970-56-9

Usage

Also known as

Ramelteon

Chemical class

Selective melatonin receptor agonist

Use

Treatment of insomnia

Mechanism of action

Affects the body's natural sleep-wake cycle to help regulate sleep

Duration of use

Short-term treatment, not recommended for long-term use

Form

Tablet for oral administration

Prescription

Must be prescribed by a healthcare professional

Upstream product

• 1074-82-4 potassium phtalimide 
• 2196-99-8 2-chloro-1-(4-methoxyphenyl)ethanone 
• 136918-14-4 phthalimide 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 85-44-9 phthalic anhydride 
• 169614-59-9 2-[2-(4-methoxyphenyl)ethyl]-1H-isoindole-1,3(2H)-dione 
• 55-81-2 4-Methoxyphenethylamine 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-66-3 methoxybenzene 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 

Downstream Products

• 40513-43-7 2-amino-1-(4-methoxy-phenyl)-ethanone 
• 100423-00-5 2-(2-hydroxy-2-(4-methoxy-phenyl)-ethyl)-isoindole-1,3-dione 
• 74730-53-3 2-[2-(4-methoxyphenyl)-1,3-dioxolan-2-ylmethyl]-1H-isoindole-1,3(2H)-dione 
• 344334-51-6 4-methoxyphenacylamine ethylene ketal 
• 55275-61-1 2-amino-1-(4-methoxyphenyl)ethanol 

Relevant academic research and scientific papers

Dual Parasiticidal Activities of Phthalimides: Synthesis and Biological Profile against Trypanosoma cruzi and Plasmodium falciparum

Chagas disease and malaria are two neglected tropical diseases (NTDs) that prevail in tropical and subtropical regions in 149 countries. Chagas is also present in Europe, the US and Australia due to immigration of asymptomatic infected individuals. In the absence of an effective vaccine, the control of both diseases relies on chemotherapy. However, the emergence of parasite drug resistance is rendering currently available drugs obsolete. Hence, it is crucial to develop new molecules. Phthalimides, thiosemicarbazones, and 1,3-thiazoles have been used as scaffolds to obtain antiplasmodial and anti-Trypanosoma cruzi agents. Herein we present the synthesis of 24 phthalimido-thiosemicarbazones (3 a–x) and 14 phthalimido-thiazoles (4 a–n) and the corresponding biological activity against T. cruzi, Plasmodium falciparum, and cytotoxicity against mammalian cell lines. Some of these compounds showed potent inhibition of T. cruzi at low cytotoxic concentrations in RAW 264.7 cells. The most active compounds, 3 t (IC50=3.60 μM), 3 h (IC50=3.75 μM), and 4 j (IC50=4.48 μM), were more active than the control drug benznidazole (IC50=14.6 μM). Overall, the phthalimido-thiosemicarbazone derivatives were more potent than phthalimido-thiazole derivatives against T. cruzi. Flow cytometry assay data showed that compound 4 j was able to induce necrosis and apoptosis in trypomastigotes. Analysis by scanning electron microscopy showed that T. cruzi trypomastigote cells treated with compounds 3 h, 3 t, and 4 j at IC50 concentrations promoted changes in the shape, flagella, and surface of the parasite body similar to those observed in benznidazole-treated cells. The compounds with the highest antimalarial activity were the phthalimido-thiazoles 4 l (IC50=1.2 μM), 4 m (IC50=1.7 μM), and 4 n (IC50=2.4 μM). Together, these data revealed that phthalimido derivatives possess a dual antiparasitic profile with potential effects against T. cruzi and lead-like characteristics.

Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations

Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.

Extending the structure?activity relationship study of marine natural ningalin B analogues as P-glycoprotein inhibitors

In the present study, a total of 25 novel ningalin B analogues were synthesized and evaluated for their P-gp modulating activity in a P-gp overexpressed breast cancer cell line LCC6MDR. Preliminary structure-activity study shows that A ring and its two methoxy groups are important pharmacophores for P-gp inhibiting activity. Among all derivatives, 23 is the most potent P-gp modulator with EC50of 120–165?nM in reversing paclitaxel, DOX, vinblastine and vincristine resistance. It is relatively safe to use with selective index at least greater than 606 compared to verapamil. Mechanistic study demonstrates that compound 23 reverses P-gp mediated drug resistance by inhibiting transport activity of P-gp, thereby restoring intracellular drug accumulation. In summary, our study demonstrates that ningalin B analogue 23 is a non-cytotoxic and effective P-gp chemosensitizer that can be used in the future for reversing P-gp mediated clinical cancer drug resistance.

Efficient preparation of biologically important 1,2-amino alcohols

An efficient three-step methodology developed for the preparation of 1,2-amino alcohols. In the first step a rapid coupling between bromoketones and potassium phthalimide in ionic liquid produced-phthalimido ketones in quantitative yields, which is followed by a facile reduction using NaCNBH 3 in acetic acid to give corresponding phthalimido alcohols and finally effecting hydrazinolysis in water at 60C to yield biologically important 1,2-amino alcohols.

INDOLE-2-CARBOXYLIC ACID AMIDES

Compounds represented by Formula (I) or pharmaceutically acceptable salts thereof, are useful in the prophylactic or therapeutic treatment of diabetes, hyperglycemia, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, hypertension, atherosclerosis or

Ru-catalyzed asymmetric hydrogenation of α-phthalimide ketones and 1,3-diaryl diketones using 4,4′-substituted BINAPs

(Chemical Equation Presented) A family of tunable precatalysts [NH 2Et2][{Ru(4,4′-BINAP)Cl}2(μ-Cl) 3] was synthesized and used for highly enantioselective hydrogenation of phthalimide-protected amino ketones and

Palladium-catalyzed asymmetric hydrogenation of functionalized ketones

(Chemical Equation Presented) A novel catalytic system for asymmetric hydrogenation of functionalized ketones has been developed using a Pd/bisphosphine complex as the catalyst in 2,2,2-trifluoroethanol. The reaction exhibits high enantioselectivity, and

PYRROLOPYRIDINE-2-CARBOXYLIC ACID AMIDE INHIBITORS OF GLYCOGEN PHOSHORYLASE

Compounds represented by Formula (I): or pharmaceutically acceptable salts thereof, are inhibitors of glycogen phosphorylase and are useful in the prophylactic or therapeutic treatment of diabetes, hyperglycemia, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, hypertension, atherosclerosis or tissue ischemia e.g. myocardial ischemia, and as cardioprotectants.

Highly Enantioselective Asymmetric Hydrogenation of α-Phthalimide Ketone: An Efficient Entry to Enantiomerically Pure Amino Alcohols

A new type of α-phthalimide ketones was hydrogenated in excellent enantioselectivity by using a Ru-(C3-TunePhos) complex as the catalyst. Up to 10000 turnovers have been achieved in more than 99% ee in the hydrogenation reaction. A dynamic kinetic resolution study for the synthesis of threonine was performed, and high anti selectivity (>97:3) was observed for the first time. An efficient method to synthesize enantiomerically pure amino alcohols has been developed. Copyright