3-imidazol-1-yl-3-[4-(6-methoxy-naphthalen-2-ylamino)phenyl]-2,2-dimethyl-propan-1-ol | 1202273-81-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-imidazol-1-yl-3-[4-(6-methoxy-naphthalen-2-ylamino)phenyl]-2,2-dimethyl-propan-1-ol
• 英文别名: 3-(1H-imidazol-1-yl)-2,2-dimethyl-3-[4-(6-methoxynaphthalen-2-ylamino)phenyl]propan-1-ol；3-Imidazol-1-yl-3-[4-[(6-methoxynaphthalen-2-yl)amino]phenyl]-2,2-dimethylpropan-1-ol
• CAS: 1202273-81-1
• 化学式: C₂₅H₂₇N₃O₂
• 分子量: 401.508
• InChiKey: JTSQVNPRXLAENY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  59.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-甲氧基萘-2-硼酸 在 吡啶 、 lithium aluminium tetrahydride 、 copper diacetate 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 3-imidazol-1-yl-3-[4-(6-methoxy-naphthalen-2-ylamino)phenyl]-2,2-dimethyl-propan-1-ol
  参考文献：
  名称：

  [EN] CYP26 INHIBITORS
  [FR] INHIBITEURS DE CYP26

  摘要：

  公式（I）的化合物，其中X选择自O、S、NH或CH2；Rd和Rp是可选的萘基取代物；RHet是咪唑基、三唑基或吡啶基；Rc是C1-4烷基，通过选择的基团取代，包括：羟基、氨基、酰胺基、羧基、C1-7烷基酯、C5-7芳基-C1-2烷基酯、磺胺基、亚砜胺基、羟胺基和四唑基。

  公开号：

  WO2009153566A1

文献信息

• Synthesis and Biological Evaluation of 3-(1<i>H</i>-Imidazol- and Triazol-1-yl)-2,2-dimethyl-3-[4-(naphthalen-2-ylamino)phenyl]propyl Derivatives as Small Molecule Inhibitors of Retinoic Acid 4-Hydroxylase (CYP26)
  作者：Mohamed S. Gomaa、Caroline E. Bridgens、Gareth J. Veal、Christopher P. F. Redfern、Andrea Brancale、Jane L. Armstrong、Claire Simons

  DOI：10.1021/jm200695m

  日期：2011.10.13

  len-2-ylamino)-phenyl]-3-[1,2,4]triazol-1-yl-propionic acid methyl ester (17) (IC50 = 0.35 nM as compared with liarozole IC50 = 540 nM and R116010 IC50 = 10 nM) was evaluated for CYP selectivity and hepatic stability. Compounds with CYP26 inhibitory IC50 values ≤50 nM enhanced the biological activity of exogenous ATRA, as evidenced by a 3.7–5.8-fold increase in CYP26A1 mRNA in SH-SY5Y neuroblastoma

  新型3-（1 H-咪唑-和三唑-1-基）-2,2-二甲基-3-（4-（萘-2-基氨基）苯基）丙基衍生物的合成及其强抑制活性描述了7种CYP26A1微粒体测定法。这项研究的重点是修饰血红素结合唑基和柔性C3链对抑制活性和选择性的影响。最有希望的抑制剂2,2-二甲基-3- [4-（萘-2-基氨基）-苯基] -3- [1,2,4]三唑-1-基-丙酸甲酯（17）（IC与利拉唑IC 50 = 540 nM和R116010 IC 50 = 10 nM相比，评估了50 = 0.35 nM的CYP选择性和肝稳定性。具有CYP26抑制IC 50的化合物值≤50nM增强外源性ATRA的生物活性，与单独使用ATRA相比，SH-SY5Y神经母细胞瘤细胞中CYP26A1 mRNA的增加3.7-5.8倍证明了这一点。所有化合物均显示出与R116010相当或更好的活性，且诱导作用与CYP26抑制数据密切相关。这些研究突
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