FR264744 | 66018-39-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: FR264744
• 英文别名: (3aS,5Z,8S,15E,17aS)-11-hydroxy-13-methoxy-2,2,8-trimethyl-7,8,17,17a-tetrahydro-4H-benzo[c][1,3]dioxolo[4,5-h][1]oxacyclotetradecine-4,10(3aH)-dione；(2E,5S,9S,11Z,14S)-18-hydroxy-20-methoxy-7,7,14-trimethyl-6,8,15-trioxatricyclo[15.4.0.05,9]henicosa-1(17),2,11,18,20-pentaene-10,16-dione
• CAS: 66018-39-1
• 化学式: C₂₂H₂₆O₇
• 分子量: 402.444
• InChiKey: MFUROMODHKJRGA-VMSLBYTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  FR264744 在 碳酸氢钠 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 Hypothemycin
  参考文献：
  名称：

  Convergent stereospecific synthesis of LL-Z1640-2 (or C292), hypothemycin and related macrolides. Part 2

  摘要：

  The total synthesis of C292 (or LL-Z1640-2) and hypothemycin has been achieved. The 14-membered ring formation was achieved either via an intramolecular Suzuki coupling or much more efficiently via a Mitsunobu macrolactonisation. Reaction conditions were found to preserve the Z enone: selective epoxidation of C292 afforded hypothemycin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00871-7
• 作为产物：
  描述：

  (3aR,5Z,8S,15E)-4,11-dihydroxy-13-methoxy-2,2,8-trimethyl-3a,4,7,8,17,17a-hexahydro-10H-benzo[c][1,3]dioxolo[4,5-h][1]oxacyclotetradecin-10-one 在 1,3-二甲基吡唑 、 jones' reagent 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.17h， 生成 FR264744
  参考文献：
  名称：

  Convergent stereospecific synthesis of LL-Z1640-2 (or C292), hypothemycin and related macrolides. Part 2

  摘要：

  The total synthesis of C292 (or LL-Z1640-2) and hypothemycin has been achieved. The 14-membered ring formation was achieved either via an intramolecular Suzuki coupling or much more efficiently via a Mitsunobu macrolactonisation. Reaction conditions were found to preserve the Z enone: selective epoxidation of C292 afforded hypothemycin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00871-7

文献信息

• Isolation, semisynthesis, covalent docking and transforming growth factor beta-activated kinase 1 (TAK1)-inhibitory activities of (5Z)-7-oxozeaenol analogues
  作者：Lara Fakhouri、Tamam El-Elimat、Dow P. Hurst、Patricia H. Reggio、Cedric J. Pearce、Nicholas H. Oberlies、Mitchell P. Croatt

  DOI：10.1016/j.bmc.2015.09.037

  日期：2015.11

  (5Z)-7-Oxozeanol and related analogues were isolated and screened to explore their activity as TAK1 inhibitors. Seven analogues were synthesized and more than a score of natural products isolated that examined the role that different areas of the molecule contribute to TAK1 inhibition. A novel nonaromatic difluoro-derivative was synthesized that had similar potency compared to the lead. This is the first example of a nonaromatic compound in this class to have TAK1 inhibition. Covalent docking for the isolated and synthesized analogues was carried out and found a strong correlation between the observed activities and the calculated binding. (C) 2015 Elsevier Ltd. All rights reserved.

  (5Z)-7-氧代泽诺醇及其相关类似物被分离并筛选，以探索其作为TAK1抑制剂的活性。合成了七种类似物，并分离了二十多种天然产物，以研究分子不同区域对TAK1抑制作用的贡献。成功合成了一种新型非芳香双氟衍生物，其效力与先导化合物相当。这是该类化合物中首个具有TAK1抑制活性的非芳香化合物。对分离和合成的类似物进行了共价对接研究，发现观察到的活性与计算的结合能力之间存在显著相关性。©2015 Elsevier Ltd. 保留所有权利。
• Non-aromatic difluoro analogues of resorcylic acid lactones
  申请人：The University of North Carolina at Greensboro

  公开号：US10434085B2

  公开（公告）日：2019-10-08

  This disclosure is directed to non-aromatic difluoro analogues of resorcylic acid lactones, pharmaceutical compositions comprising non-aromatic difluoro analogues of resorcylic acid lactones, and methods of treatment comprising non-aromatic difluoro analogues of resorcylic acid lactones.

  本公开涉及非芳香族二氟类似物的间苯二酚内酯、包含非芳香族二氟类似物的间苯二酚内酯的药物组合物，以及包含非芳香族二氟类似物的间苯二酚内酯的治疗方法。
• NON-AROMATIC DIFLUORO ANALOGUES OF RESORCYLIC ACID LACTONES
  申请人：Pearce Cedric

  公开号：US20180153854A1

  公开（公告）日：2018-06-07

  This disclosure is directed to non-aromatic difluoro analogues of resorcylic acid lactones, pharmaceutical compositions comprising non-aromatic difluoro analogues of resorcylic acid lactones, and methods of treatment comprising non-aromatic difluoro analogues of resorcylic acid lactones.
• US7799827B2
  申请人：——

  公开号：US7799827B2

  公开（公告）日：2010-09-21
• US7915306B2
  申请人：——

  公开号：US7915306B2

  公开（公告）日：2011-03-29