N,N-bis(2-cyanoethyl)-5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)-pentan-3-yl)-1-ethyl-1H-pyrrole-2-carboxamide

• 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: N,N-bis(2-cyanoethyl)-5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)-pentan-3-yl)-1-ethyl-1H-pyrrole-2-carboxamide
• 英文别名: N,N-bis(2-cyanoethyl)-5-[3-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]pentan-3-yl]-1-ethylpyrrole-2-carboxamide
• 化学式: C₃₁H₄₂N₄O₃
• 分子量: 518.699
• InChiKey: CTLHKPXBIYJSSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  99.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-bis(2-cyanoethyl)-5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)-pentan-3-yl)-1-ethyl-1H-pyrrole-2-carboxamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以88%的产率得到N,N-bis(2-cyanoethyl)-1-ethyl-5-(3-(4-(2-hydroxy-3,3-dimethylbutoxy)-3-methylphenyl)pentan-3-yl)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Novel nonsecosteroidal VDR ligands with phenyl-pyrrolyl pentane skeleton for cancer therapy

  摘要：

  A series of nonsecosteroidal vitamin D-3 receptor (VDR) ligands with phenyl-pyrrolyl pentane skeleton were synthesized for cancer therapy. In contrast to 1 alpha,25-dihydroxyvitamin D-3 (Calcitriol), these VDR ligands exhibited anti-proliferative activity without inducing hypercalcemia. These compounds were evaluated for vitamin D-3-agonistic ability and anti-proliferative activity in vitro. Among them, compounds 5k and 5i exhibited equivalent vitamin D-3-agonistic activity compared with Calcitriol. Meanwhile, compound 5k displayed promising inhibiting profile against MCF-7, HepG-2 and Caco-2 with IC50 values of 0.00586 mu M, 0.176 mu M, and 1.01 mu M (Calcitriol: 5.58 mu M, 80.83 mu M and 4.46 mu M) respectively. Compound Si inhibited proliferation of PC-3 with IC50 value of 0.00798 mu M (Calcitriol: 17.25 mu M). Additionally, neither of these compounds significantly elevated serum calcium in rats. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.042
• 作为产物：
  描述：

  5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)-1-ethylpyrrole-2-carboxylic acid 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 N,N-bis(2-cyanoethyl)-5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)-pentan-3-yl)-1-ethyl-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Novel nonsecosteroidal VDR ligands with phenyl-pyrrolyl pentane skeleton for cancer therapy

  摘要：

  A series of nonsecosteroidal vitamin D-3 receptor (VDR) ligands with phenyl-pyrrolyl pentane skeleton were synthesized for cancer therapy. In contrast to 1 alpha,25-dihydroxyvitamin D-3 (Calcitriol), these VDR ligands exhibited anti-proliferative activity without inducing hypercalcemia. These compounds were evaluated for vitamin D-3-agonistic ability and anti-proliferative activity in vitro. Among them, compounds 5k and 5i exhibited equivalent vitamin D-3-agonistic activity compared with Calcitriol. Meanwhile, compound 5k displayed promising inhibiting profile against MCF-7, HepG-2 and Caco-2 with IC50 values of 0.00586 mu M, 0.176 mu M, and 1.01 mu M (Calcitriol: 5.58 mu M, 80.83 mu M and 4.46 mu M) respectively. Compound Si inhibited proliferation of PC-3 with IC50 value of 0.00798 mu M (Calcitriol: 17.25 mu M). Additionally, neither of these compounds significantly elevated serum calcium in rats. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.042