2454-39-9

Usage

Uses

Used in Chemical Synthesis:
2-AMINO-THIOBENZAMIDE is used as a chemical intermediate for the production of 2-trifluoromethyl-3H-quinazoline-4-thione. This synthesis process involves heating the compound in the presence of reagent molecular sieves and solvent CHCl3 for a reaction time of 2 hours.
Used in Agrochemicals:
2-AMINO-THIOBENZAMIDE is used as an intermediate in the agrochemical industry, contributing to the development of various agricultural chemicals that help in pest control, crop protection, and overall improvement of crop yield.
Used in Pharmaceuticals:
In the pharmaceutical industry, 2-AMINO-THIOBENZAMIDE is utilized as a key intermediate for the synthesis of various drugs. Its unique chemical structure allows it to be a building block in the development of new medications with potential therapeutic applications.
Used in Dyestuff:
The dyestuff industry also benefits from the use of 2-AMINO-THIOBENZAMIDE as an intermediate. It plays a role in the production of different types of dyes, which are essential for coloring fabrics, plastics, and other materials in various applications.

InChI:InChI=1/C7H8N2S/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H2,9,10)

Upstream product

• 1885-29-6 anthranilic acid nitrile 
• 612-24-8 o-nitrobenzonitrile 
• 28144-70-9 anthranilic acid amide 
• 7783-06-4 hydrogen sulfide 
• 7664-41-7 ammonia 
• 100698-06-4 2-mercapto-2-thioxo-2,3-dihydro-1H-2λ⁵-benzo[1,3,2]diazaphosphinine-4-thione pyridinium salt 
• 100698-05-3 2,3-dihydro-2-mercapto-2,1,3-benzophosphadiazine-4(1H)-thione 2-sulphide 

Downstream Products

• 6484-28-2 2-methyl-4(3H)-quinazolinethione 
• 91760-82-6 2,2-dimethyl-2,3-dihydro-1H-quinazoline-4-thione 
• 2536-88-1 3H-benzo[1,2,3]triazine-4-thione 
• 37802-50-9 [2-(2-amino-phenyl)-4-oxo-4H-thiazol-5-ylidene]-acetic acid methyl ester 
• 793716-07-1 4-imino-1,4-dihydro-benzo[d][1,3]thiazine-2-thione 
• 33759-66-9 2-oxo-2,3-dihydro-1H-2λ⁴-benzo[1,2,6]thiadiazine-4-thione 
• 153076-83-6 2-methyl-1-oxo-5-thioxo-1,2,3,3a,4,5-hexahydropyrrolo<1,2-a>quinazoline 
• 76164-70-0 Ethyl 3-(2-Thiocarbamoylanilino)methylene-2,4-dioxovalerate 
• 35982-23-1 2-(trifluoromethyl)-4(3H)-quinazolinethione 
• 59525-07-4 4-methyl-N-(2-thiocarbamoyl-phenyl)-benzamide 
• 59525-09-6 4-chloro-N-(2-thiocarbamoyl-phenyl)-benzamide 
• 59525-08-5 4-methoxy-N-(2-thiocarbamoyl-phenyl)-benzamide 
• 396716-17-9 3-nitro-N-(2-thiocarbamoyl-phenyl)-benzamide 

Relevant academic research and scientific papers

Anithiactins A-C, modified 2-phenylthiazoles from a mudflat-derived streptomyces sp.

Intensive investigation of the chemical components of a Streptomyces sp. isolated from mudflat sediments collected on the southern coast of the Korean peninsula led to the isolation of three new compounds, anithiactins A-C (1-3). The chemical structures of anithiactins A and C were determined by interpretation of NMR data analyses, while the chemical structure of anithiactin B was established from a combination of NMR spectroscopic and crystallographic data analyses. The structure of anithiactin A was also confirmed by total synthesis. These three anithiactins displayed moderate acetylcholinesterase inhibitory activity with no significant cytotoxicity.

Evaluation of thioamides, thiolactams and thioureas as hydrogen sulfide (H2S)donors for lowering blood pressure

Hydrogen sulfide (H2S)is a biologically important gaseous molecule that exhibits promising protective effects against a variety of pathological processes. For example, it was recognized as a blood pressure lowering agent. Aligned with the need for easily modifiable platforms for the H2S supply, we report here the preparation and the H2S release kinetics from a series of structurally diversified thioamides, thiolactams and thioureas. Three different thionation methods based on the usage of a phosphorus pentasulfide and Lawesson reagent were applied to prepare the target thioamides and thiolactams. Furthermore, obtained H2S donors were evaluated both in in vivo and in vitro studies. The kinetic parameters of the liberating H2S was determined and compared with NaHS and GYY4137 using two different detection technics i.e.; fluorescence labeling 7-azido-4-methyl-2H-chromen-2-one and 5,5‘-dithiobis (2-nitrobenzoic acid), sulfhydryl probe, also known as the Ellman's reagent. We have proved that the amount of releasing H2S from these compounds is controllable through structural modifications. Finally, the present study shows a hypotensive response to an intravenous administration of the developed donors in the anesthetized rats.

