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Pd-Catalyzed microwave-assisted synthesis of phosphonated 13?-estrones as potential OATP2B1, 17?-HSD1 and/or STS inhibitors.

ABSTRACT: Novel 2- or 4-phosphonated 13?-estrone derivatives were synthesized via the Hirao reaction. Bromo regioisomers (2- or 4-) of 13?-estrone and its 3-benzyl or 3-methyl ether were reacted with diethyl phosphite or diphenylphosphine oxide using Pd(PPh₃)₄ as catalyst under microwave irradiation. The influence of the new compounds on the transport function of the organic anion transporting polypeptide OATP2B1 was investigated by measuring Cascade Blue uptake. Derivatives bearing a 3-benzyl ether function displayed substantial submicromolar OATP2B1 inhibitory activity. The inhibitory effects of the compounds on human placental steroid sulfatase (STS) and 17?-hydroxysteroid dehydrogenase type 1 isozyme (17?-HSD1) were investigated by in vitro radiosubstrate incubation methods. None of the test compounds inhibited the STS markedly. The structure-activity relationship evaluation revealed that 2-substituted 3-hydroxy derivatives are able to inhibit the 17?-HSD1 enzyme with submicromolar IC₅₀ values. Dual OATP2B1 and 17?-HSD1 inhibitors have been identified.

SUBMITTER: Jojart R

PROVIDER: S-EPMC6244214 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Pd-Catalyzed microwave-assisted synthesis of phosphonated 13α-estrones as potential OATP2B1, 17β-HSD1 and/or STS inhibitors.

Jójárt Rebeka R Pécsy Szabolcs S Keglevich György G Szécsi Mihály M Rigó Réka R Özvegy-Laczka Csilla C Kecskeméti Gábor G Mernyák Erzsébet E

Beilstein journal of organic chemistry 20181114

Novel 2- or 4-phosphonated 13α-estrone derivatives were synthesized via the Hirao reaction. Bromo regioisomers (2- or 4-) of 13α-estrone and its 3-benzyl or 3-methyl ether were reacted with diethyl phosphite or diphenylphosphine oxide using Pd(PPh<sub>3</sub>)<sub>4</sub> as catalyst under microwave irradiation. The influence of the new compounds on the transport function of the organic anion transporting polypeptide OATP2B1 was investigated by measuring Cascade Blue uptake. Derivatives bearing ...[more]

PMID: 30498534

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Project description:To produce biodiesel cost-effective, low-cost, high free fatty acid (FFA) oil feedstock is desirable. But high FFA creates difficulty during the base-catalyzed transesterification process by yield loss due to the formation of soap. However, these problems are overcome by the use of an acid catalyst. The acid catalysts can directly convert both triglycerides and FFAs into biodiesel without the formation of soaps or emulsions. The shortcomings of mostly used inorganic acids are that they work well for esterification of FFA present in low-cost oil, but their kinetics for transesterification of triglycerides present in oils is considerably slower. Corrosion of equipment is another major problem associated with an inorganic acid catalyst. The usage of an organic acid catalyst of the alkyl benzene sulfonic type, like 4-dodecyl benzene sulfonic acid (DBSA) minimizes these disadvantages of inorganic acid-catalyzed transesterification. The aim of the present investigation was to reduce the reaction time of transesterification of triglycerides further by using microwaves as a heating source in the presence of DBSA catalyst to achieve higher conversions under mild operating conditions. To optimize the transesterification variables for the higher conversion of biodiesel, the response surface methodology was employed to design the experiment. By using the DBSA catalyst under microwave heating at a temperature of 76 °C, conversion close to 100% in only 30 min of reaction time was obtained using a 0.09 molar ratio of catalyst to oil and 9.0 molar ratio of methanol to oil. A modified polynomial model was developed and was adequately fitted with the experimental data and could be used for understanding the effect of various process parameters. The catalyst to oil molar ratio and reaction temperature created a stronger effect on the biodiesel production than that exhibited by the methanol to oil molar ratio. It was observed that the microwave heating process outperformed conventional heating, providing a rapid, easy method for biodiesel synthesis from triglycerides in the presence of DBSA, an organic acid catalyst. The produced biodiesel was of good quality, as all the properties were within the prescribed limits of the ASTM D6751 standard.

Dataset Information

Pd-Catalyzed microwave-assisted synthesis of phosphonated 13?-estrones as potential OATP2B1, 17?-HSD1 and/or STS inhibitors.

Publications

Pd-Catalyzed microwave-assisted synthesis of phosphonated 13α-estrones as potential OATP2B1, 17β-HSD1 and/or STS inhibitors.

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