研究者詳細 - 北村　充

論文 - 北村　充

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Design, Synthesis and Anticancer Evaluation of New Substituted Thiophene-Quinoline Derivatives 査読有り

Othman D., Selim K., El-Sayed M., Tantawy A., Amen Y., Shimizu K., Okauchi T., Kitamura M.

Bioorganic and Medicinal Chemistry 27 ( 19 ) 2019年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2019 Elsevier Ltd A series of new isoxazolyl, triazolyl and phenyl based 3-thiophen-2-yl-quinoline derivatives were synthesized adopting click chemistry approach. In addition, the synthesis of new useful synthon, (2-chloroquinolin-3-yl) (thiophen-2-yl) methanol, is reported. The obtained compounds were characterized by spectral data analysis and evaluated for their anticancer activity. All the derivatives were subjected to in vitro MTT cytotoxicity screening assay against a panel of four different human cancer cell lines, liver (HepG-2), colon (HCT-116), human cervical cancer (HeLa) and breast (MCF-7). Out of a library of 17 compounds, two compounds have been identified as potent and selective cytotoxic agents against HeLa and MCF-7 cell lines. SAR studies for such hybridized analogues were investigated and phenyl derivatives were proved to be more potent than isoxazole and triazole derivatives. Furthermore, the promising compounds were selected for in vitro inhibition of EGFR-TK and Topo II enzymes. Also, they were subjected to cell cycle arrest analysis and apoptosis assay on MCF-7 cells. Our recent finding highlights these thiophene-quinoline analogues as a promising class of compounds for further studies concerning new anticancer therapies.

DOI： 10.1016/j.bmc.2019.07.042

Scopus

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Direct Azidation of Phenols 査読有り

Kitamura M., Murakami K., Koga T., Eto T., Ishikawa A., Shimooka H., Okauchi T.

European Journal of Organic Chemistry 2019 ( 33 ) 5824 - 5827 2019年09月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Direct azidation of phenols was developed. By treating chloroimidazolinium chloride 1b and sodium azide with phenol in the presence of a secondary amine in methoxyethanol, ortho-azidation of phenol was achieved.

DOI： 10.1002/ejoc.201900967

Kyutacar

Scopus

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高校生のためのクロスカップリング実験査読有り

岡内　辰夫，北村　充

化学と教育 67 ( 3 ) 130 - 133 2019年03月

Pd-catalyzed cyclization of terminal alkynes using diazonaphthoquinones: Synthesis of naphtho[1,2-b]furans 査読有り国際誌

Takahashi S., Shimooka H., Okauchi T., Kitamura M.

Chemistry Letters ( 公益社団法人日本化学会 ) 48 ( 1 ) 28 - 31 2019年01月

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

© 2019 The Chemical Society of Japan. Naphtho[1,2-b]furans were synthesized via a Pd-catalyzed reaction of diazonaphthoquinones and terminal alkynes in the presence of CuI and diisopropylamine. This method was then successfully applied to the synthesis of natural product, furomollugin.

DOI： 10.1246/cl.180803

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85059438494&origin=inward

高校生のためのクロスカップリング実験:—ノーベル化学賞の鈴木-宮浦クロスカップリングを題材に— 査読有り

岡内辰夫, 北村充

化学と教育 ( 公益社団法人日本化学会 ) 67 ( 3 ) 130 - 133 2019年01月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

<p>2010年，「有機合成におけるパラジウム触媒を用いたクロスカップリングの開発」に貢献した3人（Heck，根岸，鈴木）に，ノーベル化学賞が与えられた。そのうち2人が日本人であったため，マスコミで大きく取り上げられ，クロスカップリングという言葉が広く知られるようになった。受賞者の1人である北海道大学名誉教授の鈴木　章先生らのグループが開発した反応が，鈴木-宮浦クロスカップリングである。この反応は，有機ホウ素化合物と有機ハロゲン化合物に対して，パラジウム触媒を作用させることで炭素-炭素結合が形成するというものである。この反応は，我々の身の回りの医薬品，農薬，液晶材料，EL材料などの開発・量産化に大いに貢献している。</p>

