14779-17-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Methyl-2-aminobenzothiazole is used as a pharmacological agent for its anticancer, antimicrobial, anti-inflammatory, antiviral, and antioxidant properties. It is employed in the development of drugs that target various diseases and conditions, leveraging its diverse therapeutic effects.
Used in Dye Manufacturing:
5-Methyl-2-aminobenzothiazole is used as a chemical intermediate in the production of dyes. Its unique chemical structure contributes to the color and properties of the dyes, making it a valuable component in this industry.
Used in Research Applications:
5-Methyl-2-aminobenzothiazole is used as a research compound for studying its chemical properties and potential applications in various fields. It serves as a valuable tool for scientists and researchers to explore new avenues in chemistry and related disciplines.

InChI:InChI=1/C8H8N2S/c1-5-2-3-7-6(4-5)10-8(9)11-7/h2-4H,1H3,(H2,9,10)

Upstream product

• 2942-16-7 5-methylbenzo[d]thiazole 
• 21303-50-4 5-methylbenzo[d]thiazole-2(3H)-thione 
• 333-20-0 potassium thioacyanate 
• 108-44-1 1-amino-3-methylbenzene 
• 35350-31-3 4,4′-dimethyl-2,2′-dinitrodiphenyldisulfide 
• 1236074-30-8 2-iodo-1-isothiocyanato-4-methylbenzene 
• 1221902-70-0 N-(2-iodo-4-methylphenyl)thiourea 
• 591-50-4 iodobenzene 
• 17356-08-0 thiourea 
• 591-24-2 3-Methylcyclohexanone 
• 638-03-9 m-toluidine hydrochloride 
• 1147550-11-5 ammonium thiocyanate 
• 13194-69-9 2-iodo-5-methylaniline 
• 17614-74-3 (4-methyl-2-nitrophenyl)isothiocyanate 

Downstream Products

• 1819-87-0 1-(5-methyl-benzothiazol-2-yl)-3-p-tolyl-thiourea 
• 5923-83-1 1-benzyl-3-(5-methyl-benzothiazol-2-yl)-thiourea 
• 108718-00-9 1-(5-methyl-benzothiazol-2-yl)-3-phenyl-urea 
• 5923-76-2 1-(4-chloro-phenyl)-3-(5-methyl-benzothiazol-2-yl)-thiourea 
• 3323-84-0 N-(6-methylbenzothiazol-2-yl)-2-chloroacetamide 
• 1819-83-6 1-(4-methoxy-phenyl)-3-(5-methyl-benzothiazol-2-yl)-thiourea 
• 1819-82-5 1-(4-ethoxy-phenyl)-3-(5-methyl-benzothiazol-2-yl)-thiourea 
• 63205-33-4 5-methyl-2-(5-methyl-benzothiazol-2-ylimino)-3-p-tolyl-thiazolidin-4-one 
• 1819-88-1 1-(5-methyl-benzothiazol-2-yl)-3-m-tolyl-thiourea 
• 1819-85-8 1-(4-bromo-phenyl)-3-(5-methyl-benzothiazol-2-yl)-thiourea 
• 53004-76-5 6-methyl-benzothiazole-2-diazonium; hydroxide 
• 31183-81-0 2-amino-4-methyl-benzenethiol 
• 5923-75-1 N-(5-methyl-benzothiazol-2-yl)-N'-p-tolyl-guanidine 
• 6025-31-6 N-benzyl-N'-(5-methyl-benzothiazol-2-yl)-guanidine 

Relevant academic research and scientific papers

ANTIBIOTIC COMPOUNDS, PHARMACEUTICAL FORMULATIONS THEREOF AND METHODS AND USES THEREFOR

The present invention relates to compounds of formula (I) wherein G1 to G8 are as defined herein. The compounds are PK inhibitors and as such represent a new approach to treating pathogenic infections, including multidrug resistant pathogens. Disclosed herein are the compounds of formula (I), pharmaceutical compositions comprising the compounds of formula (I) and their use in the treatment of antimicrobial infection. (Formula (1))

Synthesis of 2-arylthio arylcyanamides from 2-iodoaryl isothiocyanates: Via a one-pot three-component reaction

A one-pot three-component reaction has been described for the synthesis of substituted 2-arylthio arylcyanamides. A cheap and readily available iron source was used as a catalyst for this reaction. Consecutive addition and domino C-S cross-coupling reacti

Probing the ATP-Binding Pocket of Protein Kinase DYRK1A with Benzothiazole Fragment Molecules

DYRK1A has emerged as a potential target for therapies of Alzheimer's disease using small molecules. On the basis of the observation of selective DYRK1A inhibition by firefly d-luciferin, we have explored static and dynamic structural properties of fragment sized variants of the benzothiazole scaffold with respect to DYRK1A using X-ray crystallography and NMR techniques. The compounds have excellent ligand efficiencies and show a remarkable diversity of binding modes in dynamic equilibrium. Binding geometries are determined in part by interactions often considered "weak", including "orthogonal multipolar" types represented by, for example, F-CO, sulfur-aromatic, and halogen-aromatic interactions, together with hydrogen bonds that are modulated by variation of electron withdrawing groups. These studies show how the benzothiazole scaffold is highly promising for the development of therapeutic DYRK1A inhibitors. In addition, the subtleties of the binding interactions, including dynamics, show how full structural studies are required to fully interpret the essential physical determinants of binding.

