(R)-7-(piperidin-1-ylmethyl)chroman-4-amine | 882423-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (R)-7-(piperidin-1-ylmethyl)chroman-4-amine
• 英文别名: (4R)-7-(piperidin-1-ylmethyl)-3,4-dihydro-2H-chromen-4-amine
• CAS: 882423-82-7
• 化学式: C₁₅H₂₂N₂O
• 分子量: 246.352
• InChiKey: COAREHYAVSQKBQ-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-7-(piperidin-1-ylmethyl)chroman-4-amine 、 1,2,3,4-tetrahydro-1-[(4-methylphenyl)sulfonyl]-3-oxo-(2R)-2-quinoxalinethanoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-((R)-3-oxo-1-tosyl-1,2,3,4-tetrahydroquinoxalin-2-yl)-N-((R)-7-(piperidin-1-ylmethyl)chroman-4-yl)acetamide
  参考文献：
  名称：

  Discovery of dihydroquinoxalinone acetamides containing bicyclic amines as potent Bradykinin B1 receptor antagonists

  摘要：

  Replacement of the core P-amino acid in our previously reported piperidine acetic acid and beta-phenylalanine-based Bradykinin B1 antagonists by dihydroquinoxalinone acetic acid increases the in vitro potency and metabolic stability. The most potent compounds from this series have IC(50)s < 0.2 nM in a human B1 receptor functional assay. A molecular modeling study of the binding modes of key compounds, based on a B1 homology model, explains the structure-activity relationship (SAR) for these analogs. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.055
• 作为产物：
  描述：

  (R)-tert-butyl 7-(piperidin-1-ylmethyl)chroman-4-ylcarbamate 在 lithium aluminium tetrahydride 、 水 、 sodium sulfate 作用下， 反应 26.0h， 生成 (R)-7-(piperidin-1-ylmethyl)chroman-4-amine
  参考文献：
  名称：

  [EN] SUBSTITUTED SULFONAMIDOPROPIONAMIDES AND METHODS OF USE
  [FR] SULFONAMIDOPROPIONAMIDES SUBSTITUES ET PROCEDES D'UTILISATION

  摘要：

  这项发明属于药物代理领域，具体涉及化合物、组合物、用途和治疗与炎症相关的疾病，包括疼痛的方法。

  公开号：

  WO2006036664A1

文献信息

• [EN] SUBSTITUTED SULFONAMIDOPROPIONAMIDES AND METHODS OF USE<br/>[FR] SULFONAMIDOPROPIONAMIDES SUBSTITUES ET PROCEDES D'UTILISATION
  申请人：AMGEN INC

  公开号：WO2006036664A1

  公开（公告）日：2006-04-06

  This invention is in the field of pharmaceutical agents and specifically relates to compounds, compositions, uses and methods for treating inflammation-related disorders, including pain.

  这项发明属于药物代理领域，具体涉及化合物、组合物、用途和治疗与炎症相关的疾病，包括疼痛的方法。
• Substituted sulfones and methods of use
  申请人：Askew C. Benny

  公开号：US20060111347A1

  公开（公告）日：2006-05-25

  Selected compounds are effective for treatment of pain and diseases, such as inflammation mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable derivatives thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving pain, inflammation, and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  所选化合物对于治疗疼痛和炎症介导的疾病有效。本发明涵盖新颖的化合物、类似物、前药和其药学上可接受的衍生物、制备这些化合物的药物组合物以及预防和治疗涉及疼痛、炎症等疾病和其他不适或病况的方法。本发明还涉及制备这些化合物的过程，以及在这些过程中有用的中间体。
• 3-Oxo-2-piperazinyl acetamides as potent bradykinin B1 receptor antagonists for the treatment of pain and inflammation
  作者：Jian Jeffrey Chen、Thomas Nguyen、Derin C. D’Amico、Wenyuan Qian、Jason Human、Toshihiro Aya、Kaustav Biswas、Christopher Fotsch、Nianhe Han、Qingyian Liu、Nobuko Nishimura、Tanya A.N. Peterkin、Kevin Yang、Jiawang Zhu、Babak Bobby Riahi、Randall W. Hungate、Neil G. Andersen、John T. Colyer、Margaret M. Faul、Augustus Kamassah、Judy Wang、Janan Jona、Gondi Kumar、Eileen Johnson、Benny C. Askew

  DOI：10.1016/j.bmcl.2011.03.115

  日期：2011.6

  The discovery of novel and highly potent oxopiperazine based B1 receptor antagonists is described. Compared to the previously described arylsulfonylated (R)-3-amino-3-phenylpropionic acid series, the current compounds showed improved in vitro potency and metabolic stability. Compound 17, 2-((2R)-1-((4-methylphenyl)sulfonyl)-3-oxo-2-piperazinyl)-N-((1R)-6-(1-piperidinylmethyl)-1,2,3,4-tetrahydro-1-naphthalenyl) acetamide, showed EC(50) of 10.3 nM in a rabbit biochemical challenge model. The practical syntheses of chiral arylsulfonylated oxopiperazine acetic acids are also described. (C) 2011 Elsevier Ltd. All rights reserved.
• Discovery of dihydroquinoxalinone acetamides containing bicyclic amines as potent Bradykinin B1 receptor antagonists
  作者：Jian Jeffrey Chen、Wenyuan Qian、Kaustav Biswas、Vellarkad N. Viswanadhan、Benny C. Askew、Stephen Hitchcock、Randall W. Hungate、Leyla Arik、Eileen Johnson

  DOI：10.1016/j.bmcl.2008.07.055

  日期：2008.8

  Replacement of the core P-amino acid in our previously reported piperidine acetic acid and beta-phenylalanine-based Bradykinin B1 antagonists by dihydroquinoxalinone acetic acid increases the in vitro potency and metabolic stability. The most potent compounds from this series have IC(50)s < 0.2 nM in a human B1 receptor functional assay. A molecular modeling study of the binding modes of key compounds, based on a B1 homology model, explains the structure-activity relationship (SAR) for these analogs. (c) 2008 Elsevier Ltd. All rights reserved.