septoriamycin A | 1234619-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: septoriamycin A
• 英文别名: 1,4-dihydroxy-3-((2R,3R,5S,6R)-6-((R)-1-methylpropyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-5-phenylpyridin-2(1H)-one；3-[(2R,3R,5S,6R)-6-[(2R)-butan-2-yl]-3,5-dimethyloxan-2-yl]-1,4-dihydroxy-5-phenylpyridin-2-one
• CAS: 1234619-27-2
• 化学式: C₂₂H₂₉NO₄
• 分子量: 371.477
• InChiKey: KMGDCJDRYJVZCA-JQGYYDNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  septoriamycin A 、 碘甲烷 在 caesium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 N-(O-methyl)-septoriamycin A
  参考文献：
  名称：

  Antiprotozoal and Antimicrobial Compounds from the Plant Pathogen Septoria pistaciarum

  摘要：

  Four new 1,4-dihydroxy-5-phenyl-2-pyridinone alkaloids, 17-hydroxy-N-(O-methyl)septoriamycin A (1), 17-acetoxy-N-(O-methyl)septoriamycin A (2), 13-(S)-hydroxy-N-(O-methyl)septoriamycin A (3), and 13-(R)-hydroxy-N-(O-methyl)septoriamycin A (4), together with the known compounds (+)-cercosporin (5), (+)-14-O-acetylcercosporin (6), (+)-di-O-acetylcercosporin (7), lumichrome, and brassicasterol, were isolated from an ethyl acetate extract of a culture medium of Septoria pistaciarum. Methylation of septoriamycin A (8) with diazomethane yielded three di-O-methyl analogues, two of which existed as mixtures of rotamers. We previously reported antimalarial activity of septoriamycin A. This compound also exhibited significant activity against Leishmania donovani promastigotes. Compounds 5-7 showed moderate in vitro activity against L. donovani promastigotes and chloroquine-sensitive (D6) and -resistant (W2) strains of Plasmodium falciparum, whereas compound 5 was fairly active against methicillin-sensitive and methicillin-resistant strains of Staphylococcus aureus. Compounds 5-7 also displayed moderate phytotoxic activity against both a dicot (lettuce, Lactuca sativa) and a monocot (bentgrass, Agrostis stolonifera) and cytotoxicity against a panel of cell lines.

  DOI：

  10.1021/np200940b
• 作为产物：
  描述：

  (S)-3-((E,4S,5R,6R)-5-(hydroxy)-2,4,6-trimethyloct-2-enoyl)-4-isopropyloxazolidin-2-one 在 氨 、 lithium 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 24.55h， 生成 septoriamycin A 、
  参考文献：
  名称：

  Concise Synthesis of Reduced Propionates by Stereoselective Reductions Combined with the Kobayashi Reaction

  摘要：

  A concise and straightforward synthesis of 2,4,6-trimethyloctanoates was established by using the sequence of the vinylogous Mukalyama aldol reaction and regio- and stereoselective reduction reactions. All Isomers were obtained selectively in a few steps. The short step synthesis of septoriamycin A, an antimalarial and antileishmanial agent, has been achieved by this methodology.

  DOI：

  10.1021/ol401406m

文献信息

• Concise Synthesis of Reduced Propionates by Stereoselective Reductions Combined with the Kobayashi Reaction
  作者：Tatsuya Nakamura、Mio Harachi、Takaaki Kano、Yuki Mukaeda、Seijiro Hosokawa

  DOI：10.1021/ol401406m

  日期：2013.6.21

  A concise and straightforward synthesis of 2,4,6-trimethyloctanoates was established by using the sequence of the vinylogous Mukalyama aldol reaction and regio- and stereoselective reduction reactions. All Isomers were obtained selectively in a few steps. The short step synthesis of septoriamycin A, an antimalarial and antileishmanial agent, has been achieved by this methodology.
• Antiprotozoal and Antimicrobial Compounds from the Plant Pathogen <i>Septoria pistaciarum</i>
  作者：Mallika Kumarihamy、Shabana I. Khan、Melissa Jacob、Babu L. Tekwani、Stephen O. Duke、Daneel Ferreira、N. P. Dhammika Nanayakkara

  DOI：10.1021/np200940b

  日期：2012.5.25

  Four new 1,4-dihydroxy-5-phenyl-2-pyridinone alkaloids, 17-hydroxy-N-(O-methyl)septoriamycin A (1), 17-acetoxy-N-(O-methyl)septoriamycin A (2), 13-(S)-hydroxy-N-(O-methyl)septoriamycin A (3), and 13-(R)-hydroxy-N-(O-methyl)septoriamycin A (4), together with the known compounds (+)-cercosporin (5), (+)-14-O-acetylcercosporin (6), (+)-di-O-acetylcercosporin (7), lumichrome, and brassicasterol, were isolated from an ethyl acetate extract of a culture medium of Septoria pistaciarum. Methylation of septoriamycin A (8) with diazomethane yielded three di-O-methyl analogues, two of which existed as mixtures of rotamers. We previously reported antimalarial activity of septoriamycin A. This compound also exhibited significant activity against Leishmania donovani promastigotes. Compounds 5-7 showed moderate in vitro activity against L. donovani promastigotes and chloroquine-sensitive (D6) and -resistant (W2) strains of Plasmodium falciparum, whereas compound 5 was fairly active against methicillin-sensitive and methicillin-resistant strains of Staphylococcus aureus. Compounds 5-7 also displayed moderate phytotoxic activity against both a dicot (lettuce, Lactuca sativa) and a monocot (bentgrass, Agrostis stolonifera) and cytotoxicity against a panel of cell lines.