5-amino-1,3-dioxo-1H-benzisoquinoline-2(3H)-acetic acid methyl ester | 103884-83-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-amino-1,3-dioxo-1H-benzisoquinoline-2(3H)-acetic acid methyl ester
• 英文别名: NA-B1；methyl (5-amino-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetate；methyl 2-(5-amino-1,3-dioxobenzo[de]isoquinolin-2-yl)acetate
• CAS: 103884-83-9
• 化学式: C₁₅H₁₂N₂O₄
• 分子量: 284.271
• InChiKey: QRXLUEMJMUPTGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  89.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-amino-1,3-dioxo-1H-benzisoquinoline-2(3H)-acetic acid methyl ester 生成 5-isothiocyanato-1,3-dioxo-1H-benz(de)isoquinoline-2(3H)-acetic acid methyl ester
  参考文献：
  名称：

  ARES J. J.; KADOR P. F.; MILLER D. D., J. MED. CHEM., 29,(1986) N 11, 2384-2389

  摘要：

  DOI：
• 作为产物：
  描述：

  5-nitro-1,3-dioxo-1H-benzisoquinoline-2(3H)-acetic acid methyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以98%的产率得到5-amino-1,3-dioxo-1H-benzisoquinoline-2(3H)-acetic acid methyl ester
  参考文献：
  名称：

  结合受保护的 α-氨基酸的荧光 3-氨基-1,8-萘二甲酰亚胺 Tröger 碱（3-氨基-TBNaps）

  摘要：

  描述了从相应的 3-氨基-1,8-萘二甲酰亚胺 ( Naps ) 单元合成 3-氨基-1,8-萘二甲酰亚胺 Tröger 碱 ( TBNaps ) 2 – 4，在酰亚胺末端具有多个氨基酸。还概述了相关3-氨基-TBNaps哌啶基-乙基衍生物1的固态 X 射线晶体结构及其超分子堆积。在这些分子中（如1的 X 射线结构所示），两个Naps单元具有正交排列，使它们具有潜在的吸引力 β-转角模拟物，用于掺入肽和多肽结构。这些系统的基态和激发态特性在一系列因极性和氢键能力而异的溶剂中进行了评估。该研究表明，所有三种化合物都具有内部电荷转移 (ICT) 激发态特性。

  DOI：

  10.1016/j.tetlet.2021.153405

文献信息

• Selective irreversible inhibitors of aldose reductase
  作者：Michael W. Smar、Jeffrey J. Ares、Toshihiro Nakayama、Hiroyuki Itabe、Peter F. Kador、Duane D. Miller

  DOI：10.1021/jm00084a017

  日期：1992.3

  3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid analogues have been examined as irreversible inhibitors of aldose reductase. The 5-alpha-bromoacetamide and 5-alpha-iodoacetamide analogues 5 and 6 gave irreversible inhibition of aldose reductase while the 5-alpha-chloroacetamide analogue 3 did not show this type of inhibition. Protection studies indicate that irreversible inhibitions are occurring at the inhibitor binding

  已经研究了一系列5-取代的1,3-二氧代-1H-苯并[异]异喹啉-2（3H）-乙酸类似物作为醛糖还原酶的不可逆抑制剂。5-α-溴乙酰胺和5-α-碘乙酰胺类似物5和6对醛糖还原酶具有不可逆的抑制作用，而5-α-氯乙酰胺类似物3没有这种抑制作用。保护研究表明在抑制剂结合位点发生不可逆的抑制作用。用大鼠晶状体醛糖还原酶（RLAR）和大鼠肾醛还原酶（RKALR）进行的不可逆抑制比较研究表明，5-α-卤代乙酰胺类似物5和6是RLAR的更有效抑制剂。
• Small Molecule Modifiers of MicroRNA miR-122 Function for the Treatment of Hepatitis C Virus Infection and Hepatocellular Carcinoma
  作者：Douglas D. Young、Colleen M. Connelly、Christoph Grohmann、Alexander Deiters

  DOI：10.1021/ja910275u

  日期：2010.6.16

  MicroRNAs are a recently discovered new class of important endogenous regulators of gene function. Aberrant regulation of microRNAs has been linked to various human diseases, most importantly cancer. Small molecule intervention of microRNA misregulation has the potential to provide new therapeutic approaches to such diseases. Here, we report the first small molecule inhibitors and activators of the liver-specific microRNA miR-122. This microRNA is the most abundant microRNA in the liver and is involved in hepatocellular carcinoma development and hepatitis C virus (HCV) infection. Our small molecule inhibitors reduce viral replication in liver cells and represent a new approach to the treatment of HCV infections. Moreover, small molecule activation of miR-122 in liver cancer cells selectively induced apoptosis through caspase activation, thus having implications in cancer chemotherapy. In addition to providing a new approach for the development of therapeutics, small molecule modifiers of miR-122 function are unique tools for exploring miR-122 biogenesis.
• Synthesis and biological evaluation of irreversible inhibitors of aldose reductase
  作者：Jeffrey J. Ares、Peter F. Kador、Duane D. Miller

  DOI：10.1021/jm00161a040

  日期：1986.11

  5-Isothiocyanatoalrestatin (1b) and 5-azidoalrestatin (1c) were prepared synthetically and examined as potential affinity and photoaffinity inhibitors of rat lens aldose reductase. Both compound 1b and 1c under appropriate conditions at 10(-4) M produced a 70% irreversible inactivation of aldose reductase within 1 min. The enzyme could, in part, be protected by preincubation with sorbinil 2, a known potent inhibitor of aldose reductase.
• ARES J. J.; KADOR P. F.; MILLER D. D., J. MED. CHEM., 29,(1986) N 11, 2384-2389
  作者：ARES J. J.、 KADOR P. F.、 MILLER D. D.

  DOI：——

  日期：——
• Fluorescent 3-amino-1,8-naphthalimide Tröger’s bases (3-amino-TBNaps) incorporating protected α-amino acids
  作者：Samantha A. Murphy、Caroline Phelan、Sankarasekaran Shanmugaraju、Salvador Blasco、Thorfinnur Gunnlaugsson

  DOI：10.1016/j.tetlet.2021.153405

  日期：2021.10

  makes them potentially attractive β-turn mimics for incorporation into peptide and polypeptide structures. The ground and the excited state properties of these systems were evaluated in a range of solvents that varied by polarity and hydrogen bonding ability. This investigation demonstrated that all three compounds possess Internal Charge Transfer (ICT) excited state properties.

  描述了从相应的 3-氨基-1,8-萘二甲酰亚胺 ( Naps ) 单元合成 3-氨基-1,8-萘二甲酰亚胺 Tröger 碱 ( TBNaps ) 2 – 4，在酰亚胺末端具有多个氨基酸。还概述了相关3-氨基-TBNaps哌啶基-乙基衍生物1的固态 X 射线晶体结构及其超分子堆积。在这些分子中（如1的 X 射线结构所示），两个Naps单元具有正交排列，使它们具有潜在的吸引力 β-转角模拟物，用于掺入肽和多肽结构。这些系统的基态和激发态特性在一系列因极性和氢键能力而异的溶剂中进行了评估。该研究表明，所有三种化合物都具有内部电荷转移 (ICT) 激发态特性。