22190-40-5

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
1-acetyl-6-bromo-1,2,3,4-tetrahydroquinoline is used as a chemical building block for the development of new pharmaceuticals and medicinal agents. Its quinoline scaffold is a key structural element in many bioactive compounds, making it a promising candidate for the creation of novel drugs with potential therapeutic applications.
Used in Organic Chemistry Research:
1-acetyl-6-bromo-1,2,3,4-tetrahydroquinoline serves as a subject of study for researchers in the field of organic chemistry. Its synthesis and properties are of interest for understanding the behavior of heterocyclic compounds and for exploring new methods of synthesis that could lead to the discovery of additional related compounds with useful properties.
Used in Drug Development:
As a potential drug candidate, 1-acetyl-6-bromo-1,2,3,4-tetrahydroquinoline may be utilized in the development of new therapeutic agents. Its unique structure and the presence of the quinoline core suggest that it could have biological activity, making it a candidate for further investigation and optimization to treat various diseases or conditions.

InChI:InChI=1/C11H12BrNO/c1-8(14)13-6-2-3-9-7-10(12)4-5-11(9)13/h4-5,7H,2-3,6H2,1H3

Upstream product

• 4169-19-1 1-acetyl-1,2,3,4-tetrahydroquinoline 
• 22190-35-8 6-bromo-1,2,3,4-tetrahydroquinoline 
• 75-36-5 acetyl chloride 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 5263-87-6 6-methoxy quinoline 

Downstream Products

• 851202-94-3 1-acetyl-1,2,3,4-tetrahydroquinoline-6-carbonitrile 

Relevant academic research and scientific papers

CANCER TREATMENTS TARGETING CANCER STEM CELLS

Disclosed are compounds, methods, compositions, and kits that allow for treating cancer by, e.g., targeting cancer stem cells. In some embodiments, the cancer is colorectal cancer, gastric cancer, gastrointestinal stromal tumor, ovarian cancer, lung cancer, breast cancer, pancreatic cancer, prostate cancer, testicular cancer, or lymphoma. In some embodiments, the cancer is liver cancer, endometrial cancer, leukemia, or multiple myeloma. The compounds utilized in the disclosure are of Formula (0), (O'), and (I):

A Unique Approach to Design Potent and Selective Cyclic Adenosine Monophosphate Response Element Binding Protein, Binding Protein (CBP) Inhibitors

The epigenetic regulator CBP/P300 presents a novel therapeutic target for oncology. Previously, we disclosed the development of potent and selective CBP bromodomain inhibitors by first identifying pharmacophores that bind the KAc region and then building into the LPF shelf. Herein, we report the "hybridization" of a variety of KAc-binding fragments with a tetrahydroquinoline scaffold that makes optimal interactions with the LPF shelf, imparting enhanced potency and selectivity to the hybridized ligand. To demonstrate the utility of our hybridization approach, two analogues containing unique Asn binders and the optimized tetrahydroquinoline moiety were rapidly optimized to yield single-digit nanomolar inhibitors of CBP with exquisite selectivity over BRD4(1) and the broader bromodomain family.

THERAPEUTIC COMPOUNDS AND USES THEREOF

The present invention relates to compounds of formula (I) and formula (II): and to salts thereof, wherein R1-R4 of formula (I) and R5-R6 of formula (II) have any of the values defined herein, and compositions and uses thereof. The compounds are useful as inhibitors of CBP and/or EP300. Also included are pharmaceutical compositions comprising a compound of formula (I) of formula (II), or a pharmaceutically acceptable salt thereof, and methods of using such compounds and salts in the treatment of various CBP and/or EP300-mediated disorders.

TETRAHYDROISOQUINOLINE COMPOUNDS AND THEIR USE AS PYRUVATE DEHYDROGENASE KINASE INHIBITORS

A compound of formula (I): or a pharmaceutically acceptable salt thereof, wherein: R1 is H, Cl, F, CH3 or CF3; R2 is H, C1-C6 alkyl or optionally substituted heteroaryl or optionally substituted aryl; and R3 is (Alk)n-Rn-(Alk)n-Rn-(Alk)n-X. The compounds are useful as tetrahydroisoquinoline (THQ) compounds, which are suitable for use as PDK inhibitors, for example for inhibition of cancer cell proliferation.

N-THIAZOL-2-YL-BENZAMIDE DERIVATIVES

The invention relates to N-thiazol-2-yl-benzamide derivatives of the formula I in the description wherein the variables are as defined in the claims. The compounds are A2A-receptor ligands, such as antagonists, agonists, reverse agonists or partial agonists, and are useful in the treatment of neurological and psychiatric disorders where an A2A-receptor is implicated.

Process for substitution of aromatic organic compounds

The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula -O-R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula Mn+ [O--R]n? wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R2 --O--CO--H wherein R2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.