Tetraacetyldigitoxin | 13238-31-8

• 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: Tetraacetyldigitoxin
• 英文别名: [(2R,3R,4S,6S)-3-[(2R,4S,5R,6R)-4-acetyloxy-5-[(2R,4S,5R,6R)-4,5-diacetyloxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-[[(3S,5R,8R,9S,10S,13R,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-2-methyloxan-4-yl] acetate
• CAS: 13238-31-8
• 化学式: C₄₉H₇₂O₁₇
• 分子量: 933.1
• InChiKey: XUTZHKBFRMSIQE-REFIZGJZSA-N

物化性质

• 沸点：
  898.6±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  66
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  207
• 氢给体数：
  1
• 氢受体数：
  17

文献信息

• Process for introducing an amino group on the 14-position of a steroid nucleus
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0863149A1

  公开（公告）日：1998-09-09

  The present invention relates to oligosaccharide-containing 14-aminosteroid compounds and the pharmaceutically-acceptable acid salts or esters thereof of the general formula: wherein a) R1 is (i) COOR5, where    R5 is hydrogen, a 1-6 carbon lower alkyl ; a 1-6 carbon lower alkyl substituted by an amino group; an arylalkyl or heteroarylalkyl or a carbocyclic ring, or (ii) CHR6OH, where    R6 is a hydrogen atom or 1-6 carbon lower alkyl group, or (iii) COR''', where R''' is hydrogen; 1-6 carbon lower alkyl; 1-6 carbon lower alkyl substituted amino; amino or dialkylamino; and b) R2 is -NR7R8, where    R7 and R8, which may be the same or different, are hydrogen atoms or a 1-6 carbon lower alkyl ; and c) R3 is (i) an oligosaccharide sugar residue having the following structure: where R9 is hydrogen; methyl; hydroxy; carboxy; acetoxy; arylalkyloxy; heteroarylalkyloxy or benzoxy; R10 is hydrogen; methyl; carboxy; acetoxy; arylalkyloxy; heteroarylalkyloxy; benzoxy or hydroxy; R11 is oxygen; wherein further when R11 is a substituent on the terminal monosaccharide sugar residue; R11 is OH; methyl; acetoxy; arylalkyloxy; heteroarylalkyloxy; and R12 is a hydrogen; methyl; methylhydroxymethyl; or acetoxymethyl; or (ii) an oligosaccharide sugar residue having the following structure: where R14 and R15, which may be the same or different, are hydrogen; 1-6 carbon lower alkyl; heteroarylalkyl; arylalkyl; heteroaryl or aryl; R17 can be hydrogen; hydroxy; acetoxy or benzoxy; R18 and R19 are hydroxy; acetoxy and benzoxy; or (iii) an oligosaccharide residue having the following structure: where R14 and R15, which may be the same or different, are hydrogen; 1-6 carbon lower alkyl; heteroaryl alkyl; arylalkyl; heteroaryl or aryl; R14a is oxygen; wherein further when R14a is a substituent on the terminal monosaccharide sugar residue; R14a must be hydroxy; methyl; acetoxy; arylalkyloxy or heteroarylalkyloxy; and d) R4 is (i) OH, or (ii) H, or (iii) OR13, where R13 is a monosaccharide sugar residue; acetoxy; benzoxy; arylalkyl or heteroarylalkyl; and e) Z is (i) -CH-, where a and b are single bonds, or (ii) =C, where either a or b is a double bond. The present invention also relates to a process for introducing an amino group at the 14-position on a steroid nucleus wherein said amino group is diasteroselectively introduced onto the 14-position of the steroid nucleus via an iodoisocyanate addition comprising the steps of: a) adding the iodoisocyanate to the 14-15 position double bond on the steroid nucleus; and b) dehalogenation; and c) isocyanate conversion to the amine moiety on the 14-position of the steroid nucleus.

  本发明涉及通式如下的含寡糖的 14-氨基甾化合物及其药学上可接受的酸盐或酯： 其中 a) R1 是 (i) COOR5，其中 R5 是氢、1-6 碳低烷基、被氨基取代的 1-6 碳低烷基、芳烷基、杂芳烷基或碳环基，或 (ii) CHR6OH，其中 R6 是氢原子或 1-6 碳低烷基，或 (iii) COR'''，其中 R'''是氢；1-6 碳低烷基；1-6 碳低烷基取代的氨基；氨基或二烷基氨基；和 b) R2 是-NR7R8，其中 R7 和 R8（可以相同或不同）是氢原子或 1-6 碳低碳烷基；以及 c) R3 是 (i) 具有以下结构的寡糖残基： 其中 R9 是氢；甲基；羟基；羧基；乙酰氧基；芳烷氧基；杂芳烷氧基或苯氧基； R10 是氢；甲基；羧基；乙酰氧基；芳烷氧基；杂芳烷氧基；苯氧基或羟基； R11 是氧；其中，当 R11 是末端单糖糖残基上的取代基时，R11 是 OH；甲基；乙酰氧基；芳基烷氧基；杂芳基烷氧基；以及 R12 是氢；甲基；甲基羟甲基；或乙酰氧甲基；或 (ii) 具有以下结构的寡糖残基： 其中 R14 和 R15（可以相同或不同）是氢；1-6 碳低烷基；杂芳烷基；芳烷基；杂芳基或芳基；R17 可以是氢；羟基；乙酰氧基或苯氧基；R18 和 R19 是羟基；乙酰氧基和苯氧基；或 (iii) 具有以下结构的寡糖残基： 其中 R14 和 R15（可以相同或不同）是氢；1-6 碳低级烷基；杂芳基烷基；芳烷基；杂芳基或芳基；R14a 是氧；其中当 R14a 是末端单糖糖残基上的取代基时，R14a 必须是羟基；甲基；乙酰氧基；芳烷氧基或杂芳基烷氧基；以及 d) R4 是 (i) OH，或 (ii) H，或 (iii) OR13，其中 R13 是单糖糖残基；乙酰氧基；苯氧基；芳烷基或杂芳基；和 e) Z 是 (i) -CH-，其中 a 和 b 为单键，或 (ii) =C，其中 a 或 b 为双键。 本发明还涉及一种在类固醇核的 14 位上引入氨基的工艺，其中所述氨基是通过碘异氰酸酯加成反应，双向选择地引入类固醇核的 14 位上，包括以下步骤： a) 将碘异氰酸酯加到类固醇核的 14-15 位双键上；以及 b) 脱卤；以及 c) 将异氰酸酯转化为甾体核 14 位上的胺分子。
• NOVEL OLIGOSACCHARIDE-CONTAINING 14-AMINOSTEROID COMPOUNDS AND NOVEL DIASTEREOSELECTIVE AMINOSTEROID PROCESS CHEMISTRY
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0721459B1

  公开（公告）日：2000-05-31