72998-92-6

Usage

Chloromethyl-substituted derivative

benzimidazole The compound is derived from benzimidazole, a heterocyclic compound, by substituting a chlorine atom with a methyl group (-CH3) on the 2nd position of the molecule.

Bicyclic structure

benzene and imidazole rings The compound has a bicyclic structure consisting of a benzene ring (a six-carbon ring with alternating single and double bonds) and an imidazole ring (a five-membered ring with one nitrogen atom and four carbon atoms).

Scientific and industrial applications

Building block for synthesis The chemical is used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds due to its reactive chloromethyl group.

Reactivity

Chloromethyl group The presence of the chloromethyl group makes the compound potentially reactive, allowing it to participate in various chemical reactions and transformations.

Potential biological activities

Scaffold for drug design 1H-Benzimidazole, 2-(chloromethyl)-5,6-dimethyl-(9CI) may exhibit biological activities and could serve as a scaffold for the design of new drugs or therapeutic agents.

InChI:InChI=1/C10H11ClN2/c1-6-3-8-9(4-7(6)2)13-10(5-11)12-8/h3-4H,5H2,1-2H3,(H,12,13)

Upstream product

• 6761-86-0 (5,6-dimethyl-1H-benzo[d]imidazol-2-yl)methanol 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 79-11-8 chloroacetic acid 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 36743-66-5 ethyl chloroacetimidate hydrochloride 

Downstream Products

• 134723-98-1 C₁₅H₁₅N₃ 
• 134724-00-8 C₁₇H₂₀N₄ 
• 134724-10-0 4-Dimethylamino-1-(5,6-dimethyl-1H-benzoimidazol-2-ylmethyl)-pyridinium; chloride 

Relevant academic research and scientific papers

Synthesis, state-of-the-art NMR-binding and molecular modeling study of new benzimidazole core derivatives as Pin1 inhibitors: Targeting breast cancer

New series of benzimidazole ring core conjugated with either dithiocarbamate or thiopropyl linkers, hybridized with different secondary amines were synthesized; 5–15 and 22–31; respectively. The new compounds were characterized by different spectroscopic techniques (1H, 13C 1D & 2D NMR, ESI-MS and IR). They were screened for in vitro anticancer activity against breast cancer using MCF7 cell line. The results obtained revealed that compounds 5, 12, 15 and 25 were the most active among the synthesized series exhibiting IC50 15N-labeled Pin1 enzyme was conducted using state-of-the-art 2D NMR binding experiments. Results showed promising binding between compounds 5, 12, and 25 by chemical shift perturbation (peak shifting or peak disappearance). Molecular docking study were quite valuable to explain the binding mode of active derivatives via hydrogen bonding. Additional contact preferences and surface mapping studies stated the similarity pattern between active candidates which may pave the way for more precise anti breast cancer target optimization.

Synthesis of Benzimidazole-Fused Medium-Sized N,S-Heterocycles via Palladium-Catalyzed Cyclizations

The synthesis of unprecedented benzimidazole-fused thiazocines, thiazonines, and thiazecines having an exocyclic double bond is reported. The process proceeds through an 8-, 9-, or 10-exo-dig cyclocarbopalladation followed by reduction. The scope and limitations were established and showed the importance of the precursor structure for the success of the reaction. A competition between the exo-dig and the endo-dig cyclization was observed for two substrates bearing an N-homopropargyl chain, the endo-cyclization leading to rarely encountered 10- and 11-membered N,S-heterocycles with a trans-endocyclic double bond. X-ray structures of three products were obtained by co-crystallization with fumaric acid and show the twisted structures of these molecules.

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.

INHIBITION AND DISPERSION OF BIOFILMS IN PLANTS WITH IMIDAZOLE-TRIAZOLE DERIVATIVES

Disclosure is provided for methods of preventing, removing or inhibiting microbial biofilm formation or microbial infection in a plant or plant part thereof, including applying thereto a treatment effective amount of an active compound as described herein, or an agriculturally acceptable salt thereof. Methods of enhancing a microbicide (e.g., including a copper, antibiotic, bacteriophage, etc.) and/or plant defense activator are also provided, including applying an active compound as described herein. Compositions comprising an active compound as described herein in an agriculturally acceptable carrier are also provided, and in some embodiments the compositions further include a microbicide (e.g., including copper, antibiotic, bacteriophage, etc.) and/or plant defense activator.

INHIBITION AND DISPERSION OF BACTERIAL BIOFILMS WITH IMIDAZOLE-TRIAZOLE DERIVATIVES

Disclosure is provided for imidazole-triazole derivative compounds that prevent, remove and/or inhibit the formation of biofilms, compositions comprising these compounds, devices comprising these compounds, and methods of using the same.

Construction and screening of a 2-aminoimidazole library identifies a small molecule capable of inhibiting and dispersing bacterial biofilms across order, class, and phylum

(Chemical Equation Presented) A team of three: 2-Aminoimidazole, triazole, and tether units together resulted in conjugates (see picture, n=4-6 for the most active compounds) that are capable of inhibiting and dispersing bacteria biofilms without inducing bacterial death. Such biofilms have been implicated in a plethora of medical problems, including infection of implanted medical devices and the mortality of cystic fibrosis patients.

Chemokine receptor binding heterocyclic compounds

This invention relates to a novel class of heterocyclic compounds that bind chemokine receptors, inhibiting the binding of their natural ligands thereby. These compounds result in protective effects against infection by HIV through binding to chemokine receptors, including CXCR4 and CCR5, thus inhibiting the subsequent binding by these chemokines. The present invention provides a compound of Formula I wherein, W is a nitrogen atom and Y is absent or, W is a carbon atom and Y═H; R1to R7may be the same or different and are independently selected from hydrogen or straight, branched or cyclic C1-6alkyl; R8is a substituted heterocyclic group or a substituted aromatic group Ar is an aromatic or heteroaromatic ring each optionally substituted at single or multiple, non-linking positions with electron-donating or withdrawing groups; n and n′ are independently, 0-2; X is a group of the formula: Wherein, Ring A is an optionally substituted, saturated or unsaturated 5 or 6-membered ring, and P is an optionally substituted carbon atom, an optionally substituted nitrogen atom, sulfur or oxygen atom. Ring B is an optionally substituted 5 to 7-membered ring. Ring A and Ring B in the above formula can be connected to the group W from any position via the group V, wherein V is a chemical bond, a (CH2)n″group (where n″=0-2) or a C═O group. Z is, (1) a hydrogen atom, (2) an optionally substituted C1-6alkyl group, (3) a C0-6alkyl group substituted with an optionally substituted aromatic or heterocyclic group, (4) an optionally substituted C0-6alkylamino or C3-7cycloalkylamino group, (5) an optionally substituted carbonyl group or sulfonyl. These compounds further include any pharmaceutically acceptable acid addition salts and metal complexes thereof and any stereoisomeric forms and mixtures of stereoisomeric forms thereof.