1668-01-5

Usage

Uses

Used in Chemical Industry:
3,4-Dichloro-1,2-benzenediamine is used as a chemical intermediate for the production of dyes, specifically due to its reactive amine groups that facilitate the formation of color compounds.
Used in Cosmetics Industry:
In the cosmetics industry, 3,4-Dichloro-1,2-benzenediamine is utilized as a precursor in the synthesis of hair dyes, where it contributes to the formation of colorants that impart shades to hair.
Used in Photography:
3,4-Dichloro-1,2-benzenediamine is employed as a component in photographic developers, where it plays a crucial role in the development process of photographic films and papers.
Used in Pharmaceutical Industry:
3,4-Dichloro-1,2-benzenediamine is also used as an intermediate in the manufacturing of certain pharmaceuticals, given its ability to undergo further chemical reactions to produce medicinally active substances.
Used in Agrochemical Industry:
3,4-Dichloro-1,2-benzenediamine finds application in the production of agrochemicals, serving as a building block for the synthesis of various pesticides and other agricultural chemicals.
However, due to its status as a skin and respiratory irritant, a potential allergen, and its classification as a hazardous substance, strict regulations guide the handling and use of 3,4-Dichloro-1,2-benzenediamine in industrial settings. It is considered potentially harmful to both the environment and human health, necessitating careful handling and exposure precautions.

Upstream product

• 65078-76-4 2,3-dichloro-6-nitroacetanilide 
• 65078-77-5 2,3-dichloro-6-nitroaniline 
• 7440-02-0 nickel 
• 95-50-1 1,2-dichloro-benzene 
• 23068-36-2 N-(2,3-dichlorophenyl)-acetamide 
• 17700-09-3 4-nitro-1,2,3-trichlorobenzene 

Downstream Products

• 6662-87-9 4,5-Dichlor-benz<2,1,3>thiadiazol 
• 1447835-70-2 5,6-dichloro-1H-benzo[d]imidazol-2-yl-phenylmethanol 
• 1447835-71-3 5,6-dichloro-1H-benzo[d]imidazol-2-yl-phenylmethanol 
• 2262452-06-0 3-[1-(6,7-dichloro-1H-benzimidazol-2-yl)-5-hydroxy-3-methyl-pyrazol-4-yl]-3H-isobenzofuran-1-one 
• 173461-08-0 1-(2-Benzyloxy-1-benzyloxymethyl-ethoxymethyl)-2,4,5-trichloro-1H-benzoimidazole 
• 173460-82-7 1-(2-Benzyloxy-ethoxymethyl)-2,4,5-trichloro-1H-benzoimidazole 
• 173460-79-2 2-bromo-4,5-dichlorobenzimidazole 
• 145489-53-8 3-<2-amino-4,5-dichlorophenylimino(p-toluoyl)>-4-hydroxy-6-(p-tolyl)-2H-pyran-2-one 

Relevant academic research and scientific papers

Small molecule inhibition of cGAS reduces interferon expression in primary macrophages from autoimmune mice

Cyclic GMP-AMP synthase is essential for innate immunity against infection and cellular damage, serving as a sensor of DNA from pathogens or mislocalized self-DNA. Upon binding double-stranded DNA, cyclic GMP-AMP synthase synthesizes a cyclic dinucleotide that initiates an inflammatory cellular response. Mouse studies that recapitulate causative mutations in the autoimmune disease Aicardi-Goutières syndrome demonstrate that ablating the cyclic GMP-AMP synthase gene abolishes the deleterious phenotype. Here, we report the discovery of a class of cyclic GMP-AMP synthase inhibitors identified by a high-throughput screen. These compounds possess defined structure-activity relationships and we present crystal structures of cyclic GMP-AMP synthase, double-stranded DNA, and inhibitors within the enzymatic active site. We find that a chemically improved member, RU.521, is active and selective in cellular assays of cyclic GMP-AMP synthase-mediated signaling and reduces constitutive expression of interferon in macrophages from a mouse model of Aicardi-Goutières syndrome. RU.521 will be useful toward understanding the biological roles of cyclic GMP-AMP synthase and can serve as a molecular scaffold for development of future autoimmune therapies.

