(R)-4-((2R,4S,6R)-4-羟基-2-甲氧基-6-((S)-3-甲基戊-4-烯基)-四氢-2H-吡喃-2-基)-3-(4-甲氧基苄基)噻唑烷-2-酮 | 1056194-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (R)-4-((2R,4S,6R)-4-羟基-2-甲氧基-6-((S)-3-甲基戊-4-烯基)-四氢-2H-吡喃-2-基)-3-(4-甲氧基苄基)噻唑烷-2-酮
• 英文名称: (R)-4-((2R,4S,6R)-4-hydroxy-2-methoxy-6-((S)-3-methylpent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one
• 英文别名: (4R)-4-[(2R,4S,6R)-4-hydroxy-2-methoxy-6-[(3S)-3-methylpent-4-enyl]oxan-2-yl]-3-[(4-methoxyphenyl)methyl]-1,3-thiazolidin-2-one
• CAS: 1056194-44-5
• 化学式: C₂₃H₃₃NO₅S
• 分子量: 435.585
• InChiKey: QHWIUULXGPHHDA-WIVATLRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  93.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-4-((2R,4S,6R)-4-羟基-2-甲氧基-6-((S)-3-甲基戊-4-烯基)-四氢-2H-吡喃-2-基)-3-(4-甲氧基苄基)噻唑烷-2-酮 、 (Z)-3-甲基-2,6-庚二烯酸 在 2,6-二甲基吡啶 、 三氟甲磺酸酐 、 15-冠醚-5 、 sodium hydride 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 4.5h， 生成 (Z)-((2R,4R,6R)-2-methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-((S)-3-methylpent-4-enyl)-tetrahydro-2H-pyran-4-yl)-3-methylhepta-2,6-dienoate
  参考文献：
  名称：

  Examination of the olefin–olefin ring closing metathesis to prepare Latrunculin B

  摘要：

  Three subunits of the potent actin polymerization inhibitor Latrunculin B were synthesized and assembled using olefin-olefin ring closing metathesis chemistry to close the 14-membered macrocycle, Metathesis reactions of substrates with various remote protecting group patterns were examined and gave 6,7-E-lactones as the preferred products. (C 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.144
• 作为产物：
  描述：

  甲醇 、 (R)-4-((2R,4S,6R)-2,4-二羟基-6-((S)-3-甲基戊-4-烯基)-四氢-2H-吡喃-2-基)-3-(4-甲氧基苄基)噻唑烷-2-酮 在 camphor-10-sulfonic acid 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以88%的产率得到(R)-4-((2R,4S,6R)-4-羟基-2-甲氧基-6-((S)-3-甲基戊-4-烯基)-四氢-2H-吡喃-2-基)-3-(4-甲氧基苄基)噻唑烷-2-酮
  参考文献：
  名称：

  Examination of the olefin–olefin ring closing metathesis to prepare Latrunculin B

  摘要：

  Three subunits of the potent actin polymerization inhibitor Latrunculin B were synthesized and assembled using olefin-olefin ring closing metathesis chemistry to close the 14-membered macrocycle, Metathesis reactions of substrates with various remote protecting group patterns were examined and gave 6,7-E-lactones as the preferred products. (C 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.144

文献信息

• Cytoskeletal active compounds, compositions and use
  申请人：Lampe W. John

  公开号：US20060217427A1

  公开（公告）日：2006-09-28

  The present invention is directed to synthetic cytoskeletal active compounds that are related to natural Latrunculin A or Latrunculin B. The present invention is also directed to pharmaceutical compositions comprising such compounds and a pharmaceutically acceptable carrier. The invention is additionally directed to a method of preventing or treating diseases or conditions associated with actin polymerization. In one embodiment of the invention, the method treats increased intraocular pressure, such as primary open-angle glaucoma. The method comprises administering to a subject a therapeutically effective amount of a cytoskeletal active compound of Formula I or II, wherein said amount is effective to influence the cytoskeleton, for example by inhibiting actin polymerization.

  本发明涉及与天然拉曲林A或拉曲林B相关的合成细胞骨架活性化合物。本发明还涉及包含这些化合物和药用可接受载体的药物组合物。该发明还涉及一种预防或治疗与肌动蛋白聚合有关的疾病或症状的方法。在该发明的一个实施例中，该方法治疗增加的眼内压，如原发性开角型青光眼。该方法包括向受试者施用公式I或II的细胞骨架活性化合物的治疗有效量，其中所述量有效地影响细胞骨架，例如通过抑制肌动蛋白聚合。
• CYTOSKELETAL ACTIVE COMPOUNDS, COMPOSITION AND USE
  申请人：Lampe W. John

  公开号：US20080076735A1

  公开（公告）日：2008-03-27

  The present invention is directed to synthetic cytoskeletal active compounds that are related to natural Latrunculin A or Latrunculin B. The present invention is also directed to pharmaceutical compositions comprising such compounds and a pharmaceutically acceptable carrier. The invention is additionally directed to a method of preventing or treating diseases or conditions associated with actin polymerization. In one embodiment of the invention, the method treats increased intraocular pressure, such as primary open-angle glaucoma. The method comprises administering to a subject a therapeutically effective amount of a cytoskeletal active compound of Formula I or II, wherein said amount is effective to influence the cytoskeleton, for example by inhibiting actin polymerization.

  本发明涉及合成的细胞骨架活性化合物，其与天然拉曲林A或拉曲林B相关。本发明还涉及包含这种化合物和药学上可接受的载体的制药组合物。此外，本发明还涉及一种预防或治疗与肌动蛋白聚合有关的疾病或病症的方法。在本发明的一种实施例中，该方法治疗增加的眼内压，如原发性开角型青光眼。该方法包括向受试者给予公式I或II的细胞骨架活性化合物的治疗有效量，其中该量对细胞骨架产生影响，例如通过抑制肌动蛋白聚合。
• Cytoskeletal active compounds, composition and use
  申请人：Inspire Pharmaceuticals, Inc.

  公开号：US08039465B2

  公开（公告）日：2011-10-18

  The present invention is directed to synthetic cytoskeletal active compounds that are related to natural Latrunculin A or Latrunculin B. The present invention is also directed to pharmaceutical compositions comprising such compounds and a pharmaceutically acceptable carrier. The invention is additionally directed to a method of preventing or treating diseases or conditions associated with actin polymerization. In one embodiment of the invention, the method treats increased intraocular pressure, such as primary open-angle glaucoma. The method comprises administering to a subject a therapeutically effective amount of a cytoskeletal active compound of Formula I or II, wherein said amount is effective to influence the cytoskeleton, for example by inhibiting actin polymerization.

  本发明涉及与天然拉曲林A或拉曲林B相关的合成细胞骨架活性化合物。本发明还涉及包含这样的化合物和药用载体的制药组合物。此外，本发明还涉及一种预防或治疗与肌动蛋白聚合有关的疾病或病症的方法。在本发明的一种实施方式中，该方法用于治疗增加的眼内压，例如原发性开角型青光眼。该方法包括向受试者施用公式I或II的细胞骨架活性化合物的治疗有效量，其中该量有效地影响细胞骨架，例如通过抑制肌动蛋白聚合。
• US7320974B2
  申请人：——

  公开号：US7320974B2

  公开（公告）日：2008-01-22
• US7666861B2
  申请人：——

  公开号：US7666861B2

  公开（公告）日：2010-02-23