227940-71-8

Usage

Uses

Used in Chemical Synthesis:
7-BENZYL-3-BOC-3,7-DIAZABICYCLO[3.3.1]NONANE is used as a reactant for the preparation of chiral phosphoramidite ligands. These ligands are crucial in enantioselective conjugate addition reactions, which are essential for the synthesis of optically active compounds with specific stereochemistry. The application of 7-BENZYL-3-BOC-3,7-DIAZABICYCLO[3.3.1]NONANE in chemical synthesis allows for the creation of a wide range of chiral molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 7-BENZYL-3-BOC-3,7-DIAZABICYCLO[3.3.1]NONANE is used as a key intermediate in the synthesis of various chiral drugs and pharmaceutical compounds. The enantioselective conjugate addition reactions facilitated by the chiral phosphoramidite ligands derived from 7-BENZYL-3-BOC-3,7-DIAZABICYCLO[3.3.1]NONANE enable the production of drugs with improved efficacy and reduced side effects, as they can selectively target specific biological receptors.
Used in Research and Development:
7-BENZYL-3-BOC-3,7-DIAZABICYCLO[3.3.1]NONANE is also utilized in research and development for the exploration of new synthetic routes and the development of novel chiral catalysts. Its unique structural features make it an interesting candidate for studying the effects of stereochemistry on reaction outcomes and for designing new chiral catalysts with enhanced selectivity and reactivity.

InChI:InChI=1/C19H28N2O2/c1-19(2,3)23-18(22)21-13-16-9-17(14-21)12-20(11-16)10-15-7-5-4-6-8-15/h4-8,16-17H,9-14H2,1-3H3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 69407-32-5 3-benzyl-3,7-diaza-bicyclo[3,3,1]nonane 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 227940-70-7 7-benzyl-9-oxo-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester 

Downstream Products

• 454695-26-2 3-(tert-butyloxycarbonyl)-3-(toluene-p-sulfonyl)-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 

Relevant academic research and scientific papers

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.

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.

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.

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.

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.

NICOTINIC ACETYLCHOLINE RECEPTOR SUB-TYPE SELECTIVE AMIDES OF DIAZABICYCLOAL KANES

The present invention relates to compounds of the following formula (I) that bind to and modulate the activity of neuronal nicotinic acetylcholine receptors, to processes for preparing these compounds, to pharmaceutical compositions containing these compounds, and to methods of using these compounds for treating a wide variety of conditions and disorders, including those associated with dysfunction of the central nervous system (CNS).

HDAC INHIBITORS AND USES THEREOF

Inhibitors of histone deacetylase, including compounds having a diazabicyclo[2.2.1]heptan-2-yl moiety are described together with methods for treating various disorders with such compounds.