1,2-di(4-methylbenzoyl)lycorine | 1308667-08-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: 1,2-di(4-methylbenzoyl)lycorine
• 英文别名: (1S,2S,3a(1)S,12bS)-1-hydroxy-2,3a(1),4,5,7,12b-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diyl bis(2-methylbenzoate)；[(1S,17S,18S,19S)-18-(4-methylbenzoyl)oxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9,15-tetraen-17-yl] 4-methylbenzoate
• CAS: 1308667-08-4
• 化学式: C₃₂H₂₉NO₆
• 分子量: 523.585
• InChiKey: NMVHCFXYAOHWOQ-VZNYXHRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对甲基苯甲酰氯 、 石蒜碱 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 24.0h， 以52%的产率得到1,2-di(4-methylbenzoyl)lycorine
  参考文献：
  名称：

  Activity of Lycorine Analogues against the Fish Bacterial Pathogen Flavobacterium columnare

  摘要：

  In a continuing effort to discover natural products and natural product-based compounds for the control of columnaris disease in channel catfish (Ictalurus punctatus), 17 lycorine analogues were synthesized, including new benzoyl analogues 6-16, and evaluated for antibacterial activity against two isolates (ALM-00-173 and BioMed) of Flavobacterium columnare using a rapid bioassay. Two of the lycorine analogues had greater antibacterial activity than 1-O-acetyllycorine, an analogue of lycorine evaluated previously that is highly active against both isolates. Carbamate analogue 18 (1S,2S,3a(1)S,12bS)-2, 3a(1),4,5,7,12b-hexahydro-1H-[1,3]dioxolo [4,5-j]pyrrolo[3,2,1-de]phenanthridin-1,2-diylbis(o-tolylcarbamate) had the strongest antibacterial activity toward both F. columnare isolates ALM-00-173 and BioMed, with 24-h IC50 values of 3.0 +/- 1.3 and 3.9 +/- 2.2 mg/L, respectively, and a MIC of 5.5 +/- 0 mg/L for both isolates. Compound 18 appears to be the most promising lycorine analogue for future efficacy studies to determine its potential for use as an alternative to the currently used compounds to control columnaris disease in channel catfish.

  DOI：

  10.1021/jf200452z

文献信息

• Activity of Lycorine Analogues against the Fish Bacterial Pathogen Flavobacterium columnare
  作者：Cheng-Xia Tan、Kevin K. Schrader、Cassia S. Mizuno、Agnes M. Rimando

  DOI：10.1021/jf200452z

  日期：2011.6.8

  In a continuing effort to discover natural products and natural product-based compounds for the control of columnaris disease in channel catfish (Ictalurus punctatus), 17 lycorine analogues were synthesized, including new benzoyl analogues 6-16, and evaluated for antibacterial activity against two isolates (ALM-00-173 and BioMed) of Flavobacterium columnare using a rapid bioassay. Two of the lycorine analogues had greater antibacterial activity than 1-O-acetyllycorine, an analogue of lycorine evaluated previously that is highly active against both isolates. Carbamate analogue 18 (1S,2S,3a(1)S,12bS)-2, 3a(1),4,5,7,12b-hexahydro-1H-[1,3]dioxolo [4,5-j]pyrrolo[3,2,1-de]phenanthridin-1,2-diylbis(o-tolylcarbamate) had the strongest antibacterial activity toward both F. columnare isolates ALM-00-173 and BioMed, with 24-h IC50 values of 3.0 +/- 1.3 and 3.9 +/- 2.2 mg/L, respectively, and a MIC of 5.5 +/- 0 mg/L for both isolates. Compound 18 appears to be the most promising lycorine analogue for future efficacy studies to determine its potential for use as an alternative to the currently used compounds to control columnaris disease in channel catfish.