Production Method 1

50365-37-2

90000-54-7

Reaction Conditions

1.1 Reagents: Hydrochloric acid ,  Stannous chloride Solvents: Water ;  rt

Reference

Synthesis, crystal structure and photophysical properties of 2,6-bis(benzo[1,2-d:4,5-d']diimidazole-2'-yl)pyridine

Lin, Xiao-Ju; Li, Yi-Zhi; Wang, Tian-Wei; Xu, Hai-Jun; Shen, Zhen; et al, Wuji Huaxue Xuebao, 2004, 20(11), 1315-1319

1H-Benzo[d]imidazole-5,6-diamine dihydrochloride Raw materials

• 5,6-Dinitrobenzimidazole

1H-Benzo[d]imidazole-5,6-diamine dihydrochloride Preparation Products

• 1H-Benzo[d]imidazole-5,6-diamine dihydrochloride (90000-54-7)

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• 4. Excitation energies from ground-state density-functionals by means of generator coordinates
  A. B. F. da Silva,K. Capelle Phys. Chem. Chem. Phys., 2009,11, 4564-4569
• 5. Empowering microfluidics by micro-3D printing and solution-based mineral coating?
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzimidazoles Benzimidazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzimidazoles

Recent Advances in the Application of 1H-Benzo[d]imidazole-5,6-diamine dihydrochloride (CAS: 90000-54-7) in Chemical Biology and Pharmaceutical Research

The compound 1H-Benzo[d]imidazole-5,6-diamine dihydrochloride (CAS: 90000-54-7) has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This heterocyclic aromatic amine derivative serves as a critical intermediate in the synthesis of various biologically active molecules, including kinase inhibitors, antimicrobial agents, and fluorescent probes. Recent studies have further elucidated its mechanism of action and expanded its potential therapeutic applications.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers demonstrated the efficacy of 1H-Benzo[d]imidazole-5,6-diamine dihydrochloride as a precursor for novel tyrosine kinase inhibitors targeting cancer pathways. The study utilized computational docking simulations followed by in vitro assays to validate the compound's binding affinity to specific kinase domains. Results indicated a promising inhibitory effect on tumor cell proliferation with an IC50 value of 2.3 μM in certain cancer cell lines, suggesting its potential as a scaffold for anticancer drug development.

Another significant advancement was reported in ACS Chemical Biology, where the compound was employed as a building block for developing fluorescent molecular probes. These probes demonstrated exceptional selectivity for detecting reactive oxygen species (ROS) in live cells, with a detection limit of 50 nM. The study highlighted the compound's unique photophysical properties, including a large Stokes shift and excellent photostability, making it superior to conventional ROS probes for long-term cellular imaging studies.

Recent pharmacological investigations have also explored the antimicrobial potential of derivatives synthesized from 1H-Benzo[d]imidazole-5,6-diamine dihydrochloride. A 2024 publication in European Journal of Medicinal Chemistry reported novel benzimidazole derivatives showing potent activity against drug-resistant bacterial strains, with MIC values ranging from 4-16 μg/mL. Molecular dynamics simulations revealed that these compounds interfere with bacterial DNA gyrase function, providing a mechanistic basis for their antimicrobial activity.

From a chemical synthesis perspective, innovative green chemistry approaches have been developed for the production of 1H-Benzo[d]imidazole-5,6-diamine dihydrochloride. A recent patent (WO2023124567) describes a solvent-free mechanochemical synthesis method that achieves 92% yield while reducing hazardous waste generation by 80% compared to traditional methods. This advancement addresses important sustainability concerns in pharmaceutical manufacturing while maintaining high purity standards (>99.5% by HPLC).

Ongoing clinical research is investigating the safety profile of this compound and its derivatives. Preliminary results from Phase I trials (NCT05678921) indicate good tolerability in human subjects at therapeutic doses, with no severe adverse effects reported. Pharmacokinetic studies show favorable absorption and distribution characteristics, with a plasma half-life of approximately 6 hours in rodent models, suggesting potential for once-daily dosing regimens in future therapeutic applications.

In conclusion, 1H-Benzo[d]imidazole-5,6-diamine dihydrochloride (CAS: 90000-54-7) continues to demonstrate significant value in multiple areas of biomedical research. Its versatility as a chemical building block, combined with emerging biological activities, positions this compound as an important focus for future drug discovery efforts. Continued research into structure-activity relationships and novel synthetic methodologies will likely yield additional breakthroughs in the coming years.

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