227940-70-7

Usage

Uses

Used in Organic Synthesis:
7-BENZYL-3-BOC-3,7-DIAZABICYCLO[3.3.1]NONAN-9-ONE is used as a building block for the synthesis of complex organic molecules, leveraging its unique bicyclic structure to facilitate the creation of a variety of chemical compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 7-BENZYL-3-BOC-3,7-DIAZABICYCLO[3.3.1]NONAN-9-ONE is utilized as a valuable tool for drug development. Its distinctive structure aids in the exploration of new drug candidates and the study of chemical reactions that are crucial for medicinal chemistry advancements.
Used in Chemical Reaction Studies:
7-BENZYL-3-BOC-3,7-DIAZABICYCLO[3.3.1]NONAN-9-ONE serves as a substrate for investigating various chemical reactions, providing insights into reaction mechanisms and helping to optimize synthetic pathways in chemical research.

Upstream product

• 50-00-0 formaldehyd 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 64-19-7 acetic acid 
• 100-46-9 benzylamine 
• 885315-82-2 C₂₂H₂₆N₂O 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 227940-71-8 tert-Butyl 7-benzyl-3,7-diazabicyclo[3.3. 1]-nonane-3-carboxylate 
• 280-74-0 3,7-diazabicyclo{3.3.1}nonane 
• 58324-95-1 3-benzyl-7-methyl-3,7-diazabicyclo[3.3.1]nonane 
• 69407-32-5 3-benzyl-3,7-diaza-bicyclo[3,3,1]nonane 
• 1429773-09-0 (7-(5-chlorobenzo[d]oxazol-2-yl)-3,7-diazabicyclo[3.3.1]nonan-3-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone 
• 1429776-76-0 tert-butyl 7-(5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl)-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate 
• 313238-51-6 tert-butyl 7-benzyl-9-hydroxy-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate 

Relevant academic research and scientific papers

Modular synthesis of functionalized bis-bispidine tetraazamacrocycles

An effective synthesis is reported for the construction of highly rigid and preorganized bis-bispidine tetraazamacrocycles bearing either identical or different functionalities. Using essential building blocks derived from N-Boc-N'-allylbispidinone, the modular approach facilitates independent incorporation of the functional groups to the macrocyclic framework as well as selective derivatization of one functionality in the presence of another.

Synthesis of a bis-cationic α,α-disubstituted amino acid (9-amino-bispidine-9-carboxylic acid) and its effects on the conformational properties of peptides

A new bis-cationic cyclic amino acid, 9-amino-3,7-diazabicyclo[3.3.1]nonane-9-carboxylic acid (9-amino-bispidine-9-carboxylic acid; Abp), which is available for both solution phase and solid phase peptide synthesis, was designed and synthesized. Furthermore, a heterotripeptide Cbz-Leu-Abp-Ala-OMe (9) containing Abp was prepared, and its dominant conformation was analyzed by examining its nuclear magnetic resonance and infrared spectra and performing molecular modeling. The tripeptide 9 formed a β-turn structure as its preferred conformation in solution.

A tryptophan-containing fluorescent intramolecular complex as a designer peptidic proton sensor

Pyrene and tryptophan groups judiciously placed on a novel molecular scaffold, namely, bispidine exhibited fluorescence due to the formation of an unprecedented emissive intramolecular complex in polar solvents. Upon protonation, the emission signal from the pyrene unit enhances at the expense of the emission signal from the complex. The probe demonstrates good sensitivity, excellent selectivity, and adequate reversibility towards proton sensing. The present design based on the bispidine scaffold opens up newer opportunities for the design of novel bispidine-peptide sensors.

Methods for Treating Cognitive Disorders Using Inhibitors of Histone Deacetylase

This disclosure relates to compounds for the inhibition of histone deacetylase and treatment of a cognitive disorder or deficit. More particularly, the disclosure provides for compounds of formula (I) wherein Q, J, L and Z are as defined in the specification.

