8-(Phenylmethyl)-8-azabicyclo[3.2.1]octan-3-one Hydrochloride CAS 83393-23-1

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8-(Phenylmethyl)-8-azabicyclo[3.2.1]octan-3-one Hydrochloride is an organic compound, also known as PCC HCl, with the molecular formula C15H19NO.HCl. It is a white crystalline powder with the appearance of fine crystals and no odour. It generally exists in the form of a hygroscopic agent and has a distinct chloride smell. It is very soluble in water and methanol at room temperature, while it is less soluble in ethanol (anhydrous) and methyl chloride. Its solubility is directly proportional to the temperature, and the solubility increases with the increase of temperature. It is a relatively insensitive substance, and its chemical stability is not high. It should be noted that the substance should not be affected by factors such as high temperature, sparks and static electricity, otherwise it may cause an explosion. It is a very unparaelectric material with poor conductivity; its optical properties have not been studied.

8-(Phenylmethyl)-8-azabicyclo[3.2.1]octan-3-one Hydrochloride is a nitrogen-containing heterocyclic compound. It is also known as guinea saponin S. The chemical formula of this compound is C16H19NO.HCl. It can be used in a variety of medical and research fields.

Used as a local anesthetic

This compound belongs to heterocyclic compounds with specific chemical structures and functional groups, and can be used as a local anesthetic. It can effectively alleviate pain caused by surgery or other medical procedures. This local anesthetic has a rapid onset of action and is very useful in pain management. This local anesthetic can also provide sufficient anesthesia for minor surgeries.

Used for treating drug addiction

It can also be used to treat drug addiction. Research has shown that this compound is highly effective in alleviating withdrawal symptoms in drug users and helping them maintain abstinence. In this case, this compound is used as an important tool to prevent the recurrence of drug addiction poisoning. It usually requires interventions targeting the mechanisms of action of addictive substances and the neurobiological changes during the addiction process. This includes reducing cravings for addictive substances, alleviating withdrawal symptoms, and restoring brain function.

Used for treating mental illnesses

The treatment of psychiatric disorders typically requires interventions targeting specific neurotransmitter systems or receptors to regulate brain function and emotional states. Common mental illnesses include depression, anxiety, schizophrenia, etc., which are associated with abnormalities in various neurotransmitters such as serotonin, dopamine, norepinephrine, etc.

Used in the field of pharmaceutical research

As a chemical reagent, it is also widely used in the field of drug research. It can be used to study the chemical structure of natural medicines, chemically synthesized medicines, and new drugs extracted from plants. Due to its interaction with the nervous system, this compound can also be used to study disciplines such as neuroscience and behavior.

It can also serve as a chiral source for synthesizing new drugs with specific chiral structures, thereby improving drug efficacy and reducing side effects. This compound can also be used in combination with other drugs to enhance drug efficacy or reduce side effects. For example, it can be used as an adjuvant drug in combination with other main drugs to improve overall treatment efficacy.

Used for on-site toxicology research

It can also be used in on-site toxicology research. Routine toxicology experiments can be slow, iterative tests of the toxicity of chemicals, which takes a lot of time and research dollars. In contrast, the use of on-site toxicology testing allows for faster and more precise detection of toxicity in chemicals so that toxic substances can be removed from use more quickly reducing any potential problems risks of.In summary, It is a compound widely used in many fields such as medicine, chemical research and toxicology. It will continue to play a role in future medical and research activities.

8-(Phenylmethyl)-8-azabicyclo[3.2.1]octan-3-one Hydrochloride, also known as β-Phenyl-γ-octahydroisoquinoline hydrochloride, is a biologically active compound used in the field of medicine and organic synthesis Has important application value. The compound can be synthesized by various methods, among which the typical five-step method and the two-step method are included.

One, five steps:

The five-step method refers to first synthesizing 8-phenylmethyl-3-azabicyclo[3.3.1]nonane, and then obtaining the final product through redox, amidation, amidation and hydrochloride reactions. Concrete reaction steps are as follows:

The advantage of the five-step method is that the reaction steps are relatively direct and the yield is relatively high, but some strong reaction conditions are required to allow the reaction to proceed, and the reaction route is relatively cumbersome.

