4-Aminobenzamidine Dihydrochloride CAS 2498-50-2

4-Aminobenzamidine Dihydrochloride, also known as 4-AB dihydrochloride, is a chemical compound primarily used in biochemical research and as a diagnostic agent. This compound belongs to the category of benzamidines, characterized by the presence of a benzene ring attached to an amidine group. The addition of two hydrochloric acid molecules (dihydrochloride) renders it water-soluble and stable under a wide range of pH conditions.

In biochemical applications, it serves as a specific inhibitor for certain enzymes, particularly those belonging to the trypsin family of serine proteases. By binding to the active site of these enzymes, it effectively blocks their catalytic activity, making it a valuable tool in studying the functions and mechanisms of these enzymes in biological processes.

Moreover, due to its fluorescent properties, which can be employed as a fluorescent probe or stain in diagnostic procedures, particularly in histology and pathology. It allows for the visualization and detection of fibrin in blood clots and other related structures under a microscope, aiding in the diagnosis of various diseases and conditions.

4-aminobenzamidine dihydrochloride is a white to off white crystalline powder with a melting point above 300 ℃. This compound has demonstrated extensive application value in various fields such as medicine, biotechnology, chemical engineering, dyes, etc. due to its unique chemical structure and properties.

Pharmaceutical field: Core intermediates and active molecules

 

1. Intermediate for drug synthesis
It is an indispensable intermediate in the pharmaceutical industry, involved in the synthesis process of various drugs. The amino (- NH ₂) and amidine (- C (=NH) NH ₂) functional groups in its molecule have high reactivity and can be introduced into specific functional groups through substitution, condensation, cyclization, and other reactions to optimize the structure and properties of drug molecules. For example:
Development of anti-inflammatory drugs: By modifying their molecular structure, compounds with targeted anti-inflammatory cytokine activity can be synthesized to reduce the gastrointestinal side effects of traditional anti-inflammatory drugs.

 

Anti tumor drug design: As a precursor molecule, ligands that can specifically recognize tumor cell surface antigens can be constructed to achieve precise drug delivery.
Antibacterial drug improvement: By introducing halogen atoms or heterocyclic structures such as fluorine and chlorine, the penetration and killing ability of drugs against drug-resistant bacteria are enhanced.

 

2. Direct pharmacological activity
The compound itself has biological activity and can be directly developed as a drug candidate molecule:
Serine protease inhibitor: It is a competitive inhibitor of serine proteases (such as trypsin and thrombin), which blocks their catalytic function by occupying the active center of the enzyme. This characteristic makes it have potential application value in fields such as anticoagulation and anti fibrosis. For example, in the treatment of thrombotic diseases, inhibiting thrombin activity can prolong clotting time and prevent thrombus formation.

 

Anti inflammatory and immune regulation: Studies have shown that this compound can inhibit the activation of inflammatory signaling pathways (such as the NF - κ B pathway), reduce the release of inflammatory factors (such as TNF - α, IL-6), and alleviate inflammatory reactions. In addition, it can also regulate the function of immune cells, suppress excessive immune responses, and provide new strategies for the treatment of autoimmune diseases.
Antitumor effect: By inducing tumor cell apoptosis, inhibiting angiogenesis and other mechanisms, it exhibits anti-tumor potential. For example, it can downregulate the expression of anti apoptotic proteins (such as Bcl-2) and upregulate the activity of pro apoptotic proteins (such as Bax), triggering programmed cell death in tumor cells.

 

3. Drug analysis and quality control
As a fluorescent probe, it can be used to detect the active site of serine protease. After its amidine group binds to the serine residue in the enzyme active center, a fluorescent signal can be generated, and quantitative detection of enzyme activity can be achieved through fluorescence spectroscopy analysis. This characteristic is of great significance in drug screening, enzyme kinetics research, and drug quality control.

Biotechnology field: Biological separation and enzyme immobilization

 

1. Affinity adsorbent ligand
It can be used as the ligand of affinity adsorbent to combine with dextran gel, agarose gel and other matrices to prepare specific adsorption materials. This material achieves efficient separation and purification of target molecules through specific interactions (such as hydrogen bonding, ionic bonding, hydrophobic interactions) between ligands and target molecules (such as enzymes, antibodies, receptors). For example:

 

Enzyme purification: 4-aminobenzamidine dihydrochloride was coupled to the surface of agarose gel to prepare serine protease affinity column. When the enzyme containing mixture passes through the affinity column, the target enzyme is retained due to binding with ligands, while other impurities are eluted. Enzyme elution and collection can be achieved by changing the buffer conditions (such as pH and ionic strength).
Antibody isolation: By utilizing the specific binding of this ligand to the Fc segment of the antibody, monoclonal or polyclonal antibodies can be isolated and purified from serum or cell culture supernatant, providing key technical support for antibody drug production.

