7364-29-6

Basic information

• Product Name: 6-CHLORO-3-HYDROXY (1H)INDAZOLE
• Synonyms: 6-CHLORO-3-HYDROXY (1H)INDAZOLE;6-Chloro-1H-indazol-3-ol;6-CHLORO-3-HYDROXYINDAZOLE;6-chloro-1,2-dihydro-3H-indazol-3-one;6-Chloro-1H-indazol-3(2H)-one
• CAS NO: 7364-29-6
• Molecular Formula: C₇H₅ClN₂O
• Molecular Weight: 168.58
• Mol File: 7364-29-6.mol

Chemical Properties

• Boiling Point: 399.1 °C at 760 mmHg
• Flash Point: 195.2 °C
• Appearance: /
• Density: 1.598 g/cm³
• Vapor Pressure: 6.1E-07mmHg at 25°C
• Refractive Index: 1.759
• CAS DataBase Reference: 6-CHLORO-3-HYDROXY (1H)INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-3-HYDROXY (1H)INDAZOLE(7364-29-6)
• EPA Substance Registry System: 6-CHLORO-3-HYDROXY (1H)INDAZOLE(7364-29-6)

Safety Data

• Hazardous Substances Data: 7364-29-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
6-CHLORO-3-HYDROXY (1H)INDAZOLE is used as a pharmaceutical candidate for the development of new medications targeting various diseases and conditions. Its unique structure and potential biological activities contribute to its therapeutic potential.
Used in Organic Synthesis:
6-CHLORO-3-HYDROXY (1H)INDAZOLE serves as a building block in organic synthesis, enabling the creation of other chemical compounds with specific properties and functions. This application expands its utility beyond direct medicinal use, allowing for the development of a broader range of chemical entities with diverse applications.

InChI:InChI=1/C7H5ClN2O/c8-4-1-2-5-6(3-4)9-10-7(5)11/h1-3H,(H2,9,10,11)

Upstream product

• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 299166-41-9 4-Chloro-2-hydrazino-benzoic acid 
• 64415-09-4 4-Chloro-2-hydrazino-benzoic acid; hydrochloride 

Downstream Products

• 89438-39-1 6-Chloro-3-oxo-2,3-dihydro-indazole-1-carboxylic acid ethyl ester 

Relevant articles and documents

Discovery of isatin and 1H-indazol-3-ol derivatives as D-amino acid oxidase (DAAO) inhibitors

D-Amino acid oxidase (DAAO) is a potential target in the treatment of schizophrenia as its inhibition increases brain D-serine level and thus contributes to NMDA receptor activation. Inhibitors of DAAO were sought testing [6+5] type heterocycles and identified isatin derivatives as micromolar DAAO inhibitors. A pharmacophore and structure-activity relationship analysis of isatins and reported DAAO inhibitors led us to investigate 1H-indazol-3-ol derivatives and nanomolar inhibitors were identified. The series was further characterized by pKa and isothermal titration calorimetry measurements. Representative compounds exhibited beneficial properties in in vitro metabolic stability and PAMPA assays. 6-fluoro-1H-indazol-3-ol (37) significantly increased plasma D-serine level in an in vivo study on mice. These results show that the 1H-indazol-3-ol series represents a novel class of DAAO inhibitors with the potential to develop drug candidates.

Bacterial translation inhibitors, 1-acylindazol-3-ols as anthranilic acid mimics

The discovery and initial optimization of a novel anthranilic acid derived class of antibacterial agents has been described in a recent series of papers. This paper describes the discovery of 1-acylindazol-3-ols as a novel bioisostere of an anthranilic acid. The synthesis and structure-activity relationships of the indazol bioisosteres are described herein.

Bioisosteric modifications of 2-arylureidobenzoic acids: Selective noncompetitive antagonists for the homomeric kainate receptor subtype GluR5

2-Arylureidobenzoic acids (AUBAs) have recently been presented as the first series of selective noncompetitive GluR5 antagonists. In this paper we have modified the acidic moiety of the AUBAs by introducing different acidic and neutral groups, and similarly, we have replaced the urea linker of the AUBAs with other structurally related linkers. Replacing the acid with neutral substituents led to inactive compounds in all instances, showing that an acidic moiety is necessary for activity. Replacing the carboxylic moiety in 2a with a sulfonic acid (5c) or a tetrazole ring (5d) improved the potency at GluR5 receptors (compounds 5c and 5d showed IC50 values of 1.5 and 2.0 μM, respectively, compared to compound 2a with IC50 = 4.8 μM). Compound 5c did not show improved in vivo activity in the ATPA rigidity test compared to 2a, whereas compound 5d was 4 times more potent than 2a. All compounds wherein the urea linker had been replaced showed lower or no activity. The results described extend the knowledge of structure-activity relationships for the AUBAs, and compound 5d may prove to be a good candidate for studying GluR5 receptors in vitro and in vivo.

NOVEL ARYL UREIDO BENZOIC ACID DERIVATIVES AND THEIR USE

This invention relates to novel aryl ureido benzoic acid derivatives useful as selective and non-competitive antagonists of the ionotropic GluR5 receptor. Due to their biological activity, the aryl ureido derivatives of the invention are considered useful for treating diseases that are responsive to modulation of an aspartate or a glutamate receptor. Moreover the invention provides chemical compounds for use according to the invention, as well as pharmaceutical compositions comprising the chemical compounds, and methods of treating diseases or disorders or conditions responsive to modulation of an aspartate or a glutamate receptor.

Hypolipidemic Activity of Phthalimide Derivatives. 7. Structure-Activity Studies of Indazolone Analogues

The apparent benefit of limiting serum cholesterol and triglyceride levels either by dietary restriction or drug therapy has prompted work in our laboratories toward development of a suitable antihyperlipidemic agent.We have demonstrated the antihyperlipi