5805-57-2

Usage

Uses

Used in Pharmaceutical Research and Development:
(1H-BENZO[D]IMIDAZOL-2-YL)METHANAMINE is used as a precursor in the synthesis of various pharmaceuticals due to its ability to be incorporated into complex molecular structures. Its presence in these structures can contribute to the desired biological activity of the final product, making it a valuable component in drug discovery and design.
Used in Organic Synthesis:
In the field of organic synthesis, (1H-BENZO[D]IMIDAZOL-2-YL)METHANAMINE serves as a versatile building block. Its chemical properties allow it to be a key component in the creation of a wide range of organic compounds, facilitating the development of new materials and chemical entities with specific applications.
Used in Medicinal Chemistry:
(1H-BENZO[D]IMIDAZOL-2-YL)METHANAMINE is utilized as a starting material in medicinal chemistry for the exploration of its potential biological activities. Studies on (1H-BENZO[D]IMIDAZOL-2-YL)METHANAMINE have been conducted to understand its interactions with biological targets, which could lead to the discovery of new therapeutic agents or the enhancement of existing ones.
Overall, (1H-BENZO[D]IMIDAZOL-2-YL)METHANAMINE is a multifaceted chemical compound with applications that span across the pharmaceutical, organic synthesis, and medicinal chemistry industries, highlighting its importance in the development of new chemical entities and therapeutics.

Upstream product

• 5805-60-7 N-(1H-benzimidazole-2-yl-methyl)benzamide 
• 54220-73-4 2-methylbenzimidazole 
• 623-33-6 glycine ethyl ester hydrochloride 
• 95-54-5 1,2-diamino-benzene 
• 57097-49-1 2-cyano-benzimidazole-N-oxide 
• 100-97-0 hexamethylenetetramine 
• 189560-83-6 (1H-Benzimidazol-2-yl-methyl)-carbamic acid tert-butyl ester 
• 5993-91-9 2-(aminomethyl)benzimidazole dihydrochloride 
• 4530-20-5 BOC-glycine 
• 6868-37-7 1H-benzoimidazole-2-carbonitrile 
• 56-40-6 glycine 
• 4857-04-9 2-chloromethyl-1H-benzimidazole 
• 60603-42-1 (1H-benzoimidazol-2-ylmethyl)-carbamic acid benzyl ester 
• 133703-73-8 tert-butyl (2-((2-aminophenyl)amino)-2-oxoethyl)carbamate 

Downstream Products

• 30770-21-9 N-[(1H-benzo[d]imidazol-2-yl)methyl]acetamide 
• 99905-48-3 3-phenyl-5-thiophen-2-yl-2,3-dihydro-1H-benzo[4,5]imidazo[1,2-a][1,4]diazepine 
• 65925-15-7 3-(1H-benzimidazol-2-ylmethyl)-2-phenyl-4(3H)-quinazolinone 
• 77523-98-9 N-benzimidazol-2-ylmethyl-N'-benzyl-thiourea 
• 77523-95-6 1-[(1H-benzo[d]imidazol-2-yl) methyl]-3-phenylthiourea 
• 89334-46-3 1-[(1H-benzo[d]imidazol-2-yl) methyl]-3-(4-chlorophenyl) thiourea 
• 74461-38-4 3-(1H-Benzoimidazol-2-ylmethyl)-8-iodo-2-phenyl-3H-quinazolin-4-one 
• 105485-38-9 4-[(1H-Benzoimidazol-2-ylmethyl)-amino]-5-phenyl-1-m-tolyl-1,5-dihydro-pyrrol-2-one 
• 4744-53-0 NSC 700996 
• 135875-06-8 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole 
• 108-74-7 1,3,5-trimethyl-1,3,5-triazacyclohexane 
• 127855-51-0 6-Methyl-6,7,8,9-tetrahydro-5H-4b,6,8,10-tetraaza-benzo[a]azulene 

Relevant academic research and scientific papers

In silico and antithrombotic studies of 1,3,4-oxadiazoles derived from benzimidazole

In the present study, a series of 1,3,4-oxadiazole derivatives (4a-4k) derived from benzimidazole were docked onto factor Xa (PDB: 1NFY) protein using SYBYLX 2.1. and also evaluated for in vitro clot lysis for thrombolytic activity. The synthesized molecules were also screened for in silico ADME studies. The molecular docking studies highlighted that the molecules showed high affinity towards 1NFY with higher docking score and the in silico ADME results were promising and indicated that the molecules holds great potential as a drug candidate. The thrombolytic evaluation was performed for decrease in solid clot weight by the clot lysis study at a concentration of 6.25, 12.5 and 25 μM strengths, respectively. The results of in vitro clot lysis for thrombolytic evaluation revealed that the tested compounds 4a-4k exhibited significant clot lysis with respect to negative control phosphate buffered saline and in comparison to the reference drug streptokinase (30,000 IU). Among all the tested compounds, compound 4j, 4d and 4g exhibited potent thrombolytic activity with EC50 value of 16.2, 18.1 and 23.7 μM, respectively. The thrombolytic efficacy investigation highlights that the synthesized compound 4j could be considered for further clinical studies to ascertain its possible hit as thrombolytic agents.

Synthesis and biological research of novel azaacridine derivatives as potent DNA-binding ligands and topoisomerase II inhibitors

DNA and DNA-related enzymes are one of the most effective and common used intracellular anticancer targets in clinic and laboratory studies, however, most of DNA-targeting drugs suffered from toxic side effects. Development of new molecules with good antitumor activity and low side effects is important. Based on computer aided design and our previous studies, a series of novel azaacridine derivatives were synthesized as DNA and topoisomerases binding agents, among which compound 9 displayed the best antiproliferative activity with an IC50 value of 0.57?μM against U937 cells, which was slightly better than m-AMSA. In addition, compound 9 displayed low cytotoxicity against human normal liver cells (QSG-7701), the IC50 of which was more than 3 times lower than m-AMSA. Later study indicated that all the compounds displayed topoisomerases II inhibition activity at 50?μM. The representative compound 9 could bind with DNA and induce U937 apoptosis through the exogenous pathway.

