383902-28-1

Basic information

• Product Name: 4-bromo-2-{[(1-methyl-1H-benzimidazol-2-yl)amino]methyl}phenol
• Synonyms: 4-Bromo-2-{[(1-methyl-1H-benzimidazol-2-yl)amino]methyl}phenol; Phenol, 4-bromo-2-[[(1-methyl-1H-benzimidazol-2-yl)amino]methyl]-
• CAS NO: 383902-28-1
• Molecular Formula: C₁₅H₁₄BrN₃O
• Molecular Weight: 332.1952
• Mol File: 383902-28-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 518.5°C at 760 mmHg
• Flash Point: 267.4°C
• Density: 1.52g/cm³
• Vapor Pressure: 2.28E-11mmHg at 25°C
• Refractive Index: 1.68
• CAS DataBase Reference: 4-bromo-2-{[(1-methyl-1H-benzimidazol-2-yl)amino]methyl}phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-2-{[(1-methyl-1H-benzimidazol-2-yl)amino]methyl}phenol(383902-28-1)
• EPA Substance Registry System: 4-bromo-2-{[(1-methyl-1H-benzimidazol-2-yl)amino]methyl}phenol(383902-28-1)

Safety Data

• Hazardous Substances Data: 383902-28-1(Hazardous Substances Data)

Upstream product

• 1622-57-7 2-Amino-1-methylbenzimidazole 
• 1761-61-1 5-bromosalicyclaldehyde 

Relevant articles and documents

In vitro activity of new N-benzyl-1H-benzimidazol-2-amine derivatives against cutaneous, mucocutaneous and visceral Leishmania species

The identification of specific therapeutic targets and the development of new drugs against leishmaniasis are urgently needed, since chemotherapy currently available for its treatment has several problems including many adverse side effects. In an effort to develop new antileishmanial drugs, in the present study a series of 28 N-benzyl-1H-benzimidazol-2-amine derivatives was synthesized and evaluated in vitro against Leishmania mexicana promastigotes. Compounds 7 and 8 with the highest antileishmanial activity (micromolar) and lower cytotoxicity than miltefosine and amphotericin B were selected to evaluate their activity against L. braziliensis 9and L. donovani, species causative of mucocutaneous and visceral leishmaniasis, respectively. Compound 7 showed significantly higher activity against L. braziliensis promastigotes than compound 8 and slightly lower than miltefosine. Compounds 7 and 8 had IC50 values in the micromolar range against the amastigote of L. mexicana and L. braziliensis. However, both compounds did not show better activity against L. donovani than miltefosine. Compound 8 showed the highest SI against both parasite stages of L. mexicana. In addition, compound 8 inhibited 68.27% the activity of recombinant L. mexicana arginase (LmARG), a therapeutic target for the treatment of leishmaniasis. Docking studies were also performed in order to establish the possible mechanism of action by which this compound exerts its inhibitory effect. Compound 8 shows promising potential for the development of more potent antileishmanial benzimidazole derivatives.