14625-39-9

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(CHLOROMETHYL)-6-NITRO-1H-BENZO[D]IMIDAZOLE is used as a chemical intermediate in the synthesis of pharmaceuticals for its high reactivity and ability to be incorporated into various drug molecules.
Used in Agrochemical Synthesis:
In the agrochemical industry, 2-(CHLOROMETHYL)-6-NITRO-1H-BENZO[D]IMIDAZOLE is used as a precursor in the development of pesticides and fungicides, capitalizing on its antimicrobial and antiparasitic properties to protect crops from diseases and pests.
Used in Antimicrobial Applications:
2-(CHLOROMETHYL)-6-NITRO-1H-BENZO[D]IMIDAZOLE is utilized as an antimicrobial agent for its effectiveness against a range of microorganisms, contributing to the treatment and prevention of various infections.
Used in Antiparasitic Applications:
2-(CHLOROMETHYL)-6-NITRO-1H-BENZO[D]IMIDAZOLE is employed as an antiparasitic agent, leveraging its ability to combat parasitic infections, thus providing a therapeutic option for related health conditions.

InChI:InChI=1/C8H6ClN3O2/c9-4-8-10-6-2-1-5(12(13)14)3-7(6)11-8/h1-3H,4H2,(H,10,11)

Upstream product

• 79-11-8 chloroacetic acid 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 20034-00-8 (5-nitro-1H-benzo[d]imidazol-2-yl)methanol 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 105-39-5 chloroacetic acid ethyl ester 
• 36743-66-5 ethyl chloroacetimidate hydrochloride 
• 849435-69-4 N-(2-amino-4-nitro-phenyl)-2-chloro-acetamide 
• 6271-08-5 2-chloro-N-(2,4-dinitrophenyl)acetamide 
• 97-02-9 2,4-Dinitroanilin 

Downstream Products

• 107090-31-3 N-(5-Methyl-isoxazol-3-yl)-4-[(5-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide 
• 107090-30-2 N-(5-Methyl-[1,3,4]thiadiazol-2-yl)-4-[(5-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide 
• 107090-27-7 N-(4,6-Dimethyl-pyrimidin-2-yl)-4-[(5-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide 
• 107090-29-9 N-(2,6-Dimethyl-pyrimidin-4-yl)-4-[(5-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide 
• 107090-28-8 N-(2,6-Dimethoxy-pyrimidin-4-yl)-4-[(5-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide 
• 107090-26-6 4-[(5-Nitro-1H-benzoimidazol-2-ylmethyl)-amino]-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide 
• 107090-24-4 4-[(5-Nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide 
• 107090-10-8 Dicyclohexyl-dithiocarbamic acid 5-nitro-1H-benzoimidazol-2-ylmethyl ester 
• 107090-09-5 4-Phenyl-piperazine-1-carbodithioic acid 5-nitro-1H-benzoimidazol-2-ylmethyl ester 
• 107090-25-5 N-Acetyl-4-[(5-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide 
• 1225045-58-8 4-bromo-N-[(5-nitro-1H-benzimidazol-2-yl)methyl]aniline 
• 1310689-11-2 2-[4-(4-fluorobenzyl)piperidin-1-yl]methyl-5-aminobenzimidazol 
• 1310689-35-0 2-[4-benzylpiperidin-1-yl]methyl-5-aminobenzimidazole 
• 685841-37-6 N-(2-[(4-benzylpiperidin-1-yl)methyl]benzimidazol-5-yl)methanesulfonamide 

Relevant academic research and scientific papers

Condensation of Ortho-phenylenediamines and Phenylhydrazines with Ethyl 4-Chloro-3-oxobutanoate: A Facile Approach for the Synthesis of Substituted 1 H-Benzimidazoles, Pyrazolones, and Pyrazoles

Substituted 1H-benzimidazoles, pyrazolones, and pyrazoles have been synthesized by the condensation of ortho-phenylenediamines and phenylhydrazines, respectively, with ethyl 4-chloro-3-oxobutanoate in good yields. The present approach is novel, straightforward, and being reported for the first time with ethyl 4-chloro-3-oxobutanoate.

