3-chloro-N'-(6-methylpyridin-3-yl)pyridine-2-carboximidamide | 1187842-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-chloro-N'-(6-methylpyridin-3-yl)pyridine-2-carboximidamide
• CAS: 1187842-27-8
• 化学式: C₁₂H₁₁ClN₄
• 分子量: 246.699
• InChiKey: NTQKSYBXFAWJAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  64.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-溴-2-氧代-丁酸乙酯 、 3-chloro-N'-(6-methylpyridin-3-yl)pyridine-2-carboximidamide 以75%的产率得到ethyl 3-(3-chloro-N-(6-methylpyridin-3-yl)picolinimidamido)-2-oxobutanoate
  参考文献：
  名称：

  Synthesis and biological evaluation of imidazole derivatives as novel NOP/ORL1 receptor antagonists: Exploration and optimization of alternative pyrazole structure

  摘要：

  Nonpeptidic small-molecule NOP/ORL1 receptor antagonists with an imidazole scaffold were designed and synthesized to investigate alternatives to the pyrazole analog. Systematic modification of the original pyrazole lead [Kobayashi et al., Bioorg. Med. Chem. Lett. 2009, 19, 3627; Kobayashi et al., Bioorg. Med. Chem. Lett., in press] to change the heterocyclic core, substituted side chain, and pendant functional group demonstrated that examining the structure-activity relationship for novel templates allowed the identification of potent, fully substituted 4-aminomethyl-1H-imidazole and 2-aminomethyl-1H-imidazole. These compounds exhibited excellent potency for ORL1 receptor with minimal P-gp efflux and/or reduced hERG affinity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.095
• 作为产物：
  描述：

  3-氨基-6-甲基吡啶 、 3-氯-2-氰基吡啶 在 sodium hexamethyldisilazane 作用下， 以57%的产率得到3-chloro-N'-(6-methylpyridin-3-yl)pyridine-2-carboximidamide
  参考文献：
  名称：

  Synthesis and biological evaluation of imidazole derivatives as novel NOP/ORL1 receptor antagonists: Exploration and optimization of alternative pyrazole structure

  摘要：

  Nonpeptidic small-molecule NOP/ORL1 receptor antagonists with an imidazole scaffold were designed and synthesized to investigate alternatives to the pyrazole analog. Systematic modification of the original pyrazole lead [Kobayashi et al., Bioorg. Med. Chem. Lett. 2009, 19, 3627; Kobayashi et al., Bioorg. Med. Chem. Lett., in press] to change the heterocyclic core, substituted side chain, and pendant functional group demonstrated that examining the structure-activity relationship for novel templates allowed the identification of potent, fully substituted 4-aminomethyl-1H-imidazole and 2-aminomethyl-1H-imidazole. These compounds exhibited excellent potency for ORL1 receptor with minimal P-gp efflux and/or reduced hERG affinity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.095

文献信息

• Synthesis and biological evaluation of imidazole derivatives as novel NOP/ORL1 receptor antagonists: Exploration and optimization of alternative pyrazole structure
  作者：Yuichi Sugimoto、Kensuke Kobayashi、Masanori Asai、Akio Ohno、Koji Yamada、Satoshi Ozaki、Hisashi Ohta、Osamu Okamoto

  DOI：10.1016/j.bmcl.2009.06.095

  日期：2009.8

  Nonpeptidic small-molecule NOP/ORL1 receptor antagonists with an imidazole scaffold were designed and synthesized to investigate alternatives to the pyrazole analog. Systematic modification of the original pyrazole lead [Kobayashi et al., Bioorg. Med. Chem. Lett. 2009, 19, 3627; Kobayashi et al., Bioorg. Med. Chem. Lett., in press] to change the heterocyclic core, substituted side chain, and pendant functional group demonstrated that examining the structure-activity relationship for novel templates allowed the identification of potent, fully substituted 4-aminomethyl-1H-imidazole and 2-aminomethyl-1H-imidazole. These compounds exhibited excellent potency for ORL1 receptor with minimal P-gp efflux and/or reduced hERG affinity. (C) 2009 Elsevier Ltd. All rights reserved.