N,N-diethyl-6'-methoxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3'-amine | 1326231-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N,N-diethyl-6'-methoxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3'-amine
• 英文别名: N,N-diethyl-6'-methoxyspiro[1H-2-benzofuran-3,9'-xanthene]-3'-amine
• CAS: 1326231-94-0
• 化学式: C₂₅H₂₅NO₃
• 分子量: 387.478
• InChiKey: BCTQRKHKHLLXLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  30.93
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  methyl 2-(6-methoxy-3-oxo-3H-xanthen-9-yl)benzoate 在 吡啶 、 lithium aluminium tetrahydride 、 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.33h， 生成 N,N-diethyl-6'-methoxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3'-amine
  参考文献：
  名称：

  不对称和还原的呫吨荧光团：合成、光化学性质以及在用于检测硝基还原酶的可激活荧光探针中的应用

  摘要：

  呫吨荧光团，包括荧光素、罗多醇和罗丹明，是已应用于生物分子检测和可视化的荧光探针的代表性类别。“开启”可激活荧光探针可响应酶促反应而开启，已开发并准备好降低“始终开启”荧光探针的高背景信号。然而，用于生物应用的基于活性的荧光探针的开发，使用简单的呫吨染料，由于其低效的合成方法和化学修饰的困难而受到阻碍。因此，我们开发了一种高效、通用的合成路线，以通过连续 Pd 催化的交叉偶联开发基于荧光素、若多醇和罗丹明的化学更稳定的还原呫吨荧光团。通过监测荧光浓度、pH 值和溶剂的变化来评估它们的荧光性质。作为可激活荧光探针的应用，还使用还原的呫吨荧光团开发了硝基还原酶 (NTR) 响应荧光探针，并评估了它们的荧光特性。

  DOI：

  10.3390/molecules24173206

文献信息

• β-Galactosidase Fluorescence Probe with Improved Cellular Accumulation Based on a Spirocyclized Rhodol Scaffold
  作者：Mako Kamiya、Daisuke Asanuma、Erina Kuranaga、Asuka Takeishi、Masayo Sakabe、Masayuki Miura、Tetsuo Nagano、Yasuteru Urano

  DOI：10.1021/ja204781t

  日期：2011.8.24

  We identified a rhodol bearing a hydroxymethyl group (HMDER) as a suitable scaffold for designing fluorescence probes for various hydrolases. HMDER shows strong fluorescence at physiological pH, but phenolic O-alkylation of HMDER results in a strong preference for the spirocyclic form, which has weak fluorescence. As a proof of concept, we utilized this finding to develop a new fluorescence probe for beta-galactosidase. This probe has favorable characteristics for imaging in biological samples: it has good cellular permeability, and its hydrolysis product is well-retained intracellularly. It could rapidly and clearly visualize beta-galactosidase activity in cultured cells and in Drosophila melanogaster tissue, which has rarely been achieved with previously reported fluorescence probes.
• HEPARANASE COMPOUNDS AND METHODS OF USE
  申请人：University of Florida Research Foundation, Incorporated

  公开号：US20220202964A1

  公开（公告）日：2022-06-30

  The invention relates to compounds that interact with heparanase, uses in heparanase screening, uses in in vitro and in vivo imaging (e g , positron emission tomography (PET) and magnetic resonance imaging (MRI)), methods of synthesis, methods of modulating heparanase activity, and methods of treating disease and disorders associated with heparanase. The compounds of the invention are also useful in treating one or more diseases or disorders associated with the function of heparanase.