72752-81-9

Usage

Uses

Used in Organic Synthesis:
2-Mercaptobenzooxazole-6-carboxylic acid methyl ester is used as a building block in organic synthesis for its versatile reactivity, contributing to the creation of various pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Chemical Research:
In the realm of chemical research, 2-Mercaptobenzooxazole-6-carboxylic acid methyl ester is utilized for its unique properties, aiding in the exploration of new chemical reactions and mechanisms.
Used in Pharmaceutical Development:
2-Mercaptobenzooxazole-6-carboxylic acid methyl ester is employed as a key intermediate in the development of pharmaceuticals, owing to its potential to form complex molecular structures with therapeutic applications.
Used in Agrochemical Production:
2-Mercaptobenzooxazole-6-carboxylic acid methyl ester is also used in agrochemical production, serving as a crucial component in the synthesis of various agrochemicals that contribute to crop protection and enhancement.
Used in Specialty Chemicals:
2-Mercaptobenzooxazole-6-carboxylic acid methyl ester is utilized in the production of specialty chemicals, where its unique properties allow for the creation of compounds with specific applications in various industries.
Used in Dye and Pigment Development:
It has been studied for its potential applications in the development of dyes and pigments, where its chemical structure can contribute to the creation of novel colorants with improved properties.
Used in Materials Science for Electronic or Optical Properties:
2-Mercaptobenzooxazole-6-carboxylic acid methyl ester is explored for its potential in materials science, particularly for the development of materials with specific electronic or optical properties, such as in sensors or optoelectronic devices.
Overall, 2-Mercaptobenzooxazole-6-carboxylic acid methyl ester plays a significant role in the advancement of chemical and materials science, with applications spanning across various industries.

InChI:InChI=1/C9H7NO3S/c1-12-8(11)5-2-3-6-7(4-5)13-9(14)10-6/h2-4H,1H3,(H,10,14)

Upstream product

• 140-89-6 potassium ethyl xanthogenate 
• 63435-16-5 3-hydroxy-4-aminobenzoic acid methyl ester 
• 2374-03-0 4-aminosalicylic acid 
• 463-71-8 thiophosgene 

Downstream Products

• 819076-91-0 methyl 2-chloro-1,3-benzoxazole-6-carboxylate 
• 1160490-11-8 methyl 2-(methylthio)benzo[d]oxazole-6-carboxylate 
• 108085-62-7 2-thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid 
• 213684-99-2 N-(2,6-diisopropylphenyl)-6-((6-((N,N-dimethylamino)methyl)benzo[d]oxazol-2-yl)thio)hexanamide 
• 213684-98-1 N-(2,6-diisopropylphenyl)-6-((6-(hydroxymethyl)benzo[d]oxazol-2-yl)thio)hexanamide 
• 213684-97-0 2-((6-((2,6-diisopropylphenyl)amino)-6-oxohexyl)thio)benzo[d]oxazole-6-carboxylic acid 
• 213684-96-9 methyl 2-((6-((2,6-diisopropylphenyl)amino)-6-oxohexyl)thio)benzo[d]oxazole-6-carboxylate 
• 1393747-01-7 C₂₄H₂₄N₄O₃ 

Relevant academic research and scientific papers

The design, synthesis and evaluation of 2-aminobenzoxazole analogues as potent and orally efficacious ChemR23 inhibitors

We previously reported 2-aminobenzoxazole analogue 1 as a potent ChemR23 inhibitor. The compound showed inhibitory activity against chemerin-induced calcium signaling through ChemR23 internalization in CAL-1 cells, which are cell lines of plasmacytoid dendric cells (pDCs). Furthermore, compound 2 inhibited chemotaxis of CAL-1 triggered by chemerin in vitro. However, we noted a difference in the ChemR23 response to our inhibitor between rodents and non-rodents in a previous study. To address this issue, we performed optimization of ChemR23 inhibitors using CAL-1 cells endogenously expressing human ChemR23 and conducted a pharmacokinetics study in cynomolgus monkeys. Various substituents at the 4-position of the benzoxazole ring exhibited potent in vitro bioactivity, while those at the 6-position were not tolerated. Among substituents, a carboxyl group was identified as key for improving the oral bioavailability in cynomolgus monkeys. Compound 38a with the acidic part changed from a tetrazole group to a 1,2,4-oxadiazol-5-one group to improve bioactivity and pharmacokinetic parameters exhibited inhibitory activity against chemerin-induced chemotaxis in vitro. In addition, we confirmed the ChemR23 internalization of pDCs by compound 38a orally administered to cynomolgus monkeys. These 2-aminobenzoxazole-based ChemR23 inhibitors may be useful as novel immunotherapeutic agents capable of suppressing the migration of pDCs, which are known to be major producers of type I interferons in the lesion area of certain autoimmune diseases, such as systemic lupus erythematosus and psoriasis.

