2941-58-4

Usage

Uses

Used in Organic Synthesis:
2-Bromo-6-methoxybenzothiazole is used as an organic synthesis intermediate for the creation of various complex organic molecules. Its unique structure allows for a range of reactions, making it a valuable component in the synthesis of specialty chemicals and materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Bromo-6-methoxybenzothiazole is utilized as a pharmaceutical intermediate. It plays a crucial role in the development of new drugs and medicines, contributing to the advancement of pharmaceutical research and chemical production processes.
Used in Laboratory Research and Development:
2-Bromo-6-methoxybenzothiazole is also employed in laboratory research and development processes. Its distinctive chemical properties make it an essential tool for scientists and researchers working on the synthesis and study of novel compounds and their potential applications in various fields.

Synthesis

2-Bromo-6-methoxybenzo[d]thiazole (B2) (Scheme 1). 6- Methoxybenzo[d]thiazol-2-amine (5.0 g; 27.7 mmol) was dissolved in 125 mL CHBCN. t- Butylnitrite (3.4 mL; 28 mmol) was added slowly. CuBr (5.0 g; 34.9 mmol) was added portion-wise through a funnel. The reaction was monitored by HPLC. After 3 hours, ethyl acetate (500 mL) was added, and the mixture was filtered through celite. The organic layer was washed with brine twice (200 mL each). The organic layer was dried over MgSO4. After filtration, the solvent was removed. The residual was dissolved in 50 mL CH2Cl2, and 2 g of silica gel was added. After drying, the silica gel loaded on a silica gel cake in hexane. The product was eluted with 5% ethyl acetate and 95% hexane. A yellowish band was collected (1.5 L). The solvent was removed to afford the product. Yield: 0.81 g 12%.

InChI:InChI=1/C8H6BrNOS/c1-11-5-2-3-6-7(4-5)12-8(9)10-6/h2-4H,1H3

Upstream product

• 1747-60-0 6-methoxybenzothiazol-2-ylamine 
• 7787-70-4 copper(I) bromide 
• 110-46-3 isopentyl nitrite 

Downstream Products

• 43036-14-2 6-methoxy-2-(4-nitrophenyl)benzothiazole 
• 808755-67-1 6-hydroxy-2-bromo-benzothiazole 
• 1042131-26-9 [4-(4-isopropyl-phenyl)-6-propargyloxy-quinazolin-2-yl]-(6-methoxy-benzothiazol-2-yl)-methanone 
• 1122521-73-6 6-methoxy-2-m-tolylbenzo[d]thiazole 
• 92161-47-2 2-(4-chlorophenyl)-6-methoxybenzo[d]thiazole 
• 10205-70-6 6-methoxy-2-(4-methoxyphenyl)benzo[d]thiazole 
• 1122521-66-7 2-(2-fluorophenyl)-6-methoxybenzo[d]thiazole 
• 1122521-65-6 2-(3-fluorophenyl)-6-methoxybenzo[d]thiazole 
• 1122521-71-4 6-methoxy-2-(2-methoxyphenyl)-1,3-benzothiazole 
• 10205-71-7 4-(6-methoxybenzo[d]thiazol2-yl)-N,N-dimethylaniline 
• 1122521-72-5 N-(3-(6-methoxybenzo[d]thiazol-2-yl)phenyl)acetamide 
• 17930-13-1 4-(6-methoxybenzo[d]thiazol-2-yl)benzonitrile 
• 1122521-70-3 2-(3-(benzyloxy)phenyl)-6-methoxybenzo[d]thiazole 
• 1122521-69-0 2-(2-(benzyloxy)phenyl)-6-methoxybenzo[d]thiazole 

Relevant academic research and scientific papers

alpha-SYNUCLEIN AGGREGATE BINDING AGENT AND IMAGING METHOD

The present invention provides an α-synuclein aggregate binding agent that has high binding selectivity for an α-synuclein aggregate. The α-synuclein aggregate binding agent contains a compound represented by a formula (I), a pharmaceutically acceptable salt thereof, or a solvate thereof: in the formula (I), R1 and R2 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, acyl, and hydroxyalkyl; R3 is hydrogen or halogen; the ring A is a benzene or pyridine ring; the ring B is represented by the following formula (i) or (ii): R4 and R5 are each independently selected from the group consisting of hydrogen, hydroxy, alkoxy, haloalkoxy, halohydroxyalkoxy, and aminoalkyl.

