16-(11'-bromoundecanyl)-1,3,5(10)-estratriene-3,17β-diol | 848338-38-5

• 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: 16-(11'-bromoundecanyl)-1,3,5(10)-estratriene-3,17β-diol
• 英文别名: (8R,9S,13S,14S,17S)-16-(11-bromoundecyl)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 848338-38-5
• 化学式: C₂₉H₄₅BrO₂
• 分子量: 505.579
• InChiKey: DFYNCLVCWPEXIT-WFVPVVLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  16-(11'-bromoundecanyl)-1,3,5(10)-estratriene-3,17β-diol 、 2-氨甲基吡啶 以 甲醇 为溶剂， 反应 72.0h， 生成 16-[11'-(2''-picolylamino)undecanyl]-1,3,5(10)-estratriene-3,17β-diol
  参考文献：
  名称：

  17β-雌二醇连接的铂（II）复合物的合成及其对雌激素依赖性和非依赖性乳腺肿瘤细胞的杀细胞活性。

  摘要：

  描述了两种新型的高效17β-雌二醇连接的铂（II）配合物的合成。新分子在类固醇核的位置16与烷基链连接。它们由雌酮经九个化学步骤制得，总收率超过10％。体外评估了这些化合物对雌激素依赖性和非依赖性（ER（+）和ER（-））人乳腺肿瘤细胞系MCF-7和MDA-MB-231的生物学活性。新化合物被证明对乳腺癌细胞系具有高度的细胞毒性。具有最高细胞毒性的衍生物对雌激素受体α具有高亲和力。

  DOI：

  10.1016/j.bioorg.2004.06.009
• 作为产物：
  描述：

  3-benzyloxy-16-(11'-hydroxyundecanyl)-1,3,5(10)-estratrien-17β-ol 在 palladium on activated charcoal 四溴化碳 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 16-(11'-bromoundecanyl)-1,3,5(10)-estratriene-3,17β-diol
  参考文献：
  名称：

  17β-雌二醇连接的铂（II）复合物的合成及其对雌激素依赖性和非依赖性乳腺肿瘤细胞的杀细胞活性。

  摘要：

  描述了两种新型的高效17β-雌二醇连接的铂（II）配合物的合成。新分子在类固醇核的位置16与烷基链连接。它们由雌酮经九个化学步骤制得，总收率超过10％。体外评估了这些化合物对雌激素依赖性和非依赖性（ER（+）和ER（-））人乳腺肿瘤细胞系MCF-7和MDA-MB-231的生物学活性。新化合物被证明对乳腺癌细胞系具有高度的细胞毒性。具有最高细胞毒性的衍生物对雌激素受体α具有高亲和力。

  DOI：

  10.1016/j.bioorg.2004.06.009

文献信息

• Estrogen-linked platinum (II) complexes as anticancer agents
  申请人：Gervais Berube

  公开号：US20040006051A1

  公开（公告）日：2004-01-08

  1 wherein n may be 1, 2, 3, 4 or 5 when X is O, wherein n may be 2/3, 1, 4/3, 5/3, 2, 7/3, 8/3, 3, or 10/3 when X is C, wherein o may be 1, 2 or 3, wherein Y may be O or 17&bgr;-OH, wherein R 1 may be selected from the group consisting of H, a straight alkyl group of 1 to 5 carbon atoms, a branched alkyl group of 3 to 5 carbon atoms, wherein R 2 may be selected for the group consisting of H, a straight alkyl group of 1 to 4 carbon atoms, a branched alkyl group of 3 or 4 carbon atoms, F, Cl, Br, I, —CF 3 , —NO 2 , —OR 1 , —COR 1 and —CH 2 OH. These compounds possess anticancer activity against hormono-dependent breast, uterus as well as ovarian cancer.

  其中，当X为O时，n可以是1、2、3、4或5，当X为C时，n可以是2/3、1、4/3、5/3、2、7/3、8/3、3或10/3，o可以是1、2或3，Y可以是O或17β-OH，R1可以从H、1至5个碳原子的直链烷基或3至5个碳原子的支链烷基中选择，R2可以从H、1至4个碳原子的直链烷基或3或4个碳原子的支链烷基、F、Cl、Br、I、—CF3、—NO2、—OR1、—COR1和—CH2OH中选择。这些化合物对激素依赖性乳腺、子宫和卵巢癌具有抗癌活性。
• Improved synthesis of unique estradiol-linked platinum(II) complexes showing potent cytocidal activity and affinity for the estrogen receptor alpha and beta
  作者：Caroline Descôteaux、Valérie Leblanc、Geoffroy Bélanger、Sophie Parent、Éric Asselin、Gervais Bérubé

  DOI：10.1016/j.steroids.2008.04.009

  日期：2008.10

  We have recently reported the synthesis of a platinum(II) complex, made of estradiol, the female sex hormone, and a cisplatin analog, an anticancer drug, linked together by an eleven carbon atoms chain. The novel estradiol-Pt(II) hybrid molecule was synthesized in nine chemical steps with 10% overall yield. This new compound has been tested in Vitro on estrogen-dependent (MCF-7) and -independent (MDA-MD-231) (ER(+) and ER(-)) cell lines. Interestingly, the biological activity was quite significant, more potent than that of cisplatin, the compound currently used in chemotherapy The estrogen receptor binding affinity (ERBA) of this compound was very similar to that of 17 beta-estradiol (E(2)) on both estrogen receptors (ERs), alpha and beta. In order to further study this type of molecule, we have decided to synthesize several analogs with the same estrogenic scaffold but with various chain lengths separating the estradiol from the toxic part of the molecule. This was planned in order to study the effect of the length of the linking chain on the biological activity of the hybrids. Four E(2)-Pt(II) hybrid molecules having 6-14 carbon atoms linking chain have been synthesized using a new synthetic methodology. They are synthesized in only eight chemical steps with 21% overall yield. The 17 beta-estradiol-linked-platinum(II) complexes have been tested for their receptor binding affinity as well as for their cytocidal activity on several breast cancer cell lines. The synthesis and biological results are reported herein. (c) 2008 Elsevier Inc. All rights reserved.