21745-41-5

Usage

Uses

Used in Pharmaceutical Industry:
1,2-Diamino-3-chlorobenzene is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs and medicinal compounds.
Used in Dye and Pigment Industry:
1,2-Diamino-3-chlorobenzene is used as a precursor in the production of dyes and pigments, playing a crucial role in the creation of colorants for a wide range of applications.
Used in Agrochemical Industry:
1,2-Diamino-3-chlorobenzene is utilized in the manufacturing of agrochemicals, contributing to the development of products that aid in crop protection and enhancement of agricultural yields.
Overall, 1,2-Diamino-3-chlorobenzene is a versatile chemical intermediate with significant applications across multiple industries. However, its potential hazards, including mutagenicity and carcinogenicity, necessitate careful handling and use in laboratory and industrial settings to ensure safety and minimize health risks.

Upstream product

• 769-11-9 2-chloro-6-nitroaniline 
• 7440-02-0 nickel 
• 108-42-9 3-chloro-aniline 
• 5228-61-5 5-bromo-2-nitroaniline 
• 59483-54-4 3-chloro-2-nitro-aniline 
• 3209-22-1 1,2-Dichloro-3-nitrobenzene 
• 602-02-8 2,3-dinitrochlorobenzene 

Downstream Products

• 16931-35-4 4-chloro-1H-1,3-benzodiazole 
• 67130-04-5 4-chloro-1H-benzo[d][1,2,3]triazole 
• 71635-98-8 4-chloro-2-phenyl-1H-benzo[d]imidazole 
• 5599-82-6 7-chloro-2-methylbenzimidazole 
• 1071355-01-5 7-chloro-2-(4-fluorophenyl)-1H-benzimidazole 
• 1221265-47-9 5-chloro-3-methyl-2-[3'-(methylsulfonyl)biphenyl-4-yl]quinoxaline 
• 1221265-64-0 5-chloro-2-methyl-3-[3'-(methylsulfonyl)biphenyl-4-yl]quinoxaline 
• 1342820-78-3 (3-((4-chloro-benzimidazol-2-yl)methyl)-6-methoxy-2-methyl-1H-indol-1-yl)(4-chlorophenyl)methanone 
• 1034046-89-3 6-[(4-tert-butylphenyl)sulfonyl]-N'-hydroxy-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-7-carboximidamide 
• 16931-35-4 7-chloro-1H-benzimidazole 
• 1449690-59-8 C₁₅H₂₁ClN₂O₃ 
• 1339789-49-9 C₁₀H₉ClN₂O₂ 
• 71635-98-8 7-chloro-2-phenyl-1H-benzimidazole 
• 5227-60-1 5-chloro-2,3-diphenylquinoxaline 

Relevant academic research and scientific papers

Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines

The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.

Overcoming imatinib resistance in chronic myelogenous leukemia cells using non-cytotoxic cell death modulators

Recent studies examined the possibility to overcome imatinib resistance in chronic myeloid leukemia (CML) patients by combination therapy with peroxisome proliferator-activated receptor gamma (PPARγ) ligands. Pioglitazone, a full PPARγ agonist, improved the survival of patients by the gradual elimination of the residual CML stem cell pool. To evaluate the importance of the pharmacological profile of PPARγ agonists on the ability to circumvent resistance, the partial PPARγ agonist 4‘-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1’-biphenyl]-2-carboxylic acid, derived from telmisartan, and other related derivatives were investigated. The 4-substituted benzimidazole derivatives bearing a [1,1′-biphenyl]-2-carboxamide moiety sensitized K562-resistant cells to imatinib treatment. Especially the derivatives 18a-f, which did not activate PPARγ to more than 40% at 10 μM, retrieved the cytotoxicity of imatinib in these cells. The cell death modulating properties were higher than that of pioglitazone. It is of interest to note that all novel compounds were not cytotoxic neither on non-resistant nor on resistant cells. They exerted antitumor potency only in combination with imatinib.

Novel cathepsin K inhibitors block osteoclasts in vitro and increase spinal bone density in zebrafish

Cathepsin K (Cat K) is a predominant cysteine protease and highly potent collagenase expressed in osteoclasts. Cat K inhibitors are anti-resorptive agents to treat osteoporosis. A novel scaffold of cathepsin K inhibitors, exemplified by lead compound 1x, was used as the template for designing and synthesizing a total of 61 derivatives that have not been reported before. An exploratory structure-activity relationship analysis identified the potent Cat K inhibitor A22, which displayed an IC50 value of 0.44 μM against Cat K. A22 was very specific for Cat K and caused a significantly higher in vitro inhibition of the enzyme as compared to that of lead compound 1x. A surface plasmon resonance analysis confirmed in vitro binding of A22 to Cat K. Molecular docking studies indicated several favourable interaction sites for A22 within the active pocket of Cat K. Furthermore, A22 also blocked active osteoclasts in vitro and increased spinal bone density in zebrafish, in which it showed an activity that was higher than that of the marketed therapeutic bone metabolizer etidronate disodium. A22 represents a very promising lead compound for the development of novel antiresorptive agents functioning as orthosteric inhibitors of Cat K.

