52085-98-0

Usage

Uses

Used in Pharmaceutical Industry:
6-CHLORO-2,3-DIHYDRO-1H-INDEN-1-OL is used as a key intermediate in the synthesis of various pharmaceutical products. Its unique molecular structure and reactivity make it suitable for the development of novel substances with valuable applications in the pharmaceutical field.
Used in Agrochemical Industry:
6-CHLORO-2,3-DIHYDRO-1H-INDEN-1-OL is also utilized in the synthesis of agrochemical products. Its chemical properties allow for the production of a wide range of organic compounds that can be used in the development of effective and innovative agrochemicals.
Used as a Building Block in the Chemical Industry:
6-CHLORO-2,3-DIHYDRO-1H-INDEN-1-OL is commonly used as a building block in the chemical industry for the development of novel substances with valuable applications in different fields. Its unique molecular structure and reactivity make it an important component in the synthesis of various organic compounds.

Upstream product

• 14548-38-0 6-chloro-1-indanone 

Downstream Products

• 872181-01-6 2-(6-chloroindan-1-yloxy)-6-fluorobenzonitrile 
• 1119270-39-1 2-(5-chloro-1'H-spiro[indene-1,4'-piperidin]-1'-yl)-1-{1-[(2E)-3-(3,5-difluorophenyl)-2-propenoyl]-4-piperidinyl}ethanol 
• 872182-08-6 (R)-6-chloro-2,3-dihydro-1H-inden-1-ol 
• 872182-06-4 (S)-6-chloro-2,3-dihydro-1H-inden-1-ol 
• 14548-38-0 6-chloro-1-indanone 
• 34784-06-0 7-chloroisoquinoline 
• 1427414-93-4 (1aS,6aR)-3-chloro-6,6a-dihydro-1aH-1-oxa-cyclopropa[a]-indene 
• 3970-51-2 5-chloro-1H-indene 

Relevant academic research and scientific papers

Kinetic resolution of racemic benzofused alcohols catalysed by HMFO variants in presence of natural deep eutectic solvents

5-Hydroxymethylfurfural oxidase (HMFO) has demonstrated to be a useful biocatalyst for the selective oxidation of alcohols employing oxygen as mild oxidant with no requirement of expensive organic cofactors. This wild-type HMFO biocatalyst and an engineered thermostable variant have been tested in the kinetic resolution of different benzofused alcohols. The use of natural deep eutectic solvents was also explored in HMFO-catalysed oxidation of alcohols. The oxidation of racemic 1-indanol showed a higher conversion and selectivity in presence of 60% v/v of different NADES, especially for those containing carbohydrates. By choosing properly the biocatalyst and the NADES, good enantioselectivity values can be obtained, demonstrating the advantages of employing these neoteric solvents in biocatalysed processes.

Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions

Isoquinolines activated with sulfamoyl chlorides were reacted with indoles in a 3-component reaction to generate a library of dihydroisoquinoline derivatives. Using a differential protecting group strategy, products could be further derivatised. Synthesis of isoquinoline starting materials using several different methods is also described.

Discovery and Optimization of 1-Phenoxy-2-aminoindanes as Potent, Selective, and Orally Bioavailable Inhibitors of the Na+/H+ Exchanger Type 3 (NHE3)

The design, synthesis, and structure-activity relationship of 1-phenoxy-2-aminoindanes as inhibitors of the Na+/H+ exchanger type 3 (NHE3) are described based on a hit from high-throughput screening (HTS). The chemical optimization resulted in the discovery of potent, selective, and orally bioavailable NHE3 inhibitors with 13d as best compound, showing high in vitro permeability and lacking CYP2D6 inhibition as main optimization parameters. Aligning 1-phenoxy-2-aminoindanes onto the X-ray structure of 13d then provided 3D-QSAR models for NHE3 inhibition capturing guidelines for optimization. These models showed good correlation coefficients and allowed for activity estimation. In silico ADMET models for Caco-2 permeability and CYP2D6 inhibition were also successfully applied for this series. Moreover, docking into the CYP2D6 X-ray structure provided a reliable alignment for 3D-QSAR models. Finally 13d, renamed as SAR197, was characterized in vitro and by in vivo pharmacokinetic (PK) and pharmacological studies to unveil its potential for reduction of obstructive sleep apneas.

NOVEL 3-HYDROXY-5-ARYLISOXAZOLE DERIVATIVE

[Problem] To provide a GPR40 activating agent having, as an active ingredient, a novel compound having a GPR40 agonist action, a salt of the compound, a solvate of the salt or the compound, or the like, particularly, an insulin secretagogue and a prophylactic and/or therapeutic agent against diabetes, obesity, or other diseases. [Means of solving the problem] A compound of Formula (I): (where p is 0 to 4; j is 0 to 3; k is 0 to 2; a ring A is a specific cyclic group; a ring B is a benzene ring, a pyridine ring, or a pyrimidine ring; X is —CH2—, O, —S(O)i— (i is 0 to 2), or —NR7—; R1 to R6 are specific groups), a salt of the compound, or a solvate of the salt or the compound.

SPIROINDENES AND SPIROINDANES AS MODULATORS OF CHEMOKINE RECEPTORS

The present invention relates to a compound of the following formula (I): or a pharmaceutically acceptable salt thereof; where R1-R5, Y, m, n, and p are defined herein. Compounds and compositions of the present invention are useful the treatment of atherosclerosis.

Synthesis and biological evaluation of novel 2,4-diaminoquinazoline derivatives as SMN2 promoter activators for the potential treatment of spinal muscular atrophy

Proximal spinal muscular atrophy (SMA) is an autosomal recessive disorder characterized by death of motor neurons in the spinal cord that is caused by deletion and/or mutation of the survival motor neuron gene (SMN1). Adjacent to SMN1 are a variable number of copies of the SMN2 gene. The two genes essentially differ by a single nucleotide, which causes the majority of the RNA transcripts from SMN2 to lack exon 7. Although both SMN1 and SMN2 encode the same Smn protein amino acid sequence, the loss of SMN1 and incorrect splicing of SMN2 have the consequence that Smn protein levels are insufficient for the survival of motor neurons. The therapeutic goal of our medicinal chemistry effort was to identify small-molecule activators of the SMN2 promoter that, by up-regulating gene transcription, would produce greater quantities of full-length Smn protein. Our initial medicinal chemistry effort explored a series of C5 substituted benzyl ether based 2,4-diaminoquinazoline derivatives that were found to be potent activators of the SMN2 promoter; however, inhibition of DHFR was shown to be an off-target activity that was linked to ATP depletion. We used a structure-guided approach to overcome DHFR inhibition while retaining SMN2 promoter activation. A lead compound 11a was identified as having high potency (EC50 = 4 nM) and 2.3-fold induction of the SMN2 promoter. Compound 11a possessed desirable pharmaceutical properties, including excellent brain exposure and long brain half-life following oral dosing to mice. The piperidine compound 11a up-regulated expression of the mouse SMN gene in NSC-34 cells, a mouse motor neuron hybrid cell line. In type 1 SMA patient fibroblasts, compound 11a induced Smn in a dose-dependent manner when analyzed by immunoblotting and increased the number of intranuclear particles called gems. The compound restored gems numbers in type I SMA patient fibroblasts to levels near unaffected genetic carriers of SMA.

2,4-DIAMINOQUINAZOLINES FOR SPINAL MUSCULAR ATROPHY

2,4-Diaminoquinazolines of formulae I-IV and VI (I, II, III, IV and VI) are useful for treating spinal muscular atrophy (SMA).