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托酚酮衍生物的合成与抗肿瘤活性

Synthesis and antitumor activity of tropolone derivatives.

作者信息

Yamato M, Hashigaki K, Kokubu N, Tsuruo T, Tashiro T

出版信息

J Med Chem. 1984 Dec;27(12):1749-53. doi: 10.1021/jm00378a041.

DOI:10.1021/jm00378a041
PMID:6502608
Abstract

Treatment of tropolones with benzaldehyde diethyl acetals gave monotropolone (12) and bistropolone (13) derivatives at the benzylic position, whereas the related 1-ethoxyisochroman and the diethyl acetals of crotonaldehyde and cinnamaldehyde gave only the monotropolone derivatives (5, 10, or 11). The monotropolone derivatives (5, 10, 11, and 12) had poor potency against P388 leukemia in mice, but the bistropolone derivatives (13 and 14) showed significant potency and prolongation of life.

摘要

用苯甲醛二乙缩醛处理卓酚酮,在苄基位置得到单卓酚酮(12)和双卓酚酮(13)衍生物,而相关的1-乙氧基异苯并二氢吡喃以及巴豆醛和肉桂醛的二乙缩醛仅得到单卓酚酮衍生物(5、10或11)。单卓酚酮衍生物(5、10、11和12)对小鼠P388白血病的效力较差,但双卓酚酮衍生物(13和14)显示出显著的效力并延长了生存期。

相似文献

1
Synthesis and antitumor activity of tropolone derivatives.托酚酮衍生物的合成与抗肿瘤活性
J Med Chem. 1984 Dec;27(12):1749-53. doi: 10.1021/jm00378a041.
2
Synthesis and antitumor activity of tropolone derivatives. 2.托酚酮衍生物的合成及其抗肿瘤活性。2.
J Med Chem. 1985 Aug;28(8):1026-31. doi: 10.1021/jm00146a009.
3
Synthesis and antitumor activity of tropolone derivatives. 4.托酚酮衍生物的合成及其抗肿瘤活性。4.
J Med Chem. 1987 Jan;30(1):117-20. doi: 10.1021/jm00384a020.
4
Synthesis and antitumor activity of tropolone derivatives. 3.托酚酮衍生物的合成与抗肿瘤活性。3.
J Med Chem. 1986 Jul;29(7):1202-5. doi: 10.1021/jm00157a014.
5
Synthesis and antitumor activity of tropolone derivatives. 5.托酚酮衍生物的合成与抗肿瘤活性。5.
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Synthesis and antitumor activity of tropolone derivatives. 6. Structure-activity relationships of antitumor-active tropolone and 8-hydroxyquinoline derivatives.托酚酮衍生物的合成与抗肿瘤活性。6. 抗肿瘤活性托酚酮和8-羟基喹啉衍生物的构效关系。
J Med Chem. 1987 Oct;30(10):1897-900. doi: 10.1021/jm00393a035.
7
Antitumor activity of isochromanyltropolones.异色满基托酚酮的抗肿瘤活性。
Chem Pharm Bull (Tokyo). 1983 Aug;31(8):2952-4. doi: 10.1248/cpb.31.2952.
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Synthesis and antitumor activity of tropolone derivatives. 7. Bistropolones containing connecting methylene chains.托酚酮衍生物的合成与抗肿瘤活性。7. 含连接亚甲基链的双托酚酮
J Med Chem. 1992 Jan 24;35(2):267-73. doi: 10.1021/jm00080a010.
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The synthesis and antitumor activities of tropolone and 8-hydroxyquinoline derivatives.托酚酮和8-羟基喹啉衍生物的合成及其抗肿瘤活性
Chem Pharm Bull (Tokyo). 1986 Aug;34(8):3496-8. doi: 10.1248/cpb.34.3496.
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Synthesis and biological evaluation of O-alkylated tropolones and related alpha-ketohydroxy derivatives as ribonucleotide reductase inhibitors.
Eur J Med Chem. 2001 Jun;36(6):561-8. doi: 10.1016/s0223-5234(01)01249-1.

引用本文的文献

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2-Hetaryl-1,3-tropolones based on five-membered nitrogen heterocycles: synthesis, structure and properties.基于五元氮杂环的2-杂芳基-1,3-氧杂蒽酮:合成、结构与性质
Beilstein J Org Chem. 2015 Nov 12;11:2179-88. doi: 10.3762/bjoc.11.236. eCollection 2015.
3
Imbalance of deoxyribonucleoside triphosphates and DNA double-strand breaks in mouse mammary tumor FM3A cells treated in vitro with an antineoplastic tropolone derivative.
体外使用抗肿瘤托酚酮衍生物处理的小鼠乳腺肿瘤FM3A细胞中脱氧核糖核苷三磷酸失衡与DNA双链断裂
Jpn J Cancer Res. 1992 Jun;83(6):661-8. doi: 10.1111/j.1349-7006.1992.tb00141.x.