10.1016/j.bmcl.2009.08.072
The study focuses on the structure-activity relationship (SAR) of a novel series of piperidine-derived c-secretase modulators for the potential treatment of Alzheimer's disease (AD). The research identifies compound 10h as a potent modulator that selectively decreases Ab42 levels, increases Ab38 levels, and does not affect Ab40 levels in vitro. This compound also exhibits favorable pharmacokinetic properties in mice, rats, and dogs, along with good central nervous system (CNS) penetration in mice. The study aims to develop more potent c-secretase modulators that could slow or halt AD progression without the side effects associated with inhibitors, by modulating the enzyme's action to produce less pathogenic peptides.
10.1021/op049808k
The study investigates two synthetic routes for the kilogram-scale production of cis-N-protected-3-methylamino-4-methylpiperidine (3), a key intermediate in the synthesis of a clinical drug candidate. The first route involves electrochemical oxidation of carbamate 1 to install a ketone at the 3 position of the piperidine, followed by reductive amination. The second route includes the hydrogenation of a functionalized pyridine. Various chemicals were utilized in these processes, such as potassium acetate, acetic acid, and methyl carbamate for the electrochemical oxidation, and 4-methyl-3-aminopyridine, potassium tert-butoxide, and dimethyl carbonate for the pyridine reduction approach. These chemicals served as reactants, solvents, and reagents to facilitate the desired chemical transformations and achieve the target compound. The study concluded that the pyridine hydrogenation route was more suitable for large-scale production due to the crystallinity and purity of intermediates, ultimately achieving the desired compound in a 55% overall yield.
10.1016/S0040-4020(01)81658-6
The research focuses on the synthesis of tetracyclic 1.2.3.4.5.6-hexahydro-1.5-methanoazocino[4.3-b]indole systems with a methoxycarbonyl substituent at the C-6 position. Key chemicals involved in this research include 2-(4-pyridylmethyl)indole, which undergoes methoxycarbonylation to introduce the functionalized one-carbon substituent. Other important chemicals are 4-acetylpyridine, used in the synthesis of the required 2-cyanotetrahydropyridine, and various reagents such as sodium borohydride, n-butyllithium, and dimethyl carbonate, which play roles in different steps of the synthesis. Additionally, compounds like 1,2,3,6-tetrahydropyridine, indole, and mercuric acetate are utilized in the oxidative cyclization process to form the final tetracyclic systems. The research also involves the use of protecting groups, such as ethylene acetal, and various solvents like methanol, benzene, and chloroform to facilitate the reactions and achieve the desired products.
10.1134/S1070428018110180
The study focuses on the synthesis of 1-, 2-methoxy-, 1,3-dimethoxyadamantanes, and 1-, 4-methoxydiadamantanes using adamantyl and diadamantyl halides reacted with dimethyl carbonate in the presence of zeolite catalysts, specifically NiHY or FeHY. These catalysts, free of binders, are promoted by iron and nickel compounds and are crucial for the selective synthesis of methoxyadamantanoids. The study optimizes the ratio of catalysts and reagents and develops reaction conditions for high yield and selectivity. The chemicals involved include adamantyl and diadamantyl halides as starting materials, dimethyl carbonate as both a reagent and solvent, and zeolite catalysts (NiHY and FeHY) to facilitate the reactions. The synthesized compounds exhibit high thermal stability, resistance to light and hydrolysis, and antimicrobial properties, making them valuable additives for improving the oxidative resistance and rheological characteristics of lubricating oils and fluids.
10.1016/S0040-4020(98)00193-8
The research focuses on the synthesis of 11-methoxycarbonyl-13-phenyl-17-vinylgona-1,3,5(10)-trienes, which are significant compounds in the field of steroid chemistry. The study aims to develop a novel and efficient strategy for the synthesis of these complex molecules, leveraging the titanium tetrachloride-mediated dialkylation of methyl 4-oxo-4-(p-bromophenyl)butanoate ethylene ketal by 1,8-bis(trimethylsilyl)-2,6-octadiene (BISTRO). The process involves several steps, including methoxycarbonylation, alkylation by iodobenzocyclobutene, and pyrolysis, to yield the desired steroid compounds. The research concludes that this methodology offers a short and efficient route to 13-arylgonatrienes from 1,3-butadiene and benzocyclobutenol, with the added advantage of being able to modify the substituents on the phenyl group and transform the vinyl group through Wacker-type oxidation, thus enhancing the synthetic versatility of the method. Key chemicals used in this process include titanium tetrachloride, 1,8-bis(trimethylsilyl)-2,6-octadiene (BISTRO), methyl 4-oxo-4-(p-bromophenyl)butanoate ethylene ketal, iodobenzocyclobutene, and dimethyl carbonate, among others.
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