harzianopyridone | 137813-88-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: harzianopyridone
• 英文别名: (1R)-Perindopril Benzyl Ester；4-hydroxy-5,6-dimethoxy-3-[(E,2S)-2-methylhex-4-enoyl]-1H-pyridin-2-one
• CAS: 137813-88-8
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: FPYAYFJAGDIMEX-GJIOHYHPSA-N

物化性质

• 沸点：
  468.1±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于甲醇：

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  harzianopyridone 在 重氧水 作用下， 反应 3.0h， 生成 C₁₄H₁₉NO₄⁽¹⁸⁾O
  参考文献：
  名称：

  Iterative Catalysis in the Biosynthesis of Mitochondrial Complex II Inhibitors Harzianopyridone and Atpenin B

  摘要：

  The pentasubstituted pyridine natural products harzianopyridone and atpenins are potent inhibitors of mitochondrial complex II. We identified the pathways of these compounds from their fungal producers and uncovered that the biosynthetic steps require multiple iterative enzymes. In particular, a methyltransferase and a flavin-dependent monooxygenase are used iteratively to introduce C5 and C6 methoxy groups. The pathway unexpectedly requires the installation and removal of an N-methoxy group, which is proposed to be a directing group that tunes the reactivity of the pyridone ring, possibly through the alpha effect.

  DOI：

  10.1021/jacs.0c03438
• 作为产物：
  描述：

  在 flavin-dependent monooxygenase harC from Aspergillus nidulans A1145 ΔEM 、 O-methyltransferase harB from Aspergillus nidulans A1145 ΔEM 作用下， 反应 12.0h， 生成 harzianopyridone
  参考文献：
  名称：

  Iterative Catalysis in the Biosynthesis of Mitochondrial Complex II Inhibitors Harzianopyridone and Atpenin B

  摘要：

  The pentasubstituted pyridine natural products harzianopyridone and atpenins are potent inhibitors of mitochondrial complex II. We identified the pathways of these compounds from their fungal producers and uncovered that the biosynthetic steps require multiple iterative enzymes. In particular, a methyltransferase and a flavin-dependent monooxygenase are used iteratively to introduce C5 and C6 methoxy groups. The pathway unexpectedly requires the installation and removal of an N-methoxy group, which is proposed to be a directing group that tunes the reactivity of the pyridone ring, possibly through the alpha effect.

  DOI：

  10.1021/jacs.0c03438

文献信息

• Stereoselective Total Synthesis of Atpenins A4 and B, Harzianopyridone, and NBRI23477 B
  作者：Masaki Ohtawa、Kouhei Sugiyama、Tohru Hiura、Shujiro Izawa、Kazuro Shiomi、Satoshi Omura、Tohru Nagamitsu

  DOI：10.1248/cpb.c12-00266

  日期：——

  The stereoselective total synthesis of atpenins A4 (2) and B (3), harzianopyridone (4), and NBRI23477 B (5) have been developed using a convergent approach involving the coupling reaction of a common iodopyridine with an aldehyde corresponding to the appropriate side chain of the desired compound. Furthermore, the absolute configurations of atpenin B (3), harzianopyridone (4), and NBRI23477 B (5) have been unambiguously determined.

  利用一种收敛方法，即普通碘吡啶与对应于所需化合物适当侧链的醛发生偶联反应，开发出了立体选择性全合成阿替匹灵 A4 (2) 和 B (3)、hazianopyridone (4) 以及 NBRI23477 B (5)。此外，还明确确定了阿替匹林 B (3)、哈嗪吡啶酮 (4) 和 NBRI23477 B (5) 的绝对构型。