40019-43-0

Basic information

• Product Name: N-HYDROXY-1-NAPHTHALENE CARBOXIMIDAMIDE
• Synonyms: N-HYDROXY-1-NAPHTHALENE CARBOXIMIDAMIDE;N-Hydroxy-naphthalene-1-carboxamidine
• CAS NO: 40019-43-0
• Molecular Formula: C₁₁H₁₀N₂O
• Molecular Weight: 186.22
• Mol File: 40019-43-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-HYDROXY-1-NAPHTHALENE CARBOXIMIDAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-HYDROXY-1-NAPHTHALENE CARBOXIMIDAMIDE(40019-43-0)
• EPA Substance Registry System: N-HYDROXY-1-NAPHTHALENE CARBOXIMIDAMIDE(40019-43-0)

Safety Data

• Hazardous Substances Data: 40019-43-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-HYDROXY-1-NAPHTHALENE CARBOXIMIDAMIDE is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structural features, including the carboximidamide and hydroxy groups, make it a valuable component in the development of new drugs with specific therapeutic properties.
Used in Dye Industry:
In the dye industry, N-HYDROXY-1-NAPHTHALENE CARBOXIMIDAMIDE is utilized as a chemical intermediate for the production of dyes. Its naphthalene and functional groups contribute to the color and stability of the dyes, making it an essential component in the formulation of various dye products.
Used in Organic Compounds Synthesis:
N-HYDROXY-1-NAPHTHALENE CARBOXIMIDAMIDE is used as a building block in the synthesis of other organic compounds. Its reactivity and structural features allow it to participate in a wide range of chemical reactions, facilitating the creation of diverse organic molecules for various applications.
Used in Biological and Medicinal Research:
N-HYDROXY-1-NAPHTHALENE CARBOXIMIDAMIDE is employed in biological and medicinal research as a structural component for the development of new compounds with potential biological activities. Its unique features can be exploited to design and synthesize novel molecules with therapeutic potential, contributing to the advancement of medical science.

Upstream product

• 86-53-3 1-Cyanonaphthalene 
• 13504-46-6 1-naphtylaldehyde oxime 
• 66-77-3 1-naphthaldehyde 
• 90-14-2 1-Iodonaphthalene 
• 90-11-9 1-Bromonaphthalene 
• 3177-49-9 1-naphthyldiazonium chloride 

Downstream Products

• 1161923-87-0 5-cyclohexylamino-3-(1-naphthyl)-1,2,4-oxadiazole 

Relevant articles and documents

Fragment Growing to Design Optimized Inhibitors for Human Blood Group B Galactosyltransferase (GTB)

Human blood group B galactosyltransferase (GTB) catalyzes the galactosylation of the H antigen and is responsible for the formation of the blood group antigen of phenotype B. The ABO blood group system is well studied and routinely serotyped before transfusion and transplantation. Blood type subgroups have been repeatedly linked to an increased occurrence of diseases (e.g., a highly increased incidence rate for pancreatic cancer for individuals with blood group phenotype B). 3-Phenyl-5-(piperazin-1-yl)-1,2,4-thiadiazole 1 has previously been described to inhibit GTB with a Ki value of 800 μm. In this work, we describe a computer-guided fragment-growing approach for the optimization of this fragment that was subsequently realized by synthesizing the most promising ligands. Enlarging the phenyl moiety of fragment 1 to a naphthyl moiety resulted in ligand 3-(naphthalene-1-yl)-5-(piperazin-1-yl)-1,2,4-thiadiazole 2 a, which shows a threefold improvement in binding affinity (Ki=271 μm).

Design and synthesis of new triarylimidazole derivatives as dual inhibitors of BRAFV600E/p38α with potential antiproliferative activity

Recent studies have shown that combining kinase inhibitors has additive and synergistic effects. BRAFV600E and p38α have been extensively studied as potential therapeutic targets for a variety of diseases. In keeping with our interest in developing multi-targeted anticancer agents, a series of novel triaryl-imidazole-based analogues containing 3-aryl-1,2,4-oxadiazoles moiety (4a-h, Scaffold B) and their reaction intermediates aryl carboximidamides moiety (3a-h, Scaffold A) have been rationally designed, synthesized, and evaluated in vitro for their antiproliferative activity as dual p38α/BRAFV600E inhibitors. The results revealed that the presence of the carboximidamide moiety is required for activity, and the best activity correlates with the Ar = 1,2-benzodioxole (3e) ≥ 4-CH3O-C6H5-(3c) > 2-naphthyl (3h) > 4-Cl-C6H5 (3b). Ring closure of carboximidamide to 1,2,4-oxadiazole significantly reduces the activity. The results of docking study into p38α revealed higher binding affinities for compounds 3c, 3e, and 3h compared to the co-crystallized ligand, SB2. However, the docking study of compounds 3c and 3e into BRAFV600E revealed slightly lower affinities than vemurafenib.

Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine

Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.

Discovery of 1,2,4-oxadiazole derivatives as a novel class of noncompetitive inhibitors of 3-hydroxykynurenine transaminase (HKT) from Aedes aegypti

The mosquito Aedes aegypti is the vector of arboviruses such as Zika, Chikungunya, dengue and yellow fever. These infectious diseases have a major impact on public health. The unavailability of effective vaccines or drugs to prevent or treat most of these

SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)

A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.

Efficient Synthesis of Functionalized Indene Derivatives via Rh(III)-Catalyzed Cascade Reaction between Oxadiazoles and Allylic Alcohols

A highly efficient rhodium(III)-catalyzed synthesis of novel functionalized indene derivatives has been achieved via C?H activation/intramolecular aldol condensation. This cascade reaction is an atom economical protocol which could be further applied to build more complex compounds. (Figure presented.).

A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement

A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.

One-pot synthesis of amidoxime via Pd-catalyzed cyanation and amidoximation

A novel "one-pot" reaction was developed for the synthesis of aryl or heteroaryl-substituted amidoxime compounds containing various functional groups. Fluorescence titration experiments coupled with theoretical analysis revealed that the steric hindrance and electronic effects of substituents influence the binding ability of the amidoxime compounds to uranyl ions. This journal is

A novel one-pot synthesis of ferrocenyl-substituted 1,2,4-oxadiazoles

One-pot synthesis of 5-ferrocenyl-1,2,4-oxadiazoles via the reaction between 3-ferrocenylpropynal and amidoximes is described. 3-Ferrocenylpropynal reacts with a variety of amidoximes in the presence of KOH in refluxing dioxane to afford a broad range of

Synthesis, enzyme kinetics and computational evaluation of N-(β-d-glucopyranosyl) oxadiazolecarboxamides as glycogen phosphorylase inhibitors

All possible isomers of N-β-d-glucopyranosyl aryl-substituted oxadiazolecarboxamides were synthesised. O-Peracetylated N-cyanocarbonyl-β- d-glucopyranosylamine was transformed into the corresponding N-glucosyl tetrazole-5-carboxamide, which upon acylation