Chelonin A | 133985-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: Chelonin A
• 英文别名: (−)-chelonin A；(2R,6S)-2-(1H-indol-3-yl)-6-(3,4,5-trimethoxyphenyl)morpholine
• CAS: 133985-26-9
• 化学式: C₂₁H₂₄N₂O₄
• 分子量: 368.433
• InChiKey: APYCBBUCRVHTDX-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Chelonin A 在 吡啶 作用下， 反应 17.0h， 以73%的产率得到Chelonin A acetamide
  参考文献：
  名称：

  Aromatic alkaloids from the marine sponge Chelonaplysilla sp

  摘要：

  Four novel alkaloids derived from tryptophan and tyrosine subunits have been isolated from the marine sponge Chelonaplysilla sp. collected from a marine lake in Palau. The structures of chelonin A (3), chelonin B (4), bromochelonin B (5), and chelonin C (6) were determined by interpretation of spectral data and chemical conversions. Chelonin A (3) and C (6) are the first natural products incorporating a 2,6-disubstituted morpholine ring. Chelonin A (3), chelonin B (4), and bromochelonin B (5) exhibited antimicrobial activity against Bacillus subtilis, while chelonin A (3) showed in vivo antiinflammatory activity.

  DOI：

  10.1021/jo00014a015
• 作为产物：
  描述：

  1-甲氧基-1H-吲哚 在 盐酸 、 lithium aluminium tetrahydride 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 、 苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 42.0h， 生成 Chelonin A
  参考文献：
  名称：

  基于 1-羟基吲哚化学的 1-甲氧基吲哚及其相关类似物 Pimprinine、(±)-Chelonin A 和 B 的合成

  摘要：

  The total synthesis of pimprinine, (+/-)-chelonin A and B, and their analogs are achieved based on 1-hydroxyindole chemistry.

  DOI：

  10.3987/com-19-14031

文献信息

• N-Tosyl-1,2,3-triazoles as Scaffolds for Morpholines: The Total Synthesis of (–)-Chelonin A
  作者：Alex C. Bissember、Jason A. Smith、Scott G. Stewart、Nina Gunawan、Michael J. Nutt

  DOI：10.1055/a-1982-5433

  日期：——

  Substituted morpholine derivatives appear frequently in biologically active compounds and thus novel routes towards such structures are of great synthetic interest. Herein, we report the total syntheses of chelonin A, a morpholine-derived marine natural product with reported antibacterial and anti-inflammatory activity. The key step in this process was a rhodium carbenoid 1,3-insertion into a bromohydrin

  取代的吗啉衍生物经常出现在生物活性化合物中，因此获得此类结构的新途径具有很大的合成意义。在此，我们报告了海龟素 A 的全合成，海龟素 A 是一种吗啉衍生的海洋天然产物，据报道具有抗菌和抗炎活性。该过程的关键步骤是将铑类胡萝卜素 1,3-插入溴醇 O-H 键，然后环化，生成 2,6-二取代-3,4-二氢-2 H -1,4-恶嗪核。然后将这项工作扩展到使用富含对映体的溴醇，通过 α-溴酮的不对称转移氢化依次制备 (–)-chelonin A 的第一个不对称全合成。
• Simple Syntheses of Marine Alkaloid, (±)-Chelonin A, and Its Analogs
  作者：Masanori Somei、Kazuko Aoki、Yoshiyuki Nagahama、Kyoko Nakagawa

  DOI：10.3987/com-94-6917

  日期：——

  The first total synthesis of (+/-)-chelonin A and syntheses of its analogs are achieved based on 1-hydroxyindole chemistry.
• BOBZIN, STEVEN C.;FAULKNER, D. JOHN, J. ORG. CHEM., 56,(1991) N4, C. 4403-4407
  作者：BOBZIN, STEVEN C.、FAULKNER, D. JOHN

  DOI：——

  日期：——
• Synthesis of 1-Methoxyindoles and Related Analogs of Pimprinine, (±)-Chelonin A and B, Based on 1-Hydroxyindole Chemistry
  作者：Masanori Somei、Kazuko Aoki、Yoshiyuki Nagahama、Katsuko Sugaya、Yuki Maeda、Haruhiko Sato、Kyoko Nakagawa (Goto)

  DOI：10.3987/com-19-14031

  日期：——

  The total synthesis of pimprinine, (+/-)-chelonin A and B, and their analogs are achieved based on 1-hydroxyindole chemistry.
• Aromatic alkaloids from the marine sponge Chelonaplysilla sp
  作者：Steven C. Bobzin、D. John Faulkner

  DOI：10.1021/jo00014a015

  日期：1991.7

  Four novel alkaloids derived from tryptophan and tyrosine subunits have been isolated from the marine sponge Chelonaplysilla sp. collected from a marine lake in Palau. The structures of chelonin A (3), chelonin B (4), bromochelonin B (5), and chelonin C (6) were determined by interpretation of spectral data and chemical conversions. Chelonin A (3) and C (6) are the first natural products incorporating a 2,6-disubstituted morpholine ring. Chelonin A (3), chelonin B (4), and bromochelonin B (5) exhibited antimicrobial activity against Bacillus subtilis, while chelonin A (3) showed in vivo antiinflammatory activity.

表征谱图