92-36-4

Usage

General Description

Light tan or light orange powder. Solutions have a violet-blue fluorescence.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-(6-Methyl-2-benzothiazolyl)benzeneamine is incompatible with strong oxidizing agents, acid chlorides and acid anhydrides.

Fire Hazard

Flash point data for 4-(6-Methyl-2-benzothiazolyl)benzeneamine are not available; however, 4-(6-Methyl-2-benzothiazolyl)benzeneamine is probably combustible.

InChI:InChI=1/C14H12N2S/c1-9-2-7-12-13(8-9)17-14(16-12)10-3-5-11(15)6-4-10/h2-8H,15H2,1H3

Upstream product

• 106-49-0 p-toluidine 
• 102-08-9 N,N-diphenylthiourea 
• 621-01-2 N,N'-Bis(p-tolyl)thiourea 
• 62-53-3 aniline 
• 1145-66-0 1-(4-methylphenyl)-3-phenylthiourea 
• 79560-96-6 N-(4-amino-benzyl)-p-toluidine 
• 150-13-0 4-amino-benzoic acid 
• 23451-96-9 2-amino-5-methylthiophenol 
• 488722-57-2 6-methyl-2-(4'-nitrophenyl)-1,3-benzothiazole 
• 3622-19-3 2-bromo-6-methylbenzothiazole 
• 214360-73-3 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline 
• 2536-91-6 6-methylbenzothiazol-2-ylamine 
• 31183-91-2 2-[(2-amino-5-methylphenyl)dithio]-4-methylphenylamine 

Downstream Products

• 299164-58-2 N-[4-(6-methyl-benzothiazol-2-yl)-phenyl]-phthalamic acid 
• 2390-54-7 thioflavine T 
• 67229-93-0 4-(6-methyl-2-benzothiazolyl)phenyl isocyanate 
• 32752-83-3 [4-(6-methyl-benzothiazol-2-yl)-anilino]-methanesulfonic acid ; sodium-salt 
• 95856-69-2 formic acid-[4-(6-methyl-benzothiazol-2-yl)-anilide] 
• 10205-63-7 N,N-diethyl-4-(6-methylbenzo[d]thiazol-2-yl)aniline 
• 82654-96-4 N-benzylidene-4-(6-methyl-benzothiazol-2-yl)-aniline 
• 95856-79-4 N-[4-(6-methyl-1,3-benzothiazol-2-yl)phenyl]benzamide 
• 65175-38-4 N-(4-dimethylamino-benzylidene)-4-(6-methyl-benzothiazol-2-yl)-aniline 
• 339223-67-5 4-nitro-benzenesulfonic acid-[4-(6-methyl-benzothiazol-2-yl)-anilide] 
• 10205-62-6 N,N-dimethyl-4-(6-methylbenzo[d]thiazole-2-yl)aniline 
• 47070-20-2 [2-(4-(dimethylamino)phenyl)-3,6-dimethylbenzo[d]thiazol-3-ium] iodide 
• 17205-68-4 bis-[4-(6-methyl-benzothiazol-2-yl)-phenyl]-diazene 
• 106-49-0 p-toluidine 

Relevant academic research and scientific papers

Discovery and Characterization of Benzimidazole Derivative XY123 as a Potent, Selective, and Orally Available RORγ Inverse Agonist

Receptor-related orphan receptor γ (RORγ) has emerged as an attractive therapeutic target for the treatment of cancer and inflammatory diseases. Herein, we report our effort on the discovery, optimization, and evaluation of benzothiazole and benzimidazole derivatives as novel inverse agonists of RORγ. The representative compound27h(designated as XY123) potently inhibited the RORγ transcription activity with a half-maximal inhibitory concentration (IC50) value of 64 nM and showed excellent selectivity against other nuclear receptors.27halso potently suppressed cell proliferation, colony formation, and the expression of androgen receptor (AR)-regulated genes in AR-positive prostate cancer cell lines. In addition,27hdemonstrated good metabolic stability and a pharmacokinetic property with reasonable oral bioavailability (32.41%) and moderate half-life (t1/2= 4.98 h). Significantly, oral administration of compound27hachieved complete and long-lasting tumor regression in the 22Rv1 xenograft tumor model in mice. Compound27hmay serve as a new valuable lead compound for further development of drugs for the treatment of prostate cancer.

