4344-85-8

Usage

Uses

Used in Chemical Research:
2-Mercaptomethyl benzimidazole is used as a research compound for its antimicrobial, antifungal, and anticancer properties, contributing to the development of new pharmaceuticals and materials.
Used in Antimicrobial Applications:
2-Mercaptomethyl benzimidazole is used as an antimicrobial agent, leveraging its ability to inhibit the growth of microorganisms, which is beneficial in various industries such as healthcare and food preservation.
Used in Antifungal Applications:
2-Mercaptomethyl benzimidazole is used as an antifungal agent, helping to prevent the growth of fungi, which is particularly useful in agricultural and pharmaceutical applications.
Used in Anticancer Applications:
2-Mercaptomethyl benzimidazole is used as an anticancer agent, potentially contributing to the development of new cancer treatments by targeting cancer cells and inhibiting their growth.
Used in Corrosion Inhibition:
2-Mercaptomethyl benzimidazole is used as a corrosion inhibitor, taking advantage of its sulfur-containing structure to form a protective film on metal surfaces, thus preventing corrosion and extending the lifespan of metal components in various industries.
Used in Pharmaceutical Development:
2-Mercaptomethyl benzimidazole is used as a potential therapeutic agent in the development of new drugs, particularly in the areas of antimicrobial, antifungal, and anticancer treatments, due to its demonstrated biological activities.

InChI:InChI=1/C8H8N2S/c11-5-8-9-6-3-1-2-4-7(6)10-8/h1-4,11H,5H2,(H,9,10)

Upstream product

• 68-11-1 mercaptoacetic acid 
• 95-54-5 1,2-diamino-benzene 
• 39145-59-0 o-phenylenediamine hydrochloride 

Downstream Products

• 36000-20-1 2-(methoxymethyl)-1H-benzimidazole 
• 99069-37-1 (ethylthiomethyl)benzimidazole 
• 6017-11-4 [(1H-benzimidazol-2-ylmethyl)sulfanyl]acetic acid 
• 74460-38-1 3-(1H-Benzoimidazol-2-ylmethylsulfanyl)-1-cyclopropyl-3-phenyl-propan-1-one 
• 74460-40-5 3-(1H-Benzoimidazol-2-ylmethylsulfanyl)-1,3-diphenyl-propan-1-one 
• 56935-43-4 3-(1H-benzoimidazol-2-ylmethylsulfanyl)-1-phenyl-propan-1-one 
• 74460-39-2 2-[(1H-Benzoimidazol-2-ylmethylsulfanyl)-phenyl-methyl]-cyclohexanone 
• 74460-37-0 4-(1H-Benzoimidazol-2-ylmethylsulfanyl)-3,4-diphenyl-butan-2-one 
• 74460-35-8 4-(1H-Benzoimidazol-2-ylmethylsulfanyl)-4-phenyl-butan-2-one 
• 264923-85-5 3,4-dihydro-1H-[1,4]thiazino[4,3-a]benzimidazole 
• 397869-22-6 2-[(4-acetylphenylaminoacetyl)thiomethyl]benzimidazole 

Relevant academic research and scientific papers

The design and synthesis of potent benzimidazole derivatives via scaffold hybridization and evaluating their antiproliferative and proapoptotic activity against breast and lung cancer cell lines

One of the current approaches used in drug discovery and development is the synthesis of novel small compounds from existing structural motifs via molecular hybridization. In the current study, a new series of benzimidazo[1,5-a]imidazole, benzimidazo[1,2-c]thiazole, benzimidazotriazine, and benzimidazo[1,2-c]quinazoline scaffolds was synthesized via C-H cycloamination, using a metal-free synthetic pathway, as potent antiproliferative antiangiogenic molecules against breast (MCF-7) and lung (A549) cancer cell lines. The expansion of the benzimidazole scaffold with heterocyclic rings resulted in a tridentate cyclic system that occupied the ATP-binding site and neighboring hydrophobic pocket, eliciting promising affinity and selectivity toward VEGFR2 through extra H-bonding and completely occupying the entrance region. Molecular docking studies demonstrated that most of the designed compounds bind VEGFR-2 adopting a DFG-in conformation, where the benzimidazole scaffold occupied the hinge region, the central aromatic ring occupied hydrophobic region I adjacent to the hinge region, and the hydrogen bond donor/acceptor bound to the hydrogen-bond-rich region. In comparison to lenvatinib, which had a docking score of-12.47 kJ mol-1 and a Glide E-model value of-132.68 kcal mol-1, compound 17 had a decent docking score of-8.95 kJ mol-1 and a Glide E-model value of-92.17 kcal mol-1. The designed molecules exhibited promising in situ cytotoxic activities, with IC50 values ranging from 9.2 to 42.3 μM against MCF-7 and A549, comparable to 5-fluorouracil (which has IC50 values of 10.32 and 5.8 μM against MCF-7 and A549, respectively); they also showed selective in vitro inhibitory activity against VEGFR2 when compared with other designed kinases, with compound 17 showing an IC50 value (23 nM) as good as that of sorafenib (30 nM). Flow cytometry and cell cycle assays revealed that apoptotic cell death induction occurred in the A549 cell line through the activation of certain caspases and the tumor suppressor P53 and through repressing the generation of BAX and PUMA. Furthermore, the proposed compounds exhibited physicochemical and pharmacokinetics properties within the acceptable range for human usage, as anticipated by an in silico ADME study, making them lead molecules for developing new forms of medication.

