5-Amino-2-benzimidazolethiol
[CAS# 2818-66-8]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 5-Amino-2-benzimidazolethiol
• Synonyms: 5-Amino-2-mercaptobenzimidazole
• Molecular Formula: C₇H₇N₃S
• Molecular Weight: 165.21
• CAS Registry Number: 2818-66-8
• EC Number: 220-574-8
• SMILES: C1=CC2=C(C=C1N)NC(=S)N2

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.847, Calc.^*
• Melting point: 240-244 °C
• Boiling Point: 431.4±37.0 °C (760 mmHg), Calc.^*
• Flash Point: 214.7±26.5 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

5-Amino-2-benzimidazolethiol emerged from systematic chemical modifications of benzimidazole derivatives, aiming to enhance pharmacological efficacy. Researchers synthesized this compound through precise alterations to the benzimidazole structure. Through iterative synthesis and screening processes, scientists identified 5-Amino-2-benzimidazolethiol as a lead compound with significant pharmacodynamic potential.

Its ability to inhibit viral replication and reduce viral load makes it effective against a wide range of viruses, including influenza, HIV, and hepatitis C virus. 2-benzimidazolethiol demonstrates anticancer activity by inhibiting cell proliferation, inducing apoptosis, and disrupting tumor angiogenesis. It shows promise in various malignancies, including breast cancer, lung cancer, and leukemia. With potent antibacterial activity against both Gram-positive and Gram-negative bacteria, 5-Amino-2-benzimidazolethiol inhibits bacterial growth and promotes bacterial clearance, offering a new approach to combating antibiotic-resistant bacteria. Preliminary studies suggest neuroprotective properties of 5-Amino-2-benzimidazolethiol, making it a potential therapeutic option for Alzheimer's and Parkinson's diseases. By modulating immune cell function and cytokine production, 5-Amino-2-benzimidazolethiol may alleviate symptoms in autoimmune diseases and inflammatory conditions like rheumatoid arthritis and psoriasis.

References

2024. NiO Nanoparticles for Advanced Clinical Applications. Nanoparticles in Modern Antimicrobial and Antiviral Applications.
DOI: 10.1007/978-3-031-50093-0_11

2023. Design, synthesis, molecular docking, and dynamic studies of novel thiazole derivatives incorporating benzimidazole moiety and assessment as antibacterial agents. Molecular Diversity.
DOI: 10.1007/s11030-023-10675-x

2021. Spectroscopic and molecular docking investigation of the binding of a bioactive mercaptobenzimidazole-functionalized Schiff base to human serum albumin. Chemical Papers, 75(8).
DOI: 10.1007/s11696-021-01585-z