5774-08-3

Upstream product

• 46905-41-3 4-(6-methyl-[2]naphthyl)-4-oxo-butyric acid 
• 5156-83-2 6-methyl-2-acetonaphthone 
• 6162-30-7 6-methyl-1,2,3,4-tetrahydro-2-naphthoic acid methyl ester 
• 581-42-0 2.6-dimethylnaphthalene 
• 91-57-6 2-Methylnaphthalene 
• 33626-98-1 methyl 6-bromo-2-naphthoate 

Downstream Products

• 87700-61-6 6-Methyl-naphthalene-2-carbonyl chloride 
• 1210226-63-3 6-methylnaphthalene-2-carboxylic acid [1-(2-phenyl-1(R)-{[1-(tetrahydropyran-4-ylmethyl)piperidin-4-ylmethyl]carbamoyl}ethylcarbamoyl)cyclopentyl]amide 
• 61187-17-5 2-(chloromethyl)-(6-methyl)naphthalene 

Relevant academic research and scientific papers

Structural assignment of 2,6- and 2,7-disubstituted naphthalenes and prediction of 13C nuclear magnetic resonance chemical shifts: Applications of topology and two-dimensional NMR spectroscopy

Unambiguous assignments of monocarboxymethylnapthalenes isolated as oxidation products of dimethylnaphthalenes by Pseudomonas putida, a bacterial strain, were made using two-dimensional nuclear Overhauser enhancement correlation spectroscopy (NOESEY). The two-dimensional long-range heteronuclear correlation NMR technique was also utilized for the assignment of quaternary carbons in the naphthalene system. In addition, we describe methods for prediction of 13C NMR chemical shifts of 2,6- and 2,7-disubstituted naphthalenes using topological approach. The method involves computation of molecular descriptors from topological representation of molecule, namely Wiener (W) and Szeged (Sz) indices. The results have shown that W and Sz indices can be successfully used for predicting 13C NMR chemical shifts and that Σ13Cn can be used as a molecular property which in turn can be modeled by both W and Sz indices successfully.

Epoxides related to dioncoquinone B: Synthesis, activity against multiple myeloma cells, and search for the target protein

Epoxide 2b is an analog of the synthetic intermediate 2a en route to the polyketide-derived antitumoral naphthoquinone dioncoquinone B (1), isolated from cell cultures of the tropical liana Triphyophyllum peltatum (Dioncophyllaceae). Compound 2b was found to induce strong apoptosis in multiple myeloma cells at a concentration (EC50 = 3.5 μM), distinctly lower than that of 1 and any related analog, without exerting significant toxicity against normal blood cells. Preliminary studies showed that 2b follows different SAR rules as compared to the naphthoquinones. Among the series of synthesized epoxides, 2b was the most active one and was thus, after biotinylation, subjected to mass spectrometry-based affinity capture experiments aiming at the identification of target proteins. The MS data revealed 2b to address proteins that are associated with stress regulation processes which are critical for multiple myeloma cell survival.

ARYLCARBOXAMIDES AND USES THEREOF

The present disclosure is directed to compounds of formula (I): or a pharmaceutically acceptable salt, solvate or solvate of the salt thereof. Compounds of formula (I) are inhibitors of NOX4 and are useful in the treatment of fibrotic diseases such as scleroderma; lung disease, such as pulmonary fibrosis including idiopathic pulmonary fibrosis (IPF); heart disease, such as heart failure due to ischaemic heart disease, valvular heart disease and hypertensive heart disease, diabetic cardiomyopathy and hypertension; liver disease, such as cirrhosis of the liver; and kidney disease, such as progressive kidney disease glomerulonephritis and diabetic nephropathy; and eye disease such as diabetic retinopathy; skin or subcutaneous scarring, such as keloids, adhesions, hypertrophic scarring or cosmetic scarring; or as an adjuvant or anti-fibrotic in pancreatic cancer to increase chemotherapeutic drug penetration by reducing the density of the connective tissue stroma.

Modulation on C- and N-terminal moieties of a series of potent and selective linear tachykinin NK2 receptor antagonists

Herein we describe the synthesis of a series of new potent tachykinin NK2 receptor antagonists by the modulation of the Cand N-terminal moieties of ibodutant (MEN 15596, 1). The Nterminal benzo[b]thiophene ring was replaced by different substituted naphthalenes and benzofurans, while further modifications were evaluated at the C-terminal tetrahydropyran moiety. Most compounds demonstrated a high affinity for the human NK2 receptor and high in vitro antagonist potency, indicating that a wide range of substituents at both termini can be incorporated in the molecule without detrimental effects on the interactions with the NK2 receptor. Selected compounds were tested in vivo confirming their activity as NK2 antagonists. In particular, after both iv and id administration to guinea pig, compound 61b was able to antagonize NK2-induced colonic contractions with a potency and duration-of-action fully comparable to the reference compound 1 (MEN 15596, ibodutant).

Re2O7-catalyzed carbon-carbon bond cleavage of ketones into carboxylic acids with aq. TBHP

A mild and efficient catalytic method for the C-C bond cleavage of ketones to corresponding carboxylic acids in good yields is described using a catalytic amount of Re2O7 and 70% tert. butyl hydroperoxide (TBHP) as oxidant.

BIOSYNTHESIS OF AXENOMYCIN D: INCORPORATION OF 13C-LABELLED PRECURSORS INTO THE MENADIONE CHROMOPHORE, DESOXYSUGARS AND THE AXENOLIDE

Experiments on the biosynthesis of the menadione chromophore of axenomycin D in Streptomyces lisandri resulted in the specific incorporation of label from L-methionine, propionate, propionate, propionate, glycerol and glucose.The data indicate that the menadione chromophore is derived from a metabolite of the shikimate pathway.The mode of incorporation shows, however, that the biosynthesis of the menadione chromophore of axenomycin differs from the biosynthesis of the menadione chromophore of menaquinones.Key Word Index: Streptomyces lisandri; axenomycin; biosynthesis; 13C-NMR spectroscopy.

Kinetics of Base-catalysed Iodination of Substituted Acetonaphthones

Kinetics of iodination of 6-substituted 2-acetonaphthones and of 4-substituted 1-acetonaphthones in 20percent pyridine-20percent methanol-60percent water (v/v) have been followed at three temperatures.The Hammett equation applies very well to these reactions.The rate constants for various heterocyclic base-catalysed iodination of acetophenone and of 1- and 2-acetonaphthones in 60percent (v/v) methanol-water solvent have been correlated with pKa values of the conjugate acids of the heterocyclic bases via the Broensted equation giving β values of 0.88, 1.01 and 0.92 for acetophenone, 1-acetonaphthone and 2-acetonaphthone respectively.The influence of solvent on the rates of pyridine-catalysed iodination of acetophenone and of 1- and 2-acetonaphthones has also been studied.