106057-23-2

Basic information

• Product Name: 8-Chloro-5,6,7,8-Tetrahydroquinoline
• Synonyms: 8-Chloro-5,6,7,8-Tetrahydroquinoline
• CAS NO: 106057-23-2
• Molecular Formula: C9H10ClN
• Molecular Weight: 168
• Mol File: 106057-23-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 8-Chloro-5,6,7,8-Tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Chloro-5,6,7,8-Tetrahydroquinoline(106057-23-2)
• EPA Substance Registry System: 8-Chloro-5,6,7,8-Tetrahydroquinoline(106057-23-2)

Safety Data

• Hazardous Substances Data: 106057-23-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-Chloro-5,6,7,8-Tetrahydroquinoline is used as a key intermediate in the synthesis of heterocyclic compounds for the development of new drugs. Its unique structural properties allow for the creation of a wide range of pharmaceuticals with diverse therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 8-Chloro-5,6,7,8-Tetrahydroquinoline serves as a vital precursor in the production of agrochemicals, such as pesticides and herbicides. Its ability to form heterocyclic compounds contributes to the development of effective and targeted agrochemicals for crop protection and management.
Used in Dye Production:
8-Chloro-5,6,7,8-Tetrahydroquinoline is utilized as a chemical intermediate in the manufacturing process of various dyes. Its structural properties enable the creation of dyes with specific color characteristics and properties, catering to the needs of different industries.
Used in Specialized Chemicals Production:
8-Chloro-5,6,7,8-Tetrahydroquinoline also finds application in the production of specialized chemicals, where its unique structural properties are leveraged to create chemicals with specific functionalities and applications in various industrial processes.

Upstream product

• 14631-48-2 5,6,7,8-tetrahydroquinoline N-oxide 
• 10500-57-9 5,6,7,8-tetrahydroquinoline 

Downstream Products

• 878025-42-4 (±)-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine 

Relevant articles and documents

Rapid and Effective Reaction of 2-Methylpyridin-N-oxides with Triphosgene via a [3,3]-Sigmatropic Rearrangement: Mechanism and Applications

A facile and effective synthesis of 2-chloromethylpyridines was developed by a one-pot reaction of 2-alkylpyridin-N-oxides and triphosgene at room temperature. As starting materials, N-oxides of 2-alkylpyridine derivatives, including 2-alkylpyridines, 2-methyl quinolines, and phenanthroline, can react rapidly with triphosgene in the presence of triethylamine, affording 2-chloromethylpyridines in good to excellent yields (52-95%). Using the 2-methylquinoline substrate for the mechanistic study, it has been well demonstrated that the chlorination reaction undergoes a [3,3]-sigmatropic rearrangement, which can be observed as a reversible process by monitoring the intermediates. Moreover, the chlorination reaction can be used to construct a rapid and sensitive fluorescent probe for the detection of phosgene.

1-Imidazolyl(alkyl)-substituted di- and tetrahydroquinolines and analogues: Syntheses and evaluation of dual inhibitors of thromboxane A2 synthase and aromatase

A series of 1-imidazolyl(alkyl)-substituted quinoline, isoquinoline, naphthalene, benzo[b]furan, and benzo[b]thiophene derivatives was synthesized as dual inhibitors of thromboxane A2 synthase (P450 TxA2) and aromatase (P450 arom). Dual inhibition of these enzymes could be a novel strategy for the treatment of mammary tumors and the prophylaxis of metastases. The most potent dual inhibitors, 5-(2-imidazol-1-ylethyl)-7,8-dihydroquinoline (31) (P450 TxA2:IC50 = 0.29/μM; P450 arom: IC50 = 0.50/μM) and its 5,6- saturated analogue 30 (P450 TxA2:IC50 = 0.68/μM; P450 arom: IC50 = 0.38/μM), showed a stronger inhibition of both target enzymes than the reference compounds (dazoxiben: IC50 = 1.1/μM; aminoglutethimide: IC50 = 18.5/μM). For the determination of the in vivo activity, the influence of selected compounds on serum TxB2 concentration was examined in rats. Compound 30 (8.5 mg/kg body weight) led to a reduction of the TxB2 serum level of 78%, 71%, and 51% after 3, 5, and 8 h, respectively (dazoxiben: 60%, 34%, and 36%). Selectivity was studied toward some enzymes of the steroidogenic and eicosanoid pathways. P450 17 was inhibited by selected compounds only at high concentrations. Compound 30 inhibited P450 scc by 13% (25/μM). Compound 31 did not affect cyclooxygenase and lipoxygenase.

HETEROARYL COMPOUNDS AS CXCR4 INHIBITORS, COMPOSITION AND METHOD USING THE SAME

The present disclosure provides heteroaryl compounds of Formula (I), processes for their preparation, pharmaceutical compositions containing them, and their use in the treatment of diseases and disorders, arising from or related to the CXCR4 pathway.

Design, synthesis, and structure-activity-relationship of a novel series of CXCR4 antagonists

The important roles of the CXCL12/CXCR4 axis in numerous pathogenic pathways involving HIV infection and cancer metastasis make the CXCR4 receptor an attractive target for the development of therapeutic agents. Through scaffold hybridization of a few known CXCR4 antagonists, a series of novel aminopyrimidine derivatives was developed. Compound 3 from this new scaffold demonstrates excellent binding affinity with CXCR4 receptor (IC50 = 54 nM) and inhibits CXCL12 induced cytosolic calcium increase (IC50 = 2.3 nM). Furthermore, compound 3 possesses good physicochemical properties (MW 353, clogP 2.0, PSA 48, pKa 6.7) and exhibits minimal hERG and CYP isozyme (e.g. 3A4, 2D6) inhibition. Collectively, these results strongly support further optimization of this novel scaffold to develop better CXCR4 antagonists.

Decahydroquinolines and analgesic use thereof

Novel enantiomeric and diastereoisomeric forms of decahydroquinolines of the formula STR1 wherein R1 and R2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken together with the n