Anti-cancer activity of two novel heterocyclic compounds through modulation of VEGFR and miR-122 in mice bearing Ehrlich ascites carcinoma

Metastasis in breast cancer is a leading cause of mortality among women in many countries. This study investigated the anti-cancer role of benzoimidazoquinazoline and benzimidazotriazin; two novel compounds that were designed, synthesized, structurally elucidated, and biologically evaluated as potent anti-angiogenic agents that act through inhibition of vascular endothelial growth factor receptor-2 (VEGFR2). Breast cancer was induced by inoculation of Ehrlich Ascites Carcinoma (EAC) cells. Seventy swiss albino mice were randomly divided into 7 groups, 10 animals each: (1) normal, (2) control EAC group, (3) cisplatin treated group, (4&5) benzoimidazoquinazoline treated (5 mg/kg and 10 mg/kg), (6&7) benzimidazotriazin treated (5 mg/kg and 10 mg/kg). The expression of miR-122 was assessed in the tumor tissue by quantitative PCR, and the VEGF level was determined in serum by ELISA. VEGFR2 and cluster of differentiation (CD)34 were assessed by immunohistochemistry. Serum ALT, AST, creatinine, and urea were measured. Treatment with benzoimidazoquinazoline and benzimidazotriazin decreased tumor weight and serum levels of VEGF, and down-regulated expression of VEGFR2 and CD34 in the tumor tissue. miR-122 was upregulated, particularly in the benzimidazotriazin (10 mg/kg) group. Relative to cisplatin, the novel compounds were less toxic to kidneys. Benzoimidazoquinazoline and benzimidazotriazin are promising anti-cancer agents that act through inhibition of angiogenesis and thus provide a new strategy for advancement of chemotherapy.

Mesoporous silica nanobeans dual-functionalized with AIEgens and leaning pillar[6]arene-based supramolecular switches for imaging and stimuli-responsive drug release

A bean-shaped and dual-functionalized organic-inorganic hybrid supramolecular system with a GSH-dependent turn-on fluorescence enhancement property and stimuli-responsive drug delivery function endowed with leaning towerarene-based switches has been const

Design, synthesis, characterization and antiproliferative activities of Ru(II) complexes of substituted benzimidazoles

Synthesis of [Ru(PPh3)2(BZM)2Cl2] (BZM= LS1, LS2, LS3, LS4 and LS5) where LS1 = (1H-benzo[d]imidazole-2-yl)methanethiol, LS2 = 2-(4-bromobutyl)-1H-benzo[d]imidazole, LS3 = 2-(4-nitrophenyl)-1H-benzo[d]imidazole, LS4 = 2-(4-chlorophenyl)-1H-benzo[d]imidazole and LS5= 4-(1H-benzo[d]imidazol-2-yl)aniline (BZM = benzimidazoles, PPh3 = triphenylphosphine) and metal complexes as MR, [Ru (PPh3)4Cl2], MLS1, MLS2, MLS3, MLS4 and MLS5 for use as potential anticancer compounds have been investigated. The complexes have been characterized by elemental analysis, IR, multinuclear NMR, UV-visible and ESI-MS spectroscopic techniques. The geometries of all complexes have been optimized by using density functional theory (DFT). The cytotoxicity effects of MR, MLS2 and LS1 were also investigated on Human cervical carcinoma cells (HeLa) by MTT assay, ROS generation and nuclear apoptosis assay. The percent cell viability assessed by MTT assay suggested that the synthesized MR, MLS2 and LS1 significantly reduce the viability of HeLa cells, in a dose-dependent manner. The inhibitory concentration (IC50) of MR, MLS2 and LS1 against HeLa cells was found 90.8, 81.8 and 115 μM, respectively. These compounds also induced the over production of intracellular reactive oxygen species (ROS) as well as the condensed and fragmented nucleus, which supports the molecular mechanism of cell death by apoptosis. The investigations suggested that the compounds MR, MLS2 and LS1 induce the cell death in HeLa cells through apoptotic pathway.

