51385-93-4

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 38, p. 2050, 1995 DOI: 10.1021/jm00012a004

InChI:InChI=1/C13H12O3/c1-15-10-5-3-9-4-6-13(16-2)12(8-14)11(9)7-10/h3-8H,1-2H3

Upstream product

• 3469-26-9 2,7-Dimethoxynaphthalene 
• 68-12-2 N,N-dimethyl-formamide 
• 141-82-2 malonic acid 
• 813-56-9 tetradeuterio-malonic acid 
• 4885-02-3 Dichloromethyl methyl ether 
• 93-61-8 N-methyl-N-phenylformamide 
• 77-78-1 dimethyl sulfate 
• 582-17-2 2,7-Dihydroxynaphthalene 
• 1535-67-7 difluoromethyl phenyl sulfide 

Downstream Products

• 75965-66-1 2-hydroxy-7-methoxynaphthalene-1-carbaldehyde 
• 4614-12-4 dibromo-1,6 dimethoxy-2,7 naphtalene 
• 66946-96-1 3-(2,7-dimethoxynaphthalen-1-yl)-1-(2-methoxyphenyl)propan-1-one 
• 78504-21-9 3-(2,7-dimethoxynaphthalen-1-yl)-1-(3,4-dimethoxyphenyl)propan-1-one 
• 78504-22-0 3-(2,7-dimethoxynaphthalen-1-yl)-1-(2,4-dimethoxyphenyl)propan-1-one 

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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

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.

Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl) methane

Difluoro(phenylsulfanyl)methane (PhSCF 2 H) was found to undergo a reaction with aromatic compounds mediated by SnCl 4, through a thionium intermediate characterized by NMR and TD-DFT analyses, leading to the formation of a mixture of S, S ′-diphenyl dithioacetal and aromatic aldehyde which, after oxidative hydrolysis, provides the aromatic aldehyde in good to excellent yields. The salient feature of the present work is the reaction of activated aromatic compounds containing a deactivating ester functional group, leading to the formylated products in good yields.

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.

Microwave-assisted Vilsmeier-Haack formylation of aromatic substrates

A microwave-assisted Vilsmeier-Haack formylation reaction has been studied on various amines, phenols and polynuclear hydrocarbons under solvent free condition that rapidly affords higher yield of products compared to traditional thermal condition.

TRICYCLIC AMIDES

The invention relates to a compound selected from these of formula (I) : STR1 in which R 7, R 8, Y, n and A are as defined in the description, and medicinal product containing the same useful for treating a disorder of the melatoninergic system.

An artificial receptor for dimethyl aspartate

[trans-5,15-Bis(2,7-dihydroxy-1-naphthyl)-2,3,7,8,12,13,17,18-octaethy lporphyrinato]zinc(II) (1), a trifunctionalized porphyrin host, was prepared as a receptor for amino acid derivatives, particularly those having a hydrogen-bonding site in the side chain. The free energy changes for the binding of Leu-OMe, Asp-OMe, and Glu-OMe to 1 were -5.8 kcal/mol, -6.6 kcal/mol, and -5.9 kcal/mol, showing a selectivity for Asp-OMe. 1H NMR titration experiments indicated that three simulteneous attractive interactions, one coordination interaction, and two hydrogen-bonding interactions, are operating in the host-guest complex. The preference for Asp-OMe over Glu-OMe was found to originate from the favorable enthalpy term for Asp-OMe. The free energy change, the enthalpy change, and the entropy change were determined and split into contributions arising from coordination interaction and from hydrogen-bonding interactions by use of reference hosts. Comparison of enthalpy and entropy changes suggests that the host-guest complex becomes more ordered as the number of recognition pairs increases.

Design and Synthesis of New Naphthalenic Derivatives as Ligands for 2-Iodomelatonin Binding Sites

New melatonin-like agents were designed from the frameworks of 2,5-dimethoxyphenethylamine, an important structural moiety for the 5-HT receptor, and (2-methoxynaphthyl)ethylamine.The compounds were synthesized by classical methods and evaluated in binding assays with chicken brain membranes using 2-(125I>iodomelatonin as the radioligand.Preliminary studies on the series of N-acyl-disubstituted phenethylamines showed the favorable role of the methoxy group in the ortho position of the side chain on the affinity for the receptor ( Ki = 8 +/- 0.2 nM ) for N-propionamide (3o).This effect was confirmed in a series of the naphthalene derivatives, a bioisosteric moiety of the indole ring, and several potent ligands for melatonin binding sites were prepared such as N-propionamide (4b) ( Ki = 0.67 +/- 0.05 nM ) and N-cyclopropylformamide (Ki = 0.05 +/- 0.004 nM ( (4k).Structure-activity relationships are discussed with regard to melatonin and bioisosteric naphthalenic compound 2.The Ki value for 4b was affected to a similar extent to that of melatonin by GTP-γ-S or Mn2+ in competition experiments, suggesting an agonist profile for this compound.

Manganese(III)-Mediated Formylation of Aromatic Compounds in the Presence of Malonic Acid

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