22246-13-5

Basic information

• Product Name: 6-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE
• Synonyms: 6-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE;6-AMINO-3,4-DIHYDRO-2(1H)-QUINOLINONE;AKOS BB-9801;6-amino-3,4-dihydro-2(1 )-quinalinone;6-AMino-1,3,4-trihydro-quinolin-2-one;6-aMino-3,4-dihydro-2(1H )-quinalinone;6-amino-3,4-dihydrocarbostyril;6-Amino-3,4-dihydroquinoline-2(1H)-one
• CAS NO: 22246-13-5
• Molecular Formula: C₉H₁₀N₂O
• Molecular Weight: 162.19
• Product Categories: pharmacetical
• Mol File: 22246-13-5.mol

Chemical Properties

• Boiling Point: 423 °C at 760 mmHg
• Flash Point: 209.7 °C
• Appearance: /
• Density: 1.237 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 6-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE(22246-13-5)
• EPA Substance Registry System: 6-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE(22246-13-5)

Safety Data

• Hazardous Substances Data: 22246-13-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE is used as a key intermediate in the synthesis of various cardiotonic agents. These agents are essential for the treatment of heart-related conditions, as they help to strengthen the contractions of the heart muscles, thereby improving cardiac function.
Used in Chemical Synthesis:
In the chemical industry, 6-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE serves as a versatile building block for the creation of a wide range of compounds with diverse applications. Its unique structure allows for further functionalization and modification, making it a valuable component in the development of new drugs, dyes, and other specialty chemicals.

Upstream product

• 22246-16-8 6-nitro-3,4-dihydro-1H-quinolin-2-one 
• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 62-53-3 aniline 
• 3460-04-6 3-chloro-N-phenylpropionamide 

Downstream Products

• 99139-81-8 N-(2-oxo-1,2,3,4-tetrahydro-[6]quinolyl)-benzamide 
• 86813-31-2 6-(1-piperazinyl)-3,4-dihydrocarbostyril hydrobromide 
• 81840-23-5 6-[1-(4-acetylpiperazynyl)]-3,4-dihydroquinolin-2(1H)-one 
• 81840-19-9 6-(4-Benzoyl-1-piperazinyl)-3,4-dihydrocarbostyril 
• 81839-69-2 6-[4-(4-chlorobenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril 
• 81839-38-5 dihydro-6-<4-(4-methoxybenzyl)-1-piperazinyl>-2(1H)-quinolinone 
• 81840-26-8 6-[4-(4-Chlorobenzoyl)-1-piperazinyl]-3,4,-dihydrocarbostyril 
• 93392-74-6 6-[4-((E)-3-p-Tolyl-acryloyl)-piperazin-1-yl]-3,4-dihydro-1H-quinolin-2-one 
• 81840-22-4 6-[4-(4-methoxybenzoyl)piperazin-1-yl]-3,4-dihydroquinolin-2(1H)-one 
• 81840-34-8 6-[4-(3,4-methylenedioxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril 
• 81840-15-5 vesnarinone 
• 81839-60-3 1-(2-propynyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril 
• 81840-41-7 1-Benzyl-6-[4-(3,4-dimethoxy-benzoyl)-piperazin-1-yl]-3,4-dihydro-1H-quinolin-2-one 
• 187739-23-7 1-benzyl-6-chloro-2-(3,4-dihydro-2(1H)-quinolinon-6-ylaminocarbonyl)benzimidazole 

Relevant articles and documents

BIFUNCTIONAL MOLECULES CONTAINING AN E3 UBIQUITINE LIGASE BINDING MOIETY LINKED TO A BCL6 TARGETING MOIETY

Bifunctional compounds, which find utility as modulators of B-cell lymphoma 6 protein (BCL6; target protein), are described herein. In particular, the bifunctional compounds of the present disclosure contain on one end a Von Hippel-Lindau, cereblon, Inhibitors of Apotosis Proteins or mouse double-minute homolog 2 ligand that binds to the respective E3 ubiquitin ligase and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The bifunctional compounds of the present disclosure exhibit a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.

TETRAHYDROQUINOLINO DERIVATIVES FOR THE TREATMENT OF METASTATIC AND CHEMORESISTANT CANCERS

Disclosed herein are compounds of Structural Formula I. Compounds of Structural Formula I inhibit aldehyde dehydrogenase isoform Ia3 (ALDHIa3) and are useful for treating cancer, for example, metastatic or chemoresistant cancer, such as metastatic cancer resistant to chemotherapy. Also disclosed herein are compositions comprising compounds of Structural Formula I and uses of compounds of Structural Formula I for treating cancer, for example, metastatic or chemoresistant cancer.

Preparation method of 6-hydroxy-3,4-dihydro-2(1H)quinolinone

The invention belongs to the field of preparation of intermediates in chemical engineering, and particularly relates to a preparation method of 6-hydroxy-3,4-dihydro-2(1H)quinolinone. The preparationmethod comprises the following steps of using aniline and 3-chloropropionyl chloride as raw materials; performing cyclization, nitrification, reduction and diazotization hydrolysis, so as to synthesize the target product, namely 6-hydroxy-3,4-dihydro-2(1H)quinolinone. The preparation method has the advantages that the reaction conditions are mild, the cost is reduced, and the yield rate is increased.

