53815-56-8

Usage

Uses

Used in Organic Synthesis:
6-Bromo-2-hydroxy-1-naphthaldehyde is used as a building block in organic synthesis for the creation of more complex molecules. Its presence of both a bromine and a hydroxyl group allows for versatile chemical reactions and the formation of a wide range of compounds.
Used in Chemical Research:
In the field of chemical research, 6-Bromo-2-hydroxy-1-naphthaldehyde is utilized for studying its unique structure and reactivity. This helps in understanding the behavior of similar compounds and contributes to the advancement of chemical knowledge.
Used in Pharmaceutical Industry:
6-Bromo-2-hydroxy-1-naphthaldehyde is used as a potential lead compound in drug discovery and development. Its unique structure and reactivity make it a promising candidate for the synthesis of new pharmaceuticals with potential therapeutic applications.
Used in Dye Industry:
Due to its chemical properties, 6-Bromo-2-hydroxy-1-naphthaldehyde is used in the dye industry for the production of various dyes. Its ability to form complex molecules makes it suitable for creating dyes with specific color properties and applications.
Used in Other Industrial Processes:
6-Bromo-2-hydroxy-1-naphthaldehyde has been studied for its potential applications in various industrial processes. Its unique structure and reactivity make it a valuable compound for developing new materials and improving existing processes.

Upstream product

• 15231-91-1 6-bromo-naphthalen-2-ol 
• 50-00-0 formaldehyd 
• 1191-17-9 1,1-dichloromethyl-methyl ether 
• 20524-86-1 dichloromethyl ether 
• 557-21-1 zinc(II) cyanide 
• 100-97-0 hexamethylenetetramine 
• 727708-53-4 6-bromo-1-(pyrrolidin-1-ylmethyl)naphthalen-2-ol 
• 542-88-1 bis(2-chloromethyl)ether 
• 4885-02-3 Dichloromethyl methyl ether 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 

Downstream Products

• 1093119-18-6 4-(5-formyl-6-hydroxynaphthalen-2-yl)-N,N-dimethylbenzamide 
• 1093119-22-2 methyl-3-(5-formyl-6-hydroxynaphthalen-2-yl)benzoate 
• 75965-73-0 nitro-2 bromo-7 naphto<2,1-b>furanne 
• 247174-18-1 6-bromo-2-methoxynaphthalene-1-carbaldehyde 

Relevant academic research and scientific papers

MLL1 INHIBITORS AND ANTI-CANCER AGENTS

The present invention provides a compound of Formula (I): or an enantiomer, an enantiomeric mixture, or a pharmaceutically acceptable salt thereof; wherein the variables are as defined herein. The present invention further provides pharmaceutical composit

Design, Synthesis and SAR Studies of Novel and Potent Dipeptidyl Peptidase 4 Inhibitors

Dipeptidyl peptidase 4 (DPP-4) is a clinically validated target for the treatment of type 2 diabetes mellitus (T2DM). To discover novel and potent DPP-4 inhibitors, three series of compounds were designed and synthesized in this study based on our previou

Discovery of selective SIRT2 inhibitors as therapeutic agents in B-cell lymphoma and other malignancies

Genetic ablation as well as pharmacological inhibition of sirtuin 2 (SIRT2), an NAD+dependent protein deacylase, have therapeutic effects in various cancers and neurodegenerative diseases. Previously, we described the discovery of a dual SIRT1/SIRT2 inhibitor called cambinol (IC50 56 and 59 μM, respectively), which showed cytotoxic activity against cancer cells in vitro and a marked anti-proliferative effect in a Burkitt lymphoma mouse xenograft model. A number of recent studies have shown a protective effect of SIRT1 and SIRT3 in neurodegenerative and metabolic diseases as well as in certain cancers prompting us to initiate a medicinal chemistry effort to develop cambinol-based SIRT2-specific inhibitors devoid of SIRT1 or SIRT3 modulating activity. Here we describe potent cambinol-based SIRT2 inhibitors, several of which show potency of ~600 nM with >300 to >800-fold selectivity over SIRT1 and 3, respectively. In vitro, these inhibitors are found to be toxic to lymphoma and epithelial cancer cell lines. In particular, compounds 55 (IC50 SIRT2 0.25 μM and 25% inhibition at 50 μM against SIRT1 and SIRT3) and 56 (IC50 SIRT2 0.78 μM and 25% inhibition at 50 μM against SIRT1 and SIRT3) showed apoptotic as well as strong anti-proliferative properties against B-cell lymphoma cells.

Sulfur-containing heterocyclic compound and application thereof as derivative of DPP4 inhibitor

The invention relates to a benzo sulfur-containing six-membered ring derivative as a DPP-4 inhibitor and application thereof, in particular to a compound shown in a formula I, a pharmaceutical composition comprising the compound of the formula I and application of the compound to the preparation of a medicament for the treatment of DPP-4 associated diseases or inhibition of DPP-4. Please see the specification for the formula I.

