中村　浩之

なかむら　ひろゆき
Hiroyuki Nakamura

学習院大学理学部化学科助教授

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専門： 有機化学・境界領域化学

担当講義： 有機化学４　有機化学実験

住所： 〒171-8588　豊島区目白 1-5-1　学習院大学理学部 

電話： 03-3986-0221（内線 6491） 

fax: 03-5992-1029（理学部） 

e-mail: hiroyuki.nakamura@gakushuin.ac.jp

学生へ一言

　病気の治療、診断、予防のための医薬開発においては、新規骨格の生理活性物質の発見が重要であり、これらは主に天然有機分子や偶然の活性発見によって見い出されてきた。これらのいわゆる天然型生理活性分子は生体内においてその標的である受容体タンパク等と相互作用して活性が発現していると考えられている。現在、がんをはじめまだまだ特効薬のない病気があり、また新しい病気の発現の可能性もある。そういった中で、２１世紀の医薬開発における生理活性分子の創製には、これまでの研究とは異なるアプローチが必要である。我々の研究室では、医薬素材として生体内に存在しないホウ素元素に着目し、これを導入した新しい生理活性分子の創製を目的として研究を進めている。我々が標的とするタンパクに特異的に作用する生理活性分子を設計・合成するだけでなく、合成した化合物の標的タンパクへの相互作用についても分子生物学的手法を用いて調べ、構造活性相関を明らかにするとともに、さらなる分子設計を行っている。このように、本研究室では有機化学を基軸として分子生物学との境界領域に挑戦しており、「新薬創製」という大きな夢に向かって日夜研究に励んでいる。
　

プロフィール

平成３年３月　　東北大学理学部化学科　卒業
平成５年３月　　東北大学大学院理学研究科化学専攻博士前期課程　修了
平成５年４月　　日本学術振興会特別研究員
平成７年２月　　東北大学大学院理学研究科化学専攻博士後期課程２年　中退
平成７年３月　　東北大学大学院理学研究科化学専攻・助手
平成７年４月　　九州大学有機化学基礎研究センター・助手（流動部門）
平成８年９月　　博士（理学）取得　（東北大学）
平成９年４月　　東北大学大学院理学研究科化学専攻・助手
平成１１年３月　日本化学会進歩賞　受賞　
平成１２年４月～平成１３年４月　文部省在外派遣研究員（米国Pittsburgh大学・D.P.Curran教授）
平成１４年４月　学習院大学理学部化学科　助教授（現在に至る）



研究業績

発表論文   

[58]

Phase-Vanishing Reactions that Use Fluorous Media as a Phase Screen.  Facile, Controlled Bromination of Alkenes by Dibromine and Dealkylation of Aromatic Ethers by Boron Tribromide. 

 

I. Ryu, H. Matsubara, S. Yasuda, H. Nakamura, D. P. Curran, J. Am. Chem. Soc. In print (2002).

[57]

Tandem Nucleophilic Allylation-Alkoxyallylation of Alkynylaldehydes via Amphiphilic Bis-p-allylapalladium Complexes

 

H. Nakamura, M. Ohtaka, Y. Yamamoto, Tetrahedron Lett. 43, In print (2002).

[56]

A Convenient Synthesis of the Novel carboranyl-substituted Tetrahydroisoquinolines:  Application to the Biologically Active Agent for BNCT

 

Lee, J-D.; Lee, C-H.: , Nakamura, H.; Ko, J.; Kang, S-O. Tetrahedron Lett. 43, 5483-5486 (2002).

[55]

Palladium-Catalyzed Aminoallylation of Activated Olefins with Allylic Halides and Certain Amines

 

K. Aoyagi, H. Nakamura, Y. Yamamoto, J. Org. Chem. 67, 5977-5980 (2002).

[54]

Nucleophilic Allylation-Heterocyclization via Bis-p-allylpalladium Complexes: Synthesis of Five- and Six-Membered Heterocycles

 

Bao, H. Nakamura, A. Inoue, Y. Yamamoto, Chem. Lett. 158-159 (2002).