DOI： 10.20665/kakyoshi.67.3_130

CiNii Article

CiNii Research

その他リンク： https://ci.nii.ac.jp/naid/130007804205

Synthesis of (±)-myo-inositol 4-methylenephosphonate via Rh-Catalyzed hydrogenation of vinylphosphonate 査読有り

T. Okauchi, S. Nakamura, K. Tsubaki, M. Asakawa, M. Kitamura

Carbohydrate Research 448 24 - 27 2017年08月

Synthesis of 1,2-naphthalenediol derivatives by Rh-catalyzed intermolecular O-H insertion reaction of 1,2-diazonaphthoquinones with water and alcohol 査読有り

M. Kitamura, K. Otsuka, S. Takahashi, T. Okauchi

Tetrahedron Letters 58 ( 36 ) 3508 - 3511 2017年07月

Azidoimidazolinium Salts: Safe and Efficient Diazo-transfer Reagents and Unique Azido-donors 査読有り

Kitamura M.

Chemical Record 17 ( 7 ) 653 - 666 2017年07月

担当区分：筆頭著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

© 2017 The Chemical Society of Japan & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2-Azido-1,3-dimethylimidazolinium chloride (ADMC) and its corresponding hexafluorophosphate (ADMP) were found to be efficient diazo-transfer reagents to various organic compounds. ADMC was prepared by the reaction of 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and sodium azide. ADMP was isolated as a crystal having good thermal stability and low explosibility. ADMC and ADMP reacted with 1,3-dicarbonyl compounds under mild basic conditions to give 2-diazo-1,3-dicarbonyl compounds in high yields, which were easily isolated in virtue of the high water solubility of the by-products. ADMP showed high diazo-transfer ability to primary amines even in the absence of metal salt such as Cu(II). Using this diazotization approach, various alkyl/aryl azides were directly obtained from their corresponding primary amines in high yields. Furthermore, naphthols reacted with ADMC to give the corresponding diazonaphthoquinones in good to high yields. In addition, 2-azido-1,3-dimethylimidazolinium salts were employed as azide-transfer and migratory amidation reagents.

DOI： 10.1002/tcr.201600118

Scopus

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Total Synthesis of Eleuthoside A; Application of Rh-Catalyzed Intramolecular Cyclization of Diazonaphthoquinone 査読有り

D. I. A. Othman, K. Otsuka, S. Takahashi, K. B. Selim, M. A. El-Sayed, A. S. Tantawy, T. Okauchi, M.u Kitamura

Synlett 29 ( 4 ) 457 - 462 2017年03月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

The first total synthesis of (±)-eleutherol and eleuthoside A, the natural cytotoxic substances extracted from medicinal Indonesian plant, is described. First, the synthesis of (±)-eleutherol has been accomplished in nine steps starting from bromo methoxy aldehyde with the aid of diazo-transfer chemistry approach. Second, a metal-catalyzed intramolecular cyclization reaction of the corresponding diazonaphthoquinone led to the desired eleuotherol, which served as a precursor to eleuthoside A. Then, several glycosidation routes, using different glucosyl donors, were experimented to reach effective O-glycosidation of eleutherol. The only successful strategy involved Koenigs-Knorr glycosidation using peracetyl glycosyl bromide in the presence of Ag 2 O and quinoline. This strategy furnished our desired acetylated glycoside of β-configuration, regioselectively. Finally, deacetylation and successive separation of diastereomers were conducted to give eleuthoside A.

DOI： 10.1055/s-0036-1589118

Kyutacar

Scopus

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85033366665&origin=inward

Diazonaphthoquinones: Synthesis, reactions and applications 招待有り査読有り

D.I.A. Othman, M. Kitamura,

Heterocycles 92 ( 10 ) 1761 - 1783 2016年08月

Axially Chiral Bifunctional 8,8′-Biquinolyl: Synthesis of 7,7′-Dihydroxymethyl-8,8′-biquinolyl via Pd-Catalyzed Double C–H Oxidation of 7,7′-Dimethyl-8,8′-biquinolyl 査読有り

M. Kitamura, H. Fukuma, M. Kobayashi, S. Okayama, T. Okauchi

J. Org. Chem. 2016年04月

Synthesis, structure, and reaction of chiral 2-azidoimidazolinium salts: (7aS)-3-azido-5,6,7,7a-tetrahydro-2-[(1R)-1-phenylethyl]-1H-pyrrolo[1,2-c]imidazolium hexafluorophosphate and 2-azido-1,3-bis[(S)-1-phenylethyl]imidazolinium hexafluorophosphate 査読有り

