메뉴 건너뛰기




Volumn 40, Issue 18, 1997, Pages 2825-2830

Synthesis of carboranes containing an azulene framework and in vitro evaluation as boron carriers

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; AZULENE DERIVATIVE; BORON 10; CARBORANE DERIVATIVE; DRUG CARRIER; PALLADIUM; SULFONIC ACID DERIVATIVE;

EID: 0030869059     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970023x     Document Type: Article
Times cited : (38)

References (29)
  • 1
    • 0002046363 scopus 로고
    • Biological Effects and the Therapeutic Possibilities of Neutrons
    • Locher, G. L. Biological Effects and the Therapeutic Possibilities of Neutrons. Am. J. Roentgenol. 1936, 36, 1.
    • (1936) Am. J. Roentgenol. , vol.36 , pp. 1
    • Locher, G.L.1
  • 2
    • 84949417496 scopus 로고
    • Molecular Design and Synthesis of B-10 Carriers for Neutron Capture Therapy
    • Review papers: (a) Yamamoto, Y. Molecular Design and Synthesis of B-10 Carriers for Neutron Capture Therapy. Pure Appl. Chem. 1991, 63, 423-426. (b) Hawthorne, M. F. The Role of Chemistry in the Development of Boron Neutron Capture Therapy. Angew. Chem., Int. Ed. Engl. 1993, 32, 950-984. (c) Barth, R. F.; Soloway, A. H.; Fairchild, R. G. Boron Neutron Capture Therapy of Cancer. Cancer Res. 1990, 50, 1061-1070.
    • (1991) Pure Appl. Chem. , vol.63 , pp. 423-426
    • Yamamoto, Y.1
  • 3
    • 33745945620 scopus 로고
    • The Role of Chemistry in the Development of Boron Neutron Capture Therapy
    • Review papers: (a) Yamamoto, Y. Molecular Design and Synthesis of B-10 Carriers for Neutron Capture Therapy. Pure Appl. Chem. 1991, 63, 423-426. (b) Hawthorne, M. F. The Role of Chemistry in the Development of Boron Neutron Capture Therapy. Angew. Chem., Int. Ed. Engl. 1993, 32, 950-984. (c) Barth, R. F.; Soloway, A. H.; Fairchild, R. G. Boron Neutron Capture Therapy of Cancer. Cancer Res. 1990, 50, 1061-1070.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 950-984
    • Hawthorne, M.F.1
  • 4
    • 0025022471 scopus 로고
    • Boron Neutron Capture Therapy of Cancer
    • Review papers: (a) Yamamoto, Y. Molecular Design and Synthesis of B-10 Carriers for Neutron Capture Therapy. Pure Appl. Chem. 1991, 63, 423-426. (b) Hawthorne, M. F. The Role of Chemistry in the Development of Boron Neutron Capture Therapy. Angew. Chem., Int. Ed. Engl. 1993, 32, 950-984. (c) Barth, R. F.; Soloway, A. H.; Fairchild, R. G. Boron Neutron Capture Therapy of Cancer. Cancer Res. 1990, 50, 1061-1070.
    • (1990) Cancer Res. , vol.50 , pp. 1061-1070
    • Barth, R.F.1    Soloway, A.H.2    Fairchild, R.G.3
  • 5
    • 33947461630 scopus 로고
    • Synthesis of Aromatic Boronic Acids. Aldehyde Boronic Acids and a Boronic Acid Analog of Tyrosine
    • (a) Synder, H. R.; Reedy, A. J.; Lennarz, W. J. Synthesis of Aromatic Boronic Acids. Aldehyde Boronic Acids and a Boronic Acid Analog of Tyrosine. J. Am. Chem. Soc. 1958, 80, 835-838.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 835-838
    • Synder, H.R.1    Reedy, A.J.2    Lennarz, W.J.3
  • 6
    • 0010036325 scopus 로고
    • A New Water-soluble p-Boronophenylalanine Derivatives for Neutron Capture Therapy
    • (b) Nemoto, H.; Iwamoto, S.; Nakamura, H.; Yamamoto, Y. A New Water-soluble p-Boronophenylalanine Derivatives for Neutron Capture Therapy. Chem. Lett. 1993, 465-468.
    • (1993) Chem. Lett. , pp. 465-468
    • Nemoto, H.1    Iwamoto, S.2    Nakamura, H.3    Yamamoto, Y.4
  • 7
    • 0029931097 scopus 로고    scopus 로고
    • Enantioselective Synthesis of L-and D-Carboranylalanine
    • (c) Radel, P. A.; Kahl, S. B. Enantioselective Synthesis of L-and D-Carboranylalanine. J. Org. Chem. 1996, 61, 4582-4588.
