N-methylcalothrixin A | 307923-53-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-methylcalothrixin A
• 英文别名: 10-Methyl-20-oxido-10-aza-20-azoniapentacyclo[11.8.0.03,11.04,9.014,19]henicosa-1(13),3(11),4,6,8,14,16,18,20-nonaene-2,12-dione；10-methyl-20-oxido-10-aza-20-azoniapentacyclo[11.8.0.03,11.04,9.014,19]henicosa-1(13),3(11),4,6,8,14,16,18,20-nonaene-2,12-dione
• CAS: 307923-53-1
• 化学式: C₂₀H₁₂N₂O₃
• 分子量: 328.327
• InChiKey: XSRRVGVAWCAYHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  12-methoxymethyl-12H-5,12-diazaindeno[1,2-b]phenanthrene-7,13-dione 在 盐酸 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 N-methylcalothrixin A
  参考文献：
  名称：

  Synthesis and antimalarial activity of calothrixins A and B, and their N-alkyl derivatives

  摘要：

  We synthesized calothrixin B using our developed biomimetic method and derived N-alkyl-calothrixins A and B. The in vitro antimalarial activity of the calothrixin derivatives, including calothrixins A and B, against the Plasmodium falciparum FCR-3 strain was evaluated. All test compounds exhibited antimalarial activity over a concentration range of 6.4 x 10(-6)-1.2 x 10(-7) M. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.064

文献信息

• Total Synthesis of Calothrixins A and B by Palladium-Catalyzed Tandem Cyclization/Cross-Coupling Reaction of Indolylborate
  作者：Takumi Abe、Toshiaki Ikeda、Tominari Choshi、Satoshi Hibino、Noriyuki Hatae、Eiko Toyata、Reiko Yanada、Minoru Ishikura

  DOI：10.1002/ejoc.201200657

  日期：2012.9

  The palladium-catalyzed tandem cyclization/cross-coupling reaction of triethyl(indol-2-yl)borate with vinyl bromide was successfully used in the concise total synthesis of the indolophenanthridine alkaloids, calothrixins A and B.

  钯催化的三乙基（吲哚-2-基）硼酸与溴乙烯的串联环化/交叉偶联反应成功地用于吲哚菲啶生物碱、calothrixins A 和 B 的简明全合成。
• Synthesis and antimalarial activity of calothrixins A and B, and their N-alkyl derivatives
  作者：Kohji Matsumoto、Tominari Choshi、Mai Hourai、Yoshito Zamami、Kenji Sasaki、Takumi Abe、Minoru Ishikura、Noriyuki Hatae、Tatsunori Iwamura、Shigeo Tohyama、Junko Nobuhiro、Satoshi Hibino

  DOI：10.1016/j.bmcl.2012.05.064

  日期：2012.7

  We synthesized calothrixin B using our developed biomimetic method and derived N-alkyl-calothrixins A and B. The in vitro antimalarial activity of the calothrixin derivatives, including calothrixins A and B, against the Plasmodium falciparum FCR-3 strain was evaluated. All test compounds exhibited antimalarial activity over a concentration range of 6.4 x 10(-6)-1.2 x 10(-7) M. (C) 2012 Elsevier Ltd. All rights reserved.