3584-65-4

Usage

Uses

Used in Pharmaceutical Industry:
2-(TRICHLOROMETHYL)-BENZIMIDAZOLE is used as an anti-tumor agent for its potential to combat cancer cells. It is being studied for its ability to target and inhibit the growth of tumors, offering a promising avenue for cancer treatment.
Used in Agrochemical Industry:
2-(TRICHLOROMETHYL)-BENZIMIDAZOLE is used as a pesticide and fungicide for its effectiveness in controlling pests and fungi that can damage crops. Its pesticidal and fungicidal properties make it a valuable tool in agricultural settings for protecting plants and ensuring crop yields.
Used in Organic Synthesis:
2-(TRICHLOROMETHYL)-BENZIMIDAZOLE is used as a reagent in the preparation of various benzimidazole-based derivatives. These derivatives possess potential biological activities and can be further developed for use in pharmaceuticals and other applications, contributing to the advancement of organic chemistry and drug discovery.

InChI:InChI=1/C8H5Cl3N2/c9-8(10,11)7-12-5-3-1-2-4-6(5)13-7/h1-4H,(H,12,13)

Upstream product

• 23170-77-6 N-methyltrichloroacetamide 
• 95-54-5 1,2-diamino-benzene 
• 2533-69-9 methyl 2,2,2-trichloroacetimidate 
• 1218786-38-9 N-Boc-2-(2',2',2'-trichloroacetylamino)-aniline 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 88-74-4 2-nitro-aniline 

Downstream Products

• 14483-99-9 2-(2-Oxazolin-2-yl)-benzimidazol 
• 14595-67-6 2-Benzoxazol-2-yl-benzimidazol 
• 2849-93-6 2-benzimidazolecarboxylic acid 
• 6868-37-7 1H-benzoimidazole-2-carbonitrile 
• 3176-72-5 2-((phenylsulfanyl)methyl)-1H-benzimidazole 
• 685141-97-3 2(RS)-{2-[(1H-benzimidazole-2-carbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid ethyl ester 
• 862279-51-4 4-(2-(1H-benzo[d]imidazol-2-yl)-1H-benzo[d]imidazol-5-yl)benzene-1,2-diamine 
• 862279-50-3 1H,1'H,1''H,1'''H-2,2':5',5'':2'',2'''-quaterbenzimidazole 
• 14483-90-0 2-(2-Imidazolin-2-yl)benzimidazol 
• 14483-93-3 2-(4,5-dihydro-4-methyl-1H-imidazol-2-yl)-1H-benzimidazole 
• 14483-74-0 benzimidazole-2-carboxamide oxime 
• 439574-23-9 C₁₅H₉Cl₃N₂O 
• 439574-24-0 C₁₅H₁₁Cl₃N₂O₂S 
• 1146213-84-4 (1H-benz[d]imidazol-2-yl)(4-(4-fluorobenzyl)piperazin-1-yl)methanone 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel scaffold benzo[4,5]imidazo [1,2-a]pyrazin-1-amine: Towards adenosine A2A receptor (A2A AR) antagonist

Antagonists of adenosine receptor are under exploration as potential drug candidates for treatment of neurological disorders, depression, certain cancers and potentially used as a cancer immunotherapy. Herein, we describe design and synthesis of novel scaffold benzo[4,5]imidazo [1,2-a]pyrazin-1-amine (6) derivatives. All the compounds were evaluated for A2A AR antagonist activity and displayed encouraging results (IC50 9–300 nM) of A2A AR antagonist binding affinity in biochemical assay. Compound 27 exhibits good activity in A2A AR antagonist cAMP functional assay (IC50 31 nM) and further this compound shows T-cell activation at the IL-2 production assay (EC50 165 nM). Molecular docking studies were carried out to rationalize the observed binding affinity of compound 27.

Facile synthesis of C6-substituted benz[4,5]imidazo[1,2-a]quinoxaline derivatives and their anticancer evaluation

Cancer remains a leading cause of death worldwide, resulting in continuous efforts to discover and develop highly efficacious anticancer drugs. High-throughput screening of heterocyclic compound libraries is one of the promising approaches that provided several new lead molecules with a novel mechanism of action. On the basis of the promising anticancer potential of imidazoquinoxaline as well as the structurally similar imidazoquinoline-derived scaffold, we prepared a set of C6-substituted benzimidazo[1,2-a]quinoxaline derivatives via two novel synthetic routes using commercially available starting materials, with good to excellent yields and evaluated their anticancer activity against the NCI-60 cancer cell lines. The one-dose (10 μM) anticancer screening of the synthesized compounds in the NCI-60 cell line panel revealed that the substituents have a significant role in the activity. In particular, the indole (7f), imidazole (7g),?and benzimidazole (7h) derivatives showed significant activity against the triple-negative breast cancer cell line, MDA-MB-468. The lead compounds also exhibited notable IC50 values against another breast cancer cell line, MCF-7. Furthermore, it was observed that these compounds were relatively nontoxic to normal cell lines: HEK293 (human embryonic kidney cell line) and MCF12A (nontumorigenic human breast epithelial cell line). The IC50 values against healthy cells were at least 5- to 11-fold higher, offering a new class of heterocycles that can be further developed as promising therapeutics for cancer treatment.