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.

Synthesis and biological activity of squaramido-tethered bisbenzimidazoles as synthetic anion transporters

A series of squaramido-tethered bisbenzimidazoles were synthesized from the reaction of diethyl squarate with substituted 2-aminomethylbenzimidazoles. These conjugates exhibit moderate binding affinity toward chloride anions. They are able to facilitate the transmembrane transport of chloride anions most probably via an anion exchange process, and tend to be more active at acidic pH than at physiological pH. The viability of these conjugates toward four selected solid tumor cell lines was evaluated using an MTT assay and the results suggest that some of these conjugates exhibit moderate cytotoxicity probably in an apoptotic fashion.

Cu(II) complex-decorated hybrid nanomaterial: a retrievable catalyst for green synthesis of 2,3-dihydroquinazolin-4(1H)-ones

The significant stability of magnetic core and ? OH functional groups on the surface of silica-coated cobalt ferrite (CoFe2O4@SiO2) nanoparticles make it a good candidate for functionalization and catalytic application. In

Dibenzimidazole conjugates with pH dependent anion trans-membrane transport activity Synthesis method and synthesis method thereof (by machine translation)

13-bis-benzimidazole conjugate is synthesized by the method, the chloride ion transport activity of each conjugate under the acidic pH condition is higher than the activity at physiological pH, and the synthesized conjugate also shows moderate intensity toxicity on selected solid tumor cells. (by machine translation)

Impact of N-Alkylamino Substituents on Serotonin Receptor (5-HTR) Affinity and Phosphodiesterase 10A (PDE10A) Inhibition of Isoindole-1,3-dione Derivatives

In this study, a series of compounds derived from 4-methoxy-1H-isoindole-1,3(2H)-dione, potential ligands of phosphodiesterase 10A and serotonin receptors, were investigated as potential antipsychotics. A library of 4-methoxy-1H-isoindole-1,3(2H)-dione derivatives with various amine moieties was synthesized and examined for their phosphodiesterase 10A (PDE10A)-inhibiting properties and their 5-HT1A and 5-HT7 receptor affinities. Based on in vitro studies, the most potent compound, 18 (2-[4-(1H-benzimidazol-2-yl)butyl]-4-methoxy-1H-isoindole-1,3(2H)-dione), was selected and its safety in vitro was evaluated. In order to explain the binding mode of compound 18 in the active site of the PDE10A enzyme and describe the molecular interactions responsible for its inhibition, computer-aided docking studies were performed. The potential antipsychotic properties of compound 18 in a behavioral model of schizophrenia were also investigated.

Cooperative Mn(i)-complex catalyzed transfer hydrogenation of ketones and imines

The synthesis and reactivity of Mn(i) complexes bearing bifunctional ligands comprising both the amine N-H and benzimidazole fragments are reported. Among the various ligands, the N-((1H-benzimidazol-2-yl)methyl)aniline ligand containing Mn(i) complex presented higher reactivity in the transfer hydrogenation (TH) of ketones in 2-propanol. Experimentally, it was established that both the benzimidazole and amine N-H proton played a vital role in the enhancement of the catalytic activity. Utilizing this system a wide range of aldehydes and ketones were reduced efficiently. Notably, the TH of several imines, as well as chemoselective reduction of unsaturated ketones, was achieved in the presence of this catalyst. DFT calculations were carried out to understand the plausible reaction mechanism which disclosed that the transfer hydrogenation reaction followed a concerted outer-sphere mechanism.

Development of dual casein kinase 1δ/1ε (CK1δ/ε) inhibitors for treatment of breast cancer

Casein kinase 1δ/ε have been identified as promising therapeutic target for oncology application, including breast and brain cancer. Here, we described our continued efforts in optimization of a lead series of purine scaffold inhibitors that led to identification of two new CK1δ/ε inhibitors 17 and 28 displaying low nanomolar values in antiproliferative assays against the human MDA-MB-231 triple negative breast cancer cell line and have physical, in vitro and in vivo pharmacokinetic properties suitable for use in proof of principle animal xenograft studies against human cancers.

Small Molecule Inhibitors Simultaneously Targeting Cancer Metabolism and Epigenetics: Discovery of Novel Nicotinamide Phosphoribosyltransferase (NAMPT) and Histone Deacetylase (HDAC) Dual Inhibitors

Cancer metabolism and epigenetics are among the most intensely pursued research areas in anticancer drug discovery. Here we report the first small molecules that simultaneously inhibit nicotinamide phosphoribosyltransferase (NAMPT) and histone deacetylase (HDAC), two important targets of cancer metabolism and epigenetics, respectively. Through iterative structure-based drug design, chemical synthesis, and biological assays, a highly potent dual NAMPT and HDAC inhibitor was successfully identified. Compound 35 possessed excellent and balanced activities against both NAMPT (IC50 = 31 nM) and HDAC1 (IC50 = 55 nM). It could effectively induce cell apoptosis and autophagy and ultimately led to cell death. Importantly, compound 35 showed excellent in vivo antitumor efficacy in the HCT116 xenograft model. This proof-of-concept study demonstrates the feasibility of discovering an inhibitor targeting cancer metabolism and epigenetics and provides an efficient strategy for multitarget antitumor drug discovery.