Two, two-step method:

The two-step method refers to preparing 8-(Phenylmethyl)-8-azabicyclo[3.2.1]octan-3-one through borane reduction reaction with phenylacetone and tetrahydropyridine, and then reacting with hydrochloric acid to generate the final product. Concrete reaction steps are as follows:

Compared with the five-step method, the advantage of the two-step method is that the reaction conditions are relatively mild and the operation is relatively simple, but at the same time, the yield is low, and certain operations and optimization of the reaction conditions are required to achieve a good enough yield.

In general, for the synthesis method of 8-(Phenylmethyl)-8-azabicyclo[3.2.1]octan-3-one Hydrochloride, it needs to be selected according to actual needs and reaction conditions. A relatively complete synthesis route can improve the yield and synthesis Efficiency, leading to further development in the fields of medicine and chemistry.

8-Benzyl-8-azabicyclo[3.2.1]octan-3-one hydrochloride (hereinafter referred to as "the compound") has a core structure of 4-oxabicyclo[3.2.1]octane-3-one, with the 8th position being substituted by a phenylmethyl group. This structure endows it with a unique rigid framework and biological activity, but it may also lead to the following structural abnormalities:

Double-ring tension and stability

The rigidity of the nitrogen-containing double-ring [3.2.1] octane skeleton may lead to the concentration of ring tension, especially at the bridgehead carbons (C3 and C8) and near the nitrogen atom. This tension may affect the thermodynamic stability of the molecule, making it prone to ring cracking or rearrangement reactions under high temperatures or extreme pH conditions.

Spatial steric hindrance of benzyl substituents

Although the introduction of benzyl groups enhances the penetration of the biological membrane, the large volume of the benzene ring may restrict the conformation of the double-ring skeleton. For example, the π-π interaction or spatial conflict between the benzene ring and the double-ring may cause the molecule to adopt an unfavorable conformation, thereby affecting its binding efficiency to the target.

Chiral centers and enantiomeric differences

If a molecule contains a chiral center (such as C8 or the α carbon of the benzyl group), different enantiomers may exhibit significantly different biological activities. For instance, one enantiomer may have analgesic effects, while the other may be inactive or cause side effects.

Conformational dynamics is an important field that studies the rate of molecular transitions between different conformations and their effects on function. For compounds, their conformational dynamics may affect biological activity through the following mechanisms:

Dynamic combination mode

 

Molecules in solution may exist in multiple conformational isomers, among which certain conformations may be more conducive to binding to the target (such as neurotransmitter receptors or enzymes). For example, the rotation of the benzyl group or the slight distortion of the bicyclic skeleton may change the charge distribution or hydrophobic regions of the molecule, thereby affecting its complementarity with the target.

Conformational entropy and binding free energy

 

The diversity of conformations may increase the binding entropy of the molecule and reduce its binding free energy with the target. However, excessive conformational flexibility may also lead to a decrease in binding affinity. Therefore, compounds need to strike a balance between conformational flexibility and stability to achieve optimal biological activity.

Time-resolved conformational changes

 

Through nuclear magnetic resonance (NMR) or molecular dynamics simulation (MD), it can be observed that compounds may undergo time-dependent conformational adjustments during the binding to the target. For example, at the initial binding, the molecule may adopt an open conformation, and then gradually transition to a tightly bound conformation through the rotation of the benzyl group or the distortion of the bicyclic structure.

For the structural abnormalities and conformational dynamics characteristics of compounds, the following strategies can be used to optimize their performance:

Structural modification to reduce ring tension

By introducing flexible chains (such as ether bonds or thioether bonds) or replacing the bridging atoms (such as replacing nitrogen with oxygen or sulfur), the tension of the bicyclic framework can be alleviated, improving the molecular stability.

Chiral control and enantiomer purification

By using chiral synthesis or resolution techniques to obtain a single enantiomer, the activity differences between enantiomers can be avoided, enhancing the safety and efficacy of the drug.

Conformational restriction design

Introducing groups that restrict the conformation (such as cyclopropane or double bonds) in the benzyl group or the bicyclic framework can fix the dominant conformation of the molecule, enhancing its binding ability to the target.

Dynamic conformation analysis for optimization guidance

Combining MD simulations and NMR experiments, the conformational dynamic characteristics of the compound can be clarified, thereby guiding structural optimization. For example, if it is found that the rotation of the benzyl group is the key factor limiting binding, substituents such as fluorine atoms can be introduced to restrict its movement.

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