(8R,9S,13S,14S,17R)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-4-carbaldehyde | 1336906-93-4

• 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: (8R,9S,13S,14S,17R)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-4-carbaldehyde
• 英文别名: (8R,9S,13S,14S,17R)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-4-carbaldehyde
• CAS: 1336906-93-4
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: GUJSHAHJIQWGNF-QRXXOTLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 α-雌二醇 在 三乙胺 、 magnesium chloride 、 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.25h， 以69%的产率得到(8R,9S,13S,14S,17R)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2-carbaldehyde
  参考文献：
  名称：

  ortho-Formylation of estrogens. Synthesis of the anti-cancer agent 2-methoxyestradiol

  摘要：

  Several estrogens were mono-formylated using a mixture of paraformaldehyde. MgCl2, and Et3N in refluxing THF. In all cases, the 2-isomer was formed as the major product with high regioselectivity compared to the 4-isomer. Excellent to high yields were obtained in all examples except one. The method was applied for an efficient synthesis of the anti-cancer agent 2-methoxyestradiol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.005

文献信息

• ESTRATRIENE DERIVATIVES COMPRISING HETEROCYCLIC BIOISOSTERES FOR THE PHENOLIC A-RING
  申请人：Blume Thorsten

  公开号：US20110190246A1

  公开（公告）日：2011-08-04

  The present invention is directed to novel pyrazolo-estrien and triazolo-estrien-derivatives, pharmaceutical compositions containing them and their use in the treatment or prevention of disorders and diseases mediated by an estrogen receptor such as hot flashes, vaginal dryness, osteopenia, osteoporosis, hyperlipidemia, loss of cognitive function, degenerative brain diseases, cardiovascular diseases, cerebrovascular diseases, hormone sensitive cancers and hyperplasia (in tissues including breast, endometrium, and cervix in women and prostate in men), endometriosis, uterine fibroids, osteoarthritis; and as contraceptive agents either alone or in combination with a progestogen or progestogen antagonist. The compounds of the invention are selective estrogen receptor modulators.

  本发明涉及新型吡唑酮-雌甾烯和三唑酮-雌甾烯衍生物，包含它们的制药组合物以及它们在治疗或预防由雌激素受体介导的疾病和疾病中的应用，例如潮热、阴道干燥、骨质疏松、骨质疏松症、高脂血症、认知功能丧失、退行性脑疾病、心血管疾病、脑血管疾病、激素敏感性癌症和增生（包括女性乳房、子宫内膜和宫颈以及男性前列腺组织），子宫内膜异位症、子宫肌瘤、骨关节炎；以及作为避孕剂，单独使用或与孕激素或孕激素拮抗剂组合使用。本发明的化合物是选择性雌激素受体调节剂。
• Estratriene derivatives comprising heterocyclic bioisosteres for the phenolic a-ring
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP2147924A1

  公开（公告）日：2010-01-27

  The present invention is directed to novel pyrazolo-estrien and triazolo-estrien-derivatives, pharmaceutical compositions containing them and their use in the treatment or prevention of disorders and diseases mediated by an estrogen receptor such as hot flashes, vaginal dryness, osteopenia, osteoporosis, hyperlipidemia, loss of cognitive function, degenerative brain diseases, cardiovascular diseases, cerebrovascular diseases, hormone sensitive cancers and hyperplasia (in tissues including breast, endometrium, and cervix in women and prostate in men), endometriosis, uterine fibroids, osteoarthritis; and as contraceptive agents either alone or in combination with a progestogen or progestogen antagonist. The compounds of the invention are selective estrogen receptor modulators.

  本发明涉及新型吡唑-雌三烯和三唑-雌三烯衍生物、含有它们的药物组合物，以及它们在治疗或预防由雌激素受体介导的紊乱和疾病中的用途，如潮热、阴道干燥、骨质疏松、骨质疏松症、高脂血症、认知功能丧失、脑退化性疾病、心血管疾病、脑血管疾病、激素敏感性癌症和增生（组织中包括乳腺、子宫内膜和子宫颈）、高脂血症、认知功能丧失、退化性脑部疾病、心血管疾病、脑血管疾病、对激素敏感的癌症和增生（女性组织包括乳腺、子宫内膜和宫颈，男性组织包括前列腺）、子宫内膜异位症、子宫肌瘤、骨关节炎；以及作为避孕药物单独使用或与孕激素或孕激素拮抗剂联合使用。本发明的化合物是选择性雌激素受体调节剂。
• [EN] ESTRATRIENE DERIVATIVES COMPRISING HETEROCYCLIC BIOISOSTERES FOR THE PHENOLIC A-RING<br/>[FR] DÉRIVÉS ESTRATRIÈNES COMPRENANT DES DIOISOSTÈRES HÉTÉROCYCLIQUES POUR LE CYCLE A PHÉNOLIQUE
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2010009828A1

  公开（公告）日：2010-01-28

  The present invention is directed to novel pyrazolo-estrien and triazolo-estrien-derivatives, pharmaceutical compositions containing them and their use in the treatment or prevention of disorders and diseases mediated by an estrogen receptor such as hot flashes, vaginal dryness, osteopenia, osteoporosis, hyperlipidemia, loss of cognitive function, degenerative brain diseases, cardiovascular diseases, cerebrovascular diseases, hormone sensitive cancers and hyperplasia (in tissues including breast, endometrium, and cervix in women and prostate in men), endometriosis, uterine fibroids, osteoarthritis; and as contraceptive agents either alone or in combination with a progestogen or progestogen antagonist. The compounds of the invention are selective estrogen receptor modulators.