Unsymmetrical pincer CNN palladium complex of 7-ferrocenylmethyl-3-methyl-3,7-diazabicyclo[3.3.1]nonane

The new unsymmetrical ferrocenyl containing bispidine derivative 7 was synthesized as a ligand precursor in five steps starting from N-Boc-4-oxopiperidine. The corresponding palladium CNN pincer complex 8 was prepared by direct cyclopalladation of the ligand 7 with Li2PdCl4 in MeOH. The molecular structure of the obtained palladacycle was determined by multinuclear NMR (1H, 13C, 15N) and confirmed by X-ray diffraction analysis. The pincer complex 8 demonstrated high catalytic activity in some cross-coupling reactions of aryl halides with phenylboronic acid, norbornene and ethyl acrylate.

Modulation of prion polymerization and toxicity by rationally designed peptidomimetics

Misfolding and aggregation of cellular prion protein is associated with a large array of neurological disorders commonly called the transmissible spongiform encephalopathies. Designing inhibitors against prions has remained a daunting task owing to limited information about mechanism(s) of their pathogenic self-assembly. Here, we explore the antiprion properties of a combinatorial library of bispidine-based peptidomimetics (BPMs) that conjugate amino acids with hydrophobic and aromatic side chains. Keeping the bispidine unit unaltered, a series of structurally diverse BPMs were synthesized and tested for their prion-modulating properties. Administration of Leu- and Trp-BPMs delayed and completely inhibited the amyloidogenic conversion of human prion protein (HuPrP), respectively. We found that each BPM induced the HuPrP to form unique oligomeric nanostructures differing in their biophysical properties, cellular toxicities and response to conformation-specific antibodies. While Leu-BPMs were found to stabilize the oligomers, Trp-BPMs effected transient oligomerization, resulting in the formation of non-toxic, nonfibrillar aggregates. Yet another aromatic residue, Phe, however, accelerated the aggregation process in HuPrP. Molecular insights obtained through MD (molecular dynamics) simulations suggested that each BPM differently engages a conserved Tyr 169 residue at the α2-β2 loop of HuPrP and affects the stability of α2 and α3 helices. Our results demonstrate that this new class of molecules having chemical scaffolds conjugating hydrophobic/aromatic residues could effectively modulate prion aggregation and toxicity.

Cyclopalladate complex of 3-benzyl-7-methyl-3,7-diazabicyclo[3.3.1]nonane

A new (C,N,N)-pincer cyclopalladate unsymmetrical complex of 3-benzyl-7-methyl-3,7-diazabicyclo[3.3.1]nonane (3-benzyl-7-methylbispidine) was synthesized and characterized. Catalytic performance of this complex was examined in the Heck and Suzuki reactions and in the norbornene hydroarylation.

3,7-DIAZABICYCLO[3.3.1 ]NONANE CARBOXAMIDES AS ANTITHROMBOTIC AGENTS

The present invention relates to the 3,7-diazabicyclo[3.3.1]nonane carboxamides and process for preparation thereof. The present invention further relates to the compounds of general formula (1) possessing anti-thrombotic (anti-platelet) activities. The invention also relates to use of these moieties as inhibitors of collagen induced platelet adhesion and aggregation mediated through collagen receptors both in vitro and in vivo. Further, invention also relates these class of compounds exhibiting anti-platelet efficacy through dual mechanism inhibited both collagen as well as U46619 (thromboxane receptor agonist) induced platelet aggregation. General formula (1) Wherein, R' is; wherein R is selected from alkyl, acyl, tosyl, tert-butyloxycarbonyl, araalkyl or substituted araalkyl groups; R'' is selected preferably from halogen, cyano, lower alkyl, aryl, substituted aryl, and tosyl groups; R1 is selected from hydrogen and lower alkyl groups; R2 is selected from lower alkyl and aryl groups; R3 is selected from tert-butyloxycarbonyl and bezyloxycarbonyl groups; n = 0,1.

3,7-DIAZABICYCLO[3.3.1]NONANE AND 9-OXA-3,7-DIAZABICYCLO[3.3.1]NONANE DERIVATIVES

The present invention relates to 3,7-diazabicyclo[3.3.1]nonane and 9-oxa-3,7- diazabicyclo[3.3.1 ]nonane derivatives of formula (I) wherein Ar1 and Ar2 are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as orexin receptor antagonists.

Bispidine as a secondary structure nucleator in peptides

Here we describe bispidine as a scaffold for inducing open turn-like and beta sheet conformations on the attached peptides depending on the mode of attachment of peptides to the scaffold. Various bispidine-peptide conjugates were designed and synthesized to demonstrate the versatility of the scaffold.