(7,15)-bis-O-TBS-ether of archazolid A | 914936-58-6

• 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: (7,15)-bis-O-TBS-ether of archazolid A
• 英文别名: [(1S)-1-[4-[(2S,3S,4E,6E,8S,9R,10R,11E,13Z,15Z,17S,18S,19E,22E)-10,18-bis[[tert-butyl(dimethyl)silyl]oxy]-8-methoxy-3,7,9,13,15,17,20,23-octamethyl-24-oxo-1-oxacyclotetracosa-4,6,11,13,15,19,22-heptaen-2-yl]-1,3-thiazol-2-yl]-3-methylbutyl] N-methylcarbamate
• CAS: 914936-58-6
• 化学式: C₅₄H₉₀N₂O₇SSi₂
• 分子量: 967.555
• InChiKey: KTFJFSRUIOBZAI-SVOWQMDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.12
• 重原子数：
  66
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (7,15)-bis-O-TBS-ether of archazolid A 在 三氯硅烷 、 氟化氢吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 1'-descarbamoyl-archazolid A
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel analogues of archazolid: A highly potent simplified V-ATPase inhibitor

  摘要：

  Novel analogues of the V-ATPase inhibitors archazolid A and B with modifications of the free hydroxyl groups and the side chain were designed by molecular modeling, synthesized by derivatization of the parent natural product and evaluated for V-ATPase inhibition and growth inhibition of murine connective tissue cells. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.073
• 作为产物：
  描述：

  archazolid A 、 叔丁基二甲基氯硅烷 在 吡啶 作用下， 反应 168.0h， 以77%的产率得到(7,15)-bis-O-TBS-ether of archazolid A
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel analogues of archazolid: A highly potent simplified V-ATPase inhibitor

  摘要：

  Novel analogues of the V-ATPase inhibitors archazolid A and B with modifications of the free hydroxyl groups and the side chain were designed by molecular modeling, synthesized by derivatization of the parent natural product and evaluated for V-ATPase inhibition and growth inhibition of murine connective tissue cells. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.073

文献信息

• Archazolid-7-O-β-D-glucopyranoside – Isolation, Structural Elucidation and Solution Conformation of a Novel V-ATPase Inhibitor from the MyxobacteriumCystobacter violaceus
  作者：Dirk Menche、Jorma Hassfeld、Heinrich Steinmetz、Markus Huss、Helmut Wieczorek、Florenz Sasse

  DOI：10.1002/ejoc.200600912

  日期：2007.3

  The novel polyketide macrolide archazolid-7-O-β-D-glucopyranoside (3) has been isolated from the myxobacterium Cystobacter violaceus and the structure of this first archazolid-glycoside has been determined by spectroscopic and degradative methods. A synthesis of simplified 7-O analogues, based on regioselective derivatisation of archazolid A, was elaborated. These structurally novel archazolids of

  新型聚酮化合物大环内酯类archazolid-7-O-β-D-吡喃葡萄糖苷 (3) 已从黏杆菌 Violaceus 中分离出来，并且已通过光谱和降解方法确定了这种第一个 archazolid 糖苷的结构。详细阐述了基于 archazolid A 的区域选择性衍生化的简化 7-O 类似物的合成。详细评估了这些结构新颖的天然和合成来源的 archazolids 对 V-ATPase 的抑制作用，并根据它们的溶液构象讨论了它们的生物活性，如由高场 NMR 研究确定的，包括基于 J 的构象分析和受约束的分子动力学模拟。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)