60553-32-4

Usage

Structure

A derivative of pyridine with a tetrahydropyridine ring, a methyl group, and a 1,3-dioxolane ring

Organic synthesis

Used as a building block for more complex molecules

Pharmaceutical research

Potential use in the development of new drugs or as a research tool for studying the biological activity of pyridine derivatives

Agrochemicals

May have uses in the field of agrochemicals

Precursor

Used as a precursor in the production of other chemicals

Tetrahydropyridine ring

A six-membered nitrogen-containing ring with four carbon atoms and two nitrogen atoms, all in a saturated state

Methyl group

A single carbon atom bonded to three hydrogen atoms (-CH3)

1,3-Dioxolane ring

A four-membered ring containing two oxygen atoms and two carbon atoms

Reactivity

May undergo various chemical reactions due to the presence of the tetrahydropyridine and 1,3-dioxolane rings

Solubility

Likely soluble in organic solvents such as ethanol, methanol, or acetone

Boiling point

Not provided, but expected to be relatively high due to the molecular size and complexity

Melting point

Not provided, but expected to be relatively low due to the presence of the 1,3-dioxolane ring

Density

Not provided, but expected to be influenced by the molecular structure and size

Appearance

Not provided, but likely a colorless to light-colored solid or liquid depending on the temperature and purity

Toxicity

Not provided, but should be handled with care due to its potential biological activity

Hazards

Not provided, but may pose risks such as flammability, irritancy, or reactivity with other chemicals

Storage

Should be stored in a cool, dry, and well-ventilated area, away from incompatible substances and sources of ignition

Synthesis

Not provided, but likely synthesized through various chemical reactions involving the formation of the tetrahydropyridine and 1,3-dioxolane rings, as well as the introduction of the methyl group.

InChI:InChI=1/C10H17NO2/c1-10(12-7-8-13-10)9-3-5-11(2)6-4-9/h3H,4-8H2,1-2H3

Upstream product

• 60553-33-5 4-(2-methyl-1,3-dioxolan-2-yl)pyridine 
• 1122-54-9 methyl (4-pyridyl) ketone 
• 60553-34-6 1-methyl-4-(2-methyl-1,3-dioxolan-2-yl)pyridinium iodide 

Downstream Products

• 100752-88-3 1-(1,2,3,6-Tetrahydro-1-methyl-4-pyridinyl)-ethanone 
• 517-81-7 20-epiuleine 
• 93841-61-3 2-<2-(methylamino)ethyl>-6-methoxy-1-methyl-9H-carbazole acetate salt 

Relevant academic research and scientific papers

Synthesis and in vivo and in vitro evaluation of isoarecolone and derivatives

The synthesis of the N-ethyl and N-phenylethyl derivatives of isoarecolone are described. These compounds were evaluated in vitro for their ability to displace [3H](±)epibatidine and/or [3H](-) nicotine from nicotinic receptors derived from rat cerebral cortex and their ability to inhibit acetylcholinesterase. The N-ethyl derivative and isoarecolone were evaluated in vivo for their antinociceptive, hypothermia and hypomotility activity in mice. The in vivo activity of isoareeolone was found to the reversible by mecamylamine, however the N-ethyl derivative was found to be insensitive to blockade by mecamylamine.

An Improved Synthesis of 1-(1,2,3,6-Tetrahydro-1-methyl-4- Pyridinyl)ethanone, Isoarecolone

A convenient synthesis of 1-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)ethanone, isoarecolone, starting with 4-acetylpyridine is presented. 4-Acetylpyridine was protected as the ketal followed by reaction with iodomethane to give the quaterary salt. The quaterary salt was reduced with sodium borohydride followed by deprotection to give isoarecolone in 80% overall yield.

Synthesis and cytotoxic activity of hydroxylated derivatives of olivacine in relation with their biotransformation

The chemical synthesis of 9-hydroxyolivacine and 7-hydroxyolivacine based on a biomimetic approach is described. These two hydroxylated derivatives have been found as main in vitro metabolites of olivacine after incubation with rat hepatic microsomes. The pretreatment of animals with benzo[a]pyrene caused a large increase in both microsomal hydroxylations, whereas the pretreatment with phenobarbital caused a weak increase, with a preservation of 9-hydroxylation/7-hydroxylation ratio >1 in both cases. The two hydroxyolivacines have been also found as principal in vivo metabolites of olivacine in rat bile as glucuronide and sulfate conjugates. The pretreatment of animals with benzo[a]pyrene reverses the 9-hydroxyolivacine/7-hydroxyolivacine ratio excretion in bile to a value that is 1H NMR spectra. Hydroxylation at position 9 increases the in vitro cytotoxicity against leukemia L1210 cells (ID50 = 0.06 μM compared to 2.03 μM for olivacine) and an opposite effect is observed for hydroxylation at position 7 (ID50 = 12.8 μM). On the other hand, hydroxylation at position 9 has no effect on the in vivo antitumor activity against L1210. This might be related to the oxidative and conjugative metabolic pathways that play an important role in antitumor activity and deactivation of olivacine and its hydroxy metabolites.