178804-18-7

Basic information

• Product Name: 6-OH-BTA-0
• Synonyms: 6-benzothiazolol, 2-(4-aminophenyl)-
• CAS NO: 178804-18-7
• Molecular Formula: C₁₃H₁₀N₂OS
• Molecular Weight: 242.2963
• Mol File: 178804-18-7.mol

Chemical Properties

• Boiling Point: 488.8 °C at 760 mmHg
• Flash Point: 249.4 °C
• Appearance: /
• Density: 1.406 g/cm³
• CAS DataBase Reference: 6-OH-BTA-0(CAS DataBase Reference)
• NIST Chemistry Reference: 6-OH-BTA-0(178804-18-7)
• EPA Substance Registry System: 6-OH-BTA-0(178804-18-7)

Safety Data

• Hazardous Substances Data: 178804-18-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellowish solid

Upstream product

• 43036-17-5 2-(4-aminophenyl)-6-methoxybenzothiazole 
• 122-04-3 4-nitro-benzoyl chloride 
• 104-94-9 4-methoxy-aniline 
• 808755-67-1 6-hydroxy-2-bromo-benzothiazole 
• 214360-73-3 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline 
• 1747-60-0 6-methoxybenzothiazol-2-ylamine 
• 89415-43-0 (4-aminophenyl)boronic acid 
• 2941-58-4 2-bromo-6-methoxy-1,3 benzothiazole 
• 62-23-7 4-nitro-benzoic acid 
• 73702-95-1 N-(4-methoxyphenyl)-4-nitrothiobenzamide 
• 43036-14-2 6-methoxy-2-(4-nitrophenyl)benzothiazole 
• 24730-11-8 N-(4-methoxyphenyl)-4-nitrobenzamide 

Downstream Products

• 566170-04-5 N-methyl[11C]2-(4'-methylaminophenyl)-6-hydroxybenzathiazole 
• 1197241-40-9 2-(4-aminophenyl)-6-(3-p-tosyloxypropoxy)-1,3-benzothiazole 
• 1563187-74-5 C₁₉H₁₉⁽¹⁸⁾FN₂O₅S 
• 1563187-70-1 C₁₉H₁₉FN₂O₅S 
• 1301256-39-2 2-(4-(N-methyl-N-tert-butoxycarbonylamino)phenyl)benzo[d]thiazol-6-ol 
• 1240379-78-5 6-(3-fluoropropoxy)-2-(4-aminophenyl)-1,3-benzothiazole 

Relevant articles and documents

TARGETED ABERRANT ALPHA-SYNUCLEIN SPECIES AND INDUCED UBIQUITINATION AND PROTEOSOMAL CLEARANCE VIA CO-RECRUITMENT OF AN E3-LIGASE SYSTEM

Disclosed are bispecific compounds (degraders) that target α-synuclein protein for degradation. Also disclosed are pharmaceutical compositions containing the degraders and methods of using the compounds to treat neurodegenerative diseases.

Synthesis of 2-arylbenzothiazoles via direct condensation between in situ generated 2-aminothiophenol from disulfide cleavage and carboxylic acids

In this work we describe a simple and efficient general methodology for 2-arylbenzothiazole preparation employing disulfides and carboxylic acids. The reaction is promoted by tributylphosphine that acts both in disulfide bond cleavage and as activating agent for coupling with carboxylic acids. The reaction scope was studied using bis(2-aminophenyl)disulfide and different carboxylic acids with donor/withdrawing substituents, which resulted in the desired 2-arylbenzothiazole with moderate to good yields. The method was tested with success in preparation of the amyloid probe 2-(4-aminophenyl)-6-methoxybenzothiazole that employed a substituted bis(2-aminophenyl)disulfide.

For nerve degenerative disease is in the field of PET imaging agent precursor and the standard method for the synthesis of (by machine translation)

A novel PET imaging agent precursor and standard and its preparation method, in order to 4-nitro cinnamic aldehyde, the methoxylphenylboronic ethylamine as a reaction initiator, synthesis of the precursor (compound 10) 4 - (6 - (2-P-toluene-sulfonic acid ethoxycarbonyl)-oxy-2-quinolyl)-N-tert-butoxy-carbonyl-N-n-pentyl-( [N-methyl-N-tert-butoxy carbonyl] - 2 - [4 ˊ - (methylamino) phenyl]-benzothiazole aniline) - 6-ether) aniline and standard (compound 25) 4 - (6 - (2-F)-oxy-2-quinolyl)-N-n-pentyl-( [N-methyl] - 2 - [4 ˊ - (methylamino) phenyl]-benzothiazole aniline) - 6-ether) aniline, at the same time provides A β protein specific binding agent 11 C-6-OH-BTA-1 an important intermediate for preparing (compound 7) method for the preparation of, the preparation method is a brand new synthetic route, step is simple, moderate reaction. (by machine translation)

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 and evaluation of two uncharged 99mTc-labeled derivatives of thioflavin-T as potential tracer agents for fibrillar brain amyloid