    • (1996) J. Org. Chem. , vol.61 , pp. 4582-4588
    • Radel, P.A.1    Kahl, S.B.2
  • 8
    • 0026501031 scopus 로고
    • Synthesis of Carboranes Containing Nucleoside Bases. Unexpectedly High Cytostatic and Cytocidal Toxicity towards Cancer Cells
    • (a) Yamamoto, Y.; Seko, T.; Nakamura, H.; Nemoto, H.; Hojo, H.; Mukai, N.; Hashimoto, Y. Synthesis of Carboranes Containing Nucleoside Bases. Unexpectedly High Cytostatic and Cytocidal Toxicity towards Cancer Cells. J. Chem. Soc., Chem. Commun. 1992, 157-158. Nemoto, H.; Wilson, J. G.; Nakamura, H.; Yamamoto, Y. Polyols of a Cascade Type as a Water-Solubilizing Element of Carborane Derivatives for Boron Neutron Capture Therapy. J. Org. Chem. 1992, 57, 435-435 and references cited therein.
    • (1992) J. Chem. Soc., Chem. Commun. , pp. 157-158
    • Yamamoto, Y.1    Seko, T.2    Nakamura, H.3    Nemoto, H.4    Hojo, H.5    Mukai, N.6    Hashimoto, Y.7
  • 9
    • 0000463634 scopus 로고
    • Polyols of a Cascade Type as a Water-Solubilizing Element of Carborane Derivatives for Boron Neutron Capture Therapy
    • and references cited therein
    • (a) Yamamoto, Y.; Seko, T.; Nakamura, H.; Nemoto, H.; Hojo, H.; Mukai, N.; Hashimoto, Y. Synthesis of Carboranes Containing Nucleoside Bases. Unexpectedly High Cytostatic and Cytocidal Toxicity towards Cancer Cells. J. Chem. Soc., Chem. Commun. 1992, 157-158. Nemoto, H.; Wilson, J. G.; Nakamura, H.; Yamamoto, Y. Polyols of a Cascade Type as a Water-Solubilizing Element of Carborane Derivatives for Boron Neutron Capture Therapy. J. Org. Chem. 1992, 57, 435-435 and references cited therein.
    • (1992) J. Org. Chem. , vol.57 , pp. 435-435
    • Nemoto, H.1    Wilson, J.G.2    Nakamura, H.3    Yamamoto, Y.4
  • 10
    • 0000956368 scopus 로고
    • Synthesis of a Carboranyl Nucleoside for Potential Use in Neutron Capture Therapy of Cancer
    • (b) Anisuzzaman, A. K. M. Q.; Alam, F.; Soloway, A. H. Synthesis of a Carboranyl Nucleoside for Potential Use in Neutron Capture Therapy of Cancer. Polyhedron 1990, 9, 891-892.
    • (1990) Polyhedron , vol.9 , pp. 891-892
    • Anisuzzaman, A.K.M.Q.1    Alam, F.2    Soloway, A.H.3
  • 11
    • 0025677140 scopus 로고
    • Synthesis of Tetrakis-carborane-carboxylate Esters of 2,4-Bis(α,β-dihydroxyethyl)deuteroporphyrin
    • Kahl, S. B.; Koo, M. S. Synthesis of Tetrakis-carborane-carboxylate Esters of 2,4-Bis(α,β-dihydroxyethyl)deuteroporphyrin. J. Chem. Soc., Chem. Commun. 1990, 1769-1771.
    • (1990) J. Chem. Soc., Chem. Commun. , pp. 1769-1771
    • Kahl, S.B.1    Koo, M.S.2
  • 12
    • 0025320318 scopus 로고
    • Glycosyl Carborane Derivatives and the Determination of the Absolute Configulation of a Diastereomeric Triol from X-ray Diffraction
    • Maurer, J. L.; Berchier, F.; Serino, A. J.; Knobler, C. B.; Hawthorne, M. F. Glycosyl Carborane Derivatives and the Determination of the Absolute Configulation of a Diastereomeric Triol from X-ray Diffraction. J. Org. Chem. 1990, 55, 838-843. Maurer, J. L.; Serino, A. J.; Hawthorne, M. F. Hydrophilically Augmented Glycosyl Carborane Derivatives for Incorporation in Antibody Conjugation Reagents. Organometallics 1988, 7, 2519-2524.
