(2S,3R)-5-fluoro-3-(4-hydroxyphenyl)-2-[4-({(2S)-2-[(3R)-3-methylpyrrolidin-1-yl] propyl}oxy)phenyl]-2,3-dihydro-1,4-benzoxathiin-6-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S,3R)-5-fluoro-3-(4-hydroxyphenyl)-2-[4-({(2S)-2-[(3R)-3-methylpyrrolidin-1-yl] propyl}oxy)phenyl]-2,3-dihydro-1,4-benzoxathiin-6-ol
• 英文别名: (2S,3R)-5-Fluoro-3-(4-hydroxy-phenyl)-2-{4-[(S)-2-((R)-3-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-2,3-dihydro-benzo[1,4]oxathiin-6-ol；(2S,3R)-5-fluoro-3-(4-hydroxyphenyl)-2-[4-[(2S)-2-[(3R)-3-methylpyrrolidin-1-yl]propoxy]phenyl]-2,3-dihydro-1,4-benzoxathiin-6-ol
• 化学式: C₂₈H₃₀FNO₄S
• 分子量: 495.615
• InChiKey: AKAPBPNIIAPPPT-JDEMJVTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R)-(+)-甲基丁二酸 在 钯 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 甲酸铵 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 24.0h， 生成 (2S,3R)-5-fluoro-3-(4-hydroxyphenyl)-2-[4-({(2S)-2-[(3R)-3-methylpyrrolidin-1-yl] propyl}oxy)phenyl]-2,3-dihydro-1,4-benzoxathiin-6-ol
  参考文献：
  名称：

  Estrogen receptor ligands. Part 13: Dihydrobenzoxathiin SERAMs with an optimized antagonist side chain

  摘要：

  An optimized side chain for dihydrobenzoxathim SERAMs was discovered and attached to four dihydrobenzoxathim platforms. The novel SERAMs show exceptional estrogen antagonist activity in uterine tissue and an MCF-7 breast cancer cell assay. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.089

文献信息

• [EN] ESTROGEN RECEPTOR MODULATORS<br/>[FR] MODULATEURS DE RECEPTEURS D'OESTROGENE
  申请人：MERCK & CO INC

  公开号：WO2003091239A1

  公开（公告）日：2003-11-06

  The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, and cancer, in particular of the breast, uterus and prostate.

  本发明涉及化合物及其衍生物，它们的合成以及作为雌激素受体调节剂的用途。本发明的化合物是雌激素受体的配体，因此可能用于治疗或预防与雌激素功能相关的各种疾病，包括：骨质疏松、骨折、骨质疏松症、软骨退化、子宫内膜异位症、子宫肌瘤病、潮热、低密度脂蛋白胆固醇水平升高、心血管疾病、认知功能受损、脑退行性疾病、再狭窄、男性乳房发育、血管平滑肌细胞增殖、肥胖、失禁和癌症，尤其是乳腺、子宫和前列腺癌。
• Estrogen receptor modulators
  申请人：DiNinno P Frank

  公开号：US20050234245A1

  公开（公告）日：2005-10-20

  The present invention relates to compounds and derivatives thereof, their cynthesis, and their use as estrogen receptor modulators. The compound of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, cartilage degeneration, endometriosis, uterine fibroid desease, hot flashes, increased levels of LDL cholestterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muschle cell proliferation, obesity, incontinence, and cancer, in particular of the breast, uterus and prostate.

  本发明涉及化合物及其衍生物，它们的合成以及它们作为雌激素受体调节剂的用途。本发明的化合物是雌激素受体的配体，因此可能对与雌激素功能相关的多种疾病的治疗或预防有用，包括：骨质流失、骨折、骨质疏松症、软骨退化、子宫内膜异位症、子宫肌瘤病、潮热、低密度脂蛋白胆固醇水平增高、心血管疾病、认知功能障碍、脑退行性疾病、再狭窄、男性乳房增大、血管平滑肌细胞增殖、肥胖、失禁以及癌症，特别是乳腺、子宫和前列腺癌。
• ESTROGEN RECEPTOR MODULATORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP1501819B1

  公开（公告）日：2010-09-15
• US7138426B2
  申请人：——

  公开号：US7138426B2

  公开（公告）日：2006-11-21
• Estrogen receptor ligands. Part 13: Dihydrobenzoxathiin SERAMs with an optimized antagonist side chain
  作者：Timothy A. Blizzard、Frank DiNinno、Helen Y. Chen、Seongkon Kim、Jane Y. Wu、Wanda Chan、Elizabeth T. Birzin、Yi Tien Yang、Lee-Yuh Pai、Edward C. Hayes、Carolyn A. DaSilva、Susan P. Rohrer、James M. Schaeffer、Milton L. Hammond

  DOI：10.1016/j.bmcl.2005.05.089

  日期：2005.9

  An optimized side chain for dihydrobenzoxathim SERAMs was discovered and attached to four dihydrobenzoxathim platforms. The novel SERAMs show exceptional estrogen antagonist activity in uterine tissue and an MCF-7 breast cancer cell assay. (c) 2005 Elsevier Ltd. All rights reserved.