68295-48-7

Usage

Bicyclic nitrogen-containing compound

Pyrrolizine derivative

Tetrahydro derivative

Contains four hydrogen atoms attached to the carbon atoms in the bicyclic ring

Carbonitrile

Contains a nitrile functional group (-C≡N)

Uses

Intermediate in the synthesis of various organic compounds, potential applications in pharmaceutical and agricultural industries

Hazards

May pose hazards if not used and stored properly

Upstream product

• 40624-07-5 1,7-dichloro-4-heptanone 
• 151-50-8 potassium cyanide 
• 19355-69-2 2-amino-2-cyanopropane 
• 107825-25-2 (E)-4,4’,5,5’-tetrahydro-2’H,3H-[2,3’-bifuranylidene]-2’-one 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Downstream Products

• 78449-73-7 7a-aminomethylhexahydro-1H-pyrrolizine 
• 1378378-67-6 4-bromo-N-((hexahydro-1H-pyrrolizin-7a-yl)methyl)benzamide trifluoroacetate 
• 1240283-09-3 4-chloro-N-((hexahydro-1H-pyrrolizin-7a-yl)methyl)benzamide 
• 96055-80-0 N-(2,6-dimethylphenyl)-8-pyrrolizidinecarboxamide 
• 80842-83-7 N-(Tetrahydro-pyrrolizin-7a-ylmethyl)-benzamide; hydrochloride 
• 167889-22-7 5-ethylaminomethyl-1-azabicyclo[3.3.0]octane 
• 412283-63-7 hexahydro-1H-pyrrolizine-7α-carboxylic acid 
• 80843-04-5 5-(methylaminomethyl)-1-azabicyclo<3.3.0>octane 
• 159329-68-7 5-chloromethyl-1-azabicyclo<3.3.0>octane hydrochloride 

Relevant academic research and scientific papers

Antimalarial activity of novel pyrrolizidinyl derivatives of 4-aminoquinoline

Two pyrrolizidinylalkyl derivatives of 4-amino-7-chloroquinoline (MG2 and MG3) were prepared and tested in vitro against CQ-sensitive and CQ-resistant strains of Plasmodium falciparum and in vivo in a Plasmodium berghei mouse model of infection. Both compounds exhibited excellent activity in all tests and low toxicity against mammalian cells. Preliminary studies of the acute toxicity and of the metabolism of the most active compound MG3 indicate a promising profile as a new antimalarial drug candidate.

Pyrrolizidines for direct air capture and CO2 conversion

Greenhouse gases such as CO2 strongly contribute to the rising temperatures of our planet, but as long as our society is dependent on fossil fuels, this trend will even increase in the near future. Therefore, CO2 capture and subseque

BICYCLOAMINE-SUBSTITUTED-N-BENZENESULFONAMIDE COMPOUNDS WITH SELECTIVE ACTIVITY IN VOLTAGE-GATED SODIUM CHANNELS

Disclosed are compounds of Formula (A-a), or a salt thereof, Where "B1" and "R1" through "R5" are as defined herein, which compounds have properties for blocking Nav 1.7 ion channels found in peripheral and sympathetic neurons. Also described are pharmaceutical formulations comprising the compounds of Formula (A-a) or their salts, and methods of treating neuropathic pain disorders using the same.

BICYCLOAMINE-SUBSTITUTED-N-BENZENESULFONAMIDE COMPOUNDS WITH SELECTIVE ACTIVITY IN VOLTAGE-GATED SODIUM CHANNELS

Disclosed are compounds of Formula A-a, or a salt thereof: Where "B1" and "R1" through "R5" are as defined herein, which compounds have properties for blocking Nav 1.7 ion channels found in peripheral and sympathetic neurons. Also described are pharmaceutical formulations comprising the compounds of Formula A-a or their salts, and methods of treating neuropathic pain disorders using the same.

