6-oxa-8α-estrone

• 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: 6-oxa-8α-estrone
• 英文别名: (3aS,3bS,9bS,11aS)-7-hydroxy-11a-methyl-2,3,3a,3b,4,9b,10,11-octahydroindeno[4,5-c]chromen-1-one
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: QDTVCCUKAKYNDR-YSLLHCQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-oxa-8α-estrone 在 sodium tetrahydroborate 作用下， 生成
  参考文献：
  名称：

  Novel structural features increase the antioxidant effect of estrogen analogues on low density lipoprotein

  摘要：

  Many known estrogens, both natural and synthetic, may act as antioxidants. We designed and synthesized 22 novel estrogen analogues with different ring junctions or substitutions, such as fluorine. We studied the antioxidant capacity in vitro of 35 synthetic estrogen analogues in aqueous lipoprotein solution by monitoring the formation of conjugated dienes. In addition to a free C-3 hydroxyl group, the two most active antioxidants had either a methyl group at C-4 and a six-carbon D-ring, or a fluorine atom at C-2 and an unsaturated B-ring. Extension of the D-ring increased the antioxidant capacity of 6-oxa estrogens. Compounds with a fluorine atom at C-2 were similar or more potent antioxidants compared with the principal endogenous estrogen, 17 beta-estradiol. In compounds with a substituted C-3 hydroxyl group, the antioxidant capacity could be significantly increased by additional double bonds in the C- or D-rings. In conclusion, we show that the antioxidant capacity of estrogen analogues could be increased by structural changes. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jsbmb.2015.08.001
• 作为产物：
  描述：

  6-oxa-8α-estrone methyl ether 在 氢溴酸 、 溶剂黄146 作用下， 反应 2.0h， 以80.5%的产率得到6-oxa-8α-estrone
  参考文献：
  名称：

  [EN] PREPARATION OF 6-OXA-8ALPHA-STEROID ESTROGEN ANALOGUES - A NEW GROUP OF UNNATURAL ESTROGENS AND THEIR USE IN MEDICINE
  [FR] PRÉPARATION D'ANALOGUES DE L'OETROGÈNE 6-OXA-8?-STÉROÏDE - UN NOUVEAU GROUPE D'OETROGÈNES NON NATURELS ET LEUR UTILISATION EN MÉDECINE

  摘要：

  公开号：

  WO2009059806A3

文献信息

• Synthesis of Tamoxifen‐Artemisinin and Estrogen‐Artemisinin Hybrids Highly Potent Against Breast and Prostate Cancer
  作者：Tony Fröhlich、Christina Mai、Roman P. Bogautdinov、Svetlana N. Morozkina、Alexander G. Shavva、Oliver Friedrich、Daniel F. Gilbert、Svetlana B. Tsogoeva

  DOI：10.1002/cmdc.202000174

  日期：2020.8.5

  for new and effective treatments of breast and prostate cancer, a series of hybrid compounds based on tamoxifen, estrogens, and artemisinin were successfully synthesized and analyzed for their in vitro activities against human prostate (PC‐3) and breast cancer (MCF‐7) cell lines. Most of the hybrid compounds exhibit a strong anticancer activity against both cancer cell lines – for example, EC50 (PC‐3)

  在寻找新的、有效的乳腺癌和前列腺癌治疗方法的过程中，成功合成了一系列基于他莫昔芬、雌激素和青蒿素的混合化合物，并分析了它们对人前列腺癌 (PC-3) 和乳腺癌 (MCF) 的体外活性。 ‐7) 细胞系。大多数杂化化合物对两种癌细胞系都表现出很强的抗癌活性——例如，EC 50 (PC-3) 低至 1.07 μM，EC 50 (MCF-7) 低至 2.08 μM——因此表现出比它们更高的活性。母体化合物 4-羟基他莫昔芬（阿莫昔芬，7；EC 50 =75.1 (PC-3) 和 19.3 μM (MCF-7)），二氢青蒿素 ( 2；EC 50 =263.6 (PC-3) 和 49.3 μM (MCF-7) ）和青蒿酸（3；EC 50 =195.1（PC-3）和32.0 μM（MCF-7））。最有效的化合物是抗前列腺癌的雌激素-青蒿素杂合体27和28（EC 50 = 1.18 和 1.07 μM），以及抗乳腺癌的杂合体23（EC
• PREPARATION OF 6-OXA-8ALPHA-STEROID ESTROGEN ANALOGUES - A NEW GROUP OF UNNATURAL ESTROGENS AND THEIR USE IN MEDICINE
  申请人：Pison Ulrich

  公开号：US20110160296A1

  公开（公告）日：2011-06-30

  The invention is related to the area of new 6-Oxa-8α-steroid estrogen analogues and the synthesis of these new biological active steroid estrogen analogues, namely, to the preparation of 6-oxa-8α-steroid estrogens and their use as estrogen receptor modulators. These new estrogen analogues are ligands for estrogen receptors and as such may be useful for the treatment and prevention of a variety of conditions related to estrogen functioning. These conditions include bone and cartilage disorders, increased levels of LDL cholesterol, cardiovascular diseases, impairment of cognitive function, cerebral degeneration disorders, endometriosis and other types of inflammation, the metabolic syndrome, and cancer, in particular of the breast, uterus and prostate.
• Novel structural features increase the antioxidant effect of estrogen analogues on low density lipoprotein
  作者：Alan F. Fidarov、Veera Vihma、Roman P. Bogautdinov、Svetlana N. Morozkina、Alexander G. Shavva、Matti J. Tikkanen

  DOI：10.1016/j.jsbmb.2015.08.001

  日期：2015.11

  Many known estrogens, both natural and synthetic, may act as antioxidants. We designed and synthesized 22 novel estrogen analogues with different ring junctions or substitutions, such as fluorine. We studied the antioxidant capacity in vitro of 35 synthetic estrogen analogues in aqueous lipoprotein solution by monitoring the formation of conjugated dienes. In addition to a free C-3 hydroxyl group, the two most active antioxidants had either a methyl group at C-4 and a six-carbon D-ring, or a fluorine atom at C-2 and an unsaturated B-ring. Extension of the D-ring increased the antioxidant capacity of 6-oxa estrogens. Compounds with a fluorine atom at C-2 were similar or more potent antioxidants compared with the principal endogenous estrogen, 17 beta-estradiol. In compounds with a substituted C-3 hydroxyl group, the antioxidant capacity could be significantly increased by additional double bonds in the C- or D-rings. In conclusion, we show that the antioxidant capacity of estrogen analogues could be increased by structural changes. (C) 2015 Elsevier Ltd. All rights reserved.
• [EN] PREPARATION OF 6-OXA-8ALPHA-STEROID ESTROGEN ANALOGUES - A NEW GROUP OF UNNATURAL ESTROGENS AND THEIR USE IN MEDICINE<br/>[FR] PRÉPARATION D'ANALOGUES DE L'OETROGÈNE 6-OXA-8?-STÉROÏDE - UN NOUVEAU GROUPE D'OETROGÈNES NON NATURELS ET LEUR UTILISATION EN MÉDECINE
  申请人：TOPASS GMBH

  公开号：WO2009059806A3

  公开（公告）日：2009-10-29