Efficient and facile protocol for one-pot synthesis of 2-amino-substituted benzothiazoles catalyzed by nano-BF3/SiO2 under mild conditions

Abstract: A highly efficient and simple protocol for the preparation of 2-aminobenzothiazoles through the reaction of potassium thiocyanate and substituted anilines in the presence of nano-BF3/SiO2 as a reusable heterogeneous catalyst is described. In this method, all of the 2-amino-substituted benzothiazoles were obtained in high to excellent yields and short reaction times under mild conditions. The structures of the resulting products were characterized and confirmed by melting point, FT-IR, 1H NMR and 13C NMR techniques. Graphical Abstract: A highly efficient and simple protocol for the preparation of 2-aminobenzothiazoles by reaction of potassium thiocyanate and substituted anilines in the presence of nano-BF3/SiO2 as a reusable heterogeneous catalyst is described.[Figure not available: see fulltext.]

Metal-free synthesis of 2-aminobenzothiazoles via aerobic oxidative cyclization/dehydrogenation of cyclohexanones and thioureas

A metal-free process for the synthesis of 2-aminobenzothiazoles from cyclohexanones and thioureas has been developed using catalytic iodine and molecular oxygen as the oxidant under mild conditions. Various 2-aminobenzothiazoles, 2-aminonaphtho[2,1-d]thiazoles, and 2-aminonaphtho[1,2-d] thiazoles were prepared via this method in satisfactory yields.

QSAR modeling of synthesized 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potent antibacterial agents

Present communication elicits the designing and synthesis of 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potential antibacterial agents. A number of substituted 2-amino benzothiazoles, 2-amino-5-[(E)-phenyl diazenyl] benzoic acid, and 2-phenyl-4H benzo[d] [1,3] oxazin-4-one were synthesized as the precursor substrates. The compounds were synthesized in excellent yields and the structures were corroborated on the basis of IR, 1H NMR, Mass, and elemental analysis data. These compounds were screened in vitro for their antibacterial activity against a representative panel of Gram positive and Gram negative bacteria and models were generated through quantitative structure-activity relationship (QSAR).The activity contributions due to structural and substituent effects were determined using sequential regression procedure. The antimicrobial assay data show that the synthesized compounds are found to manifest profound antimicrobial activity. Springer Science+Business Media, LLC 2011.

Design and synthesis of new derivatives of 3H-quinazolin-4-one as potential anticonvulsant agents

As a part of systematic investigation on synthesis and biological activities, some new derivatives of 2-ethyl-3-(substituted benzothiazole- 2′-yl)-[3H]-quinazolin-4-ones 3 have been synthesized, and the structures of the compounds were confirmed by elemental analysis and spectral data. The newly synthesized derivatives are then screened for anticonvulsant activity by maximal electroshock method. Copyright

Synthesis and antimicrobial activity of new pyridine derivatives-I

2-Amino substituted benzothiazoles 2a-l and 2-chloropyridine-3-carboxylic acid 3 were used to prepare 2-[N-(substitutedbenzothiazolyl)amino]pyridine-3- carboxylic acids (4a-l) in 2-ethoxy ethanol. Acid chlorides (5a-l) were condensed with 2-hydroxyethyl piperazine (6) and 2,3-dichloropiperazine (7) to prepare amide derivatives 2-[N-(substituted benzothiazolyl)amino]pyridin-3-yl (4-(2-hydroxyethyl)piperazin-1-yl)methanones (8a-l) and 2-[N-(substituted benzothiazolyl) amino]pyridin-3-yl(2,3- dichloropiperazine-1-yl)methanones (9a-l), respectively. The structures of new compounds have been established on the basis of elemental analysis and spectral (IR, 1H NMR, and Mass spectra) studies. The in vitro antimicrobial activity was screened for all the synthesized compounds. Variable and modest activity were observed against the investigated strains of bacteria and fungi. Springer Science+Business Media, LLC 2010.

Synthesis and antimicrobial studies of new pyridine derivatives

2-(p-Acetylaminobenzenesulfonylamido)-substituted benzothiazoles were prepared from 2-amino-substituted benzothiazoles and p-acetamidobenzenesulfonyl chloride using a mixture of pyridine and Ac2O, which formed an electrophilic N-acetyl- pyridinium complex facilitating condensation to give the desired products by removal of HCl. 2-[4-(Substituted benzothiazol-2-yl) aminosulfonylanilino]pyridine-3-carboxylic acids (synthesized from 2-chloropyridine-3-carboxylic acid and the corresponding substituted 2-(p-aminobenzenesulfonylamido)benzothiazole in 2-ethoxyethanol using Cu-powder and K2CO3) were then converted to acid chlorides, which on further reaction with piperazine and 4-methoxyphenylpiperazine yielded the corresponding 2-[4-(substituted benzothiazol-2-yl)amino-sulfonyl]anilino-3- (piperazinocarbonyl) pyridine and 2-[4-(substituted benzothiazol-2-yl)amino- sulfonyl]anilino-3-[(4-methoxyphenyl)piperazin-1-yl-carbonyl]pyridine. The structures of the new compounds have been established on the basis of their elemental analyses as well as IR, 1H NMR, and mass-spectral data. All the compounds have been screened for antimicrobial activity and found to possess considerable antibacterial activity.

Synthesis and in vivo diuretic activity of biphenyl benzothiazole-2- carboxamide derivatives

A series of N-{(substituted)1,3-benzothiazol-2-yl}-1,1'-biphenyl-4- carboxamides was synthesized by reaction between biphenyl acid chloride and 2-aminobenzothiazole. The synthesized compounds were screened in vivo for diuretic activity. Among the series, N-(1,3-benzothiazol-2-yl)-1,1'-biphenyl-4- carboxamide (II) was found to be the most promising candidate.