2-ethoxy-3-O-benzyl-estrone | 192062-25-2

• 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: 2-ethoxy-3-O-benzyl-estrone
• 英文别名: 2-Ethoxy-3-Benzyloxy-Estra-1,3,5(10)-Triene-17-One；3-benzyloxy-2-ethoxy-estra-1,3,5(10)-triene-17-one；2-ethoxy-3-(benzyloxy)estra-1,3,5(10)-trien-17-one；(8R,9S,13S,14S)-2-ethoxy-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 192062-25-2
• 化学式: C₂₇H₃₂O₃
• 分子量: 404.549
• InChiKey: NULLVRPYBQTEPV-VBXWPYOKSA-N

物化性质

• 沸点：
  547.1±50.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  2-ethoxy-3-O-benzyl-estrone 在 palladium dihydroxide 氢气 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 23.0~25.0 ℃ 、344.73 kPa 条件下， 反应 123.0h， 生成 2-ethoxy-3-hydroxy-17β-aminoestra-1,3,5(10)-triene
  参考文献：
  名称：

  Synthesis of Analogs of 2-Methoxyestradiol with Enhanced Inhibitory Effects on Tubulin Polymerization and Cancer Cell Growth

  摘要：

  A new series of estradiol analogs was synthesized in an attempt to improve on the anticancer activity of 2-methoxyestradiol, a naturally occurring mammalian tubulin polymerization inhibitor. The compounds were evaluated as inhibitors of tubulin polymerization and the binding of [H-3]colchicine to tubulin, as well as for in vitro cytotoxicity in human cancer cell cultures. Overall, the most potent of the new compounds were 2-(2',2',2'-trifluoroethoxy)-6-oximinoestradiol, 2-ethoxy-6-oximinoestradiol, and 2-ethoxy-6-methoximinoestradiol. These agents lacked significant affinity for the estrogen receptor. The cytotoxicities of the compounds correlated in general with their abilities to inhibit tubulin polymerization, thus supporting inhibition of tubulin polymerization as the primary mechanism causing inhibition of cell growth.

  DOI：

  10.1021/jm9700833
• 作为产物：
  描述：

  2-formyl-estrone 在 potassium dihydrogenphosphate 、 potassium carbonate 、 caesium carbonate 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 2-ethoxy-3-O-benzyl-estrone
  参考文献：
  名称：

  Panchapakesan, Ganapathy; Sureshbabu, Radhakrishnan; Nachiappan, Dhatchana Moorthy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 1, p. 109 - 121

  摘要：

  DOI：

文献信息

• SUBSTITUTED ESTRATRIENE DERIVATIVES AS 17BETA HSD INHIBITORS
  申请人：MESSINGER Josef

  公开号：US20080255075A1

  公开（公告）日：2008-10-16

  Substituted estratriene compounds of formula (I) useful in therapy, especially in the treatment or inhibition of a steroid hormone dependent disorder requiring the inhibition of a 17β-hydroxysteroid dehydrogenase (17β-HSD) type 1, type 2 and/or type 3 enzyme, as well as their salts, pharmaceutical compositions containing such compounds and processes for preparing such compounds.

  公式（I）中的替代雌三烯化合物在治疗中很有用，特别是在治疗或抑制需要抑制17β-羟基类固醇脱氢酶（17β-HSD）类型1、类型2和/或类型3酶的类固醇激素依赖性疾病方面，以及它们的盐、含有这种化合物的药物组合物和制备这种化合物的方法。
• 2-alkoxy estradiols and derivatives thereof
  申请人：The United States of America as represented by the Department of Health

  公开号：US06136992A1

  公开（公告）日：2000-10-24

  Compounds represented by the following structural formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined in the specification. The compounds are disclosed as useful in the treatment of various forms of cancer.

  以下结构式所代表的化合物：##STR1## 其中R.sub.1，R.sub.2和R.sub.3如规范中所定义。这些化合物被披露为治疗各种癌症形式有用的化合物。
• 17-beta HSD1 and STS Inhibitors
  申请人：Messinger Josef

  公开号：US20110021480A1

  公开（公告）日：2011-01-27

  Substituted steroid compounds which represent selective inhibitors of 17β-hydroxysteroid dehydrogenase type I (17β-HSD1) and, in addition, which may represent inhibitors of the steroid sulfatase, salts thereof, pharmaceutical preparations containing these compounds, and a process for the preparation of these compounds. Also disclosed is a therapeutic method of using such substituted steroid compounds, particularly in the treatment, inhibition, prophylaxis or prevention of steroid hormone dependent diseases or disorders, such as steroid hormone dependent diseases or disorders requiring the inhibition of 17β-hydroxysteroid dehydrogenase type I and/or steroid sulfatase enzymes and/or requiring lowering of the endogenous 17β-estradiol concentration.

  本发明涉及代替类固醇化合物，其代表选择性抑制17β-羟基类固醇脱氢酶I（17β-HSD1）并且可能代表类固醇磺酸酯酶的抑制剂，这些化合物的盐，包含这些化合物的药物制剂以及制备这些化合物的方法。此外，本发明还揭示了使用这种代替类固醇化合物的治疗方法，特别是在治疗、抑制、预防或预防类固醇激素依赖性疾病或疾病时，例如需要抑制17β-羟基类固醇脱氢酶I和/或类固醇磺酸酯酶和/或需要降低内源性17β-雌二醇浓度的类固醇激素依赖性疾病或疾病。
• 17 -HSD1 AND STS INHIBITORS
  申请人：Solvay Pharmaceuticals GmbH

  公开号：EP1888615A1

  公开（公告）日：2008-02-20
• SUBSTITUTED ESTRATRIEN DERIVATIVES AS 17BETA HSD INHIBITORS
  申请人：Solvay Pharmaceuticals GmbH

  公开号：EP2099814A1

  公开（公告）日：2009-09-16