3171-46-8

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Dimethyl-1,2-phenylenediamine is used as a reagent for the synthesis of benzimidazoles and benzimidazole conjugates, which are important in the development of pharmaceutical compounds with potential therapeutic applications.
Used in Chemical Synthesis:
3,5-Dimethyl-1,2-phenylenediamine is used as a starting material to synthesize various organic compounds, such as:
Tetramethyl quinoxaline derivatives by reacting with 1,2-dicarbonyl compounds, which have potential applications in various chemical and pharmaceutical industries.
5,7-Dimethyl-1H-benzotriazole by reacting with tert-butyl nitrite, which can be used as a corrosion inhibitor, stabilizer, and in various chemical reactions.
Dimethyl-1H-benzimidazole by reacting with dimethylformamide (DMF), which can be used in the synthesis of other organic compounds and as a reagent in various chemical processes.

InChI:InChI=1/C8H12N2/c1-5-3-7(9)8(10)4-6(5)2/h3-4H,9-10H2,1-2H3

Upstream product

• 90111-03-8 1,3-dibromo-2,4-dimethyl-5,6-dinitro-benzene 
• 90434-19-8 dibromo-m-xylene 
• 95-68-1 2,4-Xylidine 
• 99-12-7 5-nitro-m-xylene 
• 65151-56-6 3,5-dimethyl-1,2-dinitrobenzene 
• 1635-84-3 2,4-Dimethyl-6-nitroanilin 
• 2050-43-3 N-(2,4-dimethylphenyl)acetamide 
• 89209-03-0 4,6-dimethyl-2,1,3-benzothiadiazole 
• 7647-01-0 hydrogenchloride 
• 6417-44-3 2-(2,4-dimethyl-phenylazo)-4,6-dimethyl-aniline 

Downstream Products

• 4602-06-6 4,6-Dimethyl-2-phenyl-2,3-dihydro-1H-1,3,2-benzodiazaphosphol-2-oxid 
• 4600-23-1 4,6-Dimethyl-2-phenyl-2,3-dihydro-1H-1,3,2-benzodiaza-phosphol-2-sulfid 
• 111337-08-7 2,4-Bis-(4-chloro-phenyl)-2,6,8-trimethyl-2,3-dihydro-1H-benzo[b][1,4]diazepine 
• 111337-07-6 2,4-Bis-(4-ethoxy-phenyl)-2,6,8-trimethyl-2,3-dihydro-1H-benzo[b][1,4]diazepine 
• 73590-92-8 4,6-dimethylbenzimidazole-2-thione 
• 102308-68-9 4,6-dimethyl-1H-benzimidazol-2(3H)-one 

Relevant academic research and scientific papers

Synthetic method of 2-n-propyl-4-methylbenzimidazole-6-carboxylic acid

The invention relates to a synthetic method of 2-n-propyl-4-methylbenzimidazole-6-carboxylic acid. The synthetic method comprises the following steps: through nitric acid/concentrated sulfuric acid nitrification reaction of 3,5-dimethylnitrobenzene, generating an intermediate product II, namely 3,5-dimethyl-1,2-dinitrobenzene; performing Pd/C catalytic hydrogenation reaction on the intermediate product II in an ethanol solution to obtain an intermediate product III, namely 3,5-dimethyl-1,2-phenylenediamine; enabling the intermediate product III to react with N-butyric acid in a polyphosphoric acid solution to obtain an intermediate product IV, namely 2-n-propyl-4,6-dimethylbenzimidazole; performing cobalt salt air liquid-phase oxidation reaction on the intermediate product IV in an acetic acid solution to obtain a product V, namely the 2-n-propyl-4-methylbenzimidazole-6-carboxylic acid. The synthetic method provided by the invention has the benefits that the operation is simple, raw materials are easy to obtain, a used solvent can be recycled, the product content can reach 95 percent or above, the yield is up to 73.2 percent, the pollution is less, and the suitability for industrial production is realized.

