(11B)-11,17-二羟基-21-[(甲基磺酰基)氧基]-孕甾-1,4-二烯-3,20-二酮 | 35410-28-7

• 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
• 中文名称: (11B)-11,17-二羟基-21-[(甲基磺酰基)氧基]-孕甾-1,4-二烯-3,20-二酮
• 中文别名: 11Β,17Α-二羟基-21-(甲磺酰氧基)孕甾-1,4-二烯-3,20-二酮；11&Beta,17α-二羟基-21-(甲磺酰氧基)孕甾-1,4-二烯-3,20-二酮
• 英文名称: 11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione 21-mesylate
• 英文别名: prednisolone 21-mesylate；11β,17-dihydroxy-21-methanesulfonyloxy-pregna-1,4-diene-3,20-dione；11β,17-Dihydroxy-21-methansulfonyloxy-pregna-1,4-dien-3,20-dion；11β,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-methanesulfonate；11beta,17,21-Trihydroxypregna-1,4-diene-3,20-dione 21-methanesulphonate；[2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] methanesulfonate
• CAS: 35410-28-7
• 化学式: C₂₂H₃₀O₇S
• 分子量: 438.542
• InChiKey: TZEYKLAAPSZABE-CWNVBEKCSA-N

物化性质

• 熔点：
  206 °C (decomp)
• 沸点：
  656.1±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)
• 溶解度：
  二恶烷（微溶）、DMSO（微溶、加热、超声处理）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  7

制备方法与用途

化学性质：结晶，熔点为173-183℃。
用途：作为氢化泼尼松的磷酸钠的中间体。
生产方法：可通过将11β,17α,21-三羟基孕甾-1,4-二烯-3,20-二酮（即氢化泼尼松）与甲基磺酰氯进行甲磺酰化反应制得。

反应信息

• 作为反应物：
  描述：

  (11B)-11,17-二羟基-21-[(甲基磺酰基)氧基]-孕甾-1,4-二烯-3,20-二酮 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 [(8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-17-(2-isoquinolin-1-ylsulfanylacetyl)-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl] furan-2-carboxylate
  参考文献：
  名称：

  Steroidal C-21 mercapto derivatives as dissociated steroids: Discovery of an inhaled dissociated steroid

  摘要：

  A series of C-21 mercapto derivatives of hydrocortisone have been synthesized and evaluated in cell based transrepression and transactivation assays. The benzothiazole derivative, compound 6 not only showed a dissociated profile in vitro functional assays but also a pharmacological profile in a Brown-Norway rat therapeutic index model of asthma that dissociated side effects (thymolysis) while maintaining efficacy against pulmonary inflammation and lung function. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.108
• 作为产物：
  描述：

  泼尼松龙 以99%的产率得到
  参考文献：
  名称：

  RYAXOVSKAYA, M. I.;GRINENKO, G. S.;ALEKSEEVA, L. M.;ENGALYCHEVA, G. N.;NI+, XIM.-FARMATS. ZH., 25,(1991) N, S. 16-18

  摘要：

  DOI：

文献信息

• Benzyl Acetylcarbamate Potassium Salt (BENAC-K): A Simple Nucleophilic N-Acetamide Equivalent
  作者：Takeo Sakai、Toshiki Tatematsu、Ayumi Fukuta、Satomi Kasai、Kahori Hayashi、Yuji Mori

  DOI：10.1055/s-0039-1690097

  日期：2019.10

  acetamide equivalent. A broad variety of alkyl halides were converted into benzyloxycarbonyl-protected N-alkylacetamides in high yields by simple treatment with an almost equimolar (1.1 equiv) amount of BENAC-K in a polar solvent. Benzyl acetylcarbamate potassium salt (BENAC-K) has been developed as a simple nucleophilic acetamide equivalent. A broad variety of alkyl halides were converted into benzyloxycarbonyl-protected

  抽象的 苄基乙酰氨基甲酸酯钾盐（BENAC-K）已开发为简单的亲核乙酰胺等效物。通过在极性溶剂中用几乎等摩尔（1.1当量）量的BENAC-K进行简单处理，可以将多种烷基卤化物以高收率转化为苄氧羰基保护的N-烷基乙酰胺。 苄基乙酰氨基甲酸酯钾盐（BENAC-K）已开发为简单的亲核乙酰胺等效物。通过在极性溶剂中用几乎等摩尔（1.1当量）量的BENAC-K进行简单处理，可以将多种烷基卤化物以高收率转化为苄氧羰基保护的N-烷基乙酰胺。
• Synthesis of novel anti-inflammatory steroidal macrocycles using ring closing metathesis reaction
  作者：Purakkattle Biju、Rema Bitar、Yeon-Hee Lim、Ying Wang、Michael Berlin、Robert Aslanian、Kevin McCormick

  DOI：10.1016/j.tetlet.2014.12.048

  日期：2015.1

  A novel class of 13 and 16 membered steroidal macrocycles were synthesized by using ring closing metathesis reaction from the readily available anti-inflammatory steroids such as prednisolone, 6-methyl prednisolone, and 16-methyl prednisolone.

  通过使用闭环易位反应从容易获得的抗炎类固醇（如泼尼松龙，6-甲基泼尼松龙和16-甲基泼尼松龙）合成了一类新的13和16元类固醇大环化合物。
• Novel alkylated pregnanes, processes for their preparation and pharmaceutical compositions containing same
  申请人：AKZO N.V.

  公开号：EP0014005A1

  公开（公告）日：1980-08-06

  The present invention relates to novel 21-alkylated steroids of the pregnane series having the formula: wherein R1 = alkyl (1-4 C); R2 = carboxyacyl (1-18 C); X = H, F or Cl; Y = O, H(OH), H(lower acyloxy), H(F) or H(CI) with the proviso that Y is not H(F) when X is F; and the dotted line indicates the optional presence of a double bond, to processes for their preparation and to pharmaceutical compositions containing same. The novel compounds possess strong anti-inflammatory properties, when applied locally and cause little or no systemic, thymolytic, adrenolytic and salt-retaining effects.

  本发明涉及具有以下式子的新型孕烷系列 21-烷基类固醇： 其中 R1 = 烷基（1-4 C）；R2 = 羧酰基（1-18 C）；X = H、F 或 Cl；Y = O、H(OH)、H(低级酰氧基)、H(F)或 H(CI)，但当 X 为 F 时，Y 不是 H(F)；虚线表示任选存在的双键。 这些新型化合物在局部使用时具有很强的抗炎特性，对全身、胸腺溶解、肾上腺溶解和盐保留作用很小或没有。
• Corticosteroid conjugates and uses thereof
  申请人：——

  公开号：US20040157810A1

  公开（公告）日：2004-08-12

  The invention features corticosteroids conjugated to either a charged group or a bulky group in a manner that resists in vivo cleavage, the resulting conjugate is a peripherally acting steroid with reduced activity in the central nervous system. The invention provides a method for treating a patient having an inflammatory disease by administering to the patient a corticosteroid conjugate.

  本发明的特点是皮质类固醇与带电基团或膨大基团以可抵抗体内裂解的方式共轭，所产生的共轭物是一种外周作用的类固醇，在中枢神经系统中的活性降低。本发明提供了一种治疗炎症性疾病患者的方法，向患者施用皮质类固醇共轭物。
• Annen, Klaus; Hofmeister, Helmut; Laurent, Henry, Liebigs Annalen der Chemie, 1982, # 5, p. 966 - 972
  作者：Annen, Klaus、Hofmeister, Helmut、Laurent, Henry、Wiechert, Rudolf

  DOI：——

  日期：——