N-[3-[5-[3-[3-(dimethylamino)propylamino]propyl]-9,9-dimethylxanthen-4-yl]propyl]-N',N'-dimethylpropane-1,3-diamine | 289719-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-[3-[5-[3-[3-(dimethylamino)propylamino]propyl]-9,9-dimethylxanthen-4-yl]propyl]-N',N'-dimethylpropane-1,3-diamine
• CAS: 289719-94-4
• 化学式: C₃₁H₅₀N₄O
• 分子量: 494.764
• InChiKey: UJXSSUJEBWHPKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  39.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-萘磺酰氯 、 N-[3-[5-[3-[3-(dimethylamino)propylamino]propyl]-9,9-dimethylxanthen-4-yl]propyl]-N',N'-dimethylpropane-1,3-diamine 在 polymer supported morpholine 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到N-(3-dimethylaminopropyl)-N-[3-(5-{3-[(3-dimethylaminopropyl)-2-naphthalenesulphonylamino]propyl}-9,9-dimethyl-9H-xanthen-4-yl)propyl]-2-naphthalenesulphonamide
  参考文献：
  名称：

  探索of吨衍生物作为锥虫硫磷还原酶抑制剂和氯喹增强剂的潜力

  摘要：

  合成了an吨衍生物，并评估了其作为锥虫硫磷还原酶（TryR）抑制剂和氯喹（CQ）增强剂的潜力。与已知的三环抗抑郁药相比，某些衍生物显示出对TryR的抑制活性。另一方面，许多衍生物在恶性疟原虫的抗性菌株中增加了CQ的积累和增强作用，其中一种化合物还表现出很强的固有抗疟活性。

  DOI：

  10.1016/s0040-4020(03)00240-0
• 作为产物：
  描述：

  9,9-二甲基氧杂蒽 在 palladium on activated charcoal 咪唑 、 lithium aluminium tetrahydride 、 正丁基锂 、 四甲基乙二胺 、 氢气 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 43.5h， 生成 N-[3-[5-[3-[3-(dimethylamino)propylamino]propyl]-9,9-dimethylxanthen-4-yl]propyl]-N',N'-dimethylpropane-1,3-diamine
  参考文献：
  名称：

  Synthesis and evaluation of 9,9-dimethylxanthene tricyclics against trypanothione reductase, Trypanosoma brucei , Trypanosoma cruzi and Leishmania donovani

  摘要：

  Derivatives of 9,9-dimethylxanthene were synthesised and evaluated against trypanothione reductase (TR) and in vitro against parasitic trypanosomes and leishmania. High in vitro antiparasitic activity was observed for some derivatives with one compound showing high activity against all three parasites (ED50 values of 0.02, 0.48 and 0.32 mu M, for Trypanosoma brucei, Trypanosoma cruzi, and Leishmania donovani, respectively). The lack of correlation between inhibitory activity against TR and ED50 values suggests that TR is not the target. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00154-2

文献信息

• Synthesis and evaluation of 9,9-dimethylxanthene tricyclics against trypanothione reductase, Trypanosoma brucei , Trypanosoma cruzi and Leishmania donovani
  作者：Kelly Chibale、Mark Visser、Vanessa Yardley、Simon L. Croft、Alan H. Fairlamb

  DOI：10.1016/s0960-894x(00)00154-2

  日期：2000.6

  Derivatives of 9,9-dimethylxanthene were synthesised and evaluated against trypanothione reductase (TR) and in vitro against parasitic trypanosomes and leishmania. High in vitro antiparasitic activity was observed for some derivatives with one compound showing high activity against all three parasites (ED50 values of 0.02, 0.48 and 0.32 mu M, for Trypanosoma brucei, Trypanosoma cruzi, and Leishmania donovani, respectively). The lack of correlation between inhibitory activity against TR and ED50 values suggests that TR is not the target. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents
  作者：Kelly Chibale、Mark Visser、Donelly van Schalkwyk、Peter J Smith、Ahilan Saravanamuthu、Alan H Fairlamb

  DOI：10.1016/s0040-4020(03)00240-0

  日期：2003.3

  Xanthene derivatives were synthesized and evaluated for their potential as trypanothione reductase (TryR) inhibitors and chloroquine (CQ) potentiating agents. Some derivatives displayed inhibitory activity against TryR comparable to known tricyclic anti-depressants. On the other hand a number of derivatives increased CQ accumulation and potentiating effects in a resistant strain of Plasmodium falciparum

  合成了an吨衍生物，并评估了其作为锥虫硫磷还原酶（TryR）抑制剂和氯喹（CQ）增强剂的潜力。与已知的三环抗抑郁药相比，某些衍生物显示出对TryR的抑制活性。另一方面，许多衍生物在恶性疟原虫的抗性菌株中增加了CQ的积累和增强作用，其中一种化合物还表现出很强的固有抗疟活性。