M. Kitamura, A. Ishikawa, T. Okauchi

Tetrahedron Lett. 57 ( 16 ) 1794 - 1797 2016年03月

Rh-Catalyzed Cyclization of 3-Aryloxycarbonyldiazonaphthoquinones for the Synthesis of β-Phenylnaphthalene Lactones and Formal Synthesis of Pradimicinone 査読有り

M. Kitamura, S. Takahashi, T. Okauchi

J. Org. Chem. 80 ( 16 ) 8406 - 8416 2015年08月

Synthesis of 2-Azido-1,3-dimethylimidazolinium Hexafluorophosphate 査読有り

M. Kitamura, K. Murakami

Organic Syntheses 92 171 - 181 2015年05月

Synthesis of the Cyclic Prenylguanidine Nitensidine E using a Palladium-Catalyzed Carbenylative Amination 査読有り

M. Kitamura, R. Yuasa, D. L. Van Vranken

Tetrahedron Lett. 2014年11月

A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate 査読有り

Kitamura M., Kato S., Yano M., Tashiro N., Shiratake Y., Sando M., Okauchi T.

Organic and Biomolecular Chemistry 12 ( 25 ) 4397 - 4406 2014年07月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

Organic azides were prepared from primary amines in high yields by a metal free diazo-transfer reaction using 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP), which is safe and stable crystalline. The choice of base was important in the diazo-transfer reaction. In general, 4-(N,N-dimethyl)aminopyridine (DMAP) was efficient, but a stronger base such as alkylamine or DBU was more appropriate for the reaction of nucleophilic primary amines. X-ray single crystal structural analysis and geometry optimization using density functional theory (B3LYP/6-31G**) were conducted to study the ADMP structure, and the diazo-transfer reaction mechanism was explained with the help of the results of these analyses. © the Partner Organisations 2014.

DOI： 10.1039/c4ob00515e

Scopus

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Reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate 査読有り

M. Kitamura, S. Kato, M. Yano, N. Tashiro, Y. Shiratake, M. Sando, T. Okauchi

Org. Biomol. Chem. in press 2014年05月

Pd(OAc)2-Catalyzed Macrocyclization of 1,2-Diazonaphthoquinones with Cyclic Ethers 査読有り

M. Kitamura, M. Kisanuki, K. Kanemura, T. Okauchi

Org. Lett. 16 1554 - 1557 2014年04月

Development of safe diazo-transfer reagent: Synthesis and reaction of guanidino diazoninm salt (azide imidazolinium salt) 査読有り

Kitamura M.

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry 72 ( 1 ) 14 - 25 2014年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

2-Azido-l,3-dimethylimidazolinium chloride (ADMC) and its corresponding hexafluorophosphate (ADMP) were found to be safe and efficient diazo-transfer reagents to various organic compounds. ADMC was prepared by the reaction of 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and sodium azide. ADMP was isolated as a crystal having thermal stability and low explo- sibility. ADMC and ADMP reacted with 1,3-dicarbonyl compounds under mild basic conditions to give 2-diazo-1,3-dicarbonyl compounds in high yields, which are easily isolated because the byproducts are highly soluble in water. Naphthols also reacted with ADMC to give corresponding diazonaphthoquinones in good to high yields. Furthermore, ADMP shows efficient diazo-transfer ability to primary amines even without the aid of a metal salt such as Cu(ll). Using this diazoti- zation approach, various alkyl/aryl azides were obtained directly from corresponding primary amines in high yields. In addition, ADMC/ADMP could be used as azide-transfer and amidation reagents.

DOI： 10.5059/yukigoseikyokaishi.72.14

Scopus

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Synthetic study of kosinostatin aglycone: Synthesis of BCDE rings using alkoxycarbonylmethylation of diazonaphthoquinone 査読有り

M. Kitamura, K. Kubo, S. Yoshinaga, H. Matsuzaki, K. Ezaki, T. Matsuura, D. Matsuura, N. Fukuzumi, K. Araki, M. Narasaki

Tetrahedron Lett. 55 1653 - 1656 2014年01月

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