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平成29年度大阪薬科大学研究振興基金助成の受賞者が決定

 大阪薬科大学研究振興基金助成は、若手専任教員が本学で行った研究成果の中で、特に優れた研究論文を発表した者を顕彰し、更なる研究活動の発展を支援することを目的としたものです。
 平成29年度は下記の3名が受賞となりました。

助成対象者 米山弘樹 助教(有機薬化学研究室)
論文名 Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions : Fragmentation of Tetrazoles Deriverd from Cyanophosphates

掲載雑誌

The Journal of Organic Chemistry, 82, 5538-5556 (2017)

概要

ケトンから容易に調製することができるシアノホスフェート(CP)を、NaN3-Et3N・HClで処理するとアジドテトラゾールが生成した。そのアジドテトラゾールにマイクロ波を照射し加熱すると、アルキリデンカルベンが発生し、[1,2]転位によって、アルキンに変換出来ることを見出した。一方で、アルデヒドから合成したCPを、THF中NaN3-Et3N・HClと反応させると、一挙に末端アルキンへと変化させる事が出来た。さらに検討を進め、CPをTMSN3と触媒量のBu2SnOと共にトルエン中還流することによって、良好な収率でアルキンへ変換出来ることを見出した。これらの反応は、中性条件下で起こせるため、従来、塩基性条件下で用いられてきたOhira-Bestmann法やShioiri法からは得られないアルキンを得ることを可能とした。

Cyanophosphates (CPs) can be easily prepared from either ketones or aldehydes, and their reaction with NaN3−Et3N·HCl results in the formation of azidotetrazoles. Under microwave irradiation, successive fragmentation of the azidotetrazoles generates alkylidene carbenes that undergo [1,2]-rearrangement and are transformed into homologous alkynes. Treatment of ketone-derived CPs with TMSN3 and Bu2SnO as catalyst in toluene at reflux directly yields the corresponding internal alkynes, whereas the reaction of aldehyde-derived CPs with NaN3−Et3N·HCl in THF at reflux or TMSN3−Bu2SnO (cat.) in toluene at reflux provides homologous terminal alkynes in good yields. These reactions take place under neutral conditions and can be successfully extended to obtain alkynes that are not usually accessible from the corresponding carbonyl compounds by the Ohira−Bestmann or Shioiri procedures, which require basic conditions.

助成対象者 菊地 崇 助教(医薬品化学研究室)
論文名

Pleurocins A and B: Unusual 11(9→7)-abeo-ergostanes, and Eringiacetal B: a 13,14-seco-13,14-epoxy Ergostane from Fruiting Bodies of Pleurotus eryngii, and their Inhibitory Effects on Nitric Oxide Production.

掲載雑誌

The Journal of Organic Chemistry, 82, 10611–10616 (2017).

概要

Two novel 11(9→7)-abeo-ergostane-type steroids, named pleurocins A (1) and B (2), a 13,14-seco-13,14-epoxy ergostane, named eringiacetal B (3), and an ergostane steroid (4), were isolated from the fruiting bodies of Pleurotus eryngii (Pleurotaceae). Their structures were determined by spectroscopic data and X-ray crystallography. A possible biogenesis pathway for 13 was also described. Compounds 13 exhibited inhibitory activities against NO production with almost no cytotoxicity at concentrations lower than 30 μM.


助成対象者 東 剛志 助教(環境分子生理学研究室)
論文名 A method for evaluating the pharmaceutical deconjugation potential in river water environments.

掲載雑誌

Chemosphere. 180, 476-482 (2017)

概要

 A new enzymatic assay method that uses deconjugation enzymes was developed to evaluate the presence and extent of conjugated pharmaceuticals in the form of glucuronide conjugates or sulphate conjugates in river environments. First, acetaminophen glucuronide (Ace Glu) and acetaminophen sulphate (Ace Sul) were used as model conjugated pharmaceuticals to determine the appropriate combination of deconjugation enzymes and reaction conditions, including temperature, duration and pH. Next, we applied the defined method to 19 pharmaceuticals grouped into nine therapeutic classes that were chosen based on previously detected levels and frequencies in sewage and river water. The enzymatic decomposition profile varied widely depending upon the enzyme preparations available. The effect of the water reaction temperature was small between 5 and 40 °C, and the reaction proceeded in for both glucuronide conjugates and sulphate conjugates at an approximately neutral pH (corresponding to usual river water conditions) within 1 h. Application of the method to environmental samples showed that some pharmaceuticals were present in both glucuronide conjugate and sulphate conjugated forms, although glucuronide conjugates were the primary forms in the river water environment. Water treatment systems at sewage treatment plants were found to be effective for the removal of these conjugated compounds. The present results should be valuable in the environmental risk assessment of conjugated pharmaceuticals and in keeping river environments clean. To the best of our knowledge, this is the first report that enables the evaluation of the pharmaceutical deconjugation potential in a river environment.




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