Synthesis and nicotinic receptor activity of chemical space analogues of N -(3 R)-1-azabicyclo[2.2.2]oct-3-yl-4-chlorobenzamide (PNU-282,987) and 1,4-diazabicyclo[3.2.2]nonane-4-carboxylic acid 4-bromophenyl ester (SSR180711)

The Chemical Universe Generated Databases up to 11 atoms of CNOF (GDB-11) and up to 13 atoms of CNOClS (GDB-13) were used to enumerate analogues of the diamine part of two known α7 nicotinic receptor agonists and construct libraries of virtual analogues of these drugs. The libraries were scored using structure-based (docking to the nicotine binding site of the acetylcholine binding protein 1uw6.pdb) or ligand-based (similarity to the parent drugs) methods, and the top-scoring virtual ligands were inspected for easily accessible synthetic targets. In total, 21 diamines were prepared and acylated with aromatic carboxylic or oxycarbonic acids to produce 85 analogues of the parent drugs. The compounds were profiled by electrophysiology in Xenopus oocytes expressing human nicotinic acetylcholine receptor (nAChR) subtypes α7, α3β2, α4β2, α3β4, or α4β4. Characterization of selected compounds revealed eight inhibitors of the α7 nicotinic receptor and three positive allosteric modulators of the α3β2 nAChR.

Synthesis of 1-azabicyclic systems by double cyclization

5-Cyano-1-azabicyclo[3.3.0]octane (1) was prepared in one step from 1,7-dichloro-4-heptanone (4) under mild conditions. The application of this method for the preparation of 5-cyano-4,6-dimethyl-1-azabicyclo [3.3.0] octane (11) gave two diastereomers in equilibrium. The NMR measurements of 11 and its reduced compound 15 showed that the major isomer is the cis-exo form, and the minor isomer is the trans form. Molecular orbital calculations indicated that the cis-exo form is more stable than the trans form, in agreement with the experimental results. Furthermore, 6-cyano-1-azabicyclo[4.3.0]nonane (17) and 1-azabicyclo[4.4.0]decane (19), both including a six-membered ring, were prepared from appropriate haloketones by using this double cyclization method.

Synthesis and muscarinic activity of a series of quinolines and naphthalenes with a 1-azabicyclo[3.3.0]octane moiety

In order to discover a medicine effective against Alzheimer's disease, we synthesized a series of quinoline derivatives having a characteristic 1- azabicyclo[3.3.0]octane amine ring, and performed pharmacological evaluation of them. Acetylcholine esterase inhibitory activities of these derivatives were unexpectedly weak. Tests for central nervous muscarinic cholinergic receptor binding affinity indicated that these compounds had higher affinities to muscarinic M1 receptors than to M2 receptors. A series of naphthalene derivatives substituted with the 1-azabicyclo[3.3.0]octane ring were also synthesized and muscarinic M1 and M2 receptor binding affinity determined. These compounds had much higher affinity for M1 receptors than the quinoline derivatives, and 1-[N-(1-azabicyclo[3.3.0]octan-5-yl)methyl-N- methylamino]-4-nitronaphthalene showed the highest affinity and selectivity. The ability of this compound to improve cognitive function was assessed using the passive avoidance test in scopolamine-induced mice.

The novel synthesis of 5-cyano-1-azabicyclo[3.3.0]octane

5-Cyano-1-azabicyclo[3.3.0]octane (1), which is a key intermediary material to some medicines, was prepared from 1,7-dichloroheptan-4-one (7) via only one step under mild conditions. The reaction mechanism is also discussed.

Antivirally active N-cycloalkyl alkanol compounds

The compounds are of the general formula or where R1 is -OH, amino or -SH, R2 is H, α- or β-naphthyl or optionally substituted phenyl, R3 is mono-, di- or tricycloalkyl of C6-16, optionally substituted, R4

1-azoniabicyclo[3.3.0]oct-1(5)-ene salt derivatives and process for the preparation of the same

There are described 1-azoniabicyclo[3.3.0]oct-1(5)-ene salt derivatives inclusive of 1-azonia-4,6-dimethylbicyclo[3.3.0]oct-1(5)-ene perchlorate, and a process for the preparation of the same. The derivatives can be prepared by heating dicyclopropylmethanimine salt derivative in a solvent, in the presence or absence of an ammonium salt. Each of the derivatives is employed as an intermediate for preparing various medicines and agricultural chemicals.