A O-phenylenediamine and its derivatives of the preparation method

The invention relates to a method for synthesizing organic compounds, and provides a method for preparing o-phenylenediamine and a derivative of o-phenylenediamine, for solving the problems that the process route is complex, a great amount of byproducts can be generated and are hard to purify, the reaction condition is rigorous, the environment pollution is severe and the like in a conventional method for synthesizing o-phenylenediamine derivatives. The method disclosed by the invention comprises the following steps: by taking azobenzene and a derivative of the azobenzene as raw materials, synthesizing the o-nitro azobenzene and the derivative of the o-nitro azobenzene under the coactions of a catalyst, an oxidant and a nitrating agent, and further reducing by using a reducing agent, thereby obtaining the o-phenylenediamine and the derivative of the o-phenylenediamine. The method provided by the invention has the advantages that the raw materials are cheap and easy to obtain, the operation is simple, convenient and safe, the synthesis steps are short, the purification is simple, no great waste acid pollution is caused, and the like.

First demonstration of positive allosteric-like modulation at the human wild type translocator protein (TSPO)

We show that changing the number and position of nitrogen atoms in the heteroatomic core of a pyrazolopyrimidine acetamide is sufficient to induce complex binding to wild type human TSPO. Only compounds with this complex binding profile lacked intrinsic effect on glioblastoma proliferation but positively modulated the antiproliferative effects of a synthetic TSPO ligand. To the best of our knowledge this is the first demonstration of allosteric-like interaction at the wild type human TSPO.

Heterocyclic compounds as inhibitors of factor VIIa

The present invention relates generally to compounds that inhibit serine proteases. In particular it is directed to novel heterocyclic compounds, or a stereoisomer or pharmaceutically acceptable salt, solvate, or prodrug form thereof, which are useful as selective inhibitors of serine protease enzymes of the coagulation cascade; for example thrombin, factor VIIa, factor Xa, factor XIa, factor IXa, and/or plasma kallikrein. In particular, it relates to compounds that are factor VIIa inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of using the same.

BICYCLIC ANILIDE SPIROLACTAM CGRP RECEPTOR ANTAGONISTS

The present invention is directed to compounds of Formula (I): (where variables A1, A2, B, J, K, m, n, R4, R5a, R5b and R5c are as defined herein) useful as antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which the CGRP is involved, such as headache, migraine and cluster headache. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

A practical method for the reduction of 2,1,3-benzothiadiazoles to 1,2-benzenediamines with magnesium and methanol

A new and practical method for the reduction of 2,1,3-benzothiadiazoles to 1,2-benzenediamines with magnesium and methanol is described. Sensitive functional groups such as bromo, chloro, cyano, and ester are well tolerated under these new conditions.

Alkyl, azido, alkoxy, and fluoro-substituted and fused quinoxalinediones

Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia, and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease, and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions, and inducing anesthesia are disclosed by administering to an animal in need of such treatment an alkyl or azido-substituted 1,4-dihydroquinoxaline-2,3-dione or pharmaceutically acceptable salts thereof, which have high binding to the glycine receptor.

Synthesis and structure-activity relationships of 1,2,3,4- tetrahydroquinoline-2,3,4-trione 3-oximes: Novel and highly potent antagonists for NMDA receptor glycine site

A series of 1,2,3,4-tetrahydroquinoline-2,3,4-trione 3-oximes (QTOs) was synthesized and evaluated for antagonism of NMDA receptor glycine site. Glycine site affinity was determined using a [3H]DCKA binding assay in rat brain membranes and electrophysiologically in Xenopus oocytes expressing 1a/2C subunits of cloned rat NMDA receptors. Selected compounds were also assayed for antagonism of AMPA receptors in Xenopus oocytes expressing rat brain poly-(A)+ RNA. QTOs were prepared by nitrosation of 2,4- quinolinediols. Structure-activity studies indicated that substitutions in the 5-, 6-, and 7-positions increase potency, whereas substitution in the 8- position causes a decrease in potency. Among the derivatives evaluated, 5,6,7-trichloro-QTO was the most potent antagonist with an IC50 of 7 nM in the [3H]DCKA binding assay and a K(b) of 1-2 nM for NMDA receptors expressed in Xenopus oocytes. 5,6,7-Trichloro-QTO also had a K(b) of 180 nM for AMPA receptors in electrophysiological assays. The SAR of QTOs was compared with the SAR of 1,4-dihydroquinoxaline-2,3-diones (QXs). For compounds with the same benzene ring substitution pattern, QTOs were generally 5-10 times more potent than the corresponding QXs. QTOs represent a new class of inhibitors of the NMDA receptor which, when appropriately substituted, are among the most potent glycine site antagonists known.