methyl N-(2-(tert-butyloxycarbonyl)aminoethyl)-N-(7-chloro-2(1H)-oxo-1,8-naphthyridin-3-yl)acetylglycinate | 216678-65-8

• 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: methyl N-(2-(tert-butyloxycarbonyl)aminoethyl)-N-(7-chloro-2(1H)-oxo-1,8-naphthyridin-3-yl)acetylglycinate
• CAS: 216678-65-8
• 化学式: C₂₀H₂₅ClN₄O₆
• 分子量: 452.895
• InChiKey: XJKARPCBAOJDHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  130.69
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl N-(2-(tert-butyloxycarbonyl)aminoethyl)-N-(7-chloro-2(1H)-oxo-1,8-naphthyridin-3-yl)acetylglycinate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以60%的产率得到N-(2-(tert-butyloxycarbonyl)aminoethyl)-N-(7-chloro-2(1H)-oxo-1,8-naphthyridin-3-yl)acetylglycine
  参考文献：
  名称：

  Substituted 1,8-Naphthyridin-2(1H)-ones Are Superior to Thymine in the Recognition of Adenine in Duplex as Well as Triplex Structures

  摘要：

  The synthesis and evaluation of a series of novel nucleobases based on substituted 1,8-naphthyridin-2(1H)-ones are reported. The nucleobases were designed to meet the requirements for incorporation into peptide nucleic acids (PNAs) and were evaluated as part of PNA duplex and triplex nucleic acid recognition systems. Of the various nucleobases tested, only the 7-chloro-1,8-naphthyridin-2(1H)-one (7-Cl-bT) nucleobase led to consistently increased affinity in all recognition systems, duplex (Watson-Crick) as well as triplex (Hoogsteen). For multiply modified systems, the increase in thermal stability per modification was dependent on the sequence context, ranging from 2.0 degreesC (in separate positions) to 3.5 degreesC (in adjacent positions) in PNA-DNA duplexes and from 1.2 degreesC (in separate positions) to 3.2 degreesC (in adjacent positions) in PNA-RNA duplexes. Singly mismatched oligonucleotide targets were employed to demonstrate uncompromised sequence discrimination. When part of multiply modified triplex (Hoogsteen) recognition systems, the 7-Cl-bT unit gave rise to increases in the thermal stability ranging from 2.7 to 3.5 degreesC when incorporated into separated and adjacent positions, respectively. Our results furthermore indicate that the duplex stabilization is predominantly enthalpic and therefore most likely not a consequence of single-strand preorganization. Finally, and most surprisingly, we find no direct correlation between the endstacking efficiency of this type of nucleobase and its helix stabilization when involved in Watson-Crick base pairing within a helix.

  DOI：

  10.1021/ja0117027
• 作为产物：
  描述：

  在 盐酸 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.67h， 生成 methyl N-(2-(tert-butyloxycarbonyl)aminoethyl)-N-(7-chloro-2(1H)-oxo-1,8-naphthyridin-3-yl)acetylglycinate
  参考文献：
  名称：

  Substituted 1,8-Naphthyridin-2(1H)-ones Are Superior to Thymine in the Recognition of Adenine in Duplex as Well as Triplex Structures

  摘要：

  The synthesis and evaluation of a series of novel nucleobases based on substituted 1,8-naphthyridin-2(1H)-ones are reported. The nucleobases were designed to meet the requirements for incorporation into peptide nucleic acids (PNAs) and were evaluated as part of PNA duplex and triplex nucleic acid recognition systems. Of the various nucleobases tested, only the 7-chloro-1,8-naphthyridin-2(1H)-one (7-Cl-bT) nucleobase led to consistently increased affinity in all recognition systems, duplex (Watson-Crick) as well as triplex (Hoogsteen). For multiply modified systems, the increase in thermal stability per modification was dependent on the sequence context, ranging from 2.0 degreesC (in separate positions) to 3.5 degreesC (in adjacent positions) in PNA-DNA duplexes and from 1.2 degreesC (in separate positions) to 3.2 degreesC (in adjacent positions) in PNA-RNA duplexes. Singly mismatched oligonucleotide targets were employed to demonstrate uncompromised sequence discrimination. When part of multiply modified triplex (Hoogsteen) recognition systems, the 7-Cl-bT unit gave rise to increases in the thermal stability ranging from 2.7 to 3.5 degreesC when incorporated into separated and adjacent positions, respectively. Our results furthermore indicate that the duplex stabilization is predominantly enthalpic and therefore most likely not a consequence of single-strand preorganization. Finally, and most surprisingly, we find no direct correlation between the endstacking efficiency of this type of nucleobase and its helix stabilization when involved in Watson-Crick base pairing within a helix.

  DOI：

  10.1021/ja0117027