[53]

Novel Carboranes with a DNA Binding Unit for the Treatment of Cancer by Boron Neutron Capture Therapy

 

L.F. Tietze, U. Griesbach, U. Bothe, H. Nakamura, Y. Yamamoto, CHEMBIOCHEM 3, 219-225 (2002).

[52]

Formation of Cyclic Ethers via the Palladium-Catalyzed Cycloaddition of Activated Olefins with Allylic Carbonates Having a Hydroxy Group at the Terminus of the Carbon Chain

 

M. Sekido, K. Aoyagi, H. Nakamura, C. Kabuto, Y. Yamamoto, J. Org. Chem. 66, 7142-7147 (2001).

[51]

Fluorous Triphasic Reactions: Transportative Deprotection of Fluorous Silyl Ethers with Concomitant Purification.

H. Nakamura, B. Linclau, D. P. Curran, J. Am. Chem. Soc. 123, 10119-10120 (2001).

[50]

Biological Evaluation of ortho-Carboranyl Glycosides for the Selective Treatment of Cancer by Boron Neutron Capture Therapy

 

L. F. Tietze, U. Bothe, U. Griesbach, M. Nakaichi, T. Hasegawa, H. Nakamura, Y. Yamamoto, Bioorg. Med. Chem. 9, 1747-1752 (2001).

[49]

The Fate of Bis-p-allylpalladium Complexes in the Co-existence of Aldehydes (or Imines) and Allylic Chlorides.  Stille Coupling versus Allylation of Aldehydes (or Imine).

 

H. Nakamura, B. Ming, Y. Yamamoto, Angew. Chem. Int. Ed. Engl. 40, 3208-3210 (2001).

[48]

Carboranyl Bisglycosides for the Treatment of Cancer by Boron Neutron Capture Therapy

 

L. F. Tietze, U. Bothe, U. Griesbach, M. Nakaichi, T. Hasegawa, H. Nakamura, Y. Yamamoto, CHEMBIOCHEM 2, 326-334 (2001).

[47]

Facile Allylative Dearomatization Catalyzed by Palladium

 

B. Ming, H. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 123, 759-760 (2001).

[46]

Catalytic Amphiphilic Allylation via Bis-p-allylpalladium Complexes and Its Application to the Synthesis of Medium-Sized Carbocycles

 

H. Nakamura, K. Aoyagi, J. Shim, Y. Yamamoto, J. Am. Chem. Soc. 123, 372-377 (2001).

[45]

A Concise Synthesis of Chiral L-(4-Boronophenyl)alanine from L-Tyrosine

 

H. Nakamura, M. Fujiwara, Y. Yamamoto, Frontiers in Neutron Capture Therapy, Eds M. F. Hawthorn, K. Shelly, R. J. Wiersema, p765-768 Kluwer Academic/Plenum Publishers, New York (2001).

[44]

In vitro Uptake Study of 5-Carboranyluridine and Its Derivatives

 

T. Hasegawa, M. Nakaichi, S. Nakama, H. Nakamura, Y. Yamamoto, M. Takagaki, A. Takeuchi, Frontiers in Neutron Capture Therapy, Eds M. F. Hawthorn, K. Shelly, R. J. Wiersema, p1003-1008 Kluwer Academic/Plenum Publishers, New York (2001).

[43]

Synthesis and in Vivo Evaluation of Carborane Gadolinium-DTPA Complex as an MR Imaging Boron Carrier.

 

H. Nakamura, H. Fukuda, F. Girard, T. Kobayashi, H. Nemoto, J. Cai, K. Yoshida, Y. Yamamoto, Chem. Pharm. Bull. 48, 1034-1038 (2000).

[42]

A Practical Method for the Synthesis of Enantiomerically Pure 4-Borono-L-phenylalanine

 

H. Nakamura, M. Fujiwara, Y. Yamamoto, Bull. Chem. Soc. Jpn. 73, 231-235 (2000).

[41]

Palladium Catalyzed Cyanoallylation of Activated Olefins

 

H. Nakamura, H. Shibata, Y. Yamamoto. Tetrahedron Lett. 41, 2911-2914 (2000).

[40]

Preparation and application of polymer-supported chiral p-allylpalladium catalyst for the allylation of imines.

