(2S,4aR,4bS,6aS,9aS,9bR,9cR,12aR,12bS)-2-((tert-butyldiphenylsilyl)oxy)-4a,6a,11,11-tetramethylhexadecahydro-7H-cyclopenta[1,2]phenanthro[9,10-d][1,3]dioxol-7-one | 537674-13-8

• 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: (2S,4aR,4bS,6aS,9aS,9bR,9cR,12aR,12bS)-2-((tert-butyldiphenylsilyl)oxy)-4a,6a,11,11-tetramethylhexadecahydro-7H-cyclopenta[1,2]phenanthro[9,10-d][1,3]dioxol-7-one
• 英文别名: (1R,2R,6R,7S,9S,12R,13S,16S,20S)-9-[tert-butyl(diphenyl)silyl]oxy-4,4,12,16-tetramethyl-3,5-dioxapentacyclo[11.7.0.02,6.07,12.016,20]icosan-17-one
• CAS: 537674-13-8
• 化学式: C₃₈H₅₂O₄Si
• 分子量: 600.914
• InChiKey: WLNVPLRUUWSMOI-BEZCTJQLSA-N

物化性质

• 沸点：
  624.1±55.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  43.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,4aR,4bS,6aS,9aS,9bR,9cR,12aR,12bS)-2-((tert-butyldiphenylsilyl)oxy)-4a,6a,11,11-tetramethylhexadecahydro-7H-cyclopenta[1,2]phenanthro[9,10-d][1,3]dioxol-7-one 在 potassium tert-butylate 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 15.17h， 生成 (Z)-6α,7β-[(methylethylidene)-bis-oxy]-5α-pregn-17(20)-en-3β-ol
  参考文献：
  名称：

  Synthesis of a transmembrane ionophore based on a C2-symmetric polyhydroxysteroid derivative

  摘要：

  The synthesis of the C-2-symmetric bis-(20S)-5alpha-23,24-bisnorchol-16-en-3beta,6alpha,7beta-triol-22-terephthaloate (1), active as Na+-transporting transmembrane channel, has been achieved in 16 steps (10% overall yield) starting from the commercially available androst-5-en-3beta-ol-17-one (3). The straightforward stereospecific functionalization of the side-chain, via the 'ene' reaction, and the successful regioselective terephthaloylation of the C-22 hydroxy group, illustrate the efficiency of the synthetic strategy. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00108-x
• 作为产物：
  描述：

  (3S,10R,13S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one 在 吡啶 、 1,3-二甲基吡唑 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 双(乙腈)氯化钯(II) 、 sodium tetrahydroborate 、 cerium(III) chloride 、 dimethyl sulfide borane 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 11.0h， 生成 (2S,4aR,4bS,6aS,9aS,9bR,9cR,12aR,12bS)-2-((tert-butyldiphenylsilyl)oxy)-4a,6a,11,11-tetramethylhexadecahydro-7H-cyclopenta[1,2]phenanthro[9,10-d][1,3]dioxol-7-one
  参考文献：
  名称：

  Synthesis of a transmembrane ionophore based on a C2-symmetric polyhydroxysteroid derivative

  摘要：

  The synthesis of the C-2-symmetric bis-(20S)-5alpha-23,24-bisnorchol-16-en-3beta,6alpha,7beta-triol-22-terephthaloate (1), active as Na+-transporting transmembrane channel, has been achieved in 16 steps (10% overall yield) starting from the commercially available androst-5-en-3beta-ol-17-one (3). The straightforward stereospecific functionalization of the side-chain, via the 'ene' reaction, and the successful regioselective terephthaloylation of the C-22 hydroxy group, illustrate the efficiency of the synthetic strategy. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00108-x

文献信息

• [EN] HEXADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHRENE DERIVATIVES USEFUL IN TREATING PAIN AND INFLAMMATION<br/>[FR] DÉRIVÉS D'HEXADÉCAHYDRO-1 H-CYCLOPENTA [A]PHÉNANTHRÈNE UTILES DANS LE TRAITEMENT DE LA DOULEUR ET DE L'INFLAMMATION
  申请人：AQUINOX PHARMACEUTICALS CANADA INC

  公开号：WO2019195692A1

  公开（公告）日：2019-10-10

  wherein,R1, R2, R3, R4a, R4b and R5 are described herein, or a stereoisomer, enantiomer or tautomer thereof or mixtures thereof, or a pharmaceutically acceptable salt or solvate thereof, are described herein, as well as other compounds. These compounds are useful in treating inflammation and/or pain. Compositions comprising a compound of the invention are also disclosed, as are methods of using the compounds to treat inflammation and/or pain.

  其中，R1、R2、R3、R4a、R4b和R5在本文中有所描述，或其立体异构体、对映体、互变异构体或混合物，或其药用可接受盐或溶剂化物，在本文中也有描述，以及其他化合物。这些化合物在治疗炎症和/或疼痛方面有用。还披露了包含本发明化合物的组合物，以及使用这些化合物治疗炎症和/或疼痛的方法。
• [EN] INDENE DERIVATIVES USEFUL IN TREATING PAIN AND INFLAMMATION<br/>[FR] DÉRIVÉS D'INDÈNE UTILES DANS LE TRAITEMENT DE LA DOULEUR ET DE L'INFLAMMATION
  申请人：AQUINOX PHARMACEUTICALS CANADA INC

  公开号：WO2019195777A1

  公开（公告）日：2019-10-10

  Compounds of formula (I): wherein,R1, R2, R3, R4a, R4b and R5 are described herein, or a stereoisomer, enantiomer or tautomer thereof or mixtures thereof, or a pharmaceutically acceptable salt or solvate thereof, are described herein, as well as other compounds. These compounds are useful in treating inflammation and/or pain. Compositions comprising a compound of the invention are also disclosed, as are methods of using the compounds to treat inflammation and/or pain.

  公式(I)的化合物：其中，R1、R2、R3、R4a、R4b和R5如本文所述，或其立体异构体、对映体、互变异构体或其混合物，或其药用可接受的盐或溶剂化物，也如本文所述，以及其他化合物。这些化合物在治疗炎症和/或疼痛方面是有用的。还披露了包含本发明化合物的组合物，以及使用这些化合物治疗炎症和/或疼痛的方法。
• [EN] SHIP1 MODULATORS AND METHODS RELATED THERETO<br/>[FR] MODULATEURS DE SHIP1 ET PROCÉDÉS ASSOCIÉS
  申请人：AQUINOX PHARMACEUTICALS INC

  公开号：WO2014158654A1

  公开（公告）日：2014-10-02

  Compounds of formula (II): wherein A, R1, R2, R5 and R13 are described herein, or a stereoisomer, enantiomer or tautomer thereof or mixtures thereof, or a pharmaceutically acceptable salt or solvate thereof, are described herein, as well as other compounds. These compounds have activity as SHIP1 modulators, and thus may be useful in treating a variety of diseases, disorders or conditions that would benefit from SHIP1 modulation. Compositions comprising a compound of the invention are also disclosed, as are methods of SHIP1 modulation by administration of such compounds to an animal in need thereof.

  公式（II）的化合物：其中A、R1、R2、R5和R13如本文所述，或其立体异构体、对映体、互变异构体或其混合物，或其药用可接受的盐或溶剂化物，本文也描述了其他化合物。这些化合物具有作为SHIP1调节剂的活性，因此可能用于治疗多种可以从SHIP1调节中受益的疾病、失调或状况。还披露了包含本发明化合物的组合物，以及通过向需要的动物施用此类化合物来进行SHIP1调节的方法。