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佛波醇衍生物的视黄酸酯的制备。

Preparation of retinoic acid esters of phorbol derivatives.

作者信息

Sorg B, Fürstenberger G, Berry D L, Hecker E, Marks F

出版信息

J Lipid Res. 1982 Mar;23(3):443-7.

PMID:7077157
Abstract

The synthesis of 12-O-retinoylphorbol-13-acetate (RPA), an incomplete tumor promoter (second stage promoter) is described. The preparation starts with phorbol-13-acetate-20-tritylether which is acylated by a carbodiimide method to yield its 12-retinoate. The latter is detritylated by acidic methanol to give RPA. Following an analogous procedure, the 4-methyl-ether of RPA is prepared from 4-O-methylphorbol-13-acetate-20-tritylether.

摘要

描述了不完全肿瘤启动子(第二阶段启动子)12-O-视黄酰佛波醇-13-乙酸酯(RPA)的合成。制备过程从佛波醇-13-乙酸酯-20-三苯甲基醚开始,通过碳二亚胺法进行酰化反应以生成其12-视黄酸酯。后者用酸性甲醇脱去三苯甲基得到RPA。按照类似的步骤,由4-O-甲基佛波醇-13-乙酸酯-20-三苯甲基醚制备RPA的4-甲基醚。

相似文献

1
Preparation of retinoic acid esters of phorbol derivatives.佛波醇衍生物的视黄酸酯的制备。
J Lipid Res. 1982 Mar;23(3):443-7.
2
12-O-retinoylphorbol-13-acetate (RPA) behaves like a retinoid-derivative in binding to retinol-binding-protein: a correlation with its specific action as an incomplete tumor promoter?
Anticancer Res. 2005 Sep-Oct;25(5):3355-65.
3
Tumor promotion by phorbol esters in skin: evidence for a memory effect.佛波酯在皮肤中的肿瘤促进作用:记忆效应的证据。
Science. 1983 Apr 1;220(4592):89-91. doi: 10.1126/science.6828884.
4
Stability of the "second stage" promoter 12-O-retinoylphorbol-13-acetate.
Cancer Res. 1985 May;45(5):2390-1.
5
Control of endogenous cell regulators by the second-stage tumor promoter phorbol-12-retinoate 13-acetate.
Int J Cancer. 1983 Apr 15;31(4):497-500. doi: 10.1002/ijc.2910310416.
6
Modulation of protein kinase C activity and [3H]phorbol 12,13-dibutyrate binding by various tumor promoters in mouse brain cytosol.多种肿瘤启动子对小鼠脑细胞质中蛋白激酶C活性及[3H]佛波醇12,13 - 二丁酸酯结合的调节作用
Cancer Res. 1985 May;45(5):1958-63.
7
Effects of complete and incomplete tumor promoters on hair growth, angiogenesis, and tenascin expression in the skin of NMRI mice.完全和不完全肿瘤启动子对NMRI小鼠皮肤毛发生长、血管生成和肌腱蛋白表达的影响。
Carcinogenesis. 1994 Dec;15(12):2739-45. doi: 10.1093/carcin/15.12.2739.
8
[Phorbols: chemical synthesis and chemical biology].
Yakugaku Zasshi. 2000 Jan;120(1):76-90. doi: 10.1248/yakushi1947.120.1_76.
9
Tumor induction in initiated mouse skin by phorbol esters and methyl methanesulfonate: correlation between chromosomal damage and conversion ('stage I of tumor promotion') in vivo.佛波酯和甲基磺酸甲酯诱导启动小鼠皮肤肿瘤:体内染色体损伤与转化(“肿瘤促进的第一阶段”)之间的相关性。
Carcinogenesis. 1989 Apr;10(4):749-52. doi: 10.1093/carcin/10.4.749.
10
Inhibition of intercellular communication by tumor-promoting phorbol esters.促癌佛波酯对细胞间通讯的抑制作用。
Cancer Res. 1980 Aug;40(8 Pt 1):2935-7.

引用本文的文献

1
Suppression of the first stage of phorbol 12-tetradecanoate 13-acetate-effected tumor promotion in mouse skin by nontoxic inhibition of DNA synthesis.通过对DNA合成的无毒抑制作用抑制佛波醇12 - 十四烷酸酯13 - 乙酸酯诱导的小鼠皮肤肿瘤促进第一阶段。
Proc Natl Acad Sci U S A. 1984 Sep;81(18):5858-62. doi: 10.1073/pnas.81.18.5858.