methyl 2-(hexadecyloxy)-4-methyl-6,7-dihydro-1,3,2-dioxaphosphepine-5-carboxylate 2-oxide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: methyl 2-(hexadecyloxy)-4-methyl-6,7-dihydro-1,3,2-dioxaphosphepine-5-carboxylate 2-oxide
• 英文别名: Methyl 2-hexadecoxy-7-methyl-2-oxo-4,5-dihydro-1,3,2lambda5-dioxaphosphepine-6-carboxylate；methyl 2-hexadecoxy-7-methyl-2-oxo-4,5-dihydro-1,3,2λ5-dioxaphosphepine-6-carboxylate
• 化学式: C₂₃H₄₃O₆P
• 分子量: 446.565
• InChiKey: UQUOYRVMTVUYSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  30
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  tert-butyl 2-acetyl-4-((4-methoxybenzyl)oxy)butanoate 在 四丁基碘化铵 、 N,N-二异丙基乙胺 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 生成 methyl 2-(hexadecyloxy)-4-methyl-6,7-dihydro-1,3,2-dioxaphosphepine-5-carboxylate 2-oxide
  参考文献：
  名称：

  [EN] FLUORESCENT LABELED INHIBITORS
  [FR] INHIBITEURS MARQUÉS PAR FLUORESCENCE

  摘要：

  本文提供了一系列荧光标记的膦酸酯和磷酸酯化合物，可用作亲和探针来检测某些酶，包括脂肪酶。同时还提供了制备和使用这些化合物的方法。

  公开号：

  WO2015127381A1

文献信息

• Rat hormone sensitive lipase inhibition by cyclipostins and their analogs
  作者：Elena Vasilieva、Supratik Dutta、Raj K. Malla、Benjamin P. Martin、Christopher D. Spilling、Cynthia M. Dupureur

  DOI：10.1016/j.bmc.2015.01.028

  日期：2015.3

  Cyclipostins are bicyclic lipophilic phosphate natural products. We report here that synthesized individual diastereomers of cyclipostins P and R have nanomolar IC(50)s toward hormone sensitive lipase (HSL). The less potent diastereomers of these compounds have 10-fold weaker IC(50)s. The monocyclic phosphate analog of cyclipostin P is nearly as potent as the bicyclic natural product. Bicyclic phosphonate analogs of both cyclipostins exhibit IC(50)s similar to those of the weaker diastereomer phosphates (about 400 nM). The monocyclic phosphonate analog of cyclipostin P has similar potency. A series of monocyclic phosphonate analogs in which a hydrophobic tail extends from the lactone side of the ring are considerably poorer inhibitors, with IC(50)s around 50 mu M. Finally cyclophostin, a related natural product inhibitor of acetylcholinesterase (AChE) that lacks the hydrocarbon tail of cyclipostins, is not active against HSL. These results indicate a critical SAR for these compounds, the hydrophobic tail. The smaller lactone ring is not critical to activity, a similarity shared with cyclophostin and AChE. The HSL kinetics of inhibition for the cyclipostin P trans diastereomer were examined in detail. The reaction is irreversible with a K-I of 40 nM and a rate constant for inactivation of 0.2 min(-1). These results are similar to those observed for cyclophostin and AChE. (C) 2015 Elsevier Ltd. All rights reserved.
• [EN] FLUORESCENT LABELED INHIBITORS<br/>[FR] INHIBITEURS MARQUÉS PAR FLUORESCENCE
  申请人：UNIV MISSOURI

  公开号：WO2015127381A1

  公开（公告）日：2015-08-27

  Provided herein are a series of fluorescently labeled phosphonate and phosphate compounds such as can be used for affinity probes to detect certain enzymes including lipases. Also provided are methods of making and using such compounds.

  本文提供了一系列荧光标记的膦酸酯和磷酸酯化合物，可用作亲和探针来检测某些酶，包括脂肪酶。同时还提供了制备和使用这些化合物的方法。