Discovery of potent and selective BRD4 inhibitors capable of blocking TLR3-induced acute airway inflammation

A series of diverse small molecules have been designed and synthesized through structure-based drug design by taking advantage of fragment merging and elaboration approaches. Compounds ZL0420 (28) and ZL0454 (35) were identified as potent and selective BRD4 inhibitors with nanomolar binding affinities to bromodomains (BDs) of BRD4. Both of them can be well docked into the acetyl-lysine (KAc) binding pocket of BRD4, forming key interactions including the critical hydrogen bonds with Asn140 directly and Tyr97 indirectly via a H2O molecule. Both compounds 28 and 35 exhibited submicromolar potency of inhibiting the TLR3-dependent innate immune gene program, including ISG54, ISG56, IL-8, and Groβ genes in cultured human small airway epithelial cells (hSAECs). More importantly, they also demonstrated potent efficacy reducing airway inflammation in a mouse model with low toxicity, indicating a proof of concept that BRD4 inhibitors may offer the therapeutic potential to block the viral-induced airway inflammation.

INHIBITORS OF BROMODOMAIN-CONTAINING PROTEIN 4 (BRD4)

Certain embodiments are directed to small molecule selective inhibitors of the BRD4 bromodomain. Compounds described herein can be used to modulate the bronchiolar NFkB-BRD4 axis, which plays a role in acute neutrophilic response to viral molecular patterns. Compounds described herein can be developed as preventive and therapeutic agents for various human diseases and conditions.

NOVEL ULK1 INHIBITORS AND METHODS USING SAME

In certain aspects, the invention provides a method for treating a disease or condition in a subject, the method comprising co-administering to a subject in need thereof a therapeutically effective amount of at least one ULK1-inhibiting pyrimidine, and a therapeutically effective amount of an mTOR inhibitor.

COMPOUNDS FOR REGULATING FAK AND/OR SRC PATHWAYS

The present application provides novel optionally substituted fused pyridine and pyrimidine bicyclic compounds and pharmaceutically acceptable salts thereof. Also provided are methods for preparing these compounds. These compounds are useful in co-regulating FAK and/or Src activity by administering a therapeutically effective amount of one or more of the compounds to a subject. By doing so, these compounds are effective in treating conditions associated with the dysregulation of the FAK and/or Src pathway. Advantageously, these compounds perform as dual FAK and/or Src inhibitors. A variety of conditions can be treated using these compounds and include diseases which are characterized by inflammation or abnormal cellular proliferation. In one embodiment, the disease is cancer.

Design, synthesis and evaluation of the antidepressant and anticonvulsant activities of triazole-containing quinolinones

A series of 1-substituted-6-(4H-1,2,4-triazol-4-yl)-3,4-dihydroquinolin- 2(1H)-ones were designed, synthesized, and screened for their antidepressant and anticonvulsant activities. Interestingly, compounds 5i, 5j, 5m, and 5n led to significant reductions in the immobility time in the forced swimming test at a dose of 50 mg/kg, and exhibited higher levels of efficacy than the reference standard fluoxetine. In addition, compound 5i exhibited greater efficacy than fluoxetine in the tail suspension test. The results of an open field test further confirmed that compound 5i provided a good antidepressant effect. In the maximal electroshock seizure screen, compounds 5c and 5d showed moderate levels of anticonvulsant activity and protected 100% of the animals at a dose of 100 mg/kg. None of the synthesized compounds showed any neurotoxicity in the rotarod test at a dose of 100 mg/kg.

Synthesis and positive inotropic activity of N-(4,5-dihydro-[1,2,4]triazolo[4,3-a]quinolin-7-yl)-2-(piperazin-1-yl)ac etamide derivatives

A series of N-(4,5-dihydro-[1,2,4]triazolo[4,3-a]quinolin-7-yl)-2-(piperazin-1-yl)ac etamide derivatives were synthesized and their positive inotropic activity was evaluated by measuring left atrium stroke volume on isolated rabbit heart preparations. Several compounds showed favorable activity compared with the standard drug, milrinone, among which N-(1-benzyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinolin-7-yl)-2-(4-benzyl piperazin-1-yl)acetamide 6j was found to be the most potent with the 13.2% increased stroke volume (milrinone 4.7%) at concentration of 3 × 10-5 M in our in vitro study. The chronotropic effects of those compounds having inotropic effects were also evaluated in this work.

Synthesis and positive inotropic evaluation of 2-(4-(4-substituted benzyloxy)-3-methoxybenzyl)-1,4-diazepan-1-yl-n-(4,5-dihydro-1-methyl[1,2,4] triazolo[4,3-a]quinolin-7-yl)-acetamides

In an attempt to search for more potent positive inotropic agents, a series of 2-(4-(4-substituted benzyloxy)-3-methoxybenzyl)-1,4-diazepan-1-yl)-N-(4,5- dihydro-1-methyl[1,2,4]triazolo[4,3-a]quinolin-7-yl)acetamides was synthesized and their positive inotropic activities were evaluated by measuring left atrium stroke volume on isolated rabbit-heart preparations. Several compounds showed favorable activity compared with the standard drug Milrinone among which 2-(4-(4-(2-chlorobenzyloxy)-3-methoxybenzyl)-1,4-diazepan-1-yl)-N-(4, 5-dihydro-1-methyl-[1,2,4]triazolo[4,3-a]quinolin-7-yl)acetamide 6e was found to have the most desirable potency with the 6.79 ± 0.18% increased stroke volume (Milrinone: 1.67 ± 0.64%) at a concentration of 1 × 10 -5 M in our in-vitro study. The chronotropic effects of those compounds having inotropic effects were also evaluated in this work.