    • (1990) J. Org. Chem. , vol.55 , pp. 838-843
    • Maurer, J.L.1    Berchier, F.2    Serino, A.J.3    Knobler, C.B.4    Hawthorne, M.F.5
  • 13
    • 0001031141 scopus 로고
    • Hydrophilically Augmented Glycosyl Carborane Derivatives for Incorporation in Antibody Conjugation Reagents
    • Maurer, J. L.; Berchier, F.; Serino, A. J.; Knobler, C. B.; Hawthorne, M. F. Glycosyl Carborane Derivatives and the Determination of the Absolute Configulation of a Diastereomeric Triol from X-ray Diffraction. J. Org. Chem. 1990, 55, 838-843. Maurer, J. L.; Serino, A. J.; Hawthorne, M. F. Hydrophilically Augmented Glycosyl Carborane Derivatives for Incorporation in Antibody Conjugation Reagents. Organometallics 1988, 7, 2519-2524.
    • (1988) Organometallics , vol.7 , pp. 2519-2524
    • Maurer, J.L.1    Serino, A.J.2    Hawthorne, M.F.3
  • 14
    • 0025256998 scopus 로고
    • Preparation of Carboranyl Porphyrins for Boron Neutron Capture Therapy
    • Miura, M.; Gabel, D.; Oenbrick, G.; Fairchild, R. G. Preparation of Carboranyl Porphyrins for Boron Neutron Capture Therapy. Tetrahedron Lett., 1990, 31, 2247. Schinazi, R. F.; Prusoff, W. H. Synthesis of 5-(Dihydroxybornyl)-2-deoxyuridine and Related Boron-containing Pyrimidines. J. Org. Chem. 1985, 50, 841.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2247
    • Miura, M.1    Gabel, D.2    Oenbrick, G.3    Fairchild, R.G.4
  • 15
    • 0001492906 scopus 로고
    • Synthesis of 5-(Dihydroxybornyl)-2-deoxyuridine and Related Boron-containing Pyrimidines
    • Miura, M.; Gabel, D.; Oenbrick, G.; Fairchild, R. G. Preparation of Carboranyl Porphyrins for Boron Neutron Capture Therapy. Tetrahedron Lett., 1990, 31, 2247. Schinazi, R. F.; Prusoff, W. H. Synthesis of 5-(Dihydroxybornyl)-2-deoxyuridine and Related Boron-containing Pyrimidines. J. Org. Chem. 1985, 50, 841.
    • (1985) J. Org. Chem. , vol.50 , pp. 841
    • Schinazi, R.F.1    Prusoff, W.H.2
  • 17
    • 0008995743 scopus 로고
    • Sesquiterpenes and Azulenes. Synthesis of Guaiazulene
    • Plattner, A.; Marti, F. L.; Schmid, H. Sesquiterpenes and Azulenes. Synthesis of Guaiazulene. Helv. Chim. Acta. 1949, 32, 2137-2144.
    • (1949) Helv. Chim. Acta. , vol.32 , pp. 2137-2144
    • Plattner, A.1    Marti, F.L.2    Schmid, H.3
  • 18
    • 0016652266 scopus 로고
    • Effects of Azulene, L-Glutamine, or Azulene and L-Gultamine on the Development or Healing of Experimental Gastic or Dudodental Ulcer and Gastric Secretion in the Rat
    • Okabe, S.; Takeuchi, K.; Honda, M.; Icshikawa, M.; Takagi, K. Effects of Azulene, L-Glutamine, or Azulene and L-Gultamine on the Development or Healing of Experimental Gastic or Dudodental Ulcer and Gastric Secretion in the Rat. Oyo Yakuri 1975, 9, 31.
    • (1975) Oyo Yakuri , vol.9 , pp. 31
    • Okabe, S.1    Takeuchi, K.2    Honda, M.3    Icshikawa, M.4    Takagi, K.5
  • 19
    • 0026072625 scopus 로고
    • Synthesis and Anti-peptic Activity of Compounds Related to the Metabolites of Sodium 3-Ethyl-7-isopropyl-1-azulenesodiumsulfonate (KT1-32)
    • Yanagisawa, T.; Kosakai, K.; Izawa, C.; Tomiyama, T.; Yasunami, Y. Synthesis and Anti-peptic Activity of Compounds Related to the Metabolites of Sodium 3-Ethyl-7-isopropyl-1-azulenesodiumsulfonate (KT1-32). Chem. Pharm. Bull. 1991, 39, 2429-2432.
    • (1991) Chem. Pharm. Bull. , vol.39 , pp. 2429-2432
    • Yanagisawa, T.1    Kosakai, K.2    Izawa, C.3    Tomiyama, T.4    Yasunami, Y.5
  • 20
    • 0004150764 scopus 로고
    • Academic Press: New York
    • Carboranes; Grimes, R. N., Ed.; Academic Press: New York, 1970; pp 66-97.
