54346-87-1

Basic information

• Product Name: 5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE
• Synonyms: 5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE;5-METHOXY-BENZOTHIAZOL-2-YLAMINE;5-methoxybenzothiazol-2-amine;2-Benzothiazolamine,5-methoxy-(9CI);5-methoxybenzo[d]thiazol-2-amine;5-Methoxy-2-benzothiazolamine;2-Amino-5-methoxybenzothiazole;5-Methoxy-1,3-benzothiazole-2-amine
• CAS NO: 54346-87-1
• Molecular Formula: C8H8N2OS
• Molecular Weight: 180.23
• EINECS: 259-118-8
• Product Categories: BENZOTHIAZOLE;Amines;Thiazoles, Isothiazoles &Benzothiazoles;Thiazoles, Isothiazoles & Benzothiazoles
• Mol File: 54346-87-1.mol

Chemical Properties

• Melting Point: 154 °C
• Boiling Point: 347.5 °C at 760 mmHg
• Flash Point: 163.9 °C
• Appearance: /
• Density: 1.359 g/cm³
• Vapor Pressure: 5.38E-05mmHg at 25°C
• Refractive Index: 1.704
• Storage Temp.: 2-8°C(protect from light)
• PKA: 4.53±0.10(Predicted)
• CAS DataBase Reference: 5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE(54346-87-1)
• EPA Substance Registry System: 5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE(54346-87-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 54346-87-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE is used as a building block for the synthesis of various heterocyclic compounds with potential biological activities. Its unique structure allows for the development of new drugs and biologically active molecules, contributing to the advancement of medicinal chemistry.
Used in Medicinal Chemistry:
5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE is used as an intermediate in the synthesis of new drugs and biologically active molecules. Its presence in the structure of these compounds can enhance their therapeutic properties and contribute to the discovery of novel pharmaceutical agents.
Used in Chemical Reactions:
5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE is used in chemical reactions such as amidation, acylation, and condensation due to the presence of the amino group. These reactions can lead to the formation of new compounds with potential applications in various fields, including pharmaceuticals and materials science.

InChI:InChI=1/C8H8N2OS/c1-11-5-2-3-7-6(4-5)10-8(9)12-7/h2-4H,1H3,(H2,9,10)

Upstream product

• 37014-08-7 3-methoxyphenylthiourea 
• 333-20-0 potassium thioacyanate 
• 536-90-3 m-Anisidine 
• 3425-46-5 potassium selenocyanate 
• 2942-14-5 5-methoxy-1,3-benzothiazole 
• 27191-09-9 m-anisidine hydrochloride 

Downstream Products

• 118526-19-5 5-hydroxy-1,3-benzothiazol-2-amine 
• 2941-72-2 6-methoxy-2-methylbenzothiazole 
• 73518-39-5 3-benzylidene-2-(5-methoxy-benzothiazol-2-yl)-2,3-dihydro-isoindol-1-one 
• 144065-28-1 4-<3-(7-methoxy imidazo<2,1-b>benzothiazolyl)>benzylphosphonate de diethyle 
• 6274-29-9 2-amino-5-methoxy-thiophenol 
• 14482-32-7 2-amino-4-methoxybenzenethiol 
• 1048025-71-3 C₁₆H₁₁N₃O₂S 

Relevant articles and documents

Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles

A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles

Novel Triapine Derivative Induces Copper-Dependent Cell Death in Hematopoietic Cancers

Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clinical trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematologic malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10) with potent antitumor activity. 10 Preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, 10 executed cytotoxic action in a copper-dependent manner. 10-Induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, 10 showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies compound 10 as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers.

Novel Triapine Derivative Induces Copper-Dependent Cell Death in Hematopoietic Cancers

Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clinical trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematologic malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10) with potent antitumor activity. 10 Preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, 10 executed cytotoxic action in a copper-dependent manner. 10-Induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, 10 showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies compound 10 as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers.

Neurodegenerative Therapies

The present invention provides a compound of formula (I) wherein: Y represents a C or N atom which may be substituted or form a cyclic group with R′″ but may not be a quaternary C atom; R′ is —OR1, —CONH2, —CF3, F, —OH, —NO2, —CN or —OCOR1 in which R1, is C1-3 alkyl and each may be in the beta or gamma position; R″ is C1-3 alkyl or H; and R′″ is H or a group consisting of 1-12 non-hydrogen atoms and may be linear, branched and/or incorporate one or more cyclic groups, cyclic groups may be aromatic and/or heterocyclic and 2 or more cyclic groups may be linked or fused and each may be substituted; or a salt, hydrate or solvate of a compound of formula (I) for use in the treatment or prevention of a neurodegenerative disorder by inhibiting formation of neurofibrillary (tau) tangles and/or by inhibiting Dyrk 1A. The invention further relates to non-therapeutic uses of these compounds.

Synthesis of thiazole linked indolyl-3-glyoxylamide derivatives as tubulin polymerization inhibitors

A series of thiazole linked indolyl-3-glyoxylamide derivatives were synthesized and evaluated for their in vitro cytotoxic activity against DU145 (prostate), PC-3 (prostate), A549 (lung) and HCT-15 (colon) cancer cell lines by employing the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among all the synthesized compounds, compound 13d displayed cytotoxicity of IC50 = 93 nM towards DU145 cancer cell line. The most active compound 13d was also tested on RWPE-1 cells and was found to be safe compared to the DU145 cells. The target compounds were also evaluated for their inhibition activity of tubulin polymerization. Further, the treatment of compound 13d on DU145 cells led to the inhibition of cell migration ability. The detailed studies such as acridine orange/ethidium Bromide (AO/EB), DAPI, annexin V-FITC/propidium iodide staining assay suggested that the compound 13d induced apoptosis in DU145 cells. The influence of the cytotoxic compound 13d on the cell cycle distribution was assessed on the DU145 cell line, exhibiting a cell cycle arrest at the G2/M phase. Moreover, the treatment with compound 13d caused collapse of mitochondrial membrane potential and elevated intracellular ROS levels in DU145 cells. The results from molecular modelling studies revealed that these compounds bind at the colchicine binding site of the tubulin. Thus, this new molecular scaffold could be a new lead for the development of anticancer agents that target tubulin.

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))

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.

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.

Imidazolothiazole compounds for the treatment of disease

Compounds, compositions and methods are provided for modulating the activity of receptor kinases and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder mediated by receptor kinases.

Mono azo dyes

The invention relates to novel azo dyestuffs of formula (I), the use of such compounds and/or mixtures for printing recording materials, especially paper or papery substrates, textile fibre materials, plastic films and plastic transparencies by the inkjet printing process and also to the recording materials printed thereby.