3-methoxy-D-homo-6-oxa-8α-estra-1,3,5(10)-trien-17a-one | 162523-66-2

• 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: 3-methoxy-D-homo-6-oxa-8α-estra-1,3,5(10)-trien-17a-one
• 英文别名: 6-oxa-D-homo-8α-estrone methyl ether；(4aS,4bS,10bS,12aS)-8-methoxy-12a-methyl-3,4,4a,4b,5,10b,11,12-octahydro-2H-naphtho[1,2-c]chromen-1-one
• CAS: 162523-66-2
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: RPUAFYGOHKRXAI-UEABVUSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-D-homo-6-oxa-8α-estra-1,3,5(10)-trien-17a-one 在 potassium tert-butylate 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到3-methoxy-17,17-dimethyl-D-homo-6-oxa-8α-estra-1,3,5(10)-trien-17a-one
  参考文献：
  名称：

  甾族雌激素8α类似物衍生的氨基磺酸酯的合成及某些生物学性质

  摘要：

  已经合成了衍生自8α系列雌激素的氨基磺酸盐，并且已经研究了它们对MCF-7乳腺癌细胞生长的影响。已发现7β-甲基-D-homo-6-oxa-8α-雌酮氨基磺酸盐和3-甲氧基-2,17β-氨磺酰氧基-8α-estra-1,3,5（10）-三烯的最佳抗癌作用几乎完全抑制癌细胞的生长。

  DOI：

  10.1134/s1070428015030215

文献信息

• 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.
• 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.
• [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：WO2009059806A2

  公开（公告）日：2009-05-14

  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.