New 7-piperazinylquinolones containing (benzo[d]imidazol-2-yl)methyl moiety as potent antibacterial agents

A series of 7-piperazinylquinolones containing a (benzo[d]imidazol-2-yl)methyl moiety were designed and synthesized as new antibacterial agents. The antibacterial activity of title compounds was evaluated against Gram-positive (Staphylococcus aureus, Staphylococcus epidermidis and Bacillus subtilis) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa and Klebsiella pneumonia) microorganisms. Among the tested compounds, the N1-cyclopropyl derivative 4a showed the highest activity against S. aureus, S. epidermidis, B. subtilis and E. coli (MIC = 0.097 μ g/mL), being 2–4 times more potent than reference drug norfloxacin. A structure-activity relationship study demonstrated that the effect of the nitro group on the benzimidazole ring depends on the pattern of substitutions on the piperazinylquinolone.

Synthesis and biological evaluation of a new series of benzimidazole derivatives as antimicrobial, antiquorum-sensing and antitumor agents

New benzimidazole derivatives were synthesized and assessed for antimicrobial efficacy toward Escherichia coli, Bacillus cereus, Staphylococcus aureus, Candida albicans and Aspergillus fumigatus 293. Results indicated that compounds 3c and 3n have promising activity toward S.?aureus, whereas 3i exhibited remarkable efficacy toward B.?cereus. Moreover, compound 3c was proved to be the most active antifungal analog toward C.?albicans. On the other hand, 3n displayed the highest activity against A.?fumigatus 293. Antiquorum-sensing activity of the same compounds was also tested against Chromobacterium violacium ATCC 12472, whereas compounds 3c-f, 3i-k and 3m-o showed acceptable activity. In?vitro antitumor testing of these compounds toward liver cancer (HepG2), colon cancer (HCT-116) and breast cancer (MCF-7) cell lines revealed that compound 3p has the highest potency against the three tested cell lines. Moreover, 3f, 3m and 3n displayed promising activity toward all tested cell lines. Compounds 3f, 3m, 3n and 3p were esteemed for in?vivo antitumor activity against EAC cells. The active antimicrobial and antitumor analogs, 3a, 3c, 3f, 3i-k, 3m, 3n and 3p were assessed for DNA-binding affinity, and results indicated that 3c, 3f, 3i, 3k and 3n have strong DNA-binding affinity. The computational studies affirmed that almost all of the inspected compounds meet the optimal requirements for good absorption and oral bioavailability.

Discovery and antitumor activity of Benzo[d]imidazol-containing 2,4-diarylaminopyrimidine analogues as ALK inhibitors with mutation-combating effects

To address drug resistance caused by ALK kinase mutations, a series of novel 2,4-diarylaminopyrimidine (DAAP) analogues were designed by incorporating 1H-benzo[d]imidazol motif onto the maternal framework. All compounds were efficiently synthesized and an

Purine derivative and preparation method and application thereof

The invention discloses a purine derivative and a preparation method and application thereof, belongs to the technical field of medicines, and designs and synthesizes a series of purine derivatives and optical isomers, pharmaceutically acceptable salts, solvates or prodrugs of the purine derivatives. Experiments show that the compound has outstanding anti-cell proliferation activity and DOT1L enzyme inhibition effect, shows good tumor growth inhibition activity in a tumor transplantation tumor model, and has a good application prospect.

Design, synthesis, and evaluation of different scaffold derivatives against NS2B-NS3 protease of dengue virus

The number of deaths or critical health issues is a threat in the infection caused by Dengue virus, which complicates the situation, as only symptomatic treatment is the current solution. In this regard we have targeted the dengue protease NS2B-NS3 that is responsible for the replication. The series was designed with the help of molecular modeling approach using docking protocols. The series comprised of different scaffolds viz. cinnamic acid analogs (CA1–CA11), chalcone (C1–C10) and their molecular hybrids (Lik1–Lik10), analogs of benzimidazole (BZ1-BZ5), mercaptobenzimidazole (BS1-BS4), and phenylsulfanylmethylbenzimidazole (PS1-PS4). Virtual screening of various natural phytoconstituents was employed to determine the interactions of designed analogs with the residues of catalytic triad in the active site of NS2B-NS3. We have further synthesized the selected leads. The synthesized analogs were evaluated for the cytotoxicity and NS2B-NS3 protease inhibition activity and compared with known anti-dengue natural phytoconstituent quercetin as the standard. CA2, BZ1, and BS2 were found to be more potent and efficacious than the standard quercetin as evident from the protease inhibition assay.

