17beta-羧基-17-去氧基地塞米松 | 75262-69-0

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: 17beta-羧基-17-去氧基地塞米松
• 中文别名: 17β-羧基-17-脱氧地塞米松；地塞米松酸杂质
• 英文名称: (8S,9R,10S,11S,13S,14S,16R,17S)-9-Fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid
• 英文别名: 17beta-Carboxy-17-desoxy Dexamethasone；(8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-7,8,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylic acid
• CAS: 75262-69-0
• 化学式: C₂₁H₂₇FO₄
• 分子量: 362.441
• InChiKey: VNEWQJPVNZRHHG-MIESIBRYSA-N

物化性质

• 熔点：
  294-296°C (dec.)
• 沸点：
  529.4±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  17beta-羧基-17-去氧基地塞米松 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-propyl 9α-fluoro-16α-methyl-11β-hydroxy-3-oxo-1,4-androstadiene-17β-carboxamide
  参考文献：
  名称：

  Synthesis of steroidal 17 β-carboxamide derivatives

  摘要：

  Several 17 beta-carboxamide derivatives of natural and fluorinated glucocorticoids have been synthesized. The 17 beta-carboxylic derivatives were obtained by periodic acid oxidation of their side chains. They were then activated by N-hydroxybenzotriazole (HOBT) and coupled to several primary amines. Using this method eleven 17 beta-carboxamide derivatives have been prepared in good yields.

  DOI：

  10.1016/0039-128x(80)90039-2
• 作为产物：
  描述：

  去羟米松 在 高碘酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 17beta-羧基-17-去氧基地塞米松
  参考文献：
  名称：

  大环内酯类：一类新型的抗炎化合物

  摘要：

  通过将有效的糖皮质激素类固醇与大环内酯类化合物结合在一起，引入了安全糖皮质激素治疗设计的新概念。这些化合物是由9-deokso-9a-aza-9a-同反霉素A和3-descladinosyl-9-deokso-9a-aza-9a-的各种类固醇17β-羧酸和9a- N-（3-氨基烷基）衍生物合成的使用稳定的烷基链的同型阿霉素。结合大环内酯类化合物优先在免疫细胞（特别是吞噬细胞）中积累的特性与经典类固醇的抗炎活性，我们设计了在卵白蛋白（OVA）诱导的哮喘大鼠中表现出良好抗炎活性的分子。描述了这种新型化合物的合成，体外和体内抗炎活性。

  DOI：

  10.1016/j.bmc.2012.10.036

文献信息

• Compounds, compositions and methods for treatment of inflammatory diseases and conditions
  申请人：PLIVA Pharmaceutical Industry, Incorporated

  公开号：US20040014685A1

  公开（公告）日：2004-01-22

  The present invention relates (a) to new compounds represented by Formula I: 1 wherein M represents a macrolide subunit (macrolide moiety) derived from macrolide possessing the property of accumulation in inflammatory cells, S represents a steroid subunit (steroid moiety) derived from steroid drug with anti-inflammatory activity and L represents a linker molecule linking M and S, (b) to their pharmacologically acceptable salts, prodrugs and solvates, (c) to processes and intermediates for their preparation, and (d) to their use in the treatment of inflammatory diseases and conditions in humans and animals. Such compounds inhibit many cytokines and immune mediators involved in immune responses which cause inflammation, allergy, or alloimmunity, including without limitation IL-1, 2, 4, 5, 6, 10, 12, GMCSF, ICAM, and TNF-&agr; Importantly, anti-inflammatory steroids exert a direct anti-inflammatory effect through binding to the glucocorticosteroid receptor.

  本发明涉及以下内容：(a) 由以下式I所表示的新化合物：其中M代表来源于具有在炎症细胞中积聚特性的大环内酯亚基（大环内酯基团），S代表来源于具有抗炎活性的类固醇药物的类固醇亚基（类固醇基团），L代表连接M和S的连接分子，(b) 它们的药理学可接受的盐、前药和溶剂化物，(c) 用于它们的制备的过程和中间体，以及(d) 用于治疗人类和动物的炎症性疾病和症状。这些化合物抑制许多参与导致炎症、过敏或移植免疫反应的细胞因子和免疫介质，包括但不限于IL-1、2、4、5、6、10、12、GMCSF、ICAM和TNF-α。重要的是，抗炎类固醇通过结合糖皮质类固醇受体直接发挥抗炎作用。
• Conjugates of immune cell specific macrolide compounds with anti-inflammatory compounds for improved cellular targeting of anti-inflammatory therapy
  申请人：——

  公开号：US20040198677A1

  公开（公告）日：2004-10-07

  The present invention relates to novel compounds represented by the structure I and pharmaceutical preparations thereof for the treatment of inflammatory diseases in humans and animals.

  本发明涉及一种由结构式I表示的新化合物及其制备的药物制剂，用于治疗人和动物的炎症性疾病。
• Conjugates of Immune Cell Specific Macrolide Compounds with Anti-Inflammatory Compounds for Improved Cellular Targeting of Anti-Inflammatory Therapy
  申请人：MERCEP Mladen

  公开号：US20090105163A1

  公开（公告）日：2009-04-23

  The present invention relates to novel compounds represented by the structure I and pharmaceutical preparations thereof for the treatment of inflammatory diseases in humans and animals.

  本发明涉及一类由结构式I表示的新化合物及其制药制剂，用于治疗人和动物的炎症性疾病。
• 9α-Fluoro-16α-methyl-3,11-dioxoandrosta-1,4-diene-17β-carboxylic acid: catemeric hydrogen bonding and acetic acid solvation in a steroidal keto acid related to dexamethasone
  作者：Roger A. Lalancette、Hugh W. Thompson

  DOI：10.1107/s0108270103007121

  日期：2003.5.15

  The title keto acid crystallizes as a solvate, C21H25FO4.C2H4O2, with two molecules each of steroid and acetic acid per asymmetric unit. The former are approximately parallel, with opposite end-to-end orientation, and form translational carboxyl-to-ketone hydrogen-bonding catemers [O...O = 2.679 (6) and 2.650 (5) Angstrom, and O-H...O = 165 and 162degrees] that involve the 3-ketone group and follow the a axis. The acetic acid molecules are paired by hydrogen bonding, and neither they nor the F atom nor the 11-ketone group play any overt role in the hydrogen-bonding scheme of the steroid. Intermolecular C-H...O=C close contacts involving three different neighboring molecules exist to the 11-ketone group, the steroidal carboxyl group and one of the acetic acid molecules.
• CONJUGATES OF IMMUNE CELL SPECIFIC MACROLIDE COMPOUNDS WITH ANTI-INFLAMMATORY COMPOUNDS FOR IMPROVED CELLULAR TARGETING OF ANTI-INFLAMMATORY THERAPY
  申请人：GlaxoSmithKline istrazivacki centar Zagreb d.o.o.

  公开号：EP1351973B1

  公开（公告）日：2010-03-31