3-hydroxy-17β-methylestra-1,3,5(10)-trien-2-carboxaldehyde | 208758-30-9

• 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-hydroxy-17β-methylestra-1,3,5(10)-trien-2-carboxaldehyde
• 英文别名: 2-formyl-3-hydroxy-17β-methyl estratriene；3-hydroxy-17β-methylestra-1,3,5(10)-triene-2-carboxaldehyde；3-Hydroxy-17beta-methylestra-1,3,5(10)-triene-2-carboxaldehyde；(8S,9S,13R,14S,17S)-3-hydroxy-13,17-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-2-carbaldehyde
• CAS: 208758-30-9
• 化学式: C₂₀H₂₆O₂
• 分子量: 298.425
• InChiKey: UQVDFQMUCVRNKW-IMLHEQTHSA-N

物化性质

• 熔点：
  194-196 °C
• 沸点：
  418.6±45.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-17β-methylestra-1,3,5(10)-trien-2-carboxaldehyde 在 sodium hydride 、 甲酸 、 氯磺酰异氰酸酯 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 5.0h， 以50%的产率得到17β-methylestra-1,3,5(10)-trien-[3,2,e]-1',2',3'-oxathiazine-2',2'-dioxide
  参考文献：
  名称：

  Steroidal oxathiazine inhibitors of estrone sulfatase

  摘要：

  The presence of estrone sulfatase in breast tumors and the high levels of circulating estrone sulfate may contribute the major portion of estrogen synthesized locally in breast tissues through conversion of estrone sulfate to estrone by the enzyme. Using inhibitors of estrone sulfatase for the treatment of estrogen-dependent (estrogen receptor positive, ER+) breast cancer could be a very effective therapeutic strategy for the treatment of estrogen-dependent breast tumors in postmenopausal women. Therefore, we designed and synthesized several steroidal 2',3-oxathiazines that inhibit estrone sulfatase and have greatly reduced estrogenic side effects. Our in vitro studies indicate that the oxathiazine compounds have inhibitory activity on estrone sulfatase in MCF-7 human breast cancer cells. These estrone sulfatase inhibitors (ESIs) also inhibit the growth of MCF-7 cells induced by estrone sulfate. In addition, our in vivo experiments demonstrate that our ESIs have moderate antitumor activity against MCF-7 breast cancer xenografts in Balb/c athymic nude mice. The synthesis and biological activity of a number of these unique steroidal ESIs are described. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00118-6
• 作为产物：
  描述：

  雌酚酮 在 溴乙烷 、 palladium on activated charcoal 、 氢气 、 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 45.0h， 生成 3-hydroxy-17β-methylestra-1,3,5(10)-trien-2-carboxaldehyde
  参考文献：
  名称：

  Synthesis of 2-substituted 17β-hydroxy/17-methylene estratrienes and their in vitro cytotoxicity in human cancer cell cultures

  摘要：

  Synthesis of various types of 2-(alkylaminomethyl) and 2-(aroyl) 17 beta-estradiol analogs are reported. The synthesis of similar types of 2-substituted 17-methylene estratriene analogs was also achieved. Synthesis of chalcone derivatives of 17 beta-estradiol and 17-methylene estratriene were also realized. All these 2-substituted estratrienes were tested for their antiproliferative activity by using four different cell lines from colon, lung, glioma and breast cancers. Among the various 2-substituted estratrienes, the compounds 10d, 14a-h and 17e were found to have in vitro antiproliferative activity comparable to that of parent analogs 1-4. Comparison of the SAR pattern of these 2-susbtituted estratriene derivatives confirmed that relatively, 17-methylene estratrienes are more active than that of 17 beta-estradiol analogs. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.08.004

文献信息

• Steriod inhibitors of estrone sulfatase and associated pharmaceutical
  申请人：SRI International

  公开号：US05763432A1

  公开（公告）日：1998-06-09

  Novel compounds useful as inhibitors of estrone sulfatase are provided. The compounds have the structural formula (I) ##STR1## wherein X and Y, or Y and Z, form an oxathiazine dioxide ring or a dihydro-oxathiazine dioxide ring, and the other various substituents are as defined herein. Pharmaceutical compositions and methods for using the compounds of formula (I) to treat estrogen-dependent disorders are provided as well.

  提供了作为雌酮磺酸酶抑制剂有用的新化合物。这些化合物具有结构式（I）##STR1##其中X和Y，或Y和Z，形成一个氧硫氮二氧杂环或一个二氢氧硫氮二氧杂环，其他各种取代基如本文所定义。还提供了使用式（I）化合物治疗雌激素依赖性疾病的药物组合物和方法。
• Antiangiogenic agents
  申请人：Agoston E. Gregory

  公开号：US20050192258A1

  公开（公告）日：2005-09-01

  Compositions and methods for treating mammalian disease characterized by undesirable angiogenesis by administering derivatives of 2-methoxyestradiol of the general formula: wherein the variables are defined in the specification.

  通过给予2-甲氧基雌二醇衍生物治疗哺乳动物疾病的组合物和方法，该疾病的特征是不良血管生成，其中衍生物的一般公式为：其中变量在规范中定义。
• Steroid inhibitors of estrone sulfatase and associated pharmaceutical
  申请人：SRI International

  公开号：US05861388A1

  公开（公告）日：1999-01-19

  Novel compounds useful as inhibitors of estrone sulfatase are provided. The compounds have the structural formula (I) ##STR1## wherein X and Y, or Y and Z, form an oxathiazine dioxide ring or a dihydro-oxathiazine dioxide ring, and the other various substituents are as defined herein. Pharmaceutical compositions and methods for using the compounds of formula (I) to treat estrogen-dependent disorders are provided as well.

  本发明提供了一种作为雌酮磺酸酶抑制剂有用的新化合物。该化合物具有结构式（I）##STR1##其中X和Y，或Y和Z，形成一个噁唑二氧杂环或二氢噁唑二氧杂环，其他各种取代基的定义如本文所述。还提供了制备药物组合物和使用式（I）化合物治疗雌激素依赖性疾病的方法。
• Panchapakesan, Ganapathy; Sureshbabu, Radhakrishnan; Nachiappan, Dhatchana Moorthy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 1, p. 109 - 121
  作者：Panchapakesan, Ganapathy、Sureshbabu, Radhakrishnan、Nachiappan, Dhatchana Moorthy、Mohanakrishnan, Arasambattu K.

  DOI：——

  日期：——
• EP1773349A4
  申请人：——

  公开号：EP1773349A4

  公开（公告）日：2009-07-29