(2S,4R,5R,6R)-2-benzoyloxy-7-benzyloxy-5-hydroxy-4,6-dimethylheptan-3-one | 207680-79-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4R,5R,6R)-2-benzoyloxy-7-benzyloxy-5-hydroxy-4,6-dimethylheptan-3-one
• 英文别名: (2S,4R,5R,6R)-7-(benzyloxy)-5-hydroxy-4,6-dimethyl-3-oxoheptan-2-yl benzoate；[(2S,4R,5R,6R)-5-hydroxy-4,6-dimethyl-3-oxo-7-phenylmethoxyheptan-2-yl] benzoate
• CAS: 207680-79-3
• 化学式: C₂₃H₂₈O₅
• 分子量: 384.472
• InChiKey: KBDLISLGOACHJP-DCXXXQMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4R,5R,6R)-2-benzoyloxy-7-benzyloxy-5-hydroxy-4,6-dimethylheptan-3-one 在 W-2 Raney nickel 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 samarium diiodide 、 草酰氯 、 三氟甲磺酸 、 氢气 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 tris(dimethylamino)sulfonium trimethylsilyldifluoride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 氘代苯 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 (6S,7R)-7-tert-butyldimethylsilyloxy-4,6,8-trimethylnon-4-en-3-one
  参考文献：
  名称：

  A Retro-Claisen Approach to Dolabriferol

  摘要：

  The protected precursor 30 to dolabriferol was generated by a DBU-induced, ester-forming, retro-Claisen process. The required linear carbon chain present in 22 was synthesized by a stereoselective lithium aldol reaction. The necessary aldehyde and ketone fragments were synthesized using stereocontrolled aldol reactions with the ethyl (S)-lactate derived ketone 13.

  DOI：

  10.1021/ol060347s
• 作为产物：
  描述：

  (S)-2-hydroxy-3-pentanone 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (2S,4R,5R,6R)-2-benzoyloxy-7-benzyloxy-5-hydroxy-4,6-dimethylheptan-3-one
  参考文献：
  名称：

  Polyketide Synthesis Using the Boron-Mediated, anti-Aldol Reactions of Lactate-Derived Ketones: Total Synthesis of (-)-ACRL Toxin IIIB

  摘要：

  The boron-mediated, anti-selective, aldol reactions of ketone 2 (and related derivatives) proceed with high levels of asymmetric induction, diastereoselectivities of up to 200:1 in favour of the aldol adducts 4 are obtained with achiral aldehydes and reagent control operates with chiral aldehydes. These lactate-derived ketones provide a versatile chiral auxiliary for the synthesis of beta-hydroxy carbonyl compounds. Oxidative removal of the auxiliary provides enantiomerically pure aldehydes 5, while reductive deoxygenation gives the corresponding ethyl ketones 6. This practical asymmetric methodology for generating anti-aldols is illustrated by an efficient total synthesis of (-)-ACRL toxin IIIB (7), which proceeds in 15 steps from 2 with 21% overall yield and 88% diastereoselectivity.

  DOI：

  10.1055/s-1998-5929

文献信息

• [EN] CYTOTOXIC ACTIN-TARGETING COMPOUNDS<br/>[FR] COMPOSÉS CYTOTOXIQUES CIBLANT L'ACTINE
  申请人：UNIV KINGSTON

  公开号：WO2019033219A1

  公开（公告）日：2019-02-21

  A class of compounds useful in pharmaceutical compositions and methods for treating or preventing cancer is described. Analogs of Mycalolide B have been prepared and tested in breast and ovarian cancer cell lines. The compounds show utility for inhibition of survival and proliferation of tumor cells. The compounds have been shown to disrupt actin.

