16-methylene-17α-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione | 192722-04-6

• 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: 16-methylene-17α-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione
• 英文别名: (8R,9S,10R,13S,14S,17R)-17-acetyl-13-ethyl-17-hydroxy-16-methylidene-2,6,7,8,9,10,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 192722-04-6
• 化学式: C₂₂H₃₀O₃
• 分子量: 342.478
• InChiKey: BZLUPEQWHVJLKH-ZCPXKWAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 16-methylene-17α-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione 在 高氯酸 、 溶剂黄146 作用下， 反应 0.17h， 以80%的产率得到Methylnestoron
  参考文献：
  名称：

  Synthesis and biological activity of a new progestogen, 16-methylene-17α-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione acetate

  摘要：

  The progestational activity of second- and third-generation progestins in oral contraceptives were markedly increased by addition of an 18-methyl group. A new progestin, the 18-methyl analog of Nestorone, 16-methylene-17 alpha-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione acetate (10), was synthesized. The relative binding affinity and biologic activity of 10 was compared with Nestorone, levonorgestrel. and progesterone using a binding assay for rat progesterone receptors, the Clauberg assay in the rabbit. and by assessing pregnancy maintenance in the rat. These studies, as summarized in Table 4, show that 10 is three to ten times more potent than Nestorone. The addition of the 18-merhyl group to Nestorone markedly increased its potency as noted above. but is unlikely to change its rate of delivery from sustained release systems. 10 should be ideally suited for administration by implants or small skin patches. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00109-9
• 作为产物：
  描述：

  在 正丁基锂 、 TEA 、 硫酸 、 溶剂黄146 、 三乙胺 、 mercury(II) oxide 、 三甲氧基磷 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 16.67h， 生成 16-methylene-17α-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione
  参考文献：
  名称：

  Synthesis and biological activity of a new progestogen, 16-methylene-17α-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione acetate

  摘要：

  The progestational activity of second- and third-generation progestins in oral contraceptives were markedly increased by addition of an 18-methyl group. A new progestin, the 18-methyl analog of Nestorone, 16-methylene-17 alpha-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione acetate (10), was synthesized. The relative binding affinity and biologic activity of 10 was compared with Nestorone, levonorgestrel. and progesterone using a binding assay for rat progesterone receptors, the Clauberg assay in the rabbit. and by assessing pregnancy maintenance in the rat. These studies, as summarized in Table 4, show that 10 is three to ten times more potent than Nestorone. The addition of the 18-merhyl group to Nestorone markedly increased its potency as noted above. but is unlikely to change its rate of delivery from sustained release systems. 10 should be ideally suited for administration by implants or small skin patches. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00109-9

文献信息

• [EN] 18-METHYL 16-METHYLENE 19-NOR PREGNANE DERIVATIVES AS PROGESTINS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND PROCESS FOR THE PREPARATION THEREOF<br/>[FR] DERIVES DE 18-METHYL-16-METHYLENE-19-NOR PREGNANE UTILISES EN TANT QUE PROGESTINES, COMPOSITIONS PHARMACEUTIQUES CONTENANT CES DERIVES ET PROCEDE DE PREPARATION CORRESPONDANTS
  申请人：RICHTER GEDEON VEGYÉSZETI GYÁR RT.

  公开号：WO1997023498A1

  公开（公告）日：1997-07-03

  (EN) The invention relates to novel 16-methylene-17$g(a)-acyloxy-18-methyl-19-norpregn-4-ene-3,20-dione derivatives to pharmaceutical compositions containing these compounds; to the intermediates useful for the preparation of these compounds as well as a process for the preparation of these compounds and compositions. The compounds exert a progestogenic effect.(FR) L'invention se rapporte à de nouveaux dérivés de 16-méthylène-17$g(a)-acyloxy-18-méthyl-19-norpregn-4-ène-3,20-dione, à des compositions pharmaceutiques contenant ces composés, à des intermédiaires utiles à la préparation de ces composés ainsi qu'à un procédé de préparation de ces composés et compositions. Lesdits composés ont un effet progestatif.