6-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)hexanoic acid | 202805-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)hexanoic acid
• 英文别名: 6-[1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]hexanoic acid；N-(5-carboxpentyl)naphthalene-1,8-dianhydride；1,8-naphthalimide-N-caproic acid；6-(1,3-dioxobenzo[de]isoquinolin-2-yl)hexanoic acid
• CAS: 202805-07-0
• 化学式: C₁₈H₁₇NO₄
• mdl: MFCD00181326
• 分子量: 311.337
• InChiKey: ZILJZINSEYHWLP-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C(Solv: dichloromethane (75-09-2); ethanol (64-17-5))
• 沸点：
  544.1±33.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)hexanoic acid 在 sodium nitrate 、 sodium dihydrogenphosphate 、 sodium persulfate 、 4,7-二苯基-1,10-菲罗啉 、 silver nitrate 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 以50 %的产率得到5-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)pentyl nitrate
  参考文献：
  名称：

  银催化脂肪族羧酸的脱羧硝氧基化

  摘要：

  在这里，我们通过基于自由基的方法提出了银催化脱羧硝氧基化。该反应原型的底物范围延伸至未活化的伯羧酸和仲羧酸。该方案为合成前所未有的有机硝酸盐家族提供了一种实用方法，并表现出广泛的官能团兼容性。初步机理研究表明，高价硝酸银 (II) 络合物是一种多功能的 NO 3资源库，可以轻松形成 C-O 键。

  DOI：

  10.1021/acs.orglett.4c02180
• 作为产物：
  描述：

  1,8-萘二甲酸酐 、 6-氨基己酸 以 乙醇 为溶剂， 反应 0.75h， 以83%的产率得到6-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)hexanoic acid
  参考文献：
  名称：

  A fluorescent histone deacetylase (HDAC) inhibitor for cellular imaging

  摘要：

  荧光4MS具有与scriptaid相当的HDAC和抗癌活性，并且可以实现细胞快速摄取和细胞质定位的可视化。

  DOI：

  10.1039/c5cc02059j

文献信息

• Synthesis and Modification of Terrylenediimides as High-Performance Fluorescent Dyes
  作者：Fabian Nolde、Jianqiang Qu、Christopher Kohl、Neil G. Pschirer、Erik Reuther、Klaus Müllen

  DOI：10.1002/chem.200401177

  日期：2005.6.20

  synthetic approaches to terrylenediimides, highly photostable fluorescent dyes, are described. For the first time terrylenediimide has been synthesised in a straightforward procedure that makes large quantities available. The second route includes an efficient cross-coupling reaction followed by a cyclodehydrogenation. Monofunctionalisation of the imide structure allows terrylenediimides now to be coupled

  描述了两种新的合成方法，即高光稳定性的荧光染料-ter二酰亚胺。首次以简单的方法合成了三甲苯二亚胺，该方法可大量使用。第二种途径包括有效的交叉偶联反应，然后进行环脱氢。酰亚胺结构的单官能化使三甲苯二酰亚胺现在可以与多种化合物偶联，例如通过Suzuki交叉偶联，这可以导致一系列带有新官能团（例如羟基，氨基或羧基）的三联二酰亚胺与其他分子。海湾区域中的官能化用于调节三甲苯二酰亚胺的性能并扩大应用范围，例如，通过引入水溶性。
• (2-Amino-phenyl)-amides of ω-substituted alkanoic acids as new histone deacetylase inhibitors
  作者：Arkadii Vaisburg、Naomy Bernstein、Sylvie Frechette、Martin Allan、Elie Abou-Khalil、Silvana Leit、Oscar Moradei、Giliane Bouchain、James Wang、Soon Hyung Woo、Marielle Fournel、Pu T. Yan、Marie-Claude Trachy-Bourget、Ann Kalita、Carole Beaulieu、Zuomei Li、A.Robert MacLeod、Jeffrey M. Besterman、Daniel Delorme

  DOI：10.1016/j.bmcl.2003.08.083

  日期：2004.1

  A variety of omega-substituted alkanoic acid (2-amino-phenyl)-amides were designed and synthesized. These compounds were shown to inhibit recombinant human histone deacetylases (HDACs) with IC50 values in the low micromolar range and induce hyperacetylation of histones in whole cells. They induced expression of p21WAFl/Cip1 and caused cell-cycle arrest in human cancer cells. Compounds in this class showed efficacy in human tumor xenograft models. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of 2′‐Amino‐2′‐deoxyuridine Modified by 1,8‐Naphthalimide
  作者：Heting Li、Zhiqin Jiang、Xin Wang、Chao Zheng

  DOI：10.1080/00397910600631924

  日期：2006.6

  A simple and efficient synthetic route of 2'-amino-2'-deoxyuridine was studied. 2'-Amino-2'-deoxyuridine was incorporated into 1,8-naphthalimides in the 2'-position of 2'-sugar via linking arms of different lengths. A convenient method for the synthesis of the conjugates was adopted.
• Highly fluorescent and HDAC6 selective scriptaid analogues
  作者：Cassandra L. Fleming、Anthony Natoli、Jeannette Schreuders、Mark Devlin、Prusothman Yoganantharajah、Yann Gibert、Kathryn G. Leslie、Elizabeth J. New、Trent D. Ashton、Frederick M. Pfeffer

  DOI：10.1016/j.ejmech.2018.11.020

  日期：2019.1

  Fluorescent scriptaid analogues with excellent HDAC6 selectivity (HDAC1/6 > 500) and potency (HDAC6 IC50 < 5 nM) have been synthesised and evaluated. The highly fluorescent nature of the compounds (up to Phi(F)= 0.83 in DMSO and 038 in aqueous buffer) makes them ideally suited for cellular imaging and visualisation of their cytoplasmic localisation was readily accomplished. Whole organism imaging in zebrafish confirmed both the vascular localisation of the new inhibitors and the impact of HDAC6 inhibition on in vivo development. Crown Copyright (C) 2018 Published by Elsevier Masson SAS. All rights reserved,
• A Convenient Synthesis of the New Histone Deacetylase Inhibitor Scriptaid
  作者：Mariana S. Gerova、Ognyan I. Petrov

  DOI：10.1080/00304948.2014.866471

  日期：2014.1