(6R,8R,9S,13S,14S)-3-hydroxy-6-(methoxymethyl)-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one | 1025495-82-2

• 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: (6R,8R,9S,13S,14S)-3-hydroxy-6-(methoxymethyl)-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one
• 英文别名: (6R,8R,9S,13S,14S)-3-hydroxy-6-(methoxymethyl)-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 1025495-82-2
• 化学式: C₂₀H₂₆O₃
• 分子量: 314.425
• InChiKey: MTUUPHGTRMPMQA-OVIBJMRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6R,8R,9S,13S,14S)-3-hydroxy-6-(methoxymethyl)-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one 在 吡啶 、 盐酸羟胺 、 sodium acetate 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氯化碳 、 乙醇 、 二甲基亚砜 为溶剂， 反应 5.5h， 生成 (4bS,8S,8aS,10R)-8-(2-cyanoethyl)-10-(methoxymethyl)-7-methylene-4-b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl methanesulfonate
  参考文献：
  名称：

  6-SUBSTITUTED DEMETHYL-ESTRADIOL DERIVATIVES AS SELECTIVE ER-BETA AGONISTS

  摘要：

  本文披露了作为选择性ERβ激动剂的6-取代13-去甲基雌二醇衍生物。还披露了一种通过给予这些6-取代13-去甲基雌二醇衍生物来治疗疼痛的方法。

  公开号：

  US20120071455A1
• 作为产物：
  描述：

  (6R,8R,9S,13S,14S)-6-(methoxymethyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol 在 三氧化硫吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.25h， 以76%的产率得到(6R,8R,9S,13S,14S)-3-hydroxy-6-(methoxymethyl)-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one
  参考文献：
  名称：

  6-SUBSTITUTED DEMETHYL-ESTRADIOL DERIVATIVES AS SELECTIVE ER-BETA AGONISTS

  摘要：

  本文披露了作为选择性ERβ激动剂的6-取代13-去甲基雌二醇衍生物。还披露了一种通过给予这些6-取代13-去甲基雌二醇衍生物来治疗疼痛的方法。

  公开号：

  US20120071455A1

文献信息

• METHODS FOR MODULATION OF LIPOPROTEIN LIPASE AND APOLIPOPROTEIN C2 EXPRESSION AND/OR ACTIVITY IN THE TREATMENT OF PERIPHERAL AND CENTRAL NERVOUS SYSTEM TISSUE DISEASE STATES
  申请人：ENDECE LLC

  公开号：US20210024568A1

  公开（公告）日：2021-01-28

  Methods for modulating lipoprotein lipase (LPL) and Apoliprotein C2 (ApoC2) expression and/or activity in the treatment of peripheral and central nervous system tissue disease states with C-6 substituted estradiol derivatives are presented herein.

  本文提出了使用C-6取代的雌二醇衍生物调节脂蛋白酯酶（LPL）和载脂蛋白C2（ApoC2）表达和/或活性的方法，用于治疗外周和中枢神经系统组织疾病状态。
• 6-ALKOXYALKYL ESTRADIOL DERIVATIVES AND METHODS OF USE
  申请人：Yarger James

  公开号：US20080119447A1

  公开（公告）日：2008-05-22

  A compound having the structure: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 9 are independently hydrogen, C 1 to C 6 alkyl or substituted alkyl, halogen, sulfate or glucuronide moieties; the symbol represents either a single or a double bond and when the symbol is a double bond and forms a keto group at position 3 or 17, then no R 7 or R 6 is present, respectively; the symbol represent the presence or absence of a bond at position 10; and the symbol represents any type of bond regardless of the stereochemistry. The invention also embraces the enantiomers, other stereochemical isomers, hydrates, solvates, tautomers and pharmaceutically acceptable salts of said compounds.

  一种具有以下结构的化合物：其中R1，R2，R3，R4，R5，R6，R7和R9独立地表示氢，C1至C6烷基或取代烷基，卤素，硫酸盐或葡萄糖醛酸酯基；符号表示单键或双键，当符号为双键并在3或17号位置形成酮基时，分别不存在R7或R6；符号表示在10号位置存在或不存在键；符号表示任何类型的键，不考虑立体化学。该发明还包括所述化合物的对映体、其他立体化学异构体、水合物、溶剂化物、互变异构体和药学上可接受的盐。
• 6-SUBSTITUTED ESTRADIOL DERIVATIVES AND METHODS OF USE
  申请人：YARGER JAMES

