5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)-1-ethylpyrrole-2-carboxylic acid | 1447711-41-2

• 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: 5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)-1-ethylpyrrole-2-carboxylic acid
• CAS: 1447711-41-2
• 化学式: C₂₅H₃₅NO₄
• 分子量: 413.557
• InChiKey: XIRKITXUIWWEJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  68.53
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)-1-ethylpyrrole-2-carboxylic acid 在 lithium hydroxide monohydrate 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-(5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)-1-ethylpyrrole-2-carboxamido)succinic acid
  参考文献：
  名称：

  Novel nonsecosteroidal VDR agonists with phenyl-pyrrolyl pentane skeleton

  摘要：

  In order to find the vitamin D receptor (VDR) ligand whose VDR agonistic activity is separated from the calcemic activity sufficiently, novel nonsecosteroidal analogs with phenyl pyrrolyl pentane skeleton were synthesized and evaluated for the VDR binding affinity, antiproliferative activity in vitro and serum calcium raising ability in vivo (tacalcitol used as control). Among them, several compounds showed varying degrees of VDR agonistic and growth inhibition activities of the tested cell lines. The most effective compound 2g (EC50: 1.06 nM) exhibited stronger VDR agonistic activity than tacalcitol (EC50: 7.05 nM), inhibited the proliferations of HaCaT and MCF-7 cells with IC50 of 2.06 mu M and 0.307 mu M (tacalcitol: 2.07 mu M and 0.057 mu M) and showed no significant effect on serum calcium. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.015
• 作为产物：
  描述：

  4-羟基-3-甲基苯甲酸 在 硫酸 、 palladium on activated charcoal 、 三氟化硼乙醚 、 水 、 甲酸铵 、 sodium hydride 、 potassium carbonate 、 potassium iodide 、 potassium hydroxide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 34.5h， 生成 5-(3-(4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl)pentan-3-yl)-1-ethylpyrrole-2-carboxylic acid
  参考文献：
  名称：

  Novel nonsecosteroidal VDR agonists with phenyl-pyrrolyl pentane skeleton

  摘要：

  In order to find the vitamin D receptor (VDR) ligand whose VDR agonistic activity is separated from the calcemic activity sufficiently, novel nonsecosteroidal analogs with phenyl pyrrolyl pentane skeleton were synthesized and evaluated for the VDR binding affinity, antiproliferative activity in vitro and serum calcium raising ability in vivo (tacalcitol used as control). Among them, several compounds showed varying degrees of VDR agonistic and growth inhibition activities of the tested cell lines. The most effective compound 2g (EC50: 1.06 nM) exhibited stronger VDR agonistic activity than tacalcitol (EC50: 7.05 nM), inhibited the proliferations of HaCaT and MCF-7 cells with IC50 of 2.06 mu M and 0.307 mu M (tacalcitol: 2.07 mu M and 0.057 mu M) and showed no significant effect on serum calcium. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.015

文献信息

• Novel nonsecosteroidal VDR ligands with phenyl-pyrrolyl pentane skeleton for cancer therapy
  作者：Zhixin Ge、Meixi Hao、Meng Xu、Zhigui Su、Zisheng Kang、Lingjing Xue、Can Zhang

  DOI：10.1016/j.ejmech.2015.10.042

  日期：2016.1

  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.