2-formyl estradiol 3-methyl ether 17-acetate | 1028058-66-3

• 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: 2-formyl estradiol 3-methyl ether 17-acetate
• 英文别名: [(8R,9S,13S,14S,17S)-2-formyl-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 1028058-66-3
• 化学式: C₂₂H₂₈O₄
• 分子量: 356.462
• InChiKey: XXZXGRMVMCNVAI-KOLYYURTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-formyl estradiol 3-methyl ether 17-acetate 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以81%的产率得到3,17β-dihydroxyestra-1,3,5(10)-trien-2-carboxaldehyde 17-acetate
  参考文献：
  名称：

  甾体骨架上的combrestastatin A4类似物的合成及其抗乳腺癌活性。

  摘要：

  在没食子酸的甾体骨架上合成Combretastatin A4类似物，可能具有抗乳腺癌的作用。合成了二十二种类似物，并评估了其对人乳腺癌细胞系（MCF-7和MDA-MB 231）的细胞毒性。最好的类似物22显示出有效的抗微管蛋白作用。对接实验还支持22与微管聚合酶的强结合亲和力。在细胞周期分析中，22显着诱导MCF-7细胞凋亡。在瑞士的白化病小鼠中，在急性口服毒性下，以300 mg / kg的剂量发现它是无毒的。本文是名为“类固醇衍生物作为抑制剂的合成和生物学测试”的特刊的一部分。

  DOI：

  10.1016/j.jsbmb.2013.02.009
• 作为产物：
  描述：

  17-Beta-雌二醇 3-甲醚 在 吡啶 、 三氯氧磷 作用下， 反应 3.0h， 生成 2-formyl estradiol 3-methyl ether 17-acetate
  参考文献：
  名称：

  Synthesis of chalcone derivatives on steroidal framework and their anticancer activities☆

  摘要：

  Chalcone derivatives on estradiol framework have been synthesized. Some of the derivatives showed potent anticancer activity against some human cancer cell lines. Compounds 9 and 19 showed potent activity against MCF-7, a hormone dependent breast cancer cell line. Chalcone 7 was further modified to the corresponding indanone derivative (19) using the Nazarov reaction, which showed better activity than the parent compound against the MCF-7 breast cancer cell line. Active anticancer derivatives were also evaluated for osmotic hemolysis using the erythrocyte as a model system. It was observed that chalcone derivatives showing cytotoxicity against cancer cell lines did not affect the fragility of erythrocytes and hence may be considered as non-toxic to normal cells. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.07.012

文献信息

• A simple, convenient and chemoselective formylation of sterols by Vilsmeier reagent
  作者：Vandana Srivastava、Arvind Singh Negi、J.K. Kumar、M.M. Gupta

  DOI：10.1016/j.steroids.2006.03.005

  日期：2006.7

  Vilsmeier reagent (DMF-POCl3) was used as an efficient formylating agent. Several sterols having sec-hydroxyl group at 3/17-position have been modified into respective formate esters. The method is simple, mild, chemoselective and provides sec-alcoholic protection in good yields. (c) 2006 Elsevier Inc. All rights reserved.
• Synthesis of chalcone derivatives on steroidal framework and their anticancer activities☆
  作者：H SAXENA、U FARIDI、J KUMAR、S LUQMAN、M DAROKAR、K SHANKER、C CHANOTIYA、M GUPTA、A NEGI

  DOI：10.1016/j.steroids.2007.07.012

  日期：2007.11

  Chalcone derivatives on estradiol framework have been synthesized. Some of the derivatives showed potent anticancer activity against some human cancer cell lines. Compounds 9 and 19 showed potent activity against MCF-7, a hormone dependent breast cancer cell line. Chalcone 7 was further modified to the corresponding indanone derivative (19) using the Nazarov reaction, which showed better activity than the parent compound against the MCF-7 breast cancer cell line. Active anticancer derivatives were also evaluated for osmotic hemolysis using the erythrocyte as a model system. It was observed that chalcone derivatives showing cytotoxicity against cancer cell lines did not affect the fragility of erythrocytes and hence may be considered as non-toxic to normal cells. (c) 2007 Elsevier Inc. All rights reserved.
• Synthesis of combretastatin A4 analogues on steroidal framework and their anti-breast cancer activity
  作者：Swati Parihar、Amit Kumar、Amit K. Chaturvedi、Naresh Kumar Sachan、Suaib Luqman、Bendangla Changkija、Murli Manohar、Om Prakash、D. Chanda、Feroz Khan、C.S. Chanotiya、Karuna Shanker、Anila Dwivedi、Rituraj Konwar、Arvind S. Negi

  DOI：10.1016/j.jsbmb.2013.02.009

  日期：2013.9

  Combretastatin A4 analogues were synthesized on steroidal framework from gallic acid with a possibility of anti-breast cancer agents. Twenty two analogues were synthesized and evaluated for cytotoxicity against human breast cancer cell lines (MCF-7 & MDA-MB 231). The best analogue 22 showed potent antitubulin effect. Docking experiments also supported strong binding affinity of 22 to microtubule polymerase

  在没食子酸的甾体骨架上合成Combretastatin A4类似物，可能具有抗乳腺癌的作用。合成了二十二种类似物，并评估了其对人乳腺癌细胞系（MCF-7和MDA-MB 231）的细胞毒性。最好的类似物22显示出有效的抗微管蛋白作用。对接实验还支持22与微管聚合酶的强结合亲和力。在细胞周期分析中，22显着诱导MCF-7细胞凋亡。在瑞士的白化病小鼠中，在急性口服毒性下，以300 mg / kg的剂量发现它是无毒的。本文是名为“类固醇衍生物作为抑制剂的合成和生物学测试”的特刊的一部分。