(6R,8R,9S,10R,13S,14S)-17-hydroxy-6-(methoxymethyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | 1227511-26-3

• 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,10R,13S,14S)-17-hydroxy-6-(methoxymethyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
• 英文别名: (6R,8R,9S,10R,13S,14S,17S)-17-hydroxy-6-(methoxymethyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one；(6R,8R,9S,10R,13S,14S,17S)-17-hydroxy-6-(methoxymethyl)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 1227511-26-3
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: HHATXJXODRUWHI-BQODETKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 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,10R,13S,14S)-17-hydroxy-6-(methoxymethyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one 在 联苯 、 二苯基甲烷 、 lithium 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 (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
  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,10R,13S,14S)-6-(methoxymethyl)-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione 在 sodium tetrahydroborate 、 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以94%的产率得到(6R,8R,9S,10R,13S,14S)-17-hydroxy-6-(methoxymethyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-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

• 6-SUBSTITUTED ESTRADIOL DERIVATIVES AND METHODS OF USE
  申请人：Yarger James G.

  公开号：US20100130463A1

  公开（公告）日：2010-05-27

  Disclosed are compounds of the formula: wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, halo, a sulfate, a glucuronide, —OH, a bulky group, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, —N(CH 2 ) n ; a phosphate group, and a phosphinate group; R 9 is hydrogen, halogen or alkyl; R 11 is selected from the group consisting of H, C 1 -C 6 alkyl, halogen, a sulfate, a glucoronide, —SO 2 NH 2 , —COOH, —CN, —CH 2 CN—, —NHCN—, —CHO, ═CHOCH 3 , —COO salt, —OSO 2 alkyl, —NH 2 , and —NHCO(CH 2 ) n ; R 12 is selected from the group consisting of H, a C 1 -C 6 alkyl, a sulfate, a glucoronide, a bulky group, aryl, cycloalkyl, heteroaryl and heterocycloalkyl; X is selected from the group consisting of C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, halogen, a glucoronide, —NH 2 , —SO 2 NH 2 , —COOH, —CN, —CH 2 CN, —NHCN, —CHO, —COOsalt, —OSO 2 alkyl, —SH, —SCH 3 , —CH[(CH 2 ) n CH 2 ]COOCH 2 , —(CH 2 ) m COOCH 3 , —(CH 2 ) m —O—CH 3 , —(CH 2 ) m —O—(CH 2 ) n CH 3 , (CH 2 ) m —S—CH 3 , —(CH 2 ) m —S—(CH 2 ) n CH 3 , —(CH 2 ) m —NH—(CH 2 ) n CH 3 , —C 2 -C 8 alkenyl-O—(CH 2 ) n CH 3 , —C 2 -C 8 alkenyl-S—(CH 2 ) n CH 3 , —C 2 -C 8 alkenyl-N—(CH 2 ) n CH 3 , —C 2 -C 8 alkynyl-O—(CH 2 ) n CH 3 , —C 2 -C 8 alkynyl-S—(CH 2 ) n CH 3 , —C 2 -C 8 alkynyl-N—(CH 2 ) n CH 3 , —(CH 2 ) m —OH, —(CH 2 ) m —O—NH 2 , —(CH 2 ) m —S—NH 2 , —NH(CH 2 ) m CH 3 , —NH(CH 2 ) m OCH 3 , —NH(CH 2 ) m CHOH—COOH, —N(CH 3 ) 2 , —(CH 2 ) m (NH)CH 2 OH, —NHCOOH, —(CH 2 ) m NHCOOH, —NO 2 , —SCN, —SO 2 alkyl, —B(OH) 2 , —(CH 2 ) m N(CH 3 )—SO 2 —NH 3 , —(CH 2 ) m —NH—SO 2 —NH 2 , —NHC(═S)CH 3 , and —NHNH 2 ; and Y is selected from hydrogen, ═O, —OCO(R 6 ) and —OH; wherein m is an integer between 0-20, n is an integer between 0-8, 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. The compounds are useful in the treatment of various types of cancer.

  公开了以下式子的化合物：其中R1、R2、R3和R4独立地为氢、C1-C6烷基、卤素、硫酸盐、葡萄糖醛酸盐、—OH、笨重基团、芳基、环烷基、杂芳基、杂环烷基、—N(CH2)n、磷酸盐和亚磷酸盐；R9为氢、卤素或烷基；R11选自H、C1-C6烷基、卤素、硫酸盐、葡萄糖醛酸盐、—SO2NH2、—COOH、—CN、— CN—、—NHCN—、—CHO、═CHO 、—COO盐、—OSO2烷基、—NH2和—NHCO( )n；R12选自H、C1-C6烷基、硫酸盐、葡萄糖醛酸盐、笨重基团、芳基、环烷基、杂芳基和杂环烷基；X选自C1-C12烷基、C2-C12烯基、C2-C12炔基、卤素、葡萄糖醛酸盐、—NH2、—SO2NH2、—COOH、—CN、— CN、—NHCN、—CHO、—COO盐、—OSO2烷基、—SH、—S 、—CH[( )n ]COO 、—( )mCOO 、—( )m—O—CH3、—( )m—O—( )n 、( )m—S— 、—( )m—S—( )n 、—( )m—NH—( )n 、—C2-C8烯基-O—( )n 、—C2-C8烯基-S—( )n 、—C2-C8烯基-N—( )n 、—C2-C8炔基-O—( )n 、—C2-C8炔基-S—( )n 、—C2-C8炔基-N—( )n 、—( )m—OH、—( )m—O—NH2、—( )m—S—NH2、—NH( )m 、—NH( )mO 、—NH( )mCHOH—COOH、—N( )2、—( )m(NH) OH、—NHCOOH、—( )mNHCOOH、—NO2、—SCN、—SO2烷基、—B(OH)2、—( )mN( )—SO2—NH3、—( )m—NH—SO2—NH2、—NHC(═S) 和—NHNH2；Y选自氢、═O、—OCO(R6)和—OH；其中m为0-20之间的整数，n为0-8之间的整数，符号表示能够在位置3或17形成酮基的单一或双键；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。该化合物在治疗各种类型的癌症中有用。
• 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。
• 6-SUBSTITUTED DEMETHYL-ESTRADIOL DERIVATIVES AS ER-BETA AGONISTS
  申请人：Endece, LLC

  公开号：EP2616477B1

  公开（公告）日：2016-11-09
• 6-SUBSTITUTED ESTRADIOL DERIVATIVES FOR USE IN REMYELINATION OF NERVE AXONS
  申请人：Yarger James G.

  公开号：US20120245131A1

  公开（公告）日：2012-09-27

  Disclosed is a method of remyelinating axons with 6-substituted estradiol compounds of the formula The methods can be used to treat a variety of demyelinating diseases.
• 6-Substituted Estradiol Derivatives for the Treatment of Alzheimer's Disease
  申请人：Endece LLC

  公开号：US20150265630A1

  公开（公告）日：2015-09-24

  Disclosed is a method of treating Alzheimer's Disease with 6-substituted estradiol compounds of the formula The methods can be used to treat a variety of diseases related to the up-regulation of lipoprotein lipase or apolipoprotein C2.