 

2. Enzyme immobilization carrier
Enzyme immobilization is an important means to improve enzyme stability, reusability, and operational continuity. 4-AB Dihydrochloride can be covalently or non covalently bound to enzyme molecules and immobilized on the surface or inside of a carrier. For example:

 

Covalent immobilization: Enzyme molecules are covalently attached to the carrier through condensation reactions between amino groups and carboxyl, epoxy, and other functional groups on the surface of the carrier. This method immobilizes enzymes with high stability, but may result in loss of enzyme activity due to severe reaction conditions.
Non covalent immobilization: Utilizing specific interactions between ligands and enzymes (such as biotin avidin systems) to achieve reversible immobilization of enzymes. This method is gentle in operation and has a high retention rate of enzyme activity, but the immobilization strength is relatively low.

Chemical industry: Catalysts and functional material precursors

 

1. Organic synthesis catalyst
The amidine group in this substance is alkaline and can serve as a catalyst or catalyst ligand in organic synthesis, participating in reactions such as condensation, cyclization, and oxidation. For example:

Condensation reaction catalysis: In the condensation reaction between aldehydes and amines, this compound can act as a base catalyst to promote the formation of imines. Its catalytic activity originates from the ability of the amidine group to capture protons, which can reduce the activation energy of the reaction and increase the reaction rate.

 

Cyclization reaction ligand: In metal catalyzed cyclization reactions, it can act as a ligand to coordinate with the metal center, regulate the electronic properties and spatial configuration of the metal, thereby affecting the selectivity and yield of the reaction. For example, in the Suzuki coupling reaction catalyzed by palladium, its coordination effect can promote the coupling of aryl halides with boronic esters, efficiently synthesizing aromatic compounds.

2. Functional material precursor
This compound can be used as a precursor molecule to prepare functional polymer materials through polymerization, cross-linking, and other reactions. For example:

 

Polyamidine polymer: 4-aminobenzamidine dihydrochloride can be prepared by condensation reaction using this substance as a monomer. This type of polymer has excellent thermal stability, chemical stability, and mechanical properties, and can be used to prepare high-performance fibers, membrane materials, and adsorbents.
Crosslinking agent: The amino and amidine groups in its molecules can undergo cross-linking reactions with compounds containing carboxyl, epoxy, and other functional groups, forming a three-dimensional network structure. The crosslinking agent can be used to prepare functional materials such as hydrogels and elastomers, and is widely used in biomedicine, tissue engineering, flexible electronics and other fields.

• Add 4-nitroaniline and acetic anhydride to anhydrous ethanol under stirring and heat until refluxing for 10 hours.

CH₃OC(=O)Ph(H₂N)NH₂ + CH₃C(=O)O(C=O)OCH₃ → CH₃OC(=O)Ph(N=C(CO₂CH₃)) NH2 + CH3COOH

• Filter the reaction solution, wash the filter cake with 5% sodium hydroxide solution, wash with water until neutral, and dry to obtain 4-nitrobenzoyl chloride.

CH₃OC(=O)Ph(N=C(CO₂CH₃))NH₂ → CH₃OC(=O)Ph(N=C (CO₂CH₃)) + HCl

• Add 4-nitrobenzoyl chloride to concentrated ammonia water, stir for 5 hours, filter, wash the filter cake with dilute hydrochloric acid solution to neutral, and dry to obtain 4-aminobenzoyl chloride.

CH₃OC (=O) Ph (N=C (CO₂CH₃))+NH₃H₂O → CH₃OC (=O) Ph (N=C (CO₂CH₃))+NH₄Cl

• React 4-aminobenzoyl chloride with sulfoxide chloride in chloroform, add ice water to terminate the reaction, and separate the solution to obtain 4-chloroaminobenzoyl chloride.