Fragment-Based Optimization of Dihydropyrazino-Benzimidazolones as Metabotropic Glutamate Receptor-2 Positive Allosteric Modulators against Migraine

Our previous scaffold-hopping attempts resulted in dihydropyrazino-benzimidazoles as metabotropic glutamate receptor-2 (mGluR2) positive allosteric modulators (PAMs) with suboptimal drug-like profiles. Here, we report an alternative fragment-based optimization strategy applied on the new dihydropyrazino-benzimidazolone scaffold. Analyzing published high-affinity mGluR2 PAMs, we used a pharmacophore-guided approach to identify suitable growing vectors and optimize the scaffold in these directions. This strategy resulted in a new fragment like lead (34) with improved druglike properties that were translated to sufficient pharmacokinetics and validated proof-of-concept studies in migraine. Gratifyingly, compound34showed reasonable activity in the partial infraorbital nerve ligation, a migraine disease model that might open this indication for mGluR2 PAMs.

Reversing binding sensitivity to A147T translocator protein

The translocator protein (TSPO) is a target for the development of neuroinflammation imaging agents. Clinical translation of TSPO PET ligands, such as [11C]DPA-713, has been hampered by the presence of a common polymorphism (A147T TSPO), at which all second-generation TSPO ligands lose affinity. Little is known about what drives binding at A147T compared to WT TSPO. This study aimed to identify moieties in DPA-713, and related derivatives, that influence binding at A147T compared to WT TSPO. We found changes to the nitrogen position and number in the heterocyclic core influences affinity to WT and A147T to a similar degree. Hydrogen bonding groups in molecules with an indole core improve binding at A147T compared to WT, a strategy that generated compounds that possess up to ten-times greater affinity for A147T. These results should inform the future design of compounds that bind both A147T and WT TSPO for use in neuroinflammation imaging.

Hit-to-lead optimization of novel benzimidazole phenylacetamides as broad spectrum trypanosomacides

Trypanosoma cruzi and Trypanosoma brucei are the parasitic causative agents of Chagas disease and human African trypanosomiasis (HAT), respectively. The drugs currently used to treat these diseases are not efficacious against all stages and/or parasite sub-species, often displaying side effects. Herein, we report the SAR exploration of a novel hit, 2-(4-chlorophenyl)-N-(1-propyl-1H-benzimidazol-2-yl)acetamide previously identified from high throughput screens against T. cruzi, Trypanosoma brucei brucei and Leishmania donovani. An informative set of analogues was synthesized incorporating key modifications of the scaffold resulting in improved potency whilst the majority of compounds retained low cytotoxicity against H9c2 and HEK293 cell lines. The SAR observed against T. cruzi broadly matches that observed against T.b. brucei, suggesting the possibility for a broad-spectrum candidate. This class of compounds therefore warrants further investigation towards development as a treatment for Chagas disease and HAT. This journal is

3-benzo[4,5]imidazo[1,2-a]pyrazin-1-amine compounds as well as preparation method and application thereof

The invention discloses 3-benzo[4,5]imidazo[1,2-a]pyrazin-1-amine compounds as well as a preparation method and application thereof. The general structure of the compounds is shown as a formula (I). The compounds disclosed by the invention have good inhibitory activity on an adenosine A2A receptor, and in particular, IC50 values of the compounds 1-3, compounds 7-11, compounds 13-15, and compounds18, 23, 25, 26, 29, 30 and 31 on the adenosine A2A receptor is 50 nM or below, and the IC50 values of the compounds 14, 23, 25, 30 and 31 is 10.1 nM or below. The disclosed compounds show excellent inhibitory effect on adenosine A2A receptors, can be prepared into adenosine A2A receptor inhibitors to serve as potential immune antitumor drugs, and release the scavenging function of an immune systemon tumor cells by inhibiting the activity of the adenosine A2A receptor, thereby achieving the effect of treating tumors. Meanwhile, the compounds are simple in synthesis method, mild in condition, high in product yield and purity, capable of being industrially produced and prepared on a large scale and convenient to apply and popularize.

AZA-HETEROARYL COMPOUNDS AS PI3K-GAMMA INHIBITORS

The present invention provides aza-heteroaryl derivatives of Formula I: and pharmaceutically acceptable salts thereof, wherein X, Y, Z, A, W, R4, R5, and R6 are defined herein, that inhibit the activity of phosphoinositide 3-kinases-gamma (PI3Kγ) and are useful in the treatment of diseases related to the activity of PI3Kγ including, for example, autoimmune diseases, cancer, cardiovascular diseases, and neurodegenerative diseases.

Synthesis of novel histamine H4 receptor antagonists

This letter describes the discovery and synthesis of a series of octahydropyrrolo[3,4-c]pyrrole based selective histamine hH4 receptor antagonists. The amidine compound 20 was found to be a potent and selective histamine H4 receptor antagonist with moderate clearance and a high volume of distribution.

NITROGEN HETEROCYCLIC COMPOUNDS USEFUL AS PDE10 INHIBITORS

Unsaturated nitrogen heterocyclic compounds of formula (I): (I), as defined in the specification, compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, Huntington's Disease, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

Rearrangement strategy for the synthesis of 2-aminoanilines

(Figure Presented) Treatment of N-aryl hydroxylamines with trichloroacetonitrile in the presence of imidazole provides a simple and effective method for the preparation of synthetically versatile 2-aminoanilines. Reactions proceed in DMF at 40°C, providing the products In up to 86% isolated yield.