    • (1970) Carboranes , pp. 66-97
    • Grimes, R.N.1
  • 23
    • 0000425082 scopus 로고    scopus 로고
    • o-Carborane as a Novel Protective Group of Aldehydes and Ketones
    • Nakamura, H.; Aoyagi, K.; Yamamoto, Y. o-Carborane as a Novel Protective Group of Aldehydes and Ketones. J. Org. Chem. 1997, 62, 780-781.
    • (1997) J. Org. Chem. , vol.62 , pp. 780-781
    • Nakamura, H.1    Aoyagi, K.2    Yamamoto, Y.3
  • 24
    • 0001371011 scopus 로고
    • Tropylation of Azulene, 1-Oxaazulan-2-one, and Their Derivatives, and Electrophilic Reaction of the Tropylazulene Derivatives
    • and references cited therein
    • Nozoe, T.; Toda, T.; Asao, T.; Yamanouchi, A. Tropylation of Azulene, 1-Oxaazulan-2-one, and Their Derivatives, and Electrophilic Reaction of the Tropylazulene Derivatives. Bull. Chem. Soc. Jpn. 1968, 41, 2935-2941 and references cited therein.
    • (1968) Bull. Chem. Soc. Jpn. , vol.41 , pp. 2935-2941
    • Nozoe, T.1    Toda, T.2    Asao, T.3    Yamanouchi, A.4
  • 26
    • 0029877711 scopus 로고    scopus 로고
    • Hydroxyl Forms of p-Boronophenylalanine as Potential Boron Carriers on Boron Neutron Capture Therapy
    • and references cited therein
    • Takagaki, M.; Ono, K.; Oda, Y.; Kikuchi, H.; Nemoto, H.; Iwamoto, S.; Cai, J.; Yamamoto, Y. Hydroxyl Forms of p-Boronophenylalanine as Potential Boron Carriers on Boron Neutron Capture Therapy. Cancer Res. 1996, 56, 2017-2020 and references cited therein.
    • (1996) Cancer Res. , vol.56 , pp. 2017-2020
    • Takagaki, M.1    Ono, K.2    Oda, Y.3    Kikuchi, H.4    Nemoto, H.5    Iwamoto, S.6    Cai, J.7    Yamamoto, Y.8
  • 27
    • 0027268542 scopus 로고
    • 1-Carboranyl-3-(2-methylazilidino)-2-propanol. Synthesis, Selective Uptake by B-16 Melanoma, and Selective Cytotoxicity toward Cancer Cells
    • Yamamoto, Y.; Nakamura, H. 1-Carboranyl-3-(2-methylazilidino)-2-propanol. Synthesis, Selective Uptake by B-16 Melanoma, and Selective Cytotoxicity toward Cancer Cells. J. Med. Chem. 1993, 36, 2232-2234.
    • (1993) J. Med. Chem. , vol.36 , pp. 2232-2234
    • Yamamoto, Y.1    Nakamura, H.2
  • 28
    • 0004012744 scopus 로고
    • Kabalka, G., Ed.; The Royal Society of Chemistry: Cambridge
    • In the case of carborane-containing nucleosides, the compounds with higher water solubility exhibited lower boron uptake; see: Yamamoto, Y.; Nemoto, H.; Nakamura, H.; Iwamoto, S. In Current Topics in the Chemistry of Boron; Kabalka, G., Ed.; The Royal Society of Chemistry: Cambridge, 1994; pp 149-154.
    • (1994) Current Topics in the Chemistry of Boron , pp. 149-154
    • Yamamoto, Y.1    Nemoto, H.2    Nakamura, H.3    Iwamoto, S.4
  • 29
    • 0001590298 scopus 로고
    • A Versatile Synthetic Method of 1-Alkylazulenes and Azulene by the Reaction of 3-Methoxycarbonyl-2H-cyclohepta[b]furan-2-one with in situ Generated Enamines
    • Yasunami, Y.; Miyoshi, S.; Kanegae, N.; Takase, K. A Versatile Synthetic Method of 1-Alkylazulenes and Azulene by the Reaction of 3-Methoxycarbonyl-2H-cyclohepta[b]furan-2-one with in situ Generated Enamines. Bull. Chem. Soc. Jpn. 1993, 66, 892-899.
    • (1993) Bull. Chem. Soc. Jpn. , vol.66 , pp. 892-899
    • Yasunami, Y.1    Miyoshi, S.2    Kanegae, N.3    Takase, K.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.