Multicomponent Bioluminescence Imaging with a π-Extended Luciferin

Bioluminescence imaging with luciferase-luciferin pairs is commonly used for monitoring biological processes in cells and whole organisms. Traditional bioluminescent probes are limited in scope, though, as they cannot be easily distinguished in biological environments, precluding efforts to visualize multicellular processes. Additionally, many luciferase-luciferin pairs emit light that is poorly tissue penetrant, hindering efforts to visualize targets in deep tissues. To address these issues, we synthesized a set of π-extended luciferins that were predicted to be red-shifted luminophores. The scaffolds were designed to be rotationally labile such that they produced light only when paired with luciferases capable of enforcing planarity. A luciferin comprising an intramolecular "lock"was identified as a viable light-emitting probe. Native luciferases were unable to efficiently process the analog, but a complementary luciferase was identified via Rosetta-guided enzyme design. The unique enzyme-substrate pair is red-shifted compared to well-known bioluminescent tools. The probe set is also orthogonal to other luciferase-luciferin probes and can be used for multicomponent imaging. Four substrate-resolved luciferases were imaged in a single session. Collectively, this work provides the first example of Rosetta-guided design in engineering bioluminescent tools and expands the scope of orthogonal imaging probes.

BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS

Disclosed are compounds of Formula (I) to (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII); or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a bicyclic heteroaryl group substituted with zero to 3 R3a; and R1, R2, R3a, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.

The cyclized compound, and, cyclic compound solution containing a light-emitting method

PROBLEM TO BE SOLVED: To provide a method of producing a cyclized compound, and a method of causing a solution containing the cyclized compound to emit light.SOLUTION: A method of producing a cyclized compound represented by the chemical formula (II) comprises bringing an acid into contact with a compound represented by the general formula (I). (In the formula, R, Rand Rare each independently H or a substituent that becomes H upon the contact with the acid, and Ris OH or a substituent that becomes OH upon the contact with the acid.)

Synthesis of Firefly Luciferin Analogues and Evaluation of the Luminescent Properties

Five new firefly luciferin (1) analogues were synthesized and their light emission properties were examined. Modifications of the thiazoline moiety in 1 were employed to produce analogues containing acyclic amino acid side chains (2–4) and heterocyclic rings derived from amino acids (5 and 6) linked to the benzothiazole moiety. Although methyl esters of all of the synthetic derivatives exhibited chemiluminescence activity, only carboluciferin (6), possessing a pyrroline-substituted benzothiazole structure, had bioluminescence (BL) activity (λmax=547 nm). Results of bioluminescence studies with AMP-carboluciferin (AMP=adenosine monophosphate) and AMP-firefly luciferin showed that the nature of the thiazoline mimicking moiety affected the adenylation step of the luciferin–luciferase reaction required for production of potent BL. In addition, BL of 6 in living mice differed from that of 1 in that its luminescence decay rate was slower.

Thiazolobenzyne: A versatile intermediate for multisubstituted benzothiazoles

Thiazolobenzyne, which is a benzyne species fused with a thiazole ring, was efficiently generated via an iodine-magnesium exchange reaction of an ortho-iodoaryl triflate-type precursor using a trimethylsilylmethyl Grignard reagent as an activator. A wide range of arynophiles reacted efficiently with the thiazolobenzynes generated by this method to afford various multisubstituted benzothiazoles.

PHARMACEUTICAL COMPOSITION FOR TREATING OR PREVENTING FOOT-AND-MOUTH DISEASE

The present invention refers to benzothiazole derivatives and its pharmaceutically acceptable salt as active ingredients opening including inverse number relates to a pharmaceutical composition for treating or preventing is. In addition, opening the present invention refers to treatment or prevention of inverse number relates to method. (by machine translation)

SPIRO-OXADIAZOLINE COMPOUNDS AS AGONISTS OF α-7-NICOTINIC ACETYLCHOLINE RECEPTORS

The present invention relates to novel spiro-oxadiazoline compounds that are suitable as agonists or partial agonists of a7-nAChR, and pharmaceutical compositions of the same, methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering a spiro-oxadiazoline cx7-nAChR agonist or partial agonist, to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

BETA-AMYLOID IMAGING AGENTS, METHODS OF MANUFACTURE, AND METHODS OF USE THEREOF

Derivatives of benzothiazolylbenzeneamines useful as imaging agents for nuclear imaging such as positron emission tomography of beta-amyloids are described. Methods of detecting amyloid using the compounds are described. Also disclosed is a radiolabeling

INHIBITORS OF CDC PHOSPHATASES

A subject of the present invention is novel compounds comprising 2 or 3 benzothiazole-4,7-dione- or benzooxazole-4,7-dione-type units, which inhibit the cdc25 phosphatases, in particular cdc25-C phosphatase. These compounds can in particular be used in the treatment of cancer.