Thioflavin-T is a fluorescent dye for in vitro detection of fibrillar amyloid b, a protein found in the brain of patients suffering from Alzheimer's disease. We synthesized and biologically evaluated two uncharged 99mTc-labeled derivatives of thioflavin-T. The precursors for labeling were synthesized by coupling an S,S′-bis-triphenylmethyl-N-tert- butoxycarbonyl bis-amino-bis-thiol tetradentate ligand via a propoxy spacer to 2-(4′-aminophenyl)-1,3-benzothiazole at the 6-position or the 2′-position. Deprotection and labeling with 99mTc were done via a one-pot procedure (15% yield) after which the labeled compound was isolated by high performance liquid chromatography (LC). LC in combination with mass spectrometry (MS) was used for identity confirmation of the labeled compounds. Results of electrophoresis and log P determination supported the assumption that the radiolabeled compounds could cross the blood-brain barrier by passive diffusion. However, in normal mice both compounds showed a low brain uptake 2 min post injection. They were mainly excreted through the hepatobiliary system, with some accumulation in the stomach. Sixty minutes after intravenous injection, 37% of the 99mTc-activity in the blood corresponded to the original compound. In view of the low brain uptake, it is concluded that the studied 99mTc-labeled derivatives of thioflavin-T are not suitable as tracer agents for in vivo visualization of amyloid in brain. Copyright

Therapeutic compounds

Compounds of the formula (I) for use as an estrogen receptor-β-selective ligand are described wherein: X is O or S; and R1, R3 R6 are as described in the specification. The use of these compounds in treating Alzheimer's disease, anxiety disorders, depressive disorders, osteoporosis, cardiovascular disease, rheumatoid arthritis and prostate cancer is described; as are processes for making them.

Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents.

The synthesis and evaluation of a series of neutral analogues of thioflavin-T (termed BTA's) with high affinities for aggregated amyloid and a wide range of lipophilicities are reported. Radiolabeling with high specific activity [(11)C]methyl iodide provided derivatives for in vivo evaluation. Brain entry in control mice and baboons was high for nearly all of the analogues at early times after injection, but the clearance rate of radioactivity from brain tissue varied by more than 1 order of magnitude. Upon the basis of its rapid clearance from normal mouse and baboon brain tissues, [N-methyl-(11)C]2-(4'-methylaminophenyl)-6-hydroxybenzothiazole (or [(11)C]6-OH-BTA-1) was selected as the lead compound for further evaluation. The radiolabeled metabolites of [(11)C]6-OH-BTA-1 were polar and did not enter brain. The binding affinities of [N-methyl-(3)H]6-OH-BTA-1 for homogenates of postmortem AD frontal cortex and synthetic Abeta(1-40) fibrils were similar (K(d) = 1.4 nM and 4.7 nM, respectively), but the ligand-to-Abeta peptide binding stoichiometry was approximately 400-fold higher for AD brain than Abeta(1-40) fibrils. Staining of AD frontal cortex tissue sections with 6-OH-BTA-1 indicated the selective binding of the compound to amyloid plaques and cerebrovascular amyloid. The encouraging in vitro and in vivo properties of [(11)C]6-OH-BTA-1 support the choice of this derivative for further evaluation in human subject studies of brain Abeta deposition.

Antitumor benzothiazoles. 8.1 Synthesis, metabolic formation, and biological properties of the C- and N-oxidation products of antitumor 2-(4- aminophenyl)-benzothiazoles

2-(4-Aminophenyl)benzothiazoles 1 and their N-acetylated forms have been converted to C and N-hydroxylated derivatives to investigate the role of metabolic oxidation in the mode of action of this series of compounds. 2-(4- Amino-3-methylphenyl)benzothiazole (1a, DF 203, NSC 674495) is a novel and potent antitumor agent with selective growth inhibitory properties against human cancer cell lines. Very low IC50 values (14C]1a derived radioactivity was observed in the sensitive MCF-7 cell line but not in the insensitive MDA-MB-435 cell line. The mechanism of growth inhibition by 1a, which is unknown, may be dependent on the differential metabolism of the drug to an activated form by sensitive cell lines only and its covalent binding to an intracellular protein. However, the 6-hydroxy derivative 6c is not the 'active' metabolite since, like all other C- and N-hydroxylated benzothiazoles examined in this study, it is devoid of antitumor properties in vitro.

Benzazole compounds

There are disclosed herein benzazole compounds, exemplified by 2-(4-aminophenyl)benzothiazole and analogues or salts thereof, which exhibit very significant selective cytotoxic activity in respect of tumor cells, especially breast cancer cells, and which provide potentially useful chemotherapeutic agents for treatment of breast cancer.

Antitumor benzothiazoles. 3. Synthesis of 2-(4- aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo

A new series of 2-(4-aminophenyl)benzothiazoles substituted in the phenyl ring and benzothiazole moiety has been synthesized by simple, high- yielding routes. The parent molecule 5a shows potent inhibitory activity in vitro in the nanomolar range against a panel of human breast cancer cell lines, but is inactive (IC50 > 30 μM) against other cell types: activity against the sensitive breast lines MCF-7 and MDA 468 is characterized by a biphasic dose-response relationship. Structure-activity relationships derived using these cell types has revealed that activity follows the heterocyclic sequence benzothiazole > benzoxazole >> benzimidazole and that 2-(4-aminophenyl)benzothiazoles bearing a 3'-methyl- 9a, 3'-bromo- 9c, 3'- iodo- 9f, and 3'-chloro-substituent 9i are especially potent and their activity extends to ovarian, lung, and renal cell lines. Four compounds have been evaluated in vivo against human mammary carcinoma models in nude mice. Compound 9a showed the most potent growth inhibition against the ER+ (MCF- 7 and BO) and ER- (MT-1 and MT-3) tumors. Our efforts to identify a pharmacological mechanism of action for these intriguing compounds have not, as yet, been successful.