4,6 alpha-difluoro-11 beta,17 alpha-dihydroxy-16 alpha-methyl-3-oxoandrost-4-ene-17 beta-carboxylic acid | 73205-06-8

• 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: 4,6 alpha-difluoro-11 beta,17 alpha-dihydroxy-16 alpha-methyl-3-oxoandrost-4-ene-17 beta-carboxylic acid
• 英文别名: (6S,8S,9S,10R,11S,13S,14S,16R,17R)-4,6-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid
• CAS: 73205-06-8
• 化学式: C₂₁H₂₈F₂O₅
• 分子量: 398.447
• InChiKey: AYUNBSLJWGOBIR-KGRGQMDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 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：
  94.8
• 氢给体数：
  3
• 氢受体数：
  7

文献信息

• 17-Beta-thiocarboxylic acid esters of 4-halo-3-oxoandrost-4-enes, their pharmaceutical use and processes for their preparation
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0004773A2

  公开（公告）日：1979-10-17

  17β-Thiocarboxylic acid esters of 4-halo-3-oxoandrost-4- enes of the formula: wherein X' is fluoro, chloro or bromo; X2 is fluoro, chloro or hydrogen; X3 is fluoro, chloro, bromo or hydrogen; X4 is =C=O or or may also be when X3 is chloro; R is alkyl or 1 to 6 carbon atoms or phenyl or benzyl optionally substituted with one substituent on the phenyl ring chosen from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and halo; R1 is hydrogen or alkanoyl of 2 to 6 carbon atoms when R2 is hydrogen, a-methyl or β-methyl, or OR' and R2 together are isopropylidenedioxy; and the solid and broken lines between C-1 and C-2 represent a double or a single bond; are useful as anti-inflammatory agents. They can be prepared by treating the corresponding 17β-carboxylic acid with a suitable base salt of RSH. The 17β-hydroxy compounds can be esterified to produce the 17β-alkanoyloxy compound. The double bond at the 4,5 position can be produced by contacting the corresponding Δ5 compound with a base.

  17β-Thiocarboxylic acid esters of 4-halo-3-oxoandrost-4- enes of the formula： 其中 X' 是氟、氯或溴； X2 是氟、氯或氢 X3 是氟、氯、溴或氢； X4 是 =C=O 或 或也可以是 当 X3 为氯时； R 是 1 至 6 个碳原子的烷基或苯基或苄基，可选择被苯基环上的一个取代基取代，该取代基可从 1 至 4 个碳原子的烷基、1 至 4 个碳原子的烷氧基和卤素组成的组中选择； 当 R2 为氢、a-甲基或 β-甲基时，R1 为氢或 2 至 6 个碳原子的烷酰基，或 OR' 和 R2 合在一起为异亚丙基二氧基；以及 C-1 和 C-2 之间的实线和断线代表双键或单键； 可用作抗炎剂。它们可以通过将相应的 17β- 羧酸与合适的 RSH 碱盐进行处理来制备。17β-hydroxy 化合物经酯化后可生成 17β-alkanoyloxy 化合物。4,5 位的双键可通过将相应的 Δ5 化合物与碱接触而生成。