6-(Isopropylamino)nicotinic acid | 960060-85-9

• 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: 6-(Isopropylamino)nicotinic acid
• 英文别名: 6-(propan-2-ylamino)pyridine-3-carboxylic acid
• CAS: 960060-85-9
• 化学式: C₉H₁₂N₂O₂
• mdl: MFCD11131987
• 分子量: 180.206
• InChiKey: ORJYNQYULBKEFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  6-(Isopropylamino)nicotinic acid 、 1-Boc-4-氨基哌啶 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 4-[(6-isopropylamino-pyridine-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Piperidinyl-nicotinamides as potent and selective somatostatin receptor subtype 5 antagonists

  摘要：

  Nicotinamides of benzyl-substituted 4-aminopiperidines and their seven-membered analogs of generic structure 2 and 20 have been discovered as potent and selective SST5 antagonists. The activity (K-i) ranges from 2.4 to 436 nM. Most compounds exhibit decent physicochemical properties and follow a clear SAR pattern. Interestingly enough, the receptor is strongly enantiodiscriminating and binds in the amino-azepaneseries only the (R)-enantiomer. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.026
• 作为产物：
  描述：

  6-氯烟酸 、 异丙胺 以 异丙醇 为溶剂， 反应 0.67h， 以3%的产率得到6-(Isopropylamino)nicotinic acid
  参考文献：
  名称：

  3-Nitro-4-amino benzoic acids and 6-amino nicotinic acids are highly selective agonists of GPR109b

  摘要：

  A series of 3-nitro-4-substituted-aminobenzoic acids were prepared and found to act as potent and highly selective agonists of the orphan human GPCR GPR109b, a low affinity receptor for niacin. No activity was observed at the closely homologous high affinity niacin receptor, GPR109a. A second series, comprising 6-amino-substituted nicotinic acids was, also prepared and several analogues showed comparable activity to the nitroaryl series. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.058

文献信息

• Piperidinyl-nicotinamides as potent and selective somatostatin receptor subtype 5 antagonists
  作者：André Alker、Alfred Binggeli、Andreas D. Christ、Luke Green、Hans Peter Maerki、Rainer E. Martin、Peter Mohr

  DOI：10.1016/j.bmcl.2010.06.026

  日期：2010.8

  Nicotinamides of benzyl-substituted 4-aminopiperidines and their seven-membered analogs of generic structure 2 and 20 have been discovered as potent and selective SST5 antagonists. The activity (K-i) ranges from 2.4 to 436 nM. Most compounds exhibit decent physicochemical properties and follow a clear SAR pattern. Interestingly enough, the receptor is strongly enantiodiscriminating and binds in the amino-azepaneseries only the (R)-enantiomer. (C) 2010 Elsevier Ltd. All rights reserved.
• 3-Nitro-4-amino benzoic acids and 6-amino nicotinic acids are highly selective agonists of GPR109b
  作者：Philip J. Skinner、Martin C. Cherrier、Peter J. Webb、Carleton R. Sage、Huong T. Dang、Cameron C. Pride、Ruoping Chen、Susan Y. Tamura、Jeremy G. Richman、Daniel T. Connolly、Graeme Semple

  DOI：10.1016/j.bmcl.2007.09.058

  日期：2007.12

  A series of 3-nitro-4-substituted-aminobenzoic acids were prepared and found to act as potent and highly selective agonists of the orphan human GPCR GPR109b, a low affinity receptor for niacin. No activity was observed at the closely homologous high affinity niacin receptor, GPR109a. A second series, comprising 6-amino-substituted nicotinic acids was, also prepared and several analogues showed comparable activity to the nitroaryl series. (c) 2007 Elsevier Ltd. All rights reserved.