研究者詳細 - 岡内　辰夫

論文 - 岡内　辰夫

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Novel 6–5 Fused Ring Heterocycle Antifolates with Potent Antitumor Activity: Bridge Modifications and Heterocyclic Benzoyl Isosters of 2,4-Diamino-6,7-dihydro-5H-cyclopenta[d] pyrimidine Antifolate 査読有り

Kotake Y., Okauchi T., Iijima A., Yoshimatsu K., Nomura H.

Chemical and Pharmaceutical Bulletin 43 ( 5 ) 829 - 841 1995年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

Structural modifications of an extremely potent inhibitor of dihydrofolate reductase (DHFR) activity and tumor cell growth, N-[4-[3-(2,4-diamino-6,7-dihydro-5H-cyclopenta[d]pyrimidin-5-yl)propyl]benzoyl]-L-glutamic acid (1), have led to the synthesis of new cyclopenta[d]pyrimidine-based antifolates, including those with low alkyl substituted trimethylene bridges (2a, b) and isosterically modified bridges (ethyleneoxa, 2c; ethyleneamino, 2d; the N-methyl- and N-ethyl derivatives of 2d, 2e, f) and those in which the benzene ring of 1 has been replaced by heterocyclic isosters (indole, 2g; indoline, 2h; thiophene, 2i). These new analogs are highly potent as DHFR and cell growth inhibitors, and most of them are more potent than methotrexate (MTX) and 10-ethyl-10-deazapterin (10-EDAM) in inhibiting tumor cell growth (P388 MTX-sensitive and MTX-resistant, colon 26 and KB) on 72 h drug exposure. Among them, 2a (the 10-methyl derivative of 1) and 2i were most potent, being 2- to 3-fold more potent than 10-EDAM. On 4 h drug exposure, the growth-inhibitory activity of these analogs was radically influenced by even minor structural changes. Compounds 1, 2a—e, g—i were much more cytotoxic in colon 26 cell line than were MTX and 10-EDAM, with 2d and 2i being most potent, followed by 2a. Structure-activity relationships and their possible significance are discussed. © 1995, The Pharmaceutical Society of Japan. All rights reserved.

DOI： 10.1248/cpb.43.829

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その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0029032398&origin=inward

Oxydative Generation of Thioalkyl Cation from 2-Tributylstannyl-1, 3-ditianes and 1-(Tributylstannnyl)alkyl Sulfides and Their Reactions with Olefinic Nucleophiles 査読有り

岡内　辰夫

Bulletin of the Chemical Society of Japan 66 ( 10 ) 2995 - 3003 1993年04月

Generation of Cation Radicals from 2-Tributylstannyl-1, 3-dithianes and Their Reaction with Olefins 査読有り

岡内　辰夫

Chemistry Letters ( 7 ) 1229 - 1232 1992年04月

Generation of Cation Radicals from Enamines and Their Reactions with Olefins 査読有り

岡内　辰夫

Chemistry Letters ( 10 ) 2099 - 2102 1992年04月

Generation of Cation Radicals from Allylic Sulfides and Their Reactions with Silyl Enol Ethers by the Use of Cerium(IV)Ammonium Nitrate 査読有り

岡内　辰夫

Chemistry Letters ( 3 ) 515 - 518 1991年04月

Addition Reactions of Cation Radicals of Nitroalkanes to Olefinic Compounds by the Use of Manganese((]G0003[))2-Pyridinecarboxylate 査読有り

岡内　辰夫

Chemistry Letters ( 3 ) 423 - 426 1991年04月

Stereoselective β-C-and β-S-Glycosylation of 2-Deoxyribofuranose Derivatives Controlled by the 3-Hydroxy Protecrive Group 査読有り

岡内　辰夫

Bulletin of the Chemical Society of Japan 62 ( 3 ) 845 - 852 1989年04月

The Addition Reaction of β-Keto Carboxylic Acids to Olefinic Compounds by the Use of Mn((]G0003[))Tris(2-pyridinecarboxylate)as an Oxidant 査読有り

岡内　辰夫

Chemistry Letters ( 12 ) 2169 - 2172 1989年04月

Synthesis of β-2-Deoxyribonucleosides from 1-O-Acetyl-3-O-[2-(methylsulfinyl)ethyl]-2-deoxyribose 査読有り

岡内　辰夫

Chemistry Letters ( 5 ) 801 - 804 1989年04月

The Trityl Cation Mediated Michael Reaction of Ethylthioketene Dithioacetals with Silyl Enol Ethers 査読有り

岡内　辰夫

Chemistry Letters ( 9 ) 1691 - 1694 1987年04月

The Trityl Cation Catalyzed Michael Type Reaction of Stannylated Nucleophiles with Ethylthioketene Dithioacetals 査読有り

岡内　辰夫

Chemistry Letters ( 9 ) 1695 - 1698 1987年04月

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