  公开号：US20080312202A1

  公开（公告）日：2008-12-18

  A compound having the structure: wherein R 1 and Z are as described above, X is selected from the group consisting of: C 1 -C 6 alkyl, a substituted alkyl, a halogen, a halogenated alkyl, a glucuronide, —NH 2 , —SO 2 NH 2 , —COOH, —CN, —CH 2 CN, —NHCN, —CHO, —COOsalt, —OSO 2 alkyl, —SH, —SCH 3 —CH(CH 2 ) n COOCH 3 , —(CH 2 ) n —O—CH 3 , —CH 2 OH, —(CH 2 ) n —O—NH 2 , —NH(CH 2 ) n CH 3 , NH(CH 2 ) n OCH 3 , —NH(CH 2 ) n CHOH—COOH, —N(CH 3 ) 2 , —(CH 2 ) n (NH)CH 2 OH, —NHCOOH, —(CH 2 ) n NHCOOH, —NO 2 , —SCN, —SO 2 alkyl, —B(OH) 2 , —(CH 2 ) n N(CH 3 )—SO 2 —NH 3 , —(CH 2 ) n NH—SO 2 —NH 2 , —NHC(═S)CH 3 , and —NHNH 2 ; R 3 is selected from the group consisting of: H, a C 1 -C 6 alkyl, a substituted alkyl, a halogen, and a halogenated alkyl; R 4 and Y are independently selected from a group consisting of: O, —OH, —H, a —C 1 -C 6 alkyl, a substituted alkyl, a halogen, a halogenated alkyl, a sulfate, a glucuronide, a bulky group, a phenyl or a substituted phenyl group, a cyclo- or heterocyclo group, piperidine, piperazine, morpholine, pyrimidine, —NH 2 , —N(CH 2 ) n CH 3 ; a phosphate group, a phosphinate group, wherein n is an integer and can be any number between 0 - 7 , the symbol represents either a single or a double bond capable of forming a keto group at position 3 or 17; and the symbol represents any type of bond regardless of the stereochemistry; and the respective enantiomers, other stereochemical isomers, hydrates, solvates, tautomers and pharmaceutically acceptable salts of said compounds.

  一种化合物具有以下结构：其中R1和Z如上所述，X选自以下组：C1-C6烷基，取代烷基，卤素，卤代烷基，葡萄糖酸盐，—NH2，—SO2NH2，—COOH，—CN，—CH2CN，—NHCN，—CHO，—COOsalt，—OSO2烷基，—SH，—SCH3—CH（CH2）nCOOCH3，—（CH2）n—O—CH3，—CH2OH，—（CH2）n—O—NH2，—NH（CH2）nCH3，NH（CH2）nOCH3，—NH（CH2）nCHOH—COOH，—N（CH3）2，—（CH2）n（NH）CH2OH，—NHCOOH，—（CH2）nNHCOOH，—NO2，—SCN，—SO2烷基，—B（OH）2，—（CH2）nN（CH3）—SO2—NH3，—（CH2）nNH—SO2—NH2，—NHC（═S）CH3和—NHNH2；R3选自以下组：H，C1-C6烷基，取代烷基，卤素和卤代烷基；R4和Y独立地选自以下组：O，—OH，—H，—C1-C6烷基，取代烷基，卤素，卤代烷基，硫酸盐，葡萄糖酸盐，臃肿基，苯基或取代苯基，环状或杂环基，哌啶，哌嗪，吗啉，嘧啶，—NH2，—N（CH2）nCH3；磷酸盐，磷酸酯盐，其中n是整数，可以是0-7之间的任何数字，符号表示能够在位置3或17形成酮基的单键或双键；符号表示任何类型的键，不考虑立体化学；以及所述化合物的相应对映异构体，其他立体化学异构体，水合物，溶剂化物，互变异构体和药学上可接受的盐。
• 6-Substituted Estradiol Derivatives and Methods of Use
  申请人：Yarger James G.

  公开号：US20120270817A1

  公开（公告）日：2012-10-25

  A method of inhibiting growth of cancer cells comprising contacting cancer cells with a 6-substituted estradiol derivative in an amount at least partially sufficient to inhibit said growth is disclosed. The compounds have the general formula depicted below, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are as defined herein.

  本发明涉及一种抑制癌细胞生长的方法，包括将癌细胞与6-取代雌二醇衍生物接触，其数量至少部分足以抑制该生长。所述化合物具有下图所示的一般公式，其中R1，R2，R3，R4，R5，R6和R7如本文所定义。
• 6-Substituted Demethyl-Estradiol Derivatives as Selective ER-Beta Agonists
  申请人：Yarger James G.

  公开号：US20140315874A1

  公开（公告）日：2014-10-23

  Disclosed herein are 6-substituted 13-demethyl-estradiol derivatives as selective ERβ agonists. Also disclosed is a method for treating pain by administering these 6-substituted 13-demethyl-estradiol derivatives.

  本文披露了6-取代的13-去甲基雌二醇衍生物作为选择性ERβ激动剂。同时披露了一种通过给予这些6-取代的13-去甲基雌二醇衍生物来治疗疼痛的方法。