  描述了一类在制药组合物和治疗或预防癌症方法中有用的化合物。已经制备并在乳腺癌和卵巢癌细胞系中测试了Mycalolide B的类似物。这些化合物显示出抑制肿瘤细胞存活和增殖的效用。已经证明这些化合物会破坏肌动蛋白。
• Truncated Actin-Targeting Macrolide Derivative Blocks Cancer Cell Motility and Invasion of Extracellular Matrix
  作者：Bhavin V. Pipaliya、Daria N. Trofimova、Rebecca L. Grange、Madhu Aeluri、Xu Deng、Kavan Shah、Andrew W. Craig、John S. Allingham、P. Andrew Evans

  DOI：10.1021/jacs.0c12404

  日期：2021.5.12

  rapid collapse of the actin cytoskeleton in ovarian cancer cells and impairs cancer cell motility and invasion of the extracellular matrix (ECM) by inhibiting invadopodia-mediated ECM degradation. These studies provide essential proof-of-principle for developing actin-targeting therapeutic agents to block cancer metastasis and establish a synthetically tractable barbed end-binding pharmacophore that can

  癌症转移是一个复杂的过程，涉及高度运动的肿瘤细胞，这些细胞突破组织屏障，进入血液和淋巴系统，并作为循环肿瘤细胞在全身传播。促成这些关键事件的主要细胞机制是肌动蛋白细胞骨架的重组。Mycalolide B (MycB) 是一种靶向肌动蛋白的海洋大环内酯，可以在低纳摩尔剂量下抑制乳腺癌和卵巢癌细胞的增殖、迁移和侵袭。通过关注 MycB 的肌动蛋白结合尾部区域 (C24-C35) 的结构-活性关系研究，我们确定了一种有效的截短衍生物，它通过与肌动蛋白的倒刺末端裂隙结合来抑制 G-肌动蛋白的聚合并切断 F-肌动蛋白。这种微型 MycB 衍生物的生物学分析表明，它会导致卵巢癌细胞中肌动蛋白细胞骨架的快速崩溃，并通过抑制侵袭伪足介导的 ECM 降解来损害癌细胞的运动性和细胞外基质 (ECM) 的侵袭。这些研究为开发肌动蛋白靶向治疗剂以阻断癌症转移并建立合成易处理的倒刺末端结合药效团提供了基本的原理证明
• Cytotoxic actin-targeting compounds
  申请人：Queen's University at Kingston

  公开号：US11369594B2

  公开（公告）日：2022-06-28

  A class of compounds useful in pharmaceutical compositions and methods for treating or preventing cancer is described. Analogs of Mycalolide B have been prepared and tested in breast and ovarian cancer cell lines. The compounds show utility for inhibition of survival and proliferation of tumor cells. The compounds have been shown to disrupt actin.

  本文描述了一类可用于治疗或预防癌症的药物组合物和方法的化合物。制备了霉酚酸内酯 B 的类似物，并在乳腺癌和卵巢癌细胞系中进行了测试。这些化合物显示出抑制肿瘤细胞存活和增殖的作用。研究表明，这些化合物能破坏肌动蛋白。
• Cytotoxic Actin-Targeting Compounds
  申请人：Queen's University at Kingston

  公开号：US20200306233A1

  公开（公告）日：2020-10-01

  A class of compounds useful in pharmaceutical compositions and methods for treating or preventing cancer is described. Analogs of Mycalolide B have been prepared and tested in breast and ovarian cancer cell lines. The compounds show utility for inhibition of survival and proliferation of tumor cells. The compounds have been shown to disrupt actin.
• Polyketide Synthesis Using the Boron-Mediated, anti-Aldol Reactions of Lactate-Derived Ketones: Total Synthesis of (-)-ACRL Toxin IIIB
  作者：Ian Paterson

  DOI：10.1055/s-1998-5929

  日期：1998.3

  The boron-mediated, anti-selective, aldol reactions of ketone 2 (and related derivatives) proceed with high levels of asymmetric induction, diastereoselectivities of up to 200:1 in favour of the aldol adducts 4 are obtained with achiral aldehydes and reagent control operates with chiral aldehydes. These lactate-derived ketones provide a versatile chiral auxiliary for the synthesis of beta-hydroxy carbonyl compounds. Oxidative removal of the auxiliary provides enantiomerically pure aldehydes 5, while reductive deoxygenation gives the corresponding ethyl ketones 6. This practical asymmetric methodology for generating anti-aldols is illustrated by an efficient total synthesis of (-)-ACRL toxin IIIB (7), which proceeds in 15 steps from 2 with 21% overall yield and 88% diastereoselectivity.