6-amino-2-(3,4-dimethoxyphenyl)-2-isopropyl-4-hexynenitrile | 229624-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-amino-2-(3,4-dimethoxyphenyl)-2-isopropyl-4-hexynenitrile
• CAS: 229624-43-5
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: LNXJFUWTABNGSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  68.27
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-<4,6-bis(allylamino)-1,3,5-triazin-2-yl>-4-piperidone hydrochloride 、 6-amino-2-(3,4-dimethoxyphenyl)-2-isopropyl-4-hexynenitrile 在 盐酸 、 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 6-[[1-[4,6-Bis(prop-2-enylamino)-1,3,5-triazin-2-yl]piperidin-4-yl]amino]-2-(3,4-dimethoxyphenyl)-2-propan-2-ylhex-4-ynenitrile
  参考文献：
  名称：

  Design, Synthesis, and in Vitro Activity of Catamphiphilic Reverters of Multidrug Resistance:  Discovery of a Selective, Highly Efficacious Chemosensitizer with Potency in the Nanomolar Range

  摘要：

  On the basis of the results obtained in previous research, three series of compounds (A-C), derived from verapamil, were designed and synthesized to obtain drugs able to revert multidrug resistance (MDR), an acquired resistance that frequently impairs cancer chemotherapy. The ability of the obtained compounds to revert MDR was evaluated on anthracycline-resistant erythroleukemia K 562 cells, measuring the uptake of THP-adriamycin (pirarubicin) by continuous spectrofluorometric monitoring of the decrease of the fluorescence signal of the anthracycline at 590 nm (lambda(ex) = 480 nm), after incubation with cells. Cardiovascular activity, which is responsible for unwanted side effects, was also evaluated. The results obtained show that many of the compounds studied are potent reverters of MDR and are endowed with reduced cardiovascular activity. One of the compounds (7, MM36) presents a pharmacological profile (unprecedented nanomolar potency, high reversal of MDR, low cardiovascular activity) that makes it a promising drug candidate to treat MDR and a useful tool for studying P-glycoprotein.

  DOI：

  10.1021/jm980440p
• 作为产物：
  描述：

  3-甲基-2-(3,4-二甲氧基苯基)丁腈 在 正丁基锂 、 18-冠醚-6 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 11.0h， 生成 6-amino-2-(3,4-dimethoxyphenyl)-2-isopropyl-4-hexynenitrile
  参考文献：
  名称：

  Design, Synthesis, and in Vitro Activity of Catamphiphilic Reverters of Multidrug Resistance:  Discovery of a Selective, Highly Efficacious Chemosensitizer with Potency in the Nanomolar Range

  摘要：

  On the basis of the results obtained in previous research, three series of compounds (A-C), derived from verapamil, were designed and synthesized to obtain drugs able to revert multidrug resistance (MDR), an acquired resistance that frequently impairs cancer chemotherapy. The ability of the obtained compounds to revert MDR was evaluated on anthracycline-resistant erythroleukemia K 562 cells, measuring the uptake of THP-adriamycin (pirarubicin) by continuous spectrofluorometric monitoring of the decrease of the fluorescence signal of the anthracycline at 590 nm (lambda(ex) = 480 nm), after incubation with cells. Cardiovascular activity, which is responsible for unwanted side effects, was also evaluated. The results obtained show that many of the compounds studied are potent reverters of MDR and are endowed with reduced cardiovascular activity. One of the compounds (7, MM36) presents a pharmacological profile (unprecedented nanomolar potency, high reversal of MDR, low cardiovascular activity) that makes it a promising drug candidate to treat MDR and a useful tool for studying P-glycoprotein.

  DOI：

  10.1021/jm980440p