5-(6-diethylamino-hexyl)-10,11-dihydro-5H-dibenz[b,f]azepine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 5-(6-diethylamino-hexyl)-10,11-dihydro-5H-dibenz[b,f]azepine
• 英文别名: 5-(6-Diaethylamino-hexyl)-10,11-dihydro-5H-dibenz[b,f]azepin；5-(6-(Diethylamino)hexyl)-10,11-dihydro-5H-dibenz(b,f)azepine；6-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-diethylhexan-1-amine
• 化学式: C₂₄H₃₄N₂
• 分子量: 350.547
• InChiKey: LXUIBXVPSSNUBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-氯-1-己醇 在 六氯丙酮 、 4-甲基苯磺酸吡啶 、 sodium carbonate 、 sodium amide 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 xylene 为溶剂， 生成 5-(6-diethylamino-hexyl)-10,11-dihydro-5H-dibenz[b,f]azepine
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of New Chemosensitizers in Multi-Drug-Resistant Plasmodium falciparum

  摘要：

  A series of new chemosensitizers (modulators) against chloroquine-resistant Plasmodium falciparum were designed and synthesized in an attempt to fabricate modulators with enhancing drug-resistant reversing efficacy and minimal side effects. Four aromatic amine ring systems-phenothiazine, iminodibenzyl, iminostilbene, and diphenylamine-were examined. Various tertiary amino groups including either noncyclic or cyclic aliphatic amines were introduced to explore the steric tolerance at the end of the side chain. The new compounds showed better drug-resistant reversing activity in chloroquine-resistant than in mefloquine-resistant cell lines and were generally more effective against chloroquine-resistant P. falciparum isolates from Southeast Asian (W2 and TM91C235) than those from South America (PC49 and RCS). Structure-activity relationship studies revealed that elongation of the alkyl side chain of the molecule retained the chemosensitizing activity, and analogues with four-carbon side chains showed superior activity. Furthermore, new modulators with phenothiazine ring exhibited the best chemosensitizing activity among the four different ring systems examined. Terminal amino function has limited steric tolerance as evidenced by the dramatic lose of the modulating activity, when the size of substituent at the amino group increases. The best new modulator synthesized in this study possesses all three optimized structural features, which consist of a phenothiazine ring and a pyrrolidinyl group joined by a four-carbon alkyl bridge. The fractional inhibitory concentration TIC) index of the best compound is 0.21, which is superior to that of verapamil (0.51), one of the best-known multi-drug-resistant reversing agents. Some of the analogues displayed moderate intrinsic in vitro antimalarial activity against a W-2 clone of P. falciparum.

  DOI：

  10.1021/jm010549o

文献信息

• Über Derivate des Iminodibenzyls
  作者：W. Schindler、F. Häfliger

  DOI：10.1002/hlca.19540370211

  日期：——

  1. Es wird die Darstellung von aminoalkylierten und aminoacylierten Derivaten des Iminodibenzyls (10, 11-Dihydro-5-dibenzo-[b, f]-azepin) beschrieben.

  1.描述了亚氨基二苄基（10，11-二氢-5-二苯并-[b，f]-氮杂）的氨基烷基化和氨基酰化衍生物的制备。