estra-1,3,5(10)-trien-17-on-3-yl isonicotinate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: estra-1,3,5(10)-trien-17-on-3-yl isonicotinate
• 英文别名: isonicotinic acid 17-oxoestra-1,3,5(10)-trien-3-yl ester；[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] pyridine-4-carboxylate
• 化学式: C₂₄H₂₅NO₃
• 分子量: 375.467
• InChiKey: ROXCCULUHDEPPN-YOEKFXIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异烟酸 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.33h， 生成 estra-1,3,5(10)-trien-17-on-3-yl isonicotinate
  参考文献：
  名称：

  (Arene)Cl2Ru(II) complexes with N-coordinated estrogen and androgen isonicotinates: Interaction with sex hormone binding globulin and anticancer activity

  摘要：

  (arene)二氯化二钌(II)复合物与N-配位的雄激素（6）和雌激素（9）的异烟酸酰胺衍生物已被制备，并测试了其对雌激素受体（ERα）和性激素结合球蛋白（SHBG）的亲和力以及在癌细胞中的细胞毒性。新的复合物均未明显结合ER，且其中大多数与SHBG的结合力亦弱于相应的无金属甾体（7）。在MTT实验中，2-取代雌酮的Ru(p-甲乙基环己二烯)复合物（9）对激素依赖性（MCF-7乳腺癌和KB-V1宫颈癌）及激素非依赖性（518A2黑色素瘤）细胞的毒性与金属无甾体相当甚至更高。在加入外源性SHBG至HU实验中，其对复合物9的细胞毒性有所降低，且对某些甾体（7）的降低明显，可能是通过屏蔽及减少胞内摄取的途径实现。在无SHBG的情况下，雌激素复合物9被518A2黑色素瘤细胞摄入，并以ICP-OES定量其DNA的钌化修饰。它们亦能钌化鲑鱼精子DNA，但在EMSA实验中未改变质粒DNA的拓扑结构。此外，2-乙氧雌酮的Ru(p-甲乙基环己二烯)复合物（9c）在划痕修复实验中被证实可显著降低518A2黑色素瘤细胞的迁移能力。（C）2010 Elsevier Inc. 保留所有权利。

  DOI：

  10.1016/j.steroids.2010.12.009

文献信息

• Synthesis of pyridine-carboxylate derivatives of hydroxysteroids for liquid chromatography–electrospray ionization-mass spectrometry
  作者：Kouwa Yamashita、Sayuri Kobayashi、Satoshi Tsukamoto、Mitsuteru Numazawa

  DOI：10.1016/j.steroids.2006.10.005

  日期：2007.1

  Synthesis and liquid chromatography-electrospray ionization-mass spectrometric (LC-ESI-MS) behaviors of the picolinoyl, 6-methylpicolinoyl, nicotinoyl, 2-methoxynicotinoyl and isonicotinoyl derivatives of the hydroxysteroids estrone, estradiol, 3 beta-hydroxyandrost-5en-17-one (dehydroepiandrosterone) and testosterone in positive mode were investigated. Each steroid was converted to the corresponding pyridine-carboxylate derivative by the acyl chloride method or the mixed anhydride method using the corresponding free acids and 2-methyl-6-nitrobenzoic anhydride; in each case, the latter method principally gave a better yield. The pyridine-carboxylate derivative of each steroid exhibited a clear single peak in liquid chromatography with a reversed phase column and CH3CN-0.1% CH3COOH as a mobile phase. The positive-ESI-mass spectra of the picolinoyl, 6-methylpicolinoyl and 2-methoxynicotinoyl derivatives showed a predominance of [M+H](+), whereas [M+H+CH3CN](+) was observed with high intensity in the nicotinoyl and isonicotinoyl derivatives. Even in the case of estradiol, with its two hydroxyl groups, a single charged ion of [M+H](+) or [M+H+CH3CN](+) was observed in the positive-ESI-mass spectrum of each derivative. The results revealed that picolinoyl derivatization is a simple and versatile method suitable for the sensitive and specific determination of hydroxysteroids by LC-ESI-MS (selected reaction monitoring). (c) 2006 Elsevier Inc. All rights reserved.