CARBONYL LINKED BICYCLIC HETEROARYL N-BENZIMIDAZOLES AND ANALOGS AS ANTIBIOTIC TOLERANCE INHIBITORS

The disclosure provides compounds and pharmaceutical compositions of includes carbonyl linked bicyclic heteroaryl N-benzimidazole compounds useful for treating chronic and acute bacterial infections. Certain of the compounds are compounds of general Formula (I) or a pharmaceutically acceptable salt or prodrug thereof. Certain compounds of this disclosure are MvfR inhibitors. MvfR inhibitors reduce the formation of antibiotic tolerant bacterial strains and are useful for treating Gram-negative bacterial infections and reducing the virulence of Pseudomonas aeruginosa. Methods of treating bacterial infections in a subject, including Pseudomonas aeruginosa infections, are also provided by the disclosure.

NOVEL COMPOUNDS USEFUL AS S100-INHIBITORS

A compound of formula (I) or a pharmaceutically acceptable salt thereof and a pharmaceutical composition comprising the compound. The compound is an inhibitor of interactions between S100A9 and interaction partners such as RAGE, TLR4 and EMMPRIN and as such is useful in the treatment of disorders such as cancer, autoimmune disorders, inflammatory disorders and neurodegenerative disorders.

Carbamate compositions and methods fo rmodulating the activity of the CHK1 enzyme

Described herein are carbamate compounds. Such compounds are capable of modulating the activity of a checkpoint kinase, and described herein are methods for utilizing such modulation to treat cell proliferative disorders. Also described are pharmaceutical

Benzimidazolone-, benzoxazolone-, or benzothiazolone derivatives as ion channel modulating agents

The present invention relates to ion channel modulating agents. More particularly, the present invention relates to a particular class of chemical compounds that has proven useful as modulators of SKCa, IKCa and BKCa channels. In further aspects, the present invention relates to the use of these SK/IK/BK channel modulating agents for the manufacture of medicaments, and pharmaceutical compositions comprising the SK/IK/BK channel modulating agents. The SK/IK/BK channel modulating agents of the invention are useful for the treatment or alleviation of diseases and conditions associated with the SK/IK/BK channels.

Synthesis and evaluation for biological activity of 3-alkyl and 3-halogenoalkyl-quinoxalin-2-ones variously substituted. Part 4

A new series of 3-isopropyl-, 3-trifluoromethyl- and 3-bromomethylquinoxaline-2-ones variously substituted on the benzo-moiety were synthesized and submitted to a preliminary in vitro evaluation for antibacterial, antifungal and anti-HIV activities. Furth

Benzimidazole derivatives for the treatment of viral infections

According to a first aspect of the invention there is provided compounds of formula (I): wherein: R1is hydroxy; O-acetyl; or a halo atom; R2is hydroxy; O-acetyl; or a halo atom; R3is hydrogen; a halo atom; azido; C2-6alkenyl; C2-6alkynyl; C6-14aryl C2-6alkenyl; C6-14arylC2-6alkynyl —NR8R9(where R8and R9may be the same or different and are hydrogen, C1-8alkyl, cyanoC1-8alkyl, hydroxyC1-8alkyl, haloC1-8alkyl, C3-7cycloalkyl, C1-8alkylC3-7cycloalkyl, C2-6alkenyl, C3-7cycloalkylC1-8alkyl, C2-6alkynyl, C6-14aryl, C6-14arylC1-8alkyl, heterocycleC1-8alkyl, C1-8alkylcarbonyl, C6-14arylsulfonyl, C1-8alkysulfonyl, or R8R9together with the N atom to which they are attached form a 3,4,5 or 6 membered heterocyclic ring); —OR10(where R10is hydrogen, C1-8alkyl, C6-14aryl, or C6-14arylC1-8alkyl, C2-6alkenyl, C2-6alkynyl, C6-14aryl C2-6alkenyl or C6-14arylC2-6alkynyl); or —SR11(where R11is hydrogen, C1-8alkyl, C6-14aryl, or C6-14arylC1-8alkyl).

