty acid metabolism. The antizyme is referred to as AtoC/Az, to indicate its dual function as both a transcriptional and post-translational regulator.ResultsThe roles of polyamines on the transcription of atoS and atoC genes as well as that of atoDAEB(ato) operon were studied. Polyamine-mediated induction was tested both in atoSC positive and negative E. coli backgrounds by using β-galactosidase reporter constructs carrying the appropriate promoters patoDAEB, patoS, patoC. In addition, a selection of synthetic polyamine analogues have been synthesized and tested for their effectiveness in inducing the expression of atoC/Az, the product of which plays a pivotal role in the feedback inhibition of putrescine biosynthesis and the transcriptional regulation of the ato operon. The effects of these compounds were also determined on the ato operon expression. The polyamine analogues were also tested for their effect on the activity of ornithine decarboxylase (ODC), the key enzyme of polyamine biosynthesis and on the growth of polyamine-deficient E. coli.ConclusionPolyamines, which have been reported to induce the protein levels of AtoC/Az in E. coli, act at the transcriptional level, since they cause activation of the atoC transcription. In addition, a series of polyamine analogues were studied on the transcription of atoC gene and ODC activity.

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“…For this purpose, we chose as model compound the readily available N 1 ,N 8 -ditritylspermidine (17). 9 Indeed, this compound was readily converted into the corresponding thiourea derivative 18 in 90% yield and the thus-obtained Scheme 2 Synthesis of all three N-tetrazolated isomers of linear triamine spermidine.…”

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confidence: 99%

Efficient Syntheses of Polyamines Bearing 1H-Tetrazol-5-yl Units on Their Amino Functions

Athanassopoulos¹,

Garnelis²,

Magoulas³

et al. 2006

Synthesis

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Simple syntheses of the polyamine alkaloid tenuilobine and analogues using selectively N-tritylated polyamines and dicarboxylic acids as bridging elements

Cited by 9 publications

References 25 publications

AMPA receptor ligands: Synthetic and pharmacological studies of polyamines and polyamine toxins

AMPA receptor ligands: Synthetic and pharmacological studies of polyamines and polyamine toxins

Effect of polyamines and synthetic polyamine-analogues on the expression of antizyme (AtoC) and its regulatory genes

Efficient Syntheses of Polyamines Bearing 1H-Tetrazol-5-yl Units on Their Amino Functions

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