bis-{2-[3-(7-methyl-[1,8]naphthyridin-2-ylamino)-propylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester | 656826-81-2

• 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: bis-{2-[3-(7-methyl-[1,8]naphthyridin-2-ylamino)-propylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N,N-bis[3-[3-[(7-methyl-1,8-naphthyridin-2-yl)amino]propylamino]-3-oxopropyl]carbamate
• CAS: 656826-81-2
• 化学式: C₃₅H₄₇N₉O₄
• 分子量: 657.816
• InChiKey: GJZLQVGOCBEKPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  163
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  bis-{2-[3-(7-methyl-[1,8]naphthyridin-2-ylamino)-propylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 以80%的产率得到N-[3-(7-methyl-[1,8]naphthyridin-2-ylamino)-propyl]-3-{2-[3-(7-methyl-[1,8]naphthyridin-2-ylamino)-propylcarbamoyl]-ethylamino}-propionamide
  参考文献：
  名称：

  The SPR Sensor Detecting Cytosine−Cytosine Mismatches

  摘要：

  We have synthesized the first surface plasmon resonance (SPIR) sensor that detects cytosine-cytosine (C-C) mismatches in duplex DNA by immobilizing aminonaphthyridine dinner on the gold surface. The ligand consisting of two 2-aminonaphthyridine chromophores and an alkyl linker connecting them strongly stabilized the C-C mismatches regardless of the flanking sequences. The fully matched duplexes were not stabilized at all under the same conditions. The C-T, C-A, and T-T mismatches were also stabilized with a reduced efficiency. SPR analyses of mismatch-containing 27-mer duplexes were performed with the sensor surface on which the aminonaphthyridine dimer was immobilized. The response for the C-C mismatch in 5'-GCC-3/3'-CCG-5' was about 83 times stronger than that obtained for the fully matched duplex. The sensor successfully detects the C-C mismatch at the concentration of 10 nM. SPR responses are proportional to the concentration of the C-C mismatch in a range up to 200 nM. Aminonaphthyridine dinner could bind strongly to the C-C mismatches having 10 possible flanking sequences with association constants in the order of 10(6) M-1. The facile protonation of 2-aminonaphthyridine chromophore at pH 7 producing the hydrogen-bonding surface complementary to that of cytosine was most likely due to the remarkably high selectivity of 1 to the C-C mismatch.

  DOI：

  10.1021/ja037947w
• 作为产物：
  描述：

  2-chloro-7-methyl-1,8-naphthyridine 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 20.0h， 生成 bis-{2-[3-(7-methyl-[1,8]naphthyridin-2-ylamino)-propylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  The SPR Sensor Detecting Cytosine−Cytosine Mismatches

  摘要：

  We have synthesized the first surface plasmon resonance (SPIR) sensor that detects cytosine-cytosine (C-C) mismatches in duplex DNA by immobilizing aminonaphthyridine dinner on the gold surface. The ligand consisting of two 2-aminonaphthyridine chromophores and an alkyl linker connecting them strongly stabilized the C-C mismatches regardless of the flanking sequences. The fully matched duplexes were not stabilized at all under the same conditions. The C-T, C-A, and T-T mismatches were also stabilized with a reduced efficiency. SPR analyses of mismatch-containing 27-mer duplexes were performed with the sensor surface on which the aminonaphthyridine dimer was immobilized. The response for the C-C mismatch in 5'-GCC-3/3'-CCG-5' was about 83 times stronger than that obtained for the fully matched duplex. The sensor successfully detects the C-C mismatch at the concentration of 10 nM. SPR responses are proportional to the concentration of the C-C mismatch in a range up to 200 nM. Aminonaphthyridine dinner could bind strongly to the C-C mismatches having 10 possible flanking sequences with association constants in the order of 10(6) M-1. The facile protonation of 2-aminonaphthyridine chromophore at pH 7 producing the hydrogen-bonding surface complementary to that of cytosine was most likely due to the remarkably high selectivity of 1 to the C-C mismatch.

  DOI：

  10.1021/ja037947w