Synthesis and evaluation of selected benzimidazole derivatives as potential antimicrobial agents

A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial activity of the compounds depended on the substituents attached to the bicyclic heterocycle. In particular, some compounds displayed antibacterial activity against two methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentrations (MICs) comparable to the widely-used drug ciprofloxacin. The compounds have some common features; three possess 5-halo substituents; two are derivatives of (S)-2-ethanaminebenzimidazole; and the others are derivatives of one 2-(chloromethyl)-1Hbenzo[ d]imidazole and (1H-benzo[d]imidazol-2-yl)methanethiol. The results from the antifungal screening were also very interesting: 23 compounds exhibited potent fungicidal activity against the selected fungal strains. They displayed equivalent or greater potency in their MIC values than amphotericin B. The 5-halobenzimidazole derivatives could be considered promising broad-spectrum antimicrobial candidates that deserve further study for potential therapeutic applications.

Long-chain alkylthia-benzimidazoles as corrosion inhibitors for carbon steel in H 2SO 4 solution

A series of long-chain N-arylundecanamides containing benzimidazole thioethers (2a-e) were synthesized and characterized by FT IR, 1H NMR, and elemental analysis. The corrosion inhibitory properties of these compounds on cold rolled low carbon

Synthesis, characterization and antibacterial activity of benzimidazole derivatives carrying quinoline moiety

A new series 2-(1H-benzimidazol-2-yl)-6-substitutedthieno[2, 3-b]quinolines 4 have been synthesized by a one-step process in which 2-(chloromethyl)-1H- benzimidazole 2/2-(mercaptomethyl)-1H-benzimidazoles 6 undergo nucleophilic substitution and cyclisation with 2-mercaptoquinoline-3-carbaldehyde 1/2-chloroquinoline-3-carbaldehyde 5. The compounds have been synthesized by two methods to select a method of higher yield. The newly synthesized compounds have been characterized by IR, CHNS analysis, LC-MS and 1H NMR and also screened for antibacterial activity.

Part I: Synthesis, cancer chemopreventive activity and molecular docking study of novel quinoxaline derivatives

The reaction of o-phenylene diamine and ethyl oxamate is reinvestigated and led to 3-aminoquinoxalin-2(1H)-one rather than benzimidazole-2-carboxamide as was previously reported. The structure of the obtained quinoxaline has been confirmed by X-ray. The anti-tumor activity of synthesized quinoxalines 1-21 has been evaluated by studying their possible inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13- acetate (TPA). Among the studied compounds 1-21, compounds 12, 8, 13, 18, 17 and 19, respectively, demonstrated strong inhibitory effects on the EBV-EA activation without showing any cytotoxicity and their effects being stronger than that of a representative control, oleanolic acid. Furthermore, compound 12 exhibited a remarkable inhibitory effect on skin tumor promotion in an in vivo two-stage mouse skin carcinogenesis test using 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter. The result of the present investigation indicated that compound 12 might be valuable as a potent cancer chemopreventive agent. Moreover, the molecular docking into PTK (PDB: 1t46) has been done for lead optimization of the aforementioned compounds as potential PTK inhibitors.

Synthesis, antitrichinnellosis and antiprotozoal activity of some novel thieno[2,3-d]pyrimidin-4(3H)-ones containing benzimidazole ring

Some novel thieno[2,3-d]pyrimidin-4(3H)-ones containing benzimidazol-2-yl-thioethyl- and benzimidazol-2-yl-methanethioethyl moiety in second position of the pyrimidine ring were synthesized in order to determine their antitrichinellosis and antiprotozoal effects. The structures of the compounds were confirmed by IR, 1H NMR and elemental analysis. The antiparasitic screening showed that the benzimidazole derivatives of thieno[2,3-d]pyrimidin-4(3H)-ones exhibited higher activity against Trichinella spiralis in vitro in comparison albendazole. The most active compound, 2-[2-(5-nitro-1H-benzimidazol-1-yl)ethyl]-5,6,7,8-tetrahydro[1]benzothieno[2, 3-d]pyrimidin-4(3H)-one 22 revealed 95% activity at a dosage of 5 mg/kg mw after 24 h, while compounds 8 and 10 applied at the same dose showed efficacy of 90% after 48 h. The compound 2-{2-[(5(6)-nitro-1H-benzimidazol-2-yl)thio]ethyl}-5,6, 7,8-tetrahydro[1]-benzothieno[2,3-d]pyrimidin-4(3H)-one 11 exhibited 90% efficacy after 24 h. The pharmaco-therapeutic study in vivo on invaded with Lamblia muris white mice showed 100% effectiveness of the compounds 8, 10, 11, 13-15 and 22, 23 after five-days-treatment course.

Benzimidazole compounds and their use as chromatographic ligands

The present invention provides a new method for isolation and/or purification of immunoglobulins from a solution containing one or more immunoglobulins using a solid phase matrix represented by the formula: M-SP-L, wherein M is designates a matrix backbone, SP designates a spacer and L designates a substituted benzimidazole ligand.