2-Aminopyrimidine Derivatives as New Selective Fibroblast Growth Factor Receptor 4 (FGFR4) Inhibitors

A series of 2-aminopyrimidine derivatives were designed and synthesized as highly selective FGFR4 inhibitors. One of the most promising compounds 2n tightly bound FGFR4 with a Kd value of 3.3 nM and potently inhibited its enzymatic activity with an IC50 value of 2.6 nM, but completely spared FGFR1/2/3. The compound selectively suppressed proliferation of breast cancer cells harboring dysregulated FGFR4 signaling with an IC50 value of 0.38 μM. Furthermore, 2n exhibited extraordinary target specificity in a Kinome-wide screen against 468 kinases, with S(35) and S(10) selectivity scores of 0.01 and 0.007 at 1.0 μM, respectively.

Potent, Selective, and Cell Active Protein Arginine Methyltransferase 5 (PRMT5) Inhibitor Developed by Structure-Based Virtual Screening and Hit Optimization

PRMT5 plays important roles in diverse cellular processes and is upregulated in several human malignancies. Besides, PRMT5 has been validated as an anticancer target in mantle cell lymphoma. In this study, we found a potent and selective PRMT5 inhibitor by performing structure-based virtual screening and hit optimization. The identified compound 17 (IC50 = 0.33 μM) exhibited a broad selectivity against a panel of other methyltransferases. The direct binding of 17 to PRMT5 was validated by surface plasmon resonance experiments, with a Kd of 0.987 μM. Kinetic experiments indicated that 17 was a SAM competitive inhibitor other than the substrate. In addition, 17 showed selective antiproliferative effects against MV4-11 cells, and further studies indicated that the mechanism of cellular antitumor activity was due to the inhibition of PRMT5 mediated SmD3 methylation. 17 may represent a promising lead compound to understand more about PRMT5 and potentially assist the development of treatments for leukemia indications.

Gold nanoparticles anchored onto the magnetic poly(ionic-liquid) polymer as robust and recoverable catalyst for reduction of Nitroarenes

Gold nanoparticles supported on poly ionic-liquid magnetic nanoparticles (MNP@PIL@Au) were synthesized by reduction of HAuCl4 with sodium borohydride. The synthesized catalyst was characterized using by AAS, TEM, FT-IR, EDS, TGA and XRD techniques. The performance of the synthesized catalyst was investigated in the reduction of nitroarenes with NaBH4. The reaction was carried out for various nitroarenes in water and mild conditions with high yields. The catalyst selectivity for the reduction of nitro group in the presences of other functional groups such as halides and alkynes was fairly well. The recycling of the catalyst was done 8 times without any significant loss of its catalytic activity.

HETEROCYCLIC ACETAMIDE COMPOUND

[Problem] A compound which is useful as a dopamine D1 receptor positive allosteric modulator (D1 PAM) is provided. [Means for Solution] The present inventors have studied a compound which has a dopamine D1 receptor positive allosteric modulating activity and is useful as an active ingredient of a pharmaceutical composition for preventing and/or treating cognitive impairment, negative symptoms of schizophrenia, Parkinson's disease, Alzheimer's disease, Huntington's disease, drug addictions, or the like, and they have thus found that a heterocyclic acetamide compound has a dopamine D1 receptor positive allosteric modulating activity, thereby completing the present invention. The heterocyclic acetamide compound of the present invention has a dopamine D1 receptor positive allosteric modulating activity and can be used as an agent for preventing and/or treating cognitive impairment, negative symptoms of schizophrenia, Parkinson's disease, Alzheimer's disease, Huntington's disease, drug addictions, or the like.

19-NOR NEUROACTIVE STEROIDS AND METHODS OF USE THEREOF

Provided herein are 3,3-disubstituted 19-nor-steroidal compounds according to Formula (I): and pharmaceutical compositions thereof. Such compounds are contemplated useful for the prevention and treatment of a variety of CNS-related conditions, for example, treatment of sleep disorders, mood disorders, schizophrenia spectrum disorders, disorders of memory and/or cognition, movement disorders, personality disorders, autism spectrum disorders, pain,traumatic brain injury, vascular diseases, substance abuse disorders and/or withdrawal syndromes, tinnitus, and status epilepticus.

Identification of novel HDAC inhibitors through cell based screening and their evaluation as potential anticancer agents

A series of benzimidazole based HDAC inhibitors have been rationally designed, synthesized and screened. The SAR of this new chemotype is described. The lead compound, 11e, showed strong activity in several cellular assays and demonstrated in vivo efficacy in mouse xenograft pancreatic cancer models.

Discovery of MK-7725, a potent, selective bombesin receptor subtype-3 agonist for the treatment of obesity

Extensive structure-activity relationship studies of a series derived from atropisomer 1, a previously described chiral benzodiazepine sulfonamide series, led to a potent, brain penetrant and selective compound with excellent preclinical pharmacokinetic a