1-Phenyl-: N -(benzothiazol-2-yl)methanimine derivatives as Middle East respiratory syndrome coronavirus inhibitors

Middle East respiratory syndrome coronavirus (MERS-CoV) poses a serious threat to human health, and currently there are no effective or specific therapies available to treat it. Herein a series of 1-phenyl-N-(benzothiazol-2-yl)methanimine derivatives with inhibitory activity against MERS-CoV are described. The compound 4f with a 50% inhibition concentration value of 0.09 μM is a promising inhibitor that warrants further evaluation, towards the development of potential anti-MERS-CoV drugs. This journal is

Discovery of Small Molecules that Induce the Degradation of Huntingtin

Huntington's disease (HD) is an autosomal dominant neurodegenerative disorder caused by the aggregation of mutant huntingtin (mHtt), and removal of toxic mHtt is expected to be an effective therapeutic approach. We designed two small hybrid molecules (1 and 2) by linking a ligand for ubiquitin ligase (cellular inhibitor of apoptosis protein 1; cIAP1) with probes for mHtt aggregates, anticipating that these compounds would recruit cIAP1 to mHtt and induce selective degradation by the ubiquitin-proteasome system. The synthesized compounds reduced mHtt levels in HD patient fibroblasts and appear to be promising candidates for the development of a treatment for HD.

A water-soluble benzo thiazole synthesis of dye method

The present invention discloses a water-soluble benzothiazole dye synthesis method, which comprises: mixing p-toluidine, sodium sulfide and a catalyst, carrying out a cyclization reaction to produce 2-(4-anilino)-6-methyl-benzothiazole, carrying out a sulfonation reaction on the 2-(4-anilino)-6-methyl-benzothiazole and a sulfonation agent to produce 2-(4-anilino)-6-methyl-7-sulfonic-benzothiazole, adding the 2-(4-anilino)-6-methyl-7-sulfonic-benzothiazole (III) and a sodium hydroxide aqueous solution to a solvent, adding a carbonyl-containing compound, and carrying out a reaction to obtain the water-soluble benzothiazole dye. Compared with the synthesis method in the prior art, the synthesis method of the present invention has characteristics of cheap and readily available raw materials, simple process, safety and environmental protection, and is suitable for large-scale industrial production.

Synthesis of 2-(4-aminophenyl)benzothiazoles using MF resin supported H+ under solvent free conditions

Abstract A simple and convenient approach to 2-(4-aminophenyl)benzothiazole derivatives by condensation of o-aminothiophenol with (un)substituted p-aminobenzoic acid under the action of melamine formaldehyde resin (MFR) supported sulfuric acid under microwave irradiation (MW) and solvent-free conditions has been developed. Structures of the corresponding products were elucidated by IR, 1H NMR spectra, and elemental analysis. The resin could be easily recovered and reused for subsequent reactions.

Synthesis of 2-(4-aminophenyl) benzothiazole derivatives and use thereof

The present invention provides a method of preparing a compound of formula 6 comprising: (a) reacting a compound of formula 1 with a compound of formula 2 to form a compound of formula 3 wherein X of formula 2 is Cl or OH; (b) treating the compound formula 3 with Lawesson's reagent to form a compound of formula 4 (c) reacting a compound of formula 4 with potassium ferricyanide to produce a compound of formula 5 and (d) performing catalytic reduction of nitro group of the compound of formula 5 with palladium on charcoal to generate the compound of formula 6, wherein R1 of formulae 1-6 is H, C1-10 alkyl, C1-10 alkoxy or C1-10 haloalkyl, and R2 of formulae 1-6 is H or C1-10 alkyl. The present invention also provides a photodynamic therapy to a patient having at least one tumor comprising the steps of: administering a compound of formula 6 (wherein R1 and R2 are defined as the above) in a pharmaceutically acceptable carrier to the patient; waiting for a sufficient time to allow the administered compound to be taken up by a target tissue having the at least one tumor; and irradiating a region of the patient containing the target tissue; wherein growth of the tumor is inhibited.

