6628-35-9

Upstream product

• 134-32-7 1-amino-naphthalene 
• 504-63-2 trimethyleneglycol 
• 91-20-3 naphthalene 
• 3420-41-5 2-Phenyl-5,6-dihydro-4H-[1,3]oxazine 
• 627-18-9 1-bromo-3-propanol 
• 861588-45-6 [1]naphthyl-carbamic acid-(3-chloro-propyl ester) 

Downstream Products

• 230-27-3 7,8-benzoquinoline 
• 95432-79-4 N¹,N³-di(naphthalen-1-yl)propane-1,3-diamine 
• 134-32-7 1-amino-naphthalene 

Relevant academic research and scientific papers

Functionalised benzo[a]phenoxazine dyes as long-wavelength fluorescent probes for amino acids

A series of monoreactive functional benzo[a]phenoxazinium chlorides with a carboxyl, hydroxyl, amine or chloromethyl group were used as labels in the preparation of long-wavelength fluorescent amino acid bioconjugates. UV-visible and fluorescence studies of all compounds were carried out in ethanol and water at physiological pH. The absorption and emission of all compounds synthesised were in the range 555-640 nm and 632-681 nm, respectively.

Synthesis of fluorescent water-soluble functionalised benzo[a]phenoxazinium salts

In order to develop long-wavelength functionalised oxazine dyes with good water solubility and high photostability for biological applications, a series of novel side-chain functionalised benzo[a]phenoxazinium salts were synthesised and characterised. The

Catalytic Synthesis of Substituted Indoles and Quinolines from the Dehydrative C-H Coupling of Arylamines with 1,2- and 1,3-Diols

The cationic ruthenium-hydride complex catalyzes the dehydrative C-H coupling reaction of arylamines with 1,2-diols to form the indole products. The analogous coupling of arylamines with 1,3-diols afforded the substituted quinolines. The catalytic method directly forms these coupling products in a highly regioselective manner without generating any toxic byproducts.

Heterocyclization Approach for Electrooxidative Coupling of Functional Primary Alkylamines with Aromatics

A new approach for electrooxidative coupling of aromatic compounds and primary alkylamines bearing a functional group such as a hydroxyl group and an amino group was developed. The key to the success of the transformation is heterocyclization of functional primary alkylamines. Treatment of primary alkylamines bearing a functional group with nitriles or their equivalents gives the corresponding heterocycles. The electrochemical oxidation of aromatic substrates in the presence of the heterocycles followed by chemical reaction under nonoxidative conditions gave the desired coupling products.

Ultrasound promoted synthesis of Nile Blue derivatives

Ultrasound irradiation was used for the first time towards the synthesis of new Nile Blue related benzo[a]phenoxazinium chlorides possessing isopentylamino, (2-cyclohexylethyl)amino and phenethylamino groups at 5-position of the heterocyclic system. The e

Synthesis of new benzo[a]phenoxazinium probes possessing carboxylic ester, hydroxyl and amino functional groups: Photophysical studies in dry ethanol and conjugation with CdTe quantum dots

A new series of benzo[a]phenoxazinium chlorides possessing hydroxyl, ethyl ester and amino functional groups as terminal substituents at the 9- and 5-positions of the tetracyclic aromatic system in different combinations, was synthesized. A photophysical

Synthesis and photophysical properties of side-chain chlorinated benzo[a]phenoxazinium chlorides

Novel water-soluble benzo[a]phenoxazinium chlorides mono- or disubstituted with 3-chloropropyl groups at the amine of position 9, and also at the hydroxyl function at position 2, were synthesized. These compounds possessing one, two or three chlorinated t

Click chemistry based method for the preparation of maleinimide-type thiol-reactive labels

Maleinimides are widely used to label proteins and to derivatize thiols. The so-called click reaction was shown to allow the efficient introduction of the maleinimido group into azido-modified fluorophores (benzoxazines) by reacting them with an alkyne-mo

Antimicrobial photodynamic efficacy of side-chain functionalized benzo[a]phenothiazinium dyes

5-(Ethylamino)-9-diethylaminobenzo[a]phenothiazinium chloride (EtNBS) is a photosensitizer (PS) with broad antimicrobial photodynamic activity. The objective of this study was to determine the antimicrobial photodynamic effect of side chain/end group modifications of EtNBS on two representative bacterial Gram-type-specific strains. Two EtNBS derivatives were synthesized, each functionalized with a different side-chain end-group, alcohol or carboxylic acid. In solution, both exhibited photochemical properties consistent with those of the EtNBS parent molecule. In vitro photodynamic therapy experiments revealed an initial Gram-type-specificity with two representative strains; both derivatives were phototoxic to Staphylococcus aureus 29213 but the carboxylic acid derivative was nontoxic to Escherichia coli 25922. This difference in photodynamic efficacy was not due to a difference in the binding of the two molecules to the bacteria as the amount of both derivatives bound by bacteria was identical. Interestingly, the carboxylic acid derivative produced no fluorescence emission when observed in cultures of E. coli via fluorescence microscopy. These early findings suggest that the addition of small functional groups could achieve Gram-type-specific phototoxicity through altering the photodynamic activity of PSs and deserve further exploration in a larger number of representative strains of each Gram type.

Clickable fluorophores for biological Labeling - With or without copper

The synthesis of a set of new clickable fluorophores that virtually cover the whole visible spectrum reaching the near infra-red regime is presented herein. Besides dyes that are capable of participating in classical copper catalyzed 1,3-dipolar cycloaddition reactions with the counterparting function we have also prepared dyes containing a cyclooctyne moiety, an alkyne derivative that enables copper free clicking to azides. The suitability of these dyes for fluorescent labeling of biomolecules is presented by examples on model frameworks representing major biopolymer building blocks. The versatility of these dyes is presented in cell labeling experiments as well as by labeling the azide modified surface glycans of CHO-cells either by copper catalyzed or copper-free click reaction. These dyes are expected to have a large variety of applications in (bio)orthogonal labeling schemes both in vivo and in vitro.