 

B. Ming, H. Nakamura, Y. Yamamoto, Tetrahedron Lett. 41, 131-134 (2000).

[39]

Palladium(0) Catalyzed Cope Rearrangement of Acyclic 1,5-Dienes.  Bis(p-allyl)palladium(II) Intermediate

 

H. Nakamura, H. Iwama, M. Ito, Y. Yamamoto, J. Am. Chem. Soc. 121 10850-10851 (1999).

[38]

Synthesis of a New Amphiphilic ortho-Carborane Derivative as a Potential BNCT Agent:  4-[N,N-Formyl-(ortho-carboranylmethyl)-amino]-benzoyl-L-glutamic Acid

 

K.-Y. Rho, Y.-J. Cho, C.-M. Yoon, H. Nakamura, Tetrahedron Lett. 40, 4821-4824 (1999).

[37]

A Concise and Stereospecific One-Shot Synthesis of Bicyclo[3,3,1]nonenols from Dimethyl 1,3-Acetonedicarboxylate and Enals via the Sequential Michael Addition-Intramolecular Aldolization

 

K. Aoyagi, H. Nakamura, Y. Yamamoto, J. Org. Chem. 64, 4148-4151 (1999).

[36]

Chiral p-Allylpalladium-Catalyzed Asymmetric Allylation: Replacement Allylstannanes by Allylsilanes.

 

K. Nakamura, H. Nakamura, Y. Yamamoto, J. Org. Chem. 64, 2614-2615 (1999).

[35]

Novel Addition Reactions of Silyl- and Stannyl-ortho-carboranes to Carbonyl Compounds

 

H. Nakamura, Y. Yamamoto, Collect. Czech. Chem. Commun. 64, 829-846 (1999).

[34]

The Synthesis of Carborane Gadolinium-DTPA Complex for Boron Neutron Capture Therapy

 

H. Nemoto, J. Cai, H. Nakamura, M. Fujiwara, Y. Yamamoto, J. Organomet. Chem. 581, 170-175 (1999).

[33]

Synthetic Utility of o-Carborane: Novel Protective Group for Aldehydes and Ketones.

 

H. Nakamura, K. Aoyagi, Y. Yamamoto, J. Organomet. Chem. 574, 107-115 (1999).

[32]

Characterization of a Dual Labeled Probe for MRI and Neutron Capture Therapy

 

 

A. T. Tatham, H. Nakamura, E. C. Wiener, Y. Yamamoto, Mag. Res. Med. 42, 32-36 (1999).

[31]

The Renaissance of p-Allylpalladium-catalyzed Organic Synthesis.

 

H. Nakamura, Y. Yamamoto, J. Syn. Org. Chem. Jpn. 56, 395-405（1998）.

[30]

Palladium Catalyzed Regioselective b-Acetonation-a-Allylation of Activated Olefins in One Shot.

 

J.-G. Shim, H. Nakamura, Y. Yamamoto, J. Org. Chem. 63, 8470-8474 (1998).

[29]

A Concise Synthesis of Enantiomerically Pure L-(4-Boronophenyl)alanine from L-Tyrosine

 

H. Nakamura, M. Fujiwara, Y. Yamamoto, J. Org. Chem. 63, 7529-7530 (1998).

[28]

Palladium-Catalyzed Alkoxycarbonation of Activated Olefins.

 

H. Nakamura, M. Sekido, M. Ito, Y. Yamamoto, J. Am. Chem. Soc. 120, 6838-6839 (1998).

[27]

Catalytic Asymmetric Allylation of Imines via Chiral Bis-p-allylpalladium Complexes.

 

H. Nakamura, K. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 120, 4242-4243 (1998).

[26]

TBAF Promoted Novel Reactions of ortho-Carboranes: Inter- and Intramolecular Addition to Aldehydes and Ketones, and Annulation via Enones and Enals.

 

H. Nakamura, K. Aoyagi, Y. Yamamoto, J. Am. Chem. Soc. 120, 1167-1171 (1998).

[25]

Amphiphilic Catalytic Allylating Reagent, Bis-p-allylpalladium Complex

 

H. Nakamura, J-G. Shim, Y. Yamamoto, J. Am. Chem. Soc. 119, 8113-8114 (1997).

[24]

Synthesis of Carboranes Containing Azulene Framework and In vitro Evaluation as Boron Carriers.

