6-cyclopropyl-3-nitropyridin-2-amine | 1552286-03-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-cyclopropyl-3-nitropyridin-2-amine
• 英文别名: 6-Cyclopropyl-3-nitro-pyridin-2-amine
• CAS: 1552286-03-9
• 化学式: C₈H₉N₃O₂
• 分子量: 179.178
• InChiKey: ROGFWBKFHHAGTG-UHFFFAOYSA-N

物化性质

• 沸点：
  360.5±42.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-cyclopropyl-3-nitropyridin-2-amine 在 氯化铵 、 锌 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以2.4 g的产率得到6-cyclopropylpyridine-2,3-diamine
  参考文献：
  名称：

  4-Methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes

  摘要：

  这项发明涉及一般式(I)的4-甲基-2,3,5,9,9b-五氮杂-环戊[α]萘衍生物，它们是磷酸二酯酶2和/或10的抑制剂，可用于治疗中枢神经系统疾病和其他疾病。此外，该发明涉及制备药物组合物的方法，以及根据该发明制造化合物的方法。

  公开号：

  US20140045856A1
• 作为产物：
  描述：

  2-氨基-3-硝基-6-氯吡啶 在 potassium phosphate 、 氢溴酸 、 palladium diacetate 、 溶剂黄146 、 三环己基膦 作用下， 以 水 、 甲苯 为溶剂， 反应 26.0h， 生成 6-cyclopropyl-3-nitropyridin-2-amine
  参考文献：
  名称：

  Aminoazabenzimidazoles, a Novel Class of Orally Active Antimalarial Agents

  摘要：

  Whole-cell high-throughput screening of the AstraZeneca compound library against the asexual blood stage of Plasmodium falciparum (Pf) led to the identification of amino imidazoles, a robust starting point for initiating a hit-to-lead medicinal chemistry effort. Structure-activity relationship studies followed by pharmacokinetics optimization resulted in the identification of 23 as an attractive lead with good oral bioavailability. Compound 23 was found to be efficacious (ED90 of 28.6 mg.kg(-1)) in the humanized P. falciparum mouse model of malaria (Pf/SCID model). Representative compounds displayed a moderate to fast killing profile that is comparable to that of chloroquine. This series demonstrates no cross-resistance against a panel of Pf strains with mutations to known antimalarial drugs, thereby suggesting a novel mechanism of action for this chemical class.

  DOI：

  10.1021/jm500535j

文献信息

• [EN] 4-METHYL-2,3,5,9,9B-PENTAAZA-CYCLOPENTA[A]NAPHTHALENES<br/>[FR] 4-MÉTHYL-2,3,5,9,9B-PENTAAZA-CYCLOPENTA[A]NAPHTALÈNES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2014019979A1

  公开（公告）日：2014-02-06

  The invention relates to 4-methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalene derivatives of general formula (I) which are inhibitors of phosphodiesterase 2 and/or 10, useful in treating central nervous system diseases and other diseases. In addition, the invention relates to processes for preparing pharmaceutical compositions as well as processes for manufacture the compounds according to the invention.

  该发明涉及一般式(I)的4-甲基-2,3,5,9,9b-五氮杂-环戊[α]萘衍生物，它们是磷酸二酯酶2和/或10的抑制剂，可用于治疗中枢神经系统疾病和其他疾病。此外，该发明涉及制备药物组合物的方法，以及根据该发明制造化合物的方法。
• 4-Methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes
  申请人：GIOVANNINI Riccardo

  公开号：US20140045856A1

  公开（公告）日：2014-02-13

  The invention relates to 4-methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalene derivatives of general formula (I) which are inhibitors of phosphodiesterase 2 and/or 10, useful in treating central nervous system diseases and other diseases. In addition, the invention relates to processes for preparing pharmaceutical compositions as well as processes for manufacture the compounds according to the invention.

  这项发明涉及一般式(I)的4-甲基-2,3,5,9,9b-五氮杂-环戊[α]萘衍生物，它们是磷酸二酯酶2和/或10的抑制剂，可用于治疗中枢神经系统疾病和其他疾病。此外，该发明涉及制备药物组合物的方法，以及根据该发明制造化合物的方法。
• US9085584B2
  申请人：——

  公开号：US9085584B2

  公开（公告）日：2015-07-21
• Aminoazabenzimidazoles, a Novel Class of Orally Active Antimalarial Agents
  作者：Shahul Hameed P、Murugan Chinnapattu、Gajanan Shanbag、Praveena Manjrekar、Krishna Koushik、Anandkumar Raichurkar、Vikas Patil、Sandesh Jatheendranath、Suresh S. Rudrapatna、Shubhada P. Barde、Nikhil Rautela、Disha Awasthy、Sapna Morayya、Chandan Narayan、Stefan Kavanagh、Ramanatha Saralaya、Sowmya Bharath、Pavithra Viswanath、Kakoli Mukherjee、Balachandra Bandodkar、Abhishek Srivastava、Vijender Panduga、Jitender Reddy、K. R. Prabhakar、Achyut Sinha、María Belén Jiménez-Díaz、María Santos Martínez、Iñigo Angulo-Barturen、Santiago Ferrer、Laura María Sanz、Francisco Javier Gamo、Sandra Duffy、Vicky M. Avery、Pamela A. Magistrado、Amanda K. Lukens、Dyann F. Wirth、David Waterson、V. Balasubramanian、Pravin S. Iyer、Shridhar Narayanan、Vinayak Hosagrahara、Vasan K. Sambandamurthy、Sreekanth Ramachandran

  DOI：10.1021/jm500535j

  日期：2014.7.10

  Whole-cell high-throughput screening of the AstraZeneca compound library against the asexual blood stage of Plasmodium falciparum (Pf) led to the identification of amino imidazoles, a robust starting point for initiating a hit-to-lead medicinal chemistry effort. Structure-activity relationship studies followed by pharmacokinetics optimization resulted in the identification of 23 as an attractive lead with good oral bioavailability. Compound 23 was found to be efficacious (ED90 of 28.6 mg.kg(-1)) in the humanized P. falciparum mouse model of malaria (Pf/SCID model). Representative compounds displayed a moderate to fast killing profile that is comparable to that of chloroquine. This series demonstrates no cross-resistance against a panel of Pf strains with mutations to known antimalarial drugs, thereby suggesting a novel mechanism of action for this chemical class.