369656-57-5

Usage

Uses

Used in Chemical Synthesis:
8-Quinolinamine,5,6,7,8-tetrahydro-,(8S)-(9CI) is used as an intermediate in the synthesis of various organic compounds. Its unique structure and properties make it a valuable building block for the development of new chemical entities.
Used in Pharmaceutical Industry:
8-Quinolinamine,5,6,7,8-tetrahydro-,(8S)-(9CI) is used as a precursor in the development of pharmaceuticals. Its potential biological and pharmacological activities make it a promising candidate for the treatment of various diseases and conditions.
Used in Research and Development:
8-Quinolinamine,5,6,7,8-tetrahydro-,(8S)-(9CI) is utilized in research and development for the exploration of its potential applications and properties. Its unique structure and stereochemistry provide opportunities for further investigation and discovery in the fields of chemistry and biology.

InChI:InChI=1/C9H12N2/c10-8-5-1-3-7-4-2-6-11-9(7)8/h2,4,6,8H,1,3,5,10H2/t8-/m0/s1

Upstream product

• 451466-68-5 (S)-8-azido-5,6,7,8-tetrahydroquinoline 
• 298181-83-6 5,6,7,8-tetrahydroquinolin-8-yl amine 
• 141-78-6 ethyl acetate 
• 14631-46-0 5,6,7,8-tetrahydroquinoline-8-ol 
• 502612-64-8 (8S)-N-{(1S)-1-[4-(methyloxy)phenyl]ethyl}-5,6,7,8-tetrahydro-8-quinolinamine 
• 1431726-92-9 (S)-8-amino-5,6,7,8-tetrahydroquinoline hydrochloride 
• 451466-64-1 (R)-5,6,7,8-tetrahydroquinolin-8-yl acetate 
• 451466-81-2 (R)-8-hydroxy-5,6,7,8-tetrahydroquinoline 

Downstream Products

• 558444-72-7 (S)-2-[4-(5,6,7,8-tetrahydro-quinolin-8-ylamino)-butyl]-isoindole-1,3-dione 
• 451466-71-0 (S)-N-benzylamino-5,6,7,8-tetrahydroquinolin-8-ylamine 

Relevant academic research and scientific papers

Monofunctional PtII Complexes Based on 8-Aminoquinoline: Synthesis and Pharmacological Characterization

Among the heterocyclic compounds, 8-aminoquinoline and its derivatives have become important candidates for the preparation of new antiproliferative metallo-drugs. Here, we reported the synthesis and cytotoxicity evaluation of a series of platinum complexes using 8-aminoquinoline and its chiral 5,6,7,8-tetrahydro-derivatives as chelating ligands. In the proposed complexes, a differently and opportunely alkylated imidazole was used to prepare the corresponding monofunctional platinum complexes. The preliminary cytotoxicity evaluation was carried out on the highly aggressive MDA-MB-231, invasive and poorly differentiated triple-negative breast cancer (TNBC) cell line, furnishing a significant IC50 10.9 ± 1.3 μM for Pt-IV. This series of complexes revealed an induction of p53, interfering with the progression of the G0/G1 phase of the cell cycle.

AMD070, a CXCR4 chemokine receptor antagonist: Practical large-scale laboratory synthesis

An efficient and convergent four-step synthetic route to the CXCR4 chemokine receptor antagonist AMD070 (1) has been developed which employs only a single chromatographic step in the entire sequence. Novel reductive amination methods have been developed for the coupling of 2 and 3 in which a dehydrative imine formation is followed by reduction with an attenuated borohydride reagent (zinc chloride and sodium borohydride). Selective extraction methods were employed to purify synthetic intermediates and remove reagents and impurities. A procedure has also been developed to isolate 1 in a pure crystalline form.

CHEMICAL COMPOUNDS

The present invention provides novel compounds that demonstrate protective effects on target cells from HIV infection in a manner as to bind specifically to the chemokine receptor, and which affect the binding of the natural ligand or chemokine to a receptor such as CXCR4 and/or CCR5 of a target cell.

Process for the synthesis of CXCR4 antagonist

This invention relates to a process for synthesizing heterocyclic pharmaceutical compound which binds to the CXCR4 chemokine receptor. In one embodiment, the process comprises: a) reacting a 5,6,7,8-tetrahydroquinolinylamine and an alkyl aldehyde bearing a phthalimide or a di-tertiary-butoxycarbonyl (di-BOC) protecting group to form an imine; b) reducing the imine to form a secondary amine; c) reacting the secondary amine with a haloalkyl substituted heterocyclic compound, to form a phthalimido-protected or di-tert-butoxycarbonyl protected tertiary amine; and d) hydrolyzing the protected amine to obtain a compound having Formula I′

CXCR4-ANTAGONISTIC DRUGS COMPRISING NITROGEN-CONTAINING COMPOUND

To provide novel nitrogen-containing compounds having antagonism to CXCR4 and remedies for disease, such as rheumatism, cancer metastasis, etc., based on the CXCR4 antagonism. Nitrogen-containing compounds represented by the following general formula and

Enzymatic resolution of bicyclic 1-heteroarylamines using Candida antarctica lipase B

Candida antarctica lipase B has been used to kinetically resolve a structurally diverse series of bicyclic 1-heteroaryl primary amines by enantioselective acetylation. High yields of either enantiomer could be obtained with excellent enantioselectivity (90-99% ee), while the undesired enantiomer could, in some cases, be recycled by thermal racemization. The absolute stereochemistry of the products was confirmed by an X-ray crystal structure.

Synthesis of enantiomerically pure amino-substituted fused bicyclic rings

This invention describes various processes for synthesis and resolution of racemic amino-substituted fused bicyclic ring systems. One process utilizes selective hydrogenation of an amino-substituted fused bicyclic aromatic ring system. An alternative process prepares the racemic amino-substituted fused bicyclic ring system via nitrosation. In addition, the present invention describes the enzymatic resolution of a racemic mixture to produce the (R)- and (S)-forms of amino-substituted fused bicyclic rings as well as a racemization process to recycle the unpreferred enantioner. Further provided by this invention is an asymmetric synthesis of the (R)- or (S)-enantiomer of primary amino-substituted fused bicyclic ring systems.

NITROGENOUS COMPOUNDS AND ANTIVIRAL DRUGS CONTAINING THE SAME

The present invention provides novel compounds having antiviral activities and antiviral drugs containing the compounds as the active ingredient. The compounds are shown by the following general formula (1), wherein typically A1 and A2 are each guanidine or a group of the general fomula (ia) ; A3 is a mono- or poly-cyclic heteroaromatic ring contining 1 or 2 heteroatoms ; B1 is a single bond or alkylene group; R1 is hydrogen or alkyl group; W is an alkylene having 2-3 carbons, a cycloalkylene having 5-10 carbons, aromatic ring having 6-10 carbons, or a heteroaromatic ring having 5-10 carbons; y is C(=O)-; x is -C(=O)-NH-; n1 is an integer of 1-2; n2 is an integer of 2-3; D is a substituent selected from among various groups.

Synthesis of enantiomerically pure 8-substituted 5,6,7,8-tetrahydro quinolines

Enantiomerically pure (S)-5,6,7,8-tetrahydroquinolin-8-ol [(S)-1] and (R)-8-acetoxy-5,6,7,8-tetrahydroquinoline [(R)-2] have been prepared by the lipase-catalyzed kinetic acetylation of racemic 5,6,7,8-tetrahydroquinolin-8-ol [(±)-1] in excellent chemical