10-benzylisoalloxazine | 21708-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 10-benzylisoalloxazine
• 英文别名: N10-benzylflavin；10-benzylbenzo[g]pteridine-2,4(3H,10H)-dione；10-Benzyl-isoalloxazin；9-Benzyl-isoalloxazin；10-benzyl-10H-benzo[g]pteridine-2,4-dione；10-Benzyl-10H-benzo[g]pteridin-2,4-dion；10-Benzylbenzo[g]pteridine-2,4-dione
• CAS: 21708-43-0
• 化学式: C₁₇H₁₂N₄O₂
• 分子量: 304.308
• InChiKey: SXXXKEQNJUOXFV-UHFFFAOYSA-N

物化性质

• 熔点：
  273-276 °C
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-benzylisoalloxazine 在 potassium carbonate 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Protochlorophyllide Reductase III: Synthesis of a Protochlorophyllide-Dihydroflavin Complex

  摘要：

  Abstract— A mild and efficient method of linking a dihydroflavin to the C‐17 carboxylic acid side chain of protochlorophyllide, without degradation of the sensitive E ring or loss of magnesium, is described. The appended dihydroflavin was shown to quench the fluorescence of protochlorophyllide. In contrast, a dihydronicotinamide moiety was unable to effect fluorescence quenching. The relevance of these findings to a possible mechanism of action of the enzyme protochlorophyllide reductase is discussed.

  DOI：

  10.1111/j.1751-1097.1996.tb02998.x
• 作为产物：
  描述：

  N-苄基-2-硝基苯胺 在 硼酸 、 溶剂黄146 、 锌 作用下， 以 甲醇 为溶剂， 生成 10-benzylisoalloxazine
  参考文献：
  名称：

  Discovery of isoalloxazine derivatives as a new class of potential anti-Alzheimer agents and their synthesis

  摘要：

  This article describes discovery of a novel and new class of cholinesterase inhibitors as potential therapeutics for Alzheimer's disease. A series of novel isoalloxazine derivatives were synthesized and biologically evaluated for their potential inhibitory outcome for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). These compounds exhibited high activity against both the enzymes AChE as well as BuChE. Of the synthesized compounds, the most potent isoalloxazine derivatives (7m and 7q) showed IC50 values of 4.72 mu M and 5.22 mu M respectively against AChE; and, 6.98 mu M and 5.29 mu M respectively against BuChE. These two compounds were further evaluated for their anti-aggregatory activity for beta-amyloid (A beta) in presence and absence of AChE by performing Thioflavin-T (ThT) assay and Congo red (CR) binding assay. In order to evaluate cytotoxic profile of these two potential compounds, cell viability assay of SH-SY5Y human neuroblastoma cells was performed. Further, to understand the binding behavior of these two compounds with AChE and BuChE enzymes, docking studies have been reported. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.05.005

文献信息

• Mechanistic studies on protochlorophyllide reductase: a model system for the enzymatic reaction
  作者：Parmesh Nayar、Anne M. Brun、Anthony Harriman、Tadhg P. Begley

  DOI：10.1039/c39920000395

  日期：——

  A model system for mimicry of the protochlorophyllide reductase enzymatic process, consisting of a zinc porphyrin covalently linked to a dihydroflavin, undergoes two successive one-electron transfer steps upon illumination, forming a zinc porphodimethene and the corresponding flavin.

  一种模仿原叶绿醌还原酶酶促过程的模型系统，由锌卟啉与二氢黄素共价连接而成，在光照下经历两个连续的单电子转移步骤，形成锌卟啉二甲烯和相应的黄素。
• A New and Improved<b><i>N</i></b>-3 Alkylation of 10-Substituted Isoalloxazines Using 1,8-Diazabicyclo[5.4.0]undec-7-ene in Benzene
  作者：Geetanjali、Ram Singh、S. M. S. Chauhan

  DOI：10.1081/scc-120015816

  日期：2003.1.4

  Abstract 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) has been identified as a remarkable base for the alkylation at N-3 position of 10-substituted isoalloxazines with alkyl halides in dry benzene.

  摘要 1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU) 已被鉴定为在无水苯中用烷基卤在10-取代异恶嗪的N-3 位进行烷基化反应的显着碱。
• Comparative binding study of steroidal adenine with flavin and uracil derivatives
  作者：Roopali Rai、Pramod S. Pandey

  DOI：10.1016/j.bmcl.2005.03.097

  日期：2005.6

  A comparative binding study of a steroidal adenine derivative based on lithocholic acid with N-10-benzylisoalloxazine (flavin) and N-1-iso-propyluracil has been described. (c) 2005 Elsevier Ltd. All rights reserved.
• Two‐Step Synthetic Route to 10‐Substituted Isoalloxazines
  作者：Prosenjit Chattopadhyay、Roopali Rai、Pramod S. Pandey

  DOI：10.1080/00397910600602552

  日期：2006.7

  10-Substituted isoalloxazines were synthesized in two steps starting from 1,2-phenylenediamine. Monoalkylation of the diamine resulted in 2-amino-N-alkylanilines, which were subsequently condensed with alloxan in boric acid and acetic acid to give 10-substituted isoalloxazines.
• US5153236A
  申请人：——

  公开号：US5153236A

  公开（公告）日：1992-10-06