Straightforward synthesis of PET tracer precursors used for the early diagnosis of Alzheimers disease through Suzuki-Miyaura cross-coupling reactions

In positron emission tomography [11C]PIB, Pittsburgh Compound-B, is currently the most widely used radiopharmaceutical for the early diagnosis of Alzheimer's disease. Synthetic routes for the preparation of the precursor of [11C]PIB are reported in the literature. These strategies require multiple steps and the use of protecting groups. This paper describes a simple one-step synthesis of the precursor of [11C]PIB through a Suzuki-Miyaura coupling reaction using thermal conditions or microwave activation. These methods were successfully applied to the synthesis of various 2-arylbenzothiazole and 2-pyridinylbenzothiazole compounds including [ 18F] precursor derivatives of PIB containing a nitro function.

SYNTHESIS OF 2-(4-AMINOPHENYL) BENZOTHIAZOLE DERIVATIVES AND USE THEREOF

The present invention provides a method of preparing a compound of formula 6 comprising: (a) reacting a compound of formula 1 with a compound of formula 2 to form a compound of formula 3 wherein X of formula 2 is Cl or OH; (b) treating the compound formula 3 with Lawesson's reagent to form a compound of formula 4 (c) reacting a compound of formula 4 with potassium ferricyanide to produce a compound of formula 5 and (d) performing catalytic reduction of nitro group of the compound of formula 5 with palladium on charcoal to generate the compound of formula 6, wherein R1 of formulae 1-6 is H, C1-10 alkyl, C1-10 alkoxy or C1-10 haloalkyl, and R2 of formulae 1-6 is H or C1-10 alkyl. The present invention also provides a photodynamic therapy to a patient having at least one tumor comprising the steps of: administering a compound of formula 6 (wherein R1 and R2 are defined as the above) in a pharmaceutically acceptable carrier to the patient; waiting for a sufficient time to allow the administered compound to be taken up by a target tissue having the at least one tumor; and irradiating a region of the patient containing the target tissue; wherein growth of the tumor is inhibited.

Synthesis, and biological evaluation of 2-(4-aminophenyl)benzothiazole derivatives as photosensitizing agents

Photodynamic therapy (PDT) employing exogenous photosensitizers is currently being approved for treatment of basal cell carcinoma (BCC). 2-(4-Aminophenyl)benzothiazoles (6) consist of chromophoric structure and absorb light in the UVA (315-400 nm). These results encouraged us to design and synthesize a diversity of 2-phenylbenzothiazoles (6). Studies on the apoptotic mechanism involved in photosensitive effects induced by UVA-activated 6 in BCC cells are carried out in the present article. 6-UVA-treated cells displayed several features of apoptosis, including an increase in the sub-G1 population, a significantly increased annexin V binding, and activation of caspase-3. 6-UVA induced a decrease in mitochondrial membrane potential (Δψ mt) and ATP via enhanced ROS generation and promoted phosphorylation of extracellular signal-regulated kinase (ERK) and p38 MAPK expression. These results suggest that 6-UVA elicits photosensitive effects in mitochondria processes which involve ERK and p38 activation, and ultimately lead to BCC cell apoptosis.

Evaluation of Re and 99mTc complexes of 2-(4′-aminophenyl) benzothiazole as potential breast cancer radiopharmaceuticals

The synthesis of M(I)(CO)3(NNO) (M = Re, 99mTc) complexes conjugated to the antitumor agent 2-(4′-aminophenyl) benzothiazole and to its 6-methyl derivative, as well as their in vitro and in vivo biological evaluation as breast cancer radiopharmaceuticals, is reported. The Re complexes displayed under the fluorescence microscope clear uptake by the sensitive to the 2-(4′-aminophenyl)benzothiazole pharmacophore breast cancer cell lines MCF-7 and T47D, while uptake by less sensitive lines and by normal fibroblasts was much weaker. In accordance, uptake of the corresponding radioactive 99mTc complexes was clearly higher in the breast cancer cell lines MCF-7 and MDA-231 compared to normal fibroblasts. Biodistribution of the 99mTc complexes in SCID mice bearing MCF-7 xenografts showed appreciable tumor uptake. A tumor/muscle ratio of 2.2 was measured for the complex conjugated to 2-(4′-aminophenyl)benzothiazole that led to successful tumor imaging. The results render the 2-(4′-aminophenyl) benzothiazole complexes potential candidates for imaging (99mTc) and targeted radiotherapy (188Re) of breast cancer.