strychnobrasiline | 34227-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: strychnobrasiline
• 英文别名: Strychnobrasilin；(1S,9S,10R,13R,14E,21R)-8-acetyl-13,16-dimethyl-12-oxa-8,16-diazapentacyclo[8.8.3.01,9.02,7.014,21]henicosa-2,4,6,14-tetraen-19-one
• CAS: 34227-00-4
• 化学式: C₂₂H₂₆N₂O₃
• 分子量: 366.46
• InChiKey: XZIACDKZDCVKKQ-XBJDSYLLSA-N

物化性质

• 熔点：
  205-8°C

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  strychnobrasiline 在 氢氧化钾 、 水 作用下， 生成 N_a-deacetylstrychnobrasiline
  参考文献：
  名称：

  阿根廷植物XXXI的研究：巴西马兜铃的生物碱

  摘要：

  从Strychnos brasiliensis（Spreng。）Mart。的树干树皮中，分离出了spermostrychnine（I）和六种新的吲哚啉生物碱，并确定了它们的结构和构型。它们被命名为：12-羟基-11-甲氧基金刚烷氨酸（II），士古龙碱（III），12-羟基-11-甲氧基金丝猴碱（IV），10,11-二甲氧基金丝猴碱（V），士灭灵甲硅烷基（VI）和士灭灵（VII） 。

  DOI：

  10.1016/s0040-4020(01)90755-0

文献信息

• Synthesis and chloroquine-enhancing activity of Na-deacetyl-ferrocenoyl-strychnobrasiline
  作者：Dorothée Razafimahefa、Lydie Pélinski、Marie-Thérèse Martin、David Ramanitrahasimbola、Philippe Rasoanaivo、Jacques Brocard

  DOI：10.1016/j.bmcl.2004.11.067

  日期：2005.2

  Several strychnobrasiline derivatives have been synthesized to overcome the lack of in vivo reversal activity of the parent compound. In the present study, N-a-deacetyl-ferrocenoyl-strychnobrasiline was synthesized by condensing N-a-deacetyl-strychnobrasiline with ferrocenic acid previously treated with oxalyl chloride. While the in vitro antiplasmodial activity of the test compound (IC50 = 4.83 mug/mL) was increased 15-fold compared to that of strychnobrasiline, and the in vitro enhancing activity was found to be similar to that of the parent compound, the compound was devoid of any in vivo potentiating effect, and an antagonistic effect was even observed at higher doses. Based on the overall results on the hemisynthesis of strychnobrasiline derivatives for better reversal activity, this strategy has appeared to be of little value for useful drugs. (C) 2004 Elsevier Ltd. All rights reserved.
• New indolines derivatives from strychnobrasiline, modulators of chloroquine resistance in Plasmodium falciparum
  作者：François Trigalo、Marie-Thérèse Martin、Alain Blond、Jean-Paul Brouard、Herintsoa Rafatro、David Ramanitrahasimbola、François Frappier

  DOI：10.1016/s0040-4020(99)00269-0

  日期：1999.5

  An unexpected molecular rearrangement in lithium aluminium hydride reduction of the indole alkaloid strychnobrasiline was observed. The resulting derivatives obtained were evaluated as modulators of chloroquine resistance in Plasmodium falciparum. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of modulators of chloroquine resistance in Plasmodium falciparum, analogues of malagashanine from strychnobrasiline
  作者：François Trigalo、Roger Joyeau、Van Cuong Pham、Jean Jacques Youté、Philippe Rasoanaivoa、François Frappier

  DOI：10.1016/j.tet.2004.04.068

  日期：2004.6

  The syntheses of three malagashanine analogues are reported. They involve conversion of strychnobrasiline in multiple steps and obtaining (i) unsaturation of the bond 3-14, (ii) inversion of configuration on carbon C3, (iii) inversion of configuration on carbon C3 and reduction of the benzene ring. (C) 2004 Published by Elsevier Ltd.