 

H. Nakamura, M. Sekido, Y. Yamamoto, J. Med. Chem. 40, 2825-2830 (1997).

[23]

o-Carborane as a Novel Protecting Group of Aldehydes and Ketones.

 

H. Nakamura, K. Aoyagi, Y. Yamamoto, J. Org. Chem. 62, 780-781 (1997).

[22]

A Novel [3+2] Annulation between o-Carboranyltrimethylsilane and Conjugated Carbonyl Compounds

 

H. Nakamura, K. Aoyagi, B. Singaram, J. Cai, H. Nemoto, Y. Yamamoto, Angew. Chem. Int. Ed. Engl. 36, 367-369 (1997).

[21]

Tetrabutylammonium Fluoride Promoted Regiospecific Reaction of Trimethylsilyl-o-carborane with Carbonyl Compounds.

 

J. Cai, H. Nemoto, H. Nakamura, B. Singaram, Y. Yamamoto, Advances in Boron Chemistry, Ed. W. Siebert, p112-115, The Royal Society of Chemistry (1997).

[20]

Rat Tumor Imaging with B-10 Carborane Gadolinium Complex.

 

F. Girard, H. Nakamura, H. Fukuda, Y. Yamamoto, K, Yoshida, Recent Advances in Biomedical Imaging, Ed. Y. Ishii et al., p201-207, Elsevier Science (1997).

[19]

Synthesis of Carborane Containing Azlene Framework Using New Palladium Catalyzed Reaction.

 

H. Nakamura, M. Sekido, Y. Yamamoto, Advances in Neutron Capture Therapy, Eds. B. Larsson, J. Crawford, R. Weinreich, p42-45, Plenum Press, New York (1997).

[18]

MR Imaging of Rat Tumor with 10B Carborane Gadolinium Complex.

 

F. Girard, H. Fukuda, H. Nakamura, Y. Yamamoto, K. Yoshida, Advances in Neutron Capture Therapy, Eds. B. Larsson, J. Crawford, R. Weinreich, p271-275, Plenum Press, New York (1997).

[17]

A New Synthetic Method of All Carboxylate-free DTPA Derivatives and Its Application to the Synthesis of Gd-Carborane Complex.

 

Y. Yamamoto, J. Cai. H. Nemoto, H. Nakamura, F. Girard, K. Yoshida, H. Fukuda, Advances in Neutron Capture Therapy, Eds. B. Larsson, J. Crawford, R. Weinreich, p436-439, Plenum Press, New York (1997).

[16]

Tetrabutylammonium Fluoride Promoted Regiospecific Reactions of Trimethylsilyl-o-Carborane with Aldehydes.

 

J. Cai, H. Nemoto, H. Nakamura, B. Singaram, Y. Yamamoto, Chem. Lett. 791-792 (1996).

[15]

Palladium and Platinum Catalyzed Addition of Aldehydes and Imines with Allylstannanes.  Chemoselective Allylation of Imines in the Presence of Aldehydes

 

H. Nakamura, H. Iwama, Y. Yamamoto, J. Am. Chem. Soc. 118, 6641-6647 (1996).

[14]

Unprecedented Highly Chemoselective Allylation of Imines in the Presence of Aldehydes via Palladium Catalyzed Allylstannane Reaction.

 

H. Nakamura, H. Iwama, Y. Yamamoto, J. Chem. Soc. Chem. Commun. 1459-1460(1996).

[13]

Netropsin and Distamycin Analogues Bearing ortho-Carborane

 

Y. Yamamoto, J. Cai, H. Nakamura, N. Sadayori, H. Nemoto, Cancer Neutron Capture Therapy, Ed. Y. Mishima, 177-182, Plenum Press, New York (1996).

[12]

Palladium and Platinum-catalyzed Addition of Aldehydes with Allylstannanes.

 

H. Nakamura, N. Asao, Y. Yamamoto, J. Chem. Soc. Chem. Commun. 1273-1274 (1995).

[11]

Synthesis of Netropsin and Distamycin Analogues Bearing o-Carborane and Their DNA Recognition.