3D-QSAR assisted identification of FABP4 inhibitors: An effective scaffold hopping analysis/QSAR evaluation

Following on the recent publication of pharmacologically relevant effects, small molecule inhibitors of adipocyte fatty-acid binding protein 4 (FABP4) have attracted high interest. FABP4 is mainly expressed in macrophages and adipose tissue, where it regulates fatty acid storage and lipolysis, being also an important mediator of inflammation. In this regard, FABP4 recently demonstrated an interesting molecular target for the treatment of type 2 diabetes, other metabolic diseases and some type of cancers. In the past years, hundreds of effective FABP4 inhibitors have been synthesized. In this paper, a quantitative structure-activity relationship (QSAR) model has been produced, in order to predict the bioactivity of FABP4 inhibitors. The methodology has been combined with a scaffold-hopping approach, allowing to identify three new molecules that act as effective inhibitors of this protein. These molecules, synthesized and tested for their FABP4 inhibitor activity, showed IC50 values between 3.70 and 5.59 μM, with a high level of agreement with the predicted values.

Method for synthesizing thiobenzamide derivative through CO2 regulation and control of substituted benzonitrile

The invention discloses a method for synthesizing a thiobenzamide derivative through CO2 regulation and control of substituted benzonitrile. The method comprises the following steps: taking the substituted benzonitrile as a raw material, an inorganic sulfide as a sulfur source and CO2 as an auxiliary agent for reacting in the presence of a reaction solvent, and concentrating and purifying a reaction solution to obtain the thiobenzamide derivative. The reaction system disclosed by the invention is relatively simple, other catalysts are not added outside a reactant and the inorganic sulfide, themethod is suitable for synthesis of high-additional-value thiobenzamide containing a plurality of substituent groups, the reaction is carried out at low temperature and low pressure, and the risk coefficient is reduced.

One-Pot Synthesis of 5-Hydroxy-4H-1,3-thiazin-4-ones: Structure Revision, Synthesis, and NMR Shift Dependence of Thiasporine A

An annulation of arylthioamides with 3-bromopyruvic acid chloride to 5-hydroxy-4H-1,3-thiazin-4-ones has been developed. The initial condensation affords two regioisomeric thiazolinone intermediates in a temperature-dependent manner. The synthesis of the 2-aminophenylthiazinone derivative led to the revision of the previously proposed structure of thiasporine A. Synthesis of the revised structure and NMR analysis revealed that thiasporine A had been isolated as a carboxylate.

Catalyst-free synthesis of 2-aryl-1,2-dihydro-quinazolin-4(1H)-thiones from 2-aminobenzothio-amides and aldehydes in water

2-Dihydroquinazolin-4(1H)-thiones were prepared in up to excellent yields from 2-aminobenzothioamides and aldehydes. The reaction is carried out in water without the use of any catalyst or promoter. The sulfur-containing substrate can be obtained easily by thiation of the corresponding nitrile by solid sodium hydrosulfide.

2-CYCLOQUINAZOLINE DERIVATIVES AND METHODS OF USE THEREOF

Provided herein are 2-cycloquinazoline compounds for treatment of JAK kinase mediated diseases, including JAK2 kinase-, JAK3 kinase- or TYK2 kinase- mediated diseases. Also provided are pharmaceutical compositions comprising the compounds and methods of using the compounds and compositions.

Copper(I) bromide-mediated synthesis of novel 2-arylthiazole-5-carboxylates from α-diazo-β-keto esters and aromatic thioamides

Starting from readily available α-diazo-β-keto esters 8 and aromatic primary thioamides 9 and 14, a simple synthesis of 2-aryl 4-substituted thiazole-5-carboxylate derivatives of type 10 and 16 has been accomplished. The method is based on the efficient catalysis of CuBr, which promotes the formation of the corresponding carbenoids 11 from diazo derivatives 8. These Cu-carbenoids 11 react with the thiocarbonyl group of the primary thioamides to afford presumably intermediates of the general type 12, which by subsequent cyclocondensation furnish the title thiazole derivatives.

Synthesis of substituted 2-benzoylaminothiobenzamides and their ring closure to substituted 2-phenylquinazoline-4-thiones

Acylation of 2-aminothiobenzamide or 2-methylaminothiobenzamide with substituted benzoyl chlorides has been used to synthesise the corresponding 2-benzoyl-aminothiobenzamides whose subsequent sodium methoxide-catalysed ring closure gives the corresponding quinazoline-4-thiones. These compounds were characterised by means of their 1H- and 13C-NMR spectra. The preferred tautomeric form of selected compounds has been discussed on the basis of their 13C-NMR, IR and Raman spectra. It has been found that in the given medium 1-methyl-quinazoline-4-thiones undergo a replacement of the sulphur substituent by oxygen giving 1-methyl-quinazoline-4-ones. In strong acid media, 2-benzoylaminothiobenzamide is cyclised through its sulphur atom to give 2-phenylbenzo[d-1,3]thiazin-4-one.

Reactions of 2-aminothiobenzamide with isocyanates: A new synthesis of 2,3-dihydroimidazo[1,2-c]quinazolin-5(6H)-one and 3,4-dihydro-2H-pyrimido[1,2-c]quinazolin-6(7H)-one

2-(2-Chloroethylureido)- and 2-(3-chloropropylureido)thiobenzamides 5a,b were prepared in good yields by treating 2-aminothiobenzamide with 2-chloroethyl and 3-chloropropyl isocyanates respectively. Subsequent treatment of compound 5a and 5b either with alkali or mineral acid led to the formation of 2,3-dihydro-imidazo[1,2-c]quinazolin-5(6H)-one 7a and 3,4-dihydro-2H-pyrimido[1,2-c]quinazolin-6(7H)-one 7b.