102074-47-5

Usage

Uses

Used in Pharmaceutical Industry:
6-chloro-N1-methylbenzene-1,2-diamine serves as an intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic properties, contributing to advancements in medicine.
Used in Dye and Pigment Production:
In the dye and pigment industry, 6-chloro-N1-methylbenzene-1,2-diamine is utilized in the production of a wide range of dyes and pigments. Its chemical properties enable the creation of vibrant and stable colorants for various applications.
Used in Material Development:
6-chloro-N1-methylbenzene-1,2-diamine plays a role in the development of new materials and compounds. Its versatility as a building block allows researchers and chemists to explore its potential in creating innovative materials for diverse industries.
Used in Research and Development:
Due to its potential therapeutic properties and chemical versatility, 6-chloro-N1-methylbenzene-1,2-diamine is often utilized in research and development. Scientists explore its applications in creating new compounds and improving existing ones, driving innovation in the chemical and pharmaceutical sectors.

Upstream product

• 75438-12-9 N-methyl-2-chloro-6-nitroaniline 
• 769-11-9 2-chloro-6-nitroaniline 
• 2106-49-2 1-chloro-2-fluoro-3-nitrobenzene 
• 3209-22-1 1,2-Dichloro-3-nitrobenzene 

Downstream Products

• 1191924-11-4 C₂₁H₁₆Cl₃N₅ 
• 24133-88-8 7-chloro-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 
• 4887-87-0 7-chloro-1-methyl-1H-benzo[d]imidazole 
• 1267635-68-6 C₁₆H₁₃ClN₂O₂ 
• 1267635-03-9 C₂₀H₂₀ClN₃O₃ 

Relevant academic research and scientific papers

Spiroconjugated Tetraaminospirenes as Donors in Color-Tunable Charge-Transfer Emitters with Donor-Acceptor Structure

Charge-transfer emitters are attractive due to their color tunability and potentially high photoluminescence quantum yields (PLQYs). We herein present tetraaminospirenes as donor moieties, which, in combination with a variety of acceptors, furnished 12 charge-transfer emitters with a range of emission colors and PLQYs of up to 99 %. The spatial separation of their frontier molecular orbitals was obtained through careful structural design, and two DA structures were confirmed by X-ray crystallography. A range of photophysical measurements supported by DFT calculations shed light on the optoelectronic properties of this new family of spiro-NN-donor-acceptor dyes.

Discovery of selective fragment-sized immunoproteasome inhibitors

Proteasomes contribute to maintaining protein homeostasis and their inhibition is beneficial in certain types of cancer and in autoimmune diseases. However, the inhibition of the proteasomes in healthy cells leads to unwanted side-effects and significant effort has been made to identify inhibitors specific for the immunoproteasome, especially to treat diseases which manifest increased levels and activity of this proteasome isoform. Here, we report our efforts to discover fragment-sized inhibitors of the human immunoproteasome. The screening of an in-house library of structurally diverse fragments resulted in the identification of benzo[d]oxazole-2(3H)-thiones, benzo[d]thiazole-2(3H)-thiones, benzo[d]imidazole-2(3H)-thiones, and 1-methylbenzo[d]imidazole-2(3H)-thiones (with a general term benzoXazole-2(3H)-thiones) as inhibitors of the chymotrypsin-like (β5i) subunit of the immunoproteasome. A subsequent structure-activity relationship study provided us with an insight regarding growing vectors. Binding to the β5i subunit was shown and selectivity against the β5 subunit of the constitutive proteasome was determined. Thorough characterization of these compounds suggested that they inhibit the immunoproteasome by forming a disulfide bond with the Cys48 available specifically in the β5i active site. To obtain fragments with biologically more tractable covalent interactions, we performed a warhead scan, which yielded benzoXazole-2-carbonitriles as promising starting points for the development of selective immunoproteasome inhibitors with non-peptidic scaffolds.

Discovery of 2-iminobenzimidazoles as potent hepatitis C virus inhibitors with a novel mechanism of action

In this report we describe 2-iminobenzimidazole (IBI) analogs, identified during the course of a phenotypic high-throughput screening campaign, as novel hepatitis C virus (HCV) inhibitors. A series of IBI derivatives was synthesized and evaluated for their inhibitory activity against infectious HCV. Among the IBIs derivatives studied in this work, we identified promising compounds with high antiviral efficacy, high selectivity index and good microsomal stability. Noteworthy, the IBI series exhibited inhibitory activity on early and late steps of the viral cycle, but not in the HCV replicon system demonstrating a mechanism of action distinct from clinical-stage and approved anti-HCV drugs. Overall, our results suggest that IBIs are predestinated for further exploration as lead compounds for novel HCV interventions.

Discovery of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of inhibitors of HIV-1 capsid assembly

The discovery of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of inhibitors of HIV-1 capsid assembly is described. Synthesis of analogs of the 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione hit established structure-activity relationships. Replacement of the enamine functionality of the hit series with either an imidazole or a pyrazole ring led to compounds that inhibited both capsid assembly and reverse transcriptase. Optimization of the bicyclic benzodiazepine scaffold to include a 3-phenyl substituent led to lead compound 48, a pure capsid assembly inhibitor with improved antiviral activity.

Bicyclic Benzimidazole Compounds and Their Use as Metabotropic Glutamate Receptor Potentiators

Compounds of Formula I: wherein A, B, D, L, R1, R2, R3, R4, m, and n are as defined for Formula I in the description. The invention also relates to processes for the preparation of the compounds and to new intermediates employed in the preparation, pharmaceutical compositions containing the compounds, and to the use of the compounds in therapy.

Discovery of small molecule benzimidazole antagonists of the chemokine receptor CXCR3

High-throughput screening identified a low molecular weight antagonist of CXCR3 displaying micromolar activity in a membrane filtration-binding assay. Systematic modification of the benzimidazole core and tethered acetophenone moiety established tractable SAR of analogs with improved physicochemical properties and sub-micromolar activity across both human and murine receptors.