L-benzimidazole nucleosides

The present invention relates to benzimidazole derivatives and their use in medical therapy particularly for the treatment or prophylaxis of virus infections such as those caused by herpes viruses. The invention also relates to the preparation of the benzimidazole derivatives and pharmaceutical formulations containing them.

Structure-activity relationships among 2-substituted 5,6-dichloro-, 4,6- dichloro-, and 4,5-dichloro-1-[(2-hydroxyethoxy)methyl]- and -1-[(1,3- dihydroxy-2-propoxy)methyl]benzimidazoles

The sodium salt of 2,5,6-trichlorobenzimidazole (8a) was condensed with [2-(benzyloxy)ethoxy]methyl chloride (9) and [1,3-bis(benzyloxy)-2- propoxy]methyl chloride (18) to provide the corresponding protected acyclic nucleosides 10a and 19a, which on debenzylation afforded 2,5,6-trichloro-1- [(2-hydroxyethoxy)methyl]benzimidazole (11a) and 2,5,6-trichloro-1-[(1,3- dihydroxy-2-propoxy)methyl]benzimidazole (20a), respectively. A similar condensation of 2,4,6-trichlorobenzimidazole (2a) and 2,4,5- trichlorobenzimidazole (7a) followed by debenzylation yielded 11b, 20b, 11c, and 20c, respectively. A nucleophilic displacement of the 2-chloro group of 11a-c and 20a-c with liquid ammonia, methylamine, dimethylamine, and thiourea furnished several interesting 2-substituted compounds in good yields, e.g., 12-14(a-e), 2123(a-e), 15-17, and 24-26. Alkylation of the 2-thio analogs 15- 17 and 24-26 with benzyl chloride furnished the 2-alkylthio acyclic nucleosides 12d-14d and 21d-23d. Desulfurization of 15 and 24 with Raney Ni furnished 5,6-dichloro-1-[(2-hydroxyethoxy)methyl]benzimidazole (12e) and 5,6-dichloro-1-[(1,3-dihydroxy-2-propoxy)methyl]benzimidazole (21e), respectively (acyclic analog of 5,6-dichloro-1-β-D- ribofuranosylbenzimidazole). Similarly the dihalo compounds 13e, 14e, and 23e were prepared in moderate yields from the 2-thio analogs 16, 17, and 26. Treatment of 2-bromo-5,6-dichlorobenzimidazole (8b) with 27 and 30 gave the protected acyclic compounds 28a and 31a, which on deacetylation with sodium carbonate and potassium cyanide yielded 2-bromo-5,6-dichloro-1-[(2- hydroxyethoxy)methyl]benzimidazole (29a) and 2-bromo-5,6-dichloro-1-[(1,3- dihydroxy-2-propoxy)methyl]benzimidazole (32a), respectively, in moderate yields. The 2-bromo-4,6-dichlorobenzimidazole and 2-bromo-4,5- dichlorbenzimidazole analogs 29b,c and 32b,c were prepared in a similar manner. Compounds were tested for activity against human cytomegalovirus (HCMV) and herpes simplex virus type 1 (HSV-1) and for cytotoxicity. In marked contrast to the ribosylbenzimidazoles, none of the acyclic analogs were specific and potent inhibitors of HCMV. Only the 2-thiobenzyl analogs 12d, 13d, 14d, and 23d and the 2-Br analogs 32a,b were active, but activity was not well separated from cytotoxicity. The lack of specific and potent antiviral activity strongly suggests that these acyclic nucleoside analogs are not phosphorylated by HCMV or HSV-1 gene products and that the ribosylbenzimidazoles do not require phosphorylation for antiviral activity.