5,16-dienpregnane-3,20-diol | 18586-88-4

• 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: 5,16-dienpregnane-3,20-diol
• 英文别名: 5,16-pregnadiene-3β-20 diol；(3S,8R,9S,10R,13S,14S)-17-(1-hydroxyethyl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 18586-88-4
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: AGHPIIDSYAFAJL-RRXYQKPUSA-N

物化性质

• 沸点：
  455.6±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,16-dienpregnane-3,20-diol 在 chromium(VI) oxide 作用下， 以 六甲基磷酰三胺 、 丙酮 为溶剂， 反应 168.0h， 生成 16-妊娠双烯醇酮
  参考文献：
  名称：

  Beugelmans,R.; Le Goff,M.-T., Bulletin de la Societe Chimique de France, 1969, p. 335 - 336

  摘要：

  DOI：
• 作为产物：
  描述：

  16-脱氢孕烯醇酮乙酸酯 在 aluminum isopropoxide 作用下， 以 异丙醇 为溶剂， 反应 3.0h， 以210 mg的产率得到16-妊娠双烯醇酮
  参考文献：
  名称：

  Synthesis and in vitro activity of some epimeric 20α-hydroxy, 20-oxime and aziridine pregnene derivatives as inhibitors of human 17α-hydroxylase/c 17,20 -lyase and 5α-reductase

  摘要：

  Some epimeric 20-hydroxy, 20-oxime, 16 alpha, 17 alpha-, 17,20- and 20,21-aziridine derivatives of progesterone were synthesized and evaluated as inhibitors of human 17 alpha-hydroxylase/C-17,C-20-lyase (P450(17 alpha)) and 5 alpha-reductase (5 alpha-R). The reduction of 16-dehydropregenolone acetate (3a) was reinvestigated. NaBH4 in the presence of CeCl3 gave better stereoselectivity for 20 beta-ol [20 alpha/20 beta-OH (4 alpha/4 beta)=1/2.7] than LTBAH or the Meerwein-Pondroff method reported; reduction with Zn in HOAc formed exclusively 20 alpha-ol (4 alpha b). The 20 alpha- and 20 beta-hydroxy-4,16-pregnadien-3-one (9 alpha) and (9 beta) were synthesized from the alcohols 4 alpha b and 4 beta b. Several 20-oxime pregnadienes and 16 alpha,17 alpha-, 17,20- and 20,21-aziridinyl-5-pregnene derivatives were also synthesized. LiAlH4 reduction of the 16-en-20-oxime (12b) yielded 20 (R)-(13a) and 20(S)-17 alpha,20-aziridine (13b) and 20(R)-17 beta,20-aziridine (14a). Several compounds inhibited the human P450(17 alpha) with greater potency than ketoconzole. The 5 alpha-R enzyme assay showed that while (9 alpha) did not have any activity, (9 beta) and (3b) were potent 5 alpha-reductase (IC50 = 21 and 31 nM) inhibitors with activities similar to finasteride. The 20-oximes (17a) and (17b) were potent dual inhibitors for both 5 alpha-R (IC50 = 63 and 115 nM, compared to 33 nM for finasteride) and P450(17 alpha) (IC50 = 43 and 25 nM, compared to 78 nM for ketoconazole). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00110-2

文献信息

• [EN] PROCESS FOR PREPARING GUGGULSTERONES AND GUGGULSTEROL<br/>[FR] PROCEDE DE PREPARATION DE GUGGULSTERONES ET DE GUGGULSTEROLS
  申请人：KANG HEONJOONG

  公开号：WO2004094450A1

  公开（公告）日：2004-11-04

  The present invention relates to a method for selective preparing 4,17 (20)-E-pregnadiene-3,16-dione (E-guggulsterone) of the formula (III) and 4,17 (20)-Z-pregnadiene-3,16-dione (Z-guggulsterone) of the formula (IV) having an effect of lowering the elevated low density lipoprotein (LDL) and high levels of the cholesterol effectively, and elevating the low levels of the high density lipoprotein (HDL) from a easy-available steroid of the following formula (I). Also, the present invention provides a method for preparation of the compound of the above formula (II).

  本发明涉及一种选择性制备具有降低升高的低密度脂蛋白（LDL）和胆固醇高水平的有效作用，并提高高密度脂蛋白（HDL）低水平的4,17(20)-E-孕甾二烯-3,16-二酮（E-谷胱甾醇）的方法，以及具有以下结构式(I)的易获得类固醇制备4,17(20)-Z-孕甾二烯-3,16-二酮（Z-谷胱甾醇）的方法。此外，本发明提供了上述结构式(II)化合物的制备方法。
• A process for the preparation of pharmacologically active synthetic z and e steroisomeric mixture of guggulsterones
  申请人：CIPLA LIMITED

  公开号：EP0447706A1

  公开（公告）日：1991-09-25

  There is provided a process for the preparation of pharmacologically active synthetic Z and E stereoisomeric mixture of guggulsterones by reacting a mixture of 5,17(20)-trans-pregnadiene-3β, 16β and 3β, 16∝ diols in an aromatic solvent in the presence of a catalyst using a hydrogen acceptor at reflux temperature in an inert atmosphere.

  提供了一种制备药理活性合成谷古酮的Z和E立体异构体混合物的方法，该方法通过在芳香溶剂中，在存在催化剂和氢受体的情况下，使用惰性气氛下的回流温度反应5,17（20）-顺式孕二烯-3β，16β和3β，16∝二醇的混合物。
• Process for preparing guggulsterones and guggulsterol
  申请人：Kang Heonjoong

  公开号：US20070055072A1

  公开（公告）日：2007-03-08

  The present invention relates to a method for selective preparing 4,17 (20)-E-pregnadiene-3,16-dione (E-guggul-sterone) of the formula (III) and 4,17 (20)-Z-pregnadiene-3,16-dione (Z-guggulsterone) of the formula (IV) having an effect of lowering the elevated low density lipoprotein (LDL) and high levels of the cholesterol effectively, and elevating the low levels of the high density lipoprotein (HDL) from a easy-available steroid of the following formula (I). Also, the present invention provides a method for preparation of the compound of the above formula (II).

  本发明涉及一种选择性制备公麻酮-3,16-二酮（E-古格尔甾酮）式（III）和4,17（20）-Z-孕二烯-3,16-二酮（Z-古格尔甾酮）式（IV）的方法，该方法使用易得的以下类固醇，具有有效降低升高的低密度脂蛋白（LDL）和胆固醇水平，并提高低水平的高密度脂蛋白（HDL）的作用。此外，本发明还提供了制备上述式（II）化合物的方法。
• EP1620455A4
  申请人：——

  公开号：EP1620455A4

  公开（公告）日：2009-08-05
• PROCESS FOR PREPARING GUGGULSTERONES AND GUGGULSTEROL
  申请人：Kang, Heonjoong

  公开号：EP1620455A1

  公开（公告）日：2006-02-01