Atropoenantioselective redox-neutral amination of biaryl compounds through borrowing hydrogen and dynamic kinetic resolution

We report herein a novel atropoenantioselective redox-neutral amination of biaryl compounds triggered by a cascade of borrowing hydrogen and dynamic kinetic resolution under the cooperative catalysis of a chiral iridium complex and an achiral Br?nsted acid. This protocol features broad substrate scope and good functional-group tolerance, and allows the rapid assembly of axially chiral biaryl compounds in good to high yields and with high to excellent enantioselectivity.

Atropoenantioselective Redox-Neutral Amination of Biaryl Compounds through Borrowing Hydrogen and Dynamic Kinetic Resolution

We report herein a novel atropoenantioselective redox-neutral amination of biaryl compounds triggered by a cascade of borrowing hydrogen and dynamic kinetic resolution under the cooperative catalysis of a chiral iridium complex and an achiral Br?nsted acid. This protocol features broad substrate scope and good functional-group tolerance, and allows the rapid assembly of axially chiral biaryl compounds in good to high yields and with high to excellent enantioselectivity.

Ruthenium-Catalyzed Atropoenantioselective Synthesis of Axial Biaryls via Reductive Amination and Dynamic Kinetic Resolution

The unprecedented ruthenium-catalyzed atropoenantioselective reductive amination of aldehydes with alkylamines via a cascade transfer hydrogenation and dynamic kinetic resolution strategy is described. This protocol features broad substrate scope and good functional group tolerance and allows the rapid assembly of axially chiral biaryls in good to high yields with high to excellent enantioselectivities. In addition, such structural motifs may have potential applications in enantioselective catalysis as chiral ligands or catalysts.

Three-Component Aminoalkylations Yielding Dihydronaphthoxazine-Based Sirtuin Inhibitors: Scaffold Modification and Exploration of Space for Polar Side-Chains

Nonpolar derivatives of heterocyclic aromatic screening hits like the non-selective sirtuin inhibitor splitomicin tend to be poorly soluble in biological fluids. Unlike sp3-rich natural products, flat aromatic compounds are prone to stacking and often difficult to optimize into leads with activity in cellular systems. The aim of this work was to identify anchor points for the introduction of sp3-rich fragments with polar functional groups into the newly discovered active (IC50 = 5 μM) but nonpolar scaffold 1,2-dihydro-3H-naphth[1,2-e][1,3]oxazine-3-thione by a molecular modeling approach. Docking studies were conducted with structural data from crystallized human SIRT2 enzyme. Subsequent evaluation of the in silico hypotheses through synthesis and biological evaluation of the designed structures was accomplished with the aim to discover new SIRT2 inhibitors with improved aqueous solubility. Derivatives of 8-bromo-1,2-dihydro-3H-naphth[1,2-e][1,3]oxazine-3-thione N-alkylated with a hydrophilic morpholino-alkyl chain at the thiocarbamate group intended for binding in the acetyl-lysine pocket of the enzyme appeared to be promising. Both the sulfur of the thiocarbamate and the bromo substituent were assumed to result in favorable hydrophobic interactions and the basic morpholino-nitrogen was predicted to build a hydrogen bond with the backbone Ile196. While the brominated scaffold showed moderately improved activity (IC50 = 1.8 μM), none of the new compounds displayed submicromolar activity. Synthesis and characterization of the new compounds are reported and the possible reasons for the outcome are discussed.

Discovery and Rational Design of Natural-Product-Derived 2-Phenyl-3,4-dihydro-2H-benzo[f]chromen-3-amine Analogs as Novel and Potent Dipeptidyl Peptidase 4 (DPP-4) Inhibitors for the Treatment of Type 2 Diabetes

Starting from the lead isodaphnetin, a natural product inhibitor of DPP-4 discovered through a target fishing docking based approach, a series of novel 2-phenyl-3,4-dihydro-2H-benzo[f]chromen-3-amine derivatives as potent DPP-4 inhibitors are rationally designed utilizing highly efficient 3D molecular similarity based scaffold hopping as well as electrostatic complementary methods. Those ingenious drug design strategies bring us approximate 7400-fold boost in potency. Compounds 22a and 24a are the most potent ones (IC50 ≈ 2.0 nM) with good pharmacokinetic profiles. Compound 22a demonstrated stable pharmacological effect. A 3 mg/kg oral dose provided >80% inhibition of DPP-4 activity within 24 h, which is comparable to the performance of the long-acting control omarigliptin. Moreover, the efficacy of 22a in improving the glucose tolerance is also comparable with omarigliptin. In this study, not only promising DPP-4 inhibitors as long acting antidiabetic that are clinically on demand are identified, but the target fish docking and medicinal chemistry strategies were successfully implemented.

Benzo-hexatomic ring derivative used as DPP-4 inhibitor and application of benzo-hexatomic ring derivative

The invention relates to a benzo-hexatomic ring derivative used as a DPP-4 inhibitor and application of the benzo-hexatomic ring derivative, in particular to compounds shown as in formula I, medicine compositions with the compounds shown as in the formula I and application of the compounds in preparing medicines for treating diseases related to DPP-4 or inhibiting the DPP-4.