137469-86-4

Usage

Uses

Used in Organic Synthesis:
BOC-8-AMINO-1,2,3,4-TETRAHYDROQUINOLINE is used as a building block in organic synthesis for the preparation of various pharmaceuticals, agrochemicals, and materials. Its unique structure allows for the creation of a wide range of compounds with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, BOC-8-AMINO-1,2,3,4-TETRAHYDROQUINOLINE is used as a precursor in the synthesis of peptide and oligonucleotide conjugates. Its role in the development of these conjugates is crucial for enhancing the therapeutic potential of peptides and nucleic acids in treating various diseases.
Used in Medicinal Chemistry and Drug Discovery:
BOC-8-AMINO-1,2,3,4-TETRAHYDROQUINOLINE is utilized in medicinal chemistry and drug discovery due to its structural flexibility and biological activity. Researchers leverage its properties to design and develop new drugs with improved efficacy and selectivity for various therapeutic targets.

InChI:InChI=1/C14H20N2O2/c1-14(2,3)18-13(17)16-11-8-4-6-10-7-5-9-15-12(10)11/h4,6,8,15H,5,7,9H2,1-3H3,(H,16,17)

Upstream product

• 578-66-5 8-amino quinoline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 54012-92-9 8-amino-1,2,3,4-tetrahydroquinoline 
• 607-35-2 8-nitroquinoline 
• 137469-85-3 tert-butyl (quinolin-8-yl)carbamate 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of tetrahydroquinoline-based reversible LSD1 inhibitors

The targeted regulation of LSD1, which is highly expressed in a variety of tumor cells, is a promising cancer therapy strategy. Several LSD1 inhibitors are currently under clinical evaluation, and most of these inhibitors are irreversible. Here, we report the design, synthesis and biochemical evaluation of novel tetrahydroquinoline-based reversible LSD1 inhibitors. Compounds 18s and 18x, which are selective to LSD1 over MAO-A/B, exhibit excellent LSD1 inhibition at the molecular levels with IC50 = 55 nM and 540 nM, respectively. The classic Lineweaver–Burk plots revealed that compound 18s could reversibly bind the LSD1 enzyme in a noncompetitive manner. Molecular docking was used to reveal the potential binding-mode of the compounds and interpret the structure-activity relationships. Furthermore, compounds 18s and 18x significantly inhibited proliferation (IC50 = 1.13 μM and 1.15 μM, respectively) and induced apoptosis in MGC-803 cells with high expression of LSD1. Compound 18x showed acceptable liver microsomal stability. Meanwhile, 18x did not appear to inhibit CYPs at 10 μM in vitro. Remarkably, the oral administration of compound 18x can inhibit the growth of MGC-803 xenograft tumors without significant side effects. Our findings suggest that tetrahydroquinoline-based LSD1 inhibitors deserve further investigation for the treatment of LSD1 overexpressing cancer.

Chemokine receptor binding heterocyclic compounds

This invention relates to a novel class of heterocyclic compounds that bind chemokine receptors, inhibiting the binding of their natural ligands thereby. These compounds result in protective effects against infection by HIV through binding to chemokine receptors, including CXCR4 and CCR5, thus inhibiting the subsequent binding by these chemokines. The present invention provides a compound of Formula I wherein, W is a nitrogen atom and Y is absent or, W is a carbon atom and Y═H; R1to R7may be the same or different and are independently selected from hydrogen or straight, branched or cyclic C1-6alkyl; R8is a substituted heterocyclic group or a substituted aromatic group Ar is an aromatic or heteroaromatic ring each optionally substituted at single or multiple, non-linking positions with electron-donating or withdrawing groups; n and n′ are independently, 0-2; X is a group of the formula: Wherein, Ring A is an optionally substituted, saturated or unsaturated 5 or 6-membered ring, and P is an optionally substituted carbon atom, an optionally substituted nitrogen atom, sulfur or oxygen atom. Ring B is an optionally substituted 5 to 7-membered ring. Ring A and Ring B in the above formula can be connected to the group W from any position via the group V, wherein V is a chemical bond, a (CH2)n″group (where n″=0-2) or a C═O group. Z is, (1) a hydrogen atom, (2) an optionally substituted C1-6alkyl group, (3) a C0-6alkyl group substituted with an optionally substituted aromatic or heterocyclic group, (4) an optionally substituted C0-6alkylamino or C3-7cycloalkylamino group, (5) an optionally substituted carbonyl group or sulfonyl. These compounds further include any pharmaceutically acceptable acid addition salts and metal complexes thereof and any stereoisomeric forms and mixtures of stereoisomeric forms thereof.

Sulfonamide derivatives and drugs containing the same as the active ingredient

The present invention discloses a sulfonamide derivative represented by the following formula (1): [wherein A represents a nitrogen atom, —CH═, etc.; Z represents an oxygen atom, etc.; Ar1represents an aryl group, etc.; Ar2represents an alkyl group, etc.; Rarepresents a hydrogen atom, etc.; Rbrepresents a hydrogen atom, etc.; and Rcrepresents an alkyl group, etc.], or a salt thereof; and drugs containing the derivative or a salt thereof as an active ingredient. This compound exhibits radical scavenging action, gastric mucous secretion augmenting action, and anti-HP action, and thus is effective as a peptic ulcer therapeutic agent.

Synthesis of Bi- and Tri-cyclic Tetrazepinones

Diazotization of N,N'-dialkyl-N-(o-aminophenyl) ureas 7, 13 and 17 gave 3,5-dimethyl-3H-1,2,3,5-benzotetrazepin-4(5H)-one 8, 3-methyl-6,7-dihydro-1,2,3,5-tetrazepinoquinolin-4(3H)-one 14 and 3-methyl-6,7-dihydrooxazino-1,2,3,5-benzotetrazepin-4-one 19.The structures of these bi- and tri-cyclic systems were confirmed by 1H, 13C and 15N NMR data.X-Ray diffraction of compound 14 shows that the tetrazepinone ring is nonplanar.