2-[(3-aminopropyl)amino]-8-isopropyl-5-methyl-3,6-dinitro-4H-1-benzopyran-4-one | 162255-99-4

• 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: 2-[(3-aminopropyl)amino]-8-isopropyl-5-methyl-3,6-dinitro-4H-1-benzopyran-4-one
• 英文别名: 2-(3-Aminopropylamino)-5-methyl-3,6-dinitro-8-propan-2-ylchromen-4-one
• CAS: 162255-99-4
• 化学式: C₁₆H₂₀N₄O₆
• 分子量: 364.358
• InChiKey: AMIZKSDQHSTHGY-UHFFFAOYSA-N

物化性质

• 沸点：
  495.7±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[(3-aminopropyl)amino]-8-isopropyl-5-methyl-3,6-dinitro-4H-1-benzopyran-4-one 、 在 4-二甲氨基吡啶 、 2,2'-二硫二吡啶 、 三乙胺 、 三苯基膦 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  寡核苷酸和稳定剂的缀合物的合成和杂交特性-II。

  摘要：

  合成了具有三或五亚甲基胺接头功能的新的吡喃酮衍生物。这些衍生物通过5'-磷酰胺键共价附于七核苷酸pd（CCAAACA）。测试八核苷酸pd（TGTTTGGC）和上述寡核苷酸缀合物的互补复合物的热力学响应。配合物形成的Tm数据和热力学参数表明色酮（γ-吡喃酮）和香豆素（α-吡喃酮）衍生物具有稳定7-mer / 8-mer互补复合物的能力，最可能是通过吡喃的堆积相互作用邻近核苷酸碱基的芳香系统。色酮（或香豆素）衍生物对寡核苷酸复合物（37摄氏度下的delta delta G）稳定性的影响在-1.0至-1之间。

  DOI：

  10.1016/s0968-0896(97)00127-2
• 作为产物：
  描述：

  百里酚 在 硫酸 、 硝酸 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 8.5h， 生成 2-[(3-aminopropyl)amino]-8-isopropyl-5-methyl-3,6-dinitro-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Synthesis and hybridization properties of the conjugates of oligonucleotides and stabilization agents. Part 3☆

  摘要：

  New compounds having tri- or pentamethylenamine linker functions were synthesized. These derivatives were covalently attached through the 5'-phosphoramide linkage to heptanucleotide pd(CCAAACA). Complementary complexes of the octanucleotide pd(TGTTTGGC) and above oligonucleotide conjugates were tested for their thermodynamic response. The T-m data and thermodynamic parameters for complex formation confirmed the ability of chromone (gamma-pyrone) derivatives to stabilize strongly the 7-mer/8-mer complementary complex. Moreover, benzochromone (naphthopyrane) and, surprisingly, tetrallydropyrimidinethanone derivatives showed the capacity of stabilizing this 7-mer/8-mer complementary complex. The effect of all these compounds on the stability of the oligonucleotide complexes (DeltaG at 37degreesC ranged from - 1.2 to -2.0 kcal/mol) was shown to be comparable to the effect of one nucleotide base pair and similar to the effect (DeltaDeltaG at 37degreesC ranged from -1.5 to -2.0 kcal/mol) found for acridine-oligonucleotide conjugates, which served as a reference in this study. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.030

文献信息

• Synthesis of 2-[(3-aminoalkyl or 3-bromoalkyl)amino]-4H-1-benzopyran-4-one derivatives
  作者：Enzo Sottofattori、Teresa Grandi、Alessandro Balbi

  DOI：10.1016/0040-4039(94)02469-r

  日期：1995.2

  The title compounds were advantageously synthesized from 2-(dialkylamino)chromones and 1,3-diaminopropane (or 1-amino-3-bromopropane) by amine exchange. The 3-cyano derivatives 5 were directly prepared from 2-(dimethylamino)chromones 1 and KCN by nitro displacement.
• Synthesis and hybridization properties of the conjugates of oligonucleotides and stabilization agents—II
  作者：A. Balbi、E. Sottofattori、T. Grandi、M. Mazzei、Dmitri S. Pyshnyi、Sergej G. Lokhov、Alexander V. Lebedev

  DOI：10.1016/s0968-0896(97)00127-2

  日期：1997.10

  synthesized. These derivatives were covalently attached through the 5'-phosphoramide linkage to heptanucleotide pd(CCAAACA). Complementary complexes of the octanucleotide pd(TGTTTGGC) and above oligonucleotide conjugates were tested for their thermodynamic response. The Tm data and thermodynamic parameters for complex formation have demonstrated the ability of chromone (gamma-pyrone) and coumarin (alpha-pyrone)

  合成了具有三或五亚甲基胺接头功能的新的吡喃酮衍生物。这些衍生物通过5'-磷酰胺键共价附于七核苷酸pd（CCAAACA）。测试八核苷酸pd（TGTTTGGC）和上述寡核苷酸缀合物的互补复合物的热力学响应。配合物形成的Tm数据和热力学参数表明色酮（γ-吡喃酮）和香豆素（α-吡喃酮）衍生物具有稳定7-mer / 8-mer互补复合物的能力，最可能是通过吡喃的堆积相互作用邻近核苷酸碱基的芳香系统。色酮（或香豆素）衍生物对寡核苷酸复合物（37摄氏度下的delta delta G）稳定性的影响在-1.0至-1之间。
• Synthesis and hybridization properties of the conjugates of oligonucleotides and stabilization agents. Part 3☆
  作者：Enzo Sottofattori、Maria Anzaldi、Mauro Mazzei、Mariangela Miele、Alessandro Balbi、Dmitri S. Pyshnyi、Olga D. Zakharova、Tatyana V. Abramova

  DOI：10.1016/j.bmc.2004.12.030

  日期：2005.3.1

  New compounds having tri- or pentamethylenamine linker functions were synthesized. These derivatives were covalently attached through the 5'-phosphoramide linkage to heptanucleotide pd(CCAAACA). Complementary complexes of the octanucleotide pd(TGTTTGGC) and above oligonucleotide conjugates were tested for their thermodynamic response. The T-m data and thermodynamic parameters for complex formation confirmed the ability of chromone (gamma-pyrone) derivatives to stabilize strongly the 7-mer/8-mer complementary complex. Moreover, benzochromone (naphthopyrane) and, surprisingly, tetrallydropyrimidinethanone derivatives showed the capacity of stabilizing this 7-mer/8-mer complementary complex. The effect of all these compounds on the stability of the oligonucleotide complexes (DeltaG at 37degreesC ranged from - 1.2 to -2.0 kcal/mol) was shown to be comparable to the effect of one nucleotide base pair and similar to the effect (DeltaDeltaG at 37degreesC ranged from -1.5 to -2.0 kcal/mol) found for acridine-oligonucleotide conjugates, which served as a reference in this study. (C) 2004 Elsevier Ltd. All rights reserved.