38077-75-7

Usage

Uses

Used in Pharmaceutical Industry:
1-NAPHTHALENECARBONYL CHLORIDE,2-HYDROXYis used as a key intermediate in the synthesis of pharmaceutical compounds for its ability to readily participate in organic reactions, contributing to the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
As a strong acylating agent, 1-NAPHTHALENECARBONYL CHLORIDE,2-HYDROXYis utilized in the production of esters and amides, which are fundamental building blocks in the creation of a variety of organic compounds.
Used in Chemical Research:
In the field of chemical research, 1-NAPHTHALENECARBONYL CHLORIDE,2-HYDROXYserves as a valuable reagent for exploring new reaction pathways and understanding the mechanisms of organic transformations.

Upstream product

• 2283-08-1 2-hydroxy-1-naphthalenecarboxylic acid 
• 947-65-9 methyl 2-hydroxy-1-naphthoate 

Relevant academic research and scientific papers

Triphenyl ether amide as a probe for electrochemical and optical sensing of copper, cyanide and arginine

A novel triphenyl ether amide (TPEAM) derivative has been synthesises and developed as a probe for electrochemical and optical sensing of copper, cyanide ions and arginine in the presence of other amino acids. The ionophore is selective for the copper and cyanide ions among various cations and anions, with detection limits as 40 nM and 0.4 μM, respectively. Sharp anodic and cathodic peaks in the differential pulse voltammograms of the TPEAM-Cu(II) complex indicated a good complexing tendency of the ligand molecule and it was confirmed by spectrofluorimetry and 1H NMR titrations. TPEAM-Cu2+ complex further detected arginine, a semi-essential amino acid, in aqueous medium with a lower detection limit of 4 μM. Host-guest interactions between TPEAM and Cu2+ ions and intramolecular charge transfer interactions (ICT) for CN- ions are proposed as possible mechanisms for the sensing of respective ions. Cyanide detection followed a non-sequential mechanism. The application of TPEAM as a probe for Cu2+ ions has also been validated on food samples and the results are compared with atomic absorption spectroscopy.

SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway

Disruption of cyclic adenosine monophosphate response element binding protein (CREB) provides a potential new strategy to address acute leukemia, a disease associated with poor prognosis, and for which conventional treatment options often carry a significant risk of morbidity and mortality. We describe the structure-activity relationships (SAR) for a series of XX-650-23 derived from naphthol AS-E phosphate that disrupts binding and activation of CREB by the CREB-binding protein (CBP). Through the development of this series, we identified several salicylamides that are potent inhibitors of acute leukemia cell viability through inhibition of CREB-CBP interaction. Among them, a biphenyl salicylamide, compound 71, was identified as a potent inhibitor of CREB-CBP interaction with improved physicochemical properties relative to previously described derivatives of naphthol AS-E phosphate.

Searching new structural scaffolds for BRAF inhibitors. An integrative study using theoretical and experimental techniques

The identification of the V600E activating mutation in the protein kinase BRAF in around 50% of melanoma patients has driven the development of highly potent small inhibitors (BRAFi) of the mutated protein. To date, Dabrafenib and Vemurafenib, two specifi

Enantioselective Copper-Catalyzed Electrophilic Dearomative Azidation of β-Naphthols

The first example of copper-catalyzed enantioselective dearomative azidation of β-naphthols using a readily available N3-transfer reagent is reported. A series of 2-hydroxy-1-naphthamides bearing a complex N-substituent were converted to the corresponding products in high yields with up to 96% ee, and chiral 1-azido-2-hydroxy-1-naphthoates were obtained with up to 90% ee under mild reaction conditions. The azides could be further transformed into the corresponding 1,2,3-triazoles smoothly via "click" reaction.

Scaffold Diversity Inspired by the Natural Product Evodiamine: Discovery of Highly Potent and Multitargeting Antitumor Agents

A critical question in natural product-based drug discovery is how to translate the product into drug-like molecules with optimal pharmacological properties. The generation of natural product-inspired scaffold diversity is an effective but challenging strategy to investigate the broader chemical space and identify promising drug leads. Extending our efforts to the natural product evodiamine, a diverse library containing 11 evodiamine-inspired novel scaffolds and their derivatives were designed and synthesized. Most of them showed good to excellent antitumor activity against various human cancer cell lines. In particular, 3-chloro-10-hydroxyl thio-evodiamine (66c) showed excellent in vitro and in vivo antitumor efficacy with good tolerability and low toxicity. Antitumor mechanism and target profiling studies indicate that compound 66c is the first-in-class triple topoisomerase I/topoisomerase II/tubulin inhibitor. Overall, this study provided an effective strategy for natural product-based drug discovery. (Figure Presented).

Design and synthesis of highly potent and selective (2-arylcarbamoyl- phenoxy)-acetic acid inhibitors of aldose reductase for treatment of chronic diabetic complications

Recent efforts to identify treatments for chronic diabetic complications have resulted in the discovery of a novel series of highly potent and selective (2-arylcarbamoyl-phenoxy)-acetic acid aldose reductase inhibitors. The compound class features a core template that utilizes an intramolecular hydrogen bond to position the key structural elements of the pharmacophore in a conformation, which promotes a high binding affinity. The lead candidate, example 40, 5-fluoro-2-(4-bromo-2-fluoro-benzylthiocarbamoyl)-phenoxyacetic acid, inhibits aldose reductase with an IC50 of 30 nM, while being 1100 times less active against aldehyde reductase, a related enzyme involved in the detoxification of reactive aldehydes. In addition, example 40 lowers nerve sorbitol levels with an ED50 of 31 mg/kg/d po in the 4-day STZ-induced diabetic rat model.

Intramolecular oxygen versus carbon alkylation of naphthoate esters. A caveat on the mechanistic aspects of neocarzinostatin chemistry

α-Hydroxy naphthoate esters are shown to be capable of undergoing intramolecular alkylation at carbon as well as at both oxygen centers. Basic reaction conditions favor intramolecular oxygen alkylation of the phenol moiety in addition to intramolecular carbon alkylation leading to spirolactones. Chemistry in neutral or acidic media appears to proceed via γ-oxo ketene acetal intermediates that are converted to products derived from addition of water followed by cleavage of the resultant orthoacid. γ-Oxo ketene acetal intermediates derived from naphthoate esters are at least 40 times more reactive than those derived from simple β-keto esters. These studies give credence to the proposal that the α-hydroxy naphthoate moiety in neocarzinostatin is capable of participation during the epoxide-opening reaction. Mechanistic consequences of such participation are discussed.