Design, synthesis and biological evaluation of 2-arylaminopyrimidine derivatives bearing 1,3,8-triazaspiro[4,5]decan-4-one or piperidine-3-carboxamide moiety as novel Type-I1/2 ALK inhibitors

Aiming to develop novel Type-I1/2 inhibitors of ALK to overcome extensive resistance mutations, especially the L1196M mutation surrounding the ATP pocket, two series of 2-arylaminopyrimidine derivatives (11a-f and 22a-t) were designed based on scaffold hopping. The extensive structural elaboration discovered compound 22o which possessed excellent IC50 values of 0.06 and 0.23 μM against ALK-positive Karpas299 and H2228 cell lines, respectively. Meanwhile, 22o displayed encouraging inhibitory potency in the ALKWT (2.5 nM) and ALKL1196M (6.5 nM) enzymatic assays. Furthermore, the AO/EB and Hoechst 33258 assays illustrated 22o could induce cell apoptosis in a dose-dependent manner. Eventually, the molecular docking of 22o with ALK clearly presented the vital interactions within the active site, which was in accordance with Type-I1/2 inhibitor binding mode.

Aromatic heterocycle-containing 2, 4-diarylaminopyrimidine derivative as well as preparation and application of 2, 4-diarylaminopyrimidine derivative

The invention relates to an aromatic heterocycle-containing 2, 4-diarylaminopyrimidine derivative represented by a general formula I, an optical isomer, a pharmaceutically acceptable salt, a solvate or a prodrug thereof, preparation methods of the aromatic heterocycle-containing 2, 4-diarylaminopyrimidine derivative and the optical isomer, the pharmaceutically acceptable salt, the solvate or the prodrug, and a pharmaceutical composition using the compound represented by the general formula I as an active component, wherein substituents R1, R2, R3, R4, R5, R6, X, Y and Z have meanings given inthe specification. The invention also relates to the compound shown in the general formula I, which has strong ALK and ROS1 kinase inhibition effects, and also relates to application of the compound and the optical isomer and pharmaceutically acceptable salt thereof in preparation of drugs for treatment and/or prevention of diseases caused by ALK and ROS1 abnormal expression, and application of the compound in preparation of drugs for prevention of diseases caused by ALK and ROS1 abnormal expression. Use in particular in the preparation of a medicament for treatment and/or for preventing cancer

Anti-oligomerization sheet molecules: Design, synthesis and evaluation of inhibitory activities against α-synuclein aggregation

Aggregation of α-synuclein (α-Syn) play a key role in the development of Parkinson Disease (PD). One of the effective approaches is to stabilize the native, monomeric protein with suitable molecule ligands. We have designed and synthesized a series of sheet-like conjugated compounds which possess different skeletons and various heteroatoms in the two blocks located at both ends of linker, which have good π-electron delocalization and high ability of hydrogen-bond formation. They have shown anti-aggregation activities in vitro towards α-Syn with IC50 down to 1.09 μM. The molecule is found binding in parallel to the NACore within NAC domain of α-Syn, interfering aggregation of NAC region within different α-Syn monomer, and further inhibiting or slowing down the formation of α-Syn oligomer nuclei at lag phase. The potential inhibitor obtained by our strategy is considered to be highly efficient to inhibit α-Syn aggregation.

Discovery of an MLLT1/3 YEATS Domain Chemical Probe

YEATS domain (YD) containing proteins are an emerging class of epigenetic targets in drug discovery. Dysregulation of these modified lysine-binding proteins has been linked to the onset and progression of cancers. We herein report the discovery and characterisation of the first small-molecule chemical probe, SGC-iMLLT, for the YD of MLLT1 (ENL/YEATS1) and MLLT3 (AF9/YEATS3). SGC-iMLLT is a potent and selective inhibitor of MLLT1/3–histone interactions. Excellent selectivity over other human YD proteins (YEATS2/4) and bromodomains was observed. Furthermore, our probe displays cellular target engagement of MLLT1 and MLLT3. The first small-molecule X-ray co-crystal structures with the MLLT1 YD are also reported. This first-in-class probe molecule can be used to understand MLLT1/3-associated biology and the therapeutic potential of small-molecule YD inhibitors.