tetrahydrocortexolone 21-acetate | 16065-01-3

• 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: tetrahydrocortexolone 21-acetate
• 英文别名: THS 21-acetate；3α,5β-Tetrahydro Substance S 21 Acetate；21-Acetoxy-3α,17-dihydroxy-5β-pregnan-20-on；21-acetoxy-3α,17α-dihydroxy-5β-pregnan-20-one；21-acetoxy-3α,17-dihydroxy-5β-pregnan-20-one
• CAS: 16065-01-3
• 化学式: C₂₃H₃₆O₅
• 分子量: 392.536
• InChiKey: HFKAIASGHCYYRR-NAWQHOSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tetrahydrocortexolone 21-acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 Methyl-3α,17,20β(F)-trihydroxy-5β-pregnan-21-oat
  参考文献：
  名称：

  四对侧链环氧异构体在20位碳上的合成，这些分子衍生自5-beta-pregnan-3-alpha-ol。

  摘要：

  DOI：

  10.1021/jo01269a001
• 作为产物：
  描述：

  5β-dihydro-11-deoxycortisol 21-acetate 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 生成 tetrahydrocortexolone 21-acetate
  参考文献：
  名称：

  红字：Reichstein物质S。5alpha-tetrahydro S和5 beta-tetrahydro S血管抑制特性的比较。

  摘要：

  来自不同来源的5 beta-四氢-赖希斯坦物质S（3 alpha，5 beta-THS）在雏鸡绒膜尿囊膜测定系统中产生了可变的生物测定活性。物理表征显示不纯的产物。通过两种不同的途径合成该化合物产生了活性和非活性的3α，5β-THS。在其他两个差向异构体中，3个beta，5个beta-THS（epi-THS）和3个alpha，5个alpha-THS（allo-THS），只有后者是有活性的。这些结果表明，通过还原S物质的α，β-不饱和酮合成的3 alpha，5 beta-THS中存在的杂质可能是表位/ allo表位异构体（3 beta，5 beta-THS和分别为3 alpha，5 alpha-THS），只有后者对混合物具有积极的血管抑制活性。在两种合成衍生的化合物中，

  DOI：

  10.1016/0039-128x(95)00080-a

文献信息

• Potential Corticoid Metabolites: Chemical Synthesis of 3- and 21-Monosulfates and Their Double-Conjugates of Tetrahydrocorticosteroids in the 5.ALPHA.- and 5.BETA.-Series
  作者：Rika Okihara、Kuniko Mitamura、Maki Hasegawa、Megumi Mori、Akina Muto、Genta Kakiyama、Shoujiro Ogawa、Takashi Iida、Miki Shimada、Nariyasu Mano、Shigeo Ikegawa

  DOI：10.1248/cpb.58.344

  日期：——

  Here, we describe the chemical synthesis of the complete sets of 18 novel 3- and 21-monosulfates and their double-conjugated form of tetrahydrocortisol (THF), tetrahydro-11-deoxycortisol (THS), and tetrahydrocortisone (THE) in the 5alpha- and 5beta-series. The principal reactions involved are: (1) selective protection of a specific hydroxy group in substrates; (2) catalytic hydrogenation at C-5 of

  在这里，我们描述了18种新颖的3-和21-单硫酸盐的完整化学合成及其在5alpha-中的四氢皮质醇（THF），四氢-11-脱氧皮质醇（THS）和四氢可的松（THE）的双共轭形式。和5beta系列。涉及的主要反应是：（1）选择性保护底物中的特定羟基；（2）在C-5处将具有10％Pd（OH）（2）/ C的Delta（4）-3-酮类固醇在C-5催化加氢以生成3-oxo-5beta-类固醇并以10％Pd / C进行还原异构化以产生3-氧代-5α-异构体; （3）用Zn（BH（4））（2）和K-Selectride（R）将所得的3-oxo-5beta-和3-oxo-5alpha-类固醇还原为相应的3alpha-羟基化合物，分别;
• Preparation of haptens for use in immunoassays of tetrahydro-11-deoxycortisol and its glucuronides.
  作者：HIROSHI HOSODA、HIROMITSU YOKOHAMA、KAZUO ISHII、YUKO ITO、TOSHIO NAMBARA

  DOI：10.1248/cpb.31.4001

  日期：——

  For the purpose of developing immunoassays of tetrahydro-11-deoxycortisol or its glucuronides, various haptenic derivatives were synthesized. The 3-hemisuccinate (15), 21-hemisuccinate (8), 3-hemiglutarate (16), 21-hemiglutarate (9) and glucuronides (19, 23, 25) of tetrahydro-11-deoxycortisol were prepared starting from 11-deoxycortisol 21-acetate (1). Then, antisera were elicited in two rabbits by immunization with the conjugate of tetrahydro-11-deoxycortisol 3-glucuronide (19) with bovine serum albumin. It was found that the antisera had binding affinities to enzyme-labeled antigens prepared from 15, 16 and 19 ; the binding was inhibited by the glucuronide (19) in the enzyme immunoassay procedure.

  为了开发四氢-11-脱氧皮质醇或其葡萄糖醛酸苷的免疫测定法，合成了各种半抗原衍生物。以11-脱氧皮质醇为原料制备四氢-11-脱氧皮质醇的3-半琥珀酸酯(15)、21-半琥珀酸酯(8)、3-半戊二酸酯(16)、21-半戊二酸酯(9)和葡萄糖醛酸苷(19,23,25) 21-乙酸盐(1)。然后，用四氢-11-脱氧皮质醇3-葡萄糖醛酸苷(19)与牛血清白蛋白的缀合物免疫两只兔子，以产生抗血清。发现该抗血清与15、16和19制备的酶标抗原具有结合亲和力；在酶免疫测定过程中，结合被葡萄糖醛酸苷 (19) 抑制。
• C-3 glucosiduronates of metabolites of adrenal steroids
  作者：R.Mattox Vernon、June E. Goodrich、Albert N. Nelson

  DOI：10.1016/0039-128x(82)90110-6

  日期：1982.7

  On treatment with methyl 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-alpha-D-glucuronate and silver carbonate, tetrahydrocortisone 21-acetate gave the corresponding 3-glucosiduronate triacetyl methyl ester. This product was converted into the 20-semicarbazone which, by treatment with alkali to hydrolyze the ester functions and acid to hydrolyze the semicarbazone moiety, gave tetrahydrocortisone 3-glucosiduronic acid. The acid was converted into the crystalline barium salt and into the methyl ester. An analogous series of reactions was carried out on tetrahydrocortexolone 21-acetate. Treatment of the 20-semicarbazone of tetrahydrocortisone 3-glucosiduronic acid with potassium borohydride reduced the 11-oxo function to an 11 beta hydroxyl group; acid-catalyzed removal of the semicarbazone group produced tetrahydrocortisol 3-glucosiduronic acid which also was obtained as the barium salt and the methyl ester.
• Process for producing 17-hydroxy-20-keto-21-acyloxy pregnanes
  申请人：SYNTEX SA

  公开号：US02596563A1

  公开（公告）日：1952-05-13