CH₃OC(=O)Ph(N=C(CO₂CH₃)) + SOCl₂ → CH₃OC(=O)Ph(N=C (CO₂CH₃)) + SO₂Cl₂ + HCl

• React 4-chloroaminobenzoyl chloride with sodium bicarbonate in dimethylformamide, add water to terminate the reaction, separate the solution, and adjust it to neutral with a dilute hydrochloric acid solution to obtain 4-aminobenzidine dihydrochloride dihydrochloride.

CH₃OC(=O)Ph(N=C(CO₂CH₃)) + NaHCO₃ → HCl + Ph(C=C(CO₂H)) + NaCl + CO₂H + HCOONa → HCl + Ph(C=C(CO₂H)) + NaCl + COONa + HCOOH → HCl + Ph(C=C(CO₂H)) + NaCl + COOH + HCOONa

• Add 4-nitroaniline and acetic anhydride to anhydrous ethanol under stirring and heat until refluxing for 10 hours.

CH₃OC (=O)Ph(H₂N)NH₂ + CH₃C(=O)O(C=O)OCH₃ → CH₃OC (=O)Ph(N=C(CO₂CH₃))NH₂ + CH₃COOH

• Filter the reaction solution, wash the filter cake with 5% sodium hydroxide solution, wash with water until neutral, and dry to obtain 4-nitrobenzoyl chloride.

CH₃OC(=O)Ph(N=C(CO₂CH₃))NH₂ → CH₃OC(=O)Ph(N=C(CO₂CH₃)) + HCl

• Add 4-nitrobenzoyl chloride to concentrated ammonia water, stir for 5 hours, filter, wash the filter cake with dilute hydrochloric acid solution to neutral, and dry to obtain 4-aminobenzoyl chloride.

CH₃OC (=O) Ph (N=C (CO₂CH₃))+NH₃H₂O → CH₃OC (=O) Ph (N=C (CO₂CH₃))+NH4Cl

• React 4-aminobenzoyl chloride and triethyl phosphite in dimethylformamide, add water to terminate the reaction, separate the solution, and adjust it to neutral with a dilute hydrochloric acid solution to obtain 4-aminophenylhydrazine triethyl ester.

CH₃OC (=O) Ph (N=C (CO₂CH₃))+(C₂H₅O) ₃PO → CH₃OC(=O)Ph(N=C(CO₂CH₃)) + (C₂H₅O)₂P(OH)OCH₃ → HCl + Ph (C=C(CO₂H)) + (C₂H₅O)₂P(OH)OCH₃ → HCl + Ph(C=C (CO2_H)) + (C₂H₅O)₂P(OH) OH

• React 4-aminophenylhydrazine triethyl ester with sodium nitrite in a sodium acetate solution, add water to terminate the reaction, separate the solution, and adjust it to neutral with a dilute hydrochloric acid solution to obtain 4-nitrophenylhydrazine triethyl ester.
• 4-AB Dihydrochloride with iron powder in ethyl acetate, heat and reflux for 30 minutes, and filter to obtain 4-aminobenzidine dihydrochloride.

The future research directions for 4-AB Dihydrochloride are diverse and promising, given its established roles in various biochemical and pharmacological applications. One primary area of focus will be exploring its potential as a scaffold for developing novel inhibitors targeting key enzymes involved in disease pathways. Researchers aim to refine its structure to enhance affinity and specificity for these enzymes, particularly those implicated in cancer, inflammatory disorders, and neurological conditions.

Another significant direction involves investigating the therapeutic efficacy of 4-AB Dihydrochloride in preclinical models. This will involve detailed pharmacokinetic and pharmacodynamic studies to understand its absorption, distribution, metabolism, excretion, and toxicity profiles, paving the way for potential clinical trials.

Moreover, studies into the synergistic effects of 4-AB Dihydrochloride with other therapeutic agents are anticipated. Combination therapies could offer enhanced therapeutic outcomes by targeting multiple disease mechanisms simultaneously.

Additionally, exploring the molecular mechanisms underlying its biological activities will deepen our understanding of its mode of action. This includes studying its interactions with cellular proteins and signaling pathways, which could lead to the discovery of new biomarkers and drug targets.

Finally, efforts will also be directed towards optimizing the synthesis and purification processes of 4-AB Dihydrochloride to ensure cost-effectiveness and scalability, facilitating its translation from the lab to the clinic. These multifaceted research endeavors hold the promise of unlocking new therapeutic potentials for 4-aminobenzamidine dihydrochloride in addressing unmet medical needs.

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