 

Y. Yamamoto, J. Cai, H. Nakamura, N. Sadayori, N. Asao, H, Nemoto, J. Org. Chem. 60, 3352-3357 (1995).

[10]

Palladium Catalyzed Addition of 1-Carboranyltributyltin to Aldehydes.

 

H. Nakamura, N. Sadayori, M. Sekido, Y. Yamamoto, J. Chem. Soc. Chem. Commun.  2581-2582 (1994).

[9]

Synthesis of New 10B Carriers and Their Selective Uptake by Cancer Cells.

 

Y. Yamamoto, H. Nemoto, H. Nakamura, S. Iwamoto, Current Topics in the Chemistry of Boron, Ed. G. Kabalka, p149-154, The Royal Society of Chemistry (1994).

[8]

Synthesis and Biological Properties of Carboranylaziridine.　

 

Y. Yamamoto, H. Nakamura, H. Nemoto, Advances in Neutron Capture Therapy, Eds. A.H. Soloway, R.F. Barth, D.E. Carpenter, 305-308, Plenum Press, New York (1993).

[7]

1-Carboranyl-3-methylaziridino-2-propanol. Synthesis, Selective Uptake by B-16 Melanoma, and Selective Cytotoxicity toward Cancer Cells.

 

Y. Yamamoto, H. Nakamura, J. Med. Chem. 36, 2232-2234 (1993).

[6]

Regio- and Stereo-selective Ring Opening of Epoxides with Amide Cuprate Reagents.

 

Y. Yamamoto, N. Asao, M. Meguro, N. Tsukada, H. Nemoto, S. Sadayori, J. Gerald Wilson, H. Nakamura, J. Chem. Soc. Chem. Commun. 1201-1203 (1993).

[5]

Boron-11 NMR of Boron Compounds in the Presence of Cancer Cells.

 

Y. Yamamoto, S. Takamatsu, H. Nakamura, J. Magn. Res. Series B, 101, 198-200 (1993).

[4]

A New Water-soluble p-Boronophenylalanine Derivative for Neutron Capture Therapy.

 

H. Nemoto, S. Iwamoto, H. Nakamura, Y. Yamamoto, Chem. Lett. 465-468 (1993).

[3]

Synthesis of Carboranes Containing Nucleoside Bases.

 

Y. Yamamoto, T. Seko, H. Nakamura, H. Nemoto, Heteroatom Chem. 3, 239-244 (1992).

[2]

Polyols of a Cascade Type as a Water-Solubilizing Element of Carborane Derivatives for Boron Neutron Capture Therapy.

 

H. Nemoto, J. G. Wilson, H. Nakamura, Y. Yamamoto, J. Org. Chem. 57, 435 (1992).

[1]

Synthesis of Carboranes Containing Nucleoside Bases.  Unexpectedly High Cytostatic and Cytocidal Toxicity toward Cancer Cells.

 

Y. Yamamoto, T. Seko, H. Nakamura, H. Nemoto, H. Hojo, N. Mukai, Y. Hashimoto, J. Chem. Soc. Chem. Commun. 157-158 (1992).

BOOKS AND REVIEWS

  1.  π-アリルパラジウム錯体　
中村浩之　有機合成化学協会誌　第56巻　５月号特集号, 453（1998）.
  1. 1999年の化学（注目の論文）「遷移金属が炭素―炭素結合を切る！」　
中村浩之、月刊「化学」Vol. 54, 64-65（1999）.
  1. V.2.1.9. Pd-Catalyzed Reactions of Soft Carbon Nucleophiles with Dienes, Vinylcyclopropanes and Related Compounds
H. Nakamura, Y. Yamamoto, Handbook of Organopalladium Chemistry for Organic Synthesis, E. Negishi Ed. Wiley (2002).
  1. IX.2.1 1. Cope, Claisen, and Other [3,3] Rearrangements
H. Nakamura, Y. Yamamoto, Handbook of Organopalladium Chemistry for Organic Synthesis, E. Negishi Ed. Wiley (2002).
 

Last modified: September 9, 2002
中村浩之
学習院大学理学部化学科

Hiroyuki Nakamura
Department of Chemistry, Gakushuin Univeristy
Tokyo, Japan
hiroyuki.nakamura@gakushuin.ac.jp

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