Design, synthesis and pharmacology of aortic-selective acyl-CoA: Cholesterol O-acyltransferase (ACAT/SOAT) inhibitors

We describe our molecular design of aortic-selective acyl-coenzyme A:cholesterol O-acyltransferase (ACAT, also abbreviated as SOAT) inhibitors, their structure–activity relationships (SARs) and their pharmacokinetic (PK) and pharmacological profiles. The connection of two weak ligands—N-(2,6-diisopropylphenyl)acetamide (50% inhibitory concentration [IC50] = 8.6 μM) and 2-(methylthio)benzo[d]oxazole (IC50 = 31 μM)—via a linker comprising a 6 methylene group chains yielded a highly potent molecule, 9-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)nonanamide (3h) that exhibited high potency (IC50 = 0.004 μM) toward aortic ACAT. This head-to-tail design made it possible to markedly enhance the activity to 2150- to 7750-fold and to discriminate the isoform-selectivity based on the double-induced fit mechanism. At doses of 1 and 3 mg/kg, 3h significantly decreased the lipid-accumulation areas in the aortic arch to 74 and 69%, respectively without reducing the plasma total cholesterol level in high fat- and cholesterol-fed F1B hamsters. Here, we demonstrate the antiatherosclerotic effect of 3h in vivo via its direct action on aortic ACAT and its powerful modulator of cholesterol level. This molecule is a potential therapeutic agent for the treatment of diseases involving ACAT-1 overexpression.

NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS AS FXR MODULATORS

The present technology is directed to compounds, compositions, and methods related to modulation of FXR. In particular, the present compounds and compositions may be used to treat FXR-mediated disorders and conditions, including, e.g., liver disease, hype

Benzoxazole and benzothiazole amides as novel pharmacokinetic enhancers of HIV protease inhibitors

A new class of benzoxazole and benzothiazole amide derivatives exhibiting potent CYP3A4 inhibiting properties was identified. Extensive lead optimization was aimed at improving the CYP3A4 inhibitory properties as well as overall ADME profile of these amide derivatives. This led to the identification of thiazol-5-ylmethyl (2S,3R)-4-(2-(ethyl(methyl)amino)-N-isobutylbenzo[d]oxazole- 6-carboxamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate (C1) as a lead candidate for this class. This compound together with structurally similar analogues demonstrated excellent 'boosting' properties when tested in dogs. These findings warrant further evaluation of their properties in an effort to identify valuable alternatives to Ritonavir as pharmacokinetic enhancers.

SUBSTITUTED BICYCLIC AMINES FOR THE TREATMENT OF DIABETES

Described herein are substituted bicyclic amines. In particular, described herein are substituted bicyclic amines that are effective as antagonists of SSTR5 and useful for the treatment, control or prevention of disorders responsive to antagonism of SSTR5

AMIDE COMPOUNDS AS BOOSTERS OF ANTIVIRALS

The present invention relates to compounds that have CYP450 inhibiting properties and are therefore useful as boosters of certain drugs, i.e. they are able to increase at least one of the pharmacokinetic variables of certain drugs when co-administered. The invention further provides the use of said compounds as improvers of the bioavailability of certain drugs. Methods for the preparation of the compounds of the invention and pharmaceutical compositions are also provided.

BENZOTHIAZOLE AND BENZOOXAZOLE DERIVATIVES AND METHODS OF USE

Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions of compounds of formula (I), methods for using such compounds and compositions, and a process for preparing the compounds.

Synthesis and evaluation of arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 3: Heterocyclic P3

A series of Nα-2-benzoxazolyl-α-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure-activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound 3 bound to the active site of cathepsin S is also reported.