Structural, conformational, biochemical, and pharmacological study of some amides derived from 3,7-dimethyl-3,7-diazabicyclo [3.3.1] nonan-9-amine as potential 5-HT3 receptor antagonists

Fernández, M. J.; Huertas, R.; Galvez, Enrique J.; Orjales, A.; Berisa, A.; Labeaga, Luis; Garcia, Albert; Uceda, G.; Server-Carrió, Juan; Martı́nez-Ripoll, M.

doi:10.1016/0022-2860(95)09026-6

Cited by 7 publications

(5 citation statements)

References 16 publications

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“…There are numerous X-ray studies of monoprotonated bispidine derivatives (141)(142)(143)(144). The N3 Á Á ÁN7 distances decrease to 2.66 Å , due to relief of the lonepair repulsion.…”

Section: -95mentioning

confidence: 99%

Bispidine Coordination Chemistry

Comba

Kerscher

Schiek

2007

Progress in Inorganic Chemistry

141

198

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“…There are numerous X-ray studies of monoprotonated bispidine derivatives (141)(142)(143)(144). The N3 Á Á ÁN7 distances decrease to 2.66 Å , due to relief of the lonepair repulsion.…”

Section: -95mentioning

confidence: 99%

Bispidine Coordination Chemistry

Comba

Kerscher

Schiek

2007

Progress in Inorganic Chemistry

141

198

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“…Moreover, in the case of 2,4-substituted bispidines, the substituents in positions 2 and 4 can be found in axial or equatorial positions, leading to three possible diastereoisomers per conformation (Scheme ). Derivatives in the cc conformation were found to display the best affinity for opioid and 5-HT3 receptors …”

Section: Introductionmentioning

confidence: 99%

“…Derivatives in the cc conformation were found to display the best affinity for opioid 8 and 5-HT3 receptors. 9 Moreover, the strong rigidity and preorganization of the cc conformers have promoted the use of 2,4-substituted bispidines for the synthesis of complexes with transition-metal ions, 10,11 such as V 4/5+ , 12 Fe 2+ , 13,14 Co 2+/3+ , 15 Cu 2+ , 16 and Ru 2+ . 17 Attention has been focused on their applications as models for a variety of metalloenzymes and in catalysis as well as, more recently, bifunctional chelates for Cu 2+ radioisotopes for positron emission tomography (PET).…”

Section: ■ Introductionmentioning

confidence: 99%

Substitution-Assisted Stereochemical Control of Bispidone-Based Ligands

Legdali¹,

Roux²,

Platas‐Iglesias

et al. 2012

J. Org. Chem.

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Three new bispidone derivatives substituted by methylenecarboxylic ethyl ester groups have been synthesized in high yields as potential ligands for (64)Cu complexation and PET imaging. Their solution and solid-state structures have been determined by (1)H NMR spectroscopy and X-ray crystallography. These studies reveal a strong rigidity of the bicycle, which adopts either a chair-chair or a boat-chair conformation depending on the substituents in the N3 and N7 positions. A methyl substituent at N3 stabilizes the chair-chair conformation, whereas ethylacetate or 2-pyridylmethyl groups induce a considerable stabilization of the boat-chair conformation. However, when introduced in the position N7, a 2-pyridylmethyl substituent stabilizes the chair-chair isomer. The relative energies of the isomers and the isomerization process have been modeled by density functional theory calculations on a series of six N-substituted bispidones, including those newly synthesized. The subtle influence of the substituents has been related not only to the effect of steric hindrance on the thermodynamic stability but also to the presence of weak H-bonding interactions involving hydrogen-bonding acceptors, such as pyridylmethyl or ethylacetate substituents, and donors, such as C(sp2)-H of the pyridyl rings or C(sp3)-H at various positions of the bispidone skeleton.

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“…Some bispidines have also shown an interaction with 5‐HT 3 receptors and have been studied for the prevention and treatment of nausea and vomiting associated with cancer chemotherapy [18] . Analogs of cytisine, instead, have been proved to bind nAChRs; beside smoking addiction, these receptors are involved in a variety of complex cognitive processes, such as learning and memory, and in many CNS disorders, for example, Alzheimer's and Parkinson's diseases, attention deficit hyperactivity disorder, depression, anxiety, and many more.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Natural Compounds Based on the [3,7]‐Diazabicyclo[3.3.1]nonane (Bispidine) Core

Sacchetti

Rossetti

2021

Eur J Org Chem

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The [3,7]‐diazabicyclo[3.3.1]nonane (bispidine) structure is found in several interesting naturally occurring alkaloids. The most representative components are the tetracyclic alkaloid (−)‐sparteine and the tricyclic (−)‐cytisine alkaloids. Their biological activities have been known for a long time. In the literature, different syntheses of both tetracyclic and tricyclic structures have been reported, especially in the last few years, when a number of new reports renewed the interest in these fascinating molecules. Bicyclic bispidine derivatives have been thoroughly investigated in recent times also for their applications as catalysts, metal chelating agents, and lately in coordination polymers chemistry. In this review, we describe the most relevant strategies for the synthesis of molecules based on the [3,7]‐diazabicyclo[3.3.1]nonane core, related to (−)‐sparteine and (−)‐cytisine alkaloids.

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Structural, conformational, biochemical, and pharmacological study of some amides derived from 3,7-dimethyl-3,7-diazabicyclo [3.3.1] nonan-9-amine as potential 5-HT3 receptor antagonists

Cited by 7 publications

References 16 publications

Bispidine Coordination Chemistry

Bispidine Coordination Chemistry

Substitution-Assisted Stereochemical Control of Bispidone-Based Ligands

Synthesis of Natural Compounds Based on the [3,7]‐Diazabicyclo[3.3.1]nonane (Bispidine) Core

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