(4R)-4-amino-3,4-dihydronaphthalen-1(2H)-one | 1057247-12-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (4R)-4-amino-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: (R)-4-amino-3,4-dihydronaphthalen-1(2H)-one；(4R)-4-amino-3,4-dihydro-2H-naphthalen-1-one
• CAS: 1057247-12-7
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: ZIKUGMFMPBBBDM-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R)-4-amino-3,4-dihydronaphthalen-1(2H)-one 、 (R)-2-(3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetic 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-[(3R)-4-(4-methylphenyl)sulfonyl-2-oxo-1,3-dihydropyrazin-3-yl]-N-[(1R)-4-oxo-2,3-dihydro-1H-naphthalen-1-yl]acetamide
  参考文献：
  名称：

  Discovery of dehydro-oxopiperazine acetamides as novel bradykinin B1 receptor antagonists with enhanced in vitro potency

  摘要：

  In a series of bradykinin B1 antagonists, we discovered that replacement of oxopiperazine acetamides with dehydro-oxopiperazine acetamides provided compounds with enhanced activity against the B1 receptor. The synthesis and SAR leading to potent analogs with reduced molecular weight will be discussed. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.11.112
• 作为产物：
  描述：

  (R)-N-(4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)formamide 在 乙酸乙酯 、 Sodium sulfate-III 、 SiO2 、 甲醇 作用下， 以 盐酸 、 甲醇 为溶剂， 反应 18.0h， 以flash chomatograph (SiO2, EtOAc to EtOAc/2M NH3 in MeOH=100:10 to 100:20) afforded crude (R)-4-amino-3,4-dihydronaphthalen-1(2H)-one as a sticky oil的产率得到(4R)-4-amino-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  1,2,3,4-tetrahydropyrazin-2-yl acetamides and methods of use

  摘要：

  选定的化合物对于治疗疼痛和疾病，如炎症介导的疾病具有有效性。本发明涵盖了新颖的化合物、类似物、前药和其药学上可接受的衍生物、制药组合物以及用于预防和治疗涉及疼痛、炎症等疾病和其他疾病或病症的方法。本发明还涉及制造这些化合物的过程以及在这些过程中有用的中间体。

  公开号：

  US07662811B2

文献信息

• Heterocyclic Compound
  申请人：HASHIMOTO Kentaro

  公开号：US20110034469A1

  公开（公告）日：2011-02-10

  The present invention provides a compound represented by the formula wherein each symbol is as defined in the specification, or a salt thereof. The compound of the present invention shows a strong IAP antagonistic activity.

  本发明提供了一种由下式表示的化合物 其中，每个符号如说明书中所定义，或其盐。本发明的化合物表现出强烈的IAP拮抗活性。
• 1,2,3,4-Tetrahydropyrazin-2-yl acetamides and methods of use
  申请人：Askew C. Benny

  公开号：US20060025400A1

  公开（公告）日：2006-02-02

  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疾病，如炎症介导的疾病，具有有效性。该发明涵盖了新颖的化合物、类似物、前药和其药学上可接受的衍生物，药物组合物以及用于预防和治疗涉及疼痛、炎症等疾病和其他不适或情况的方法。该发明还涉及制备此类化合物的方法，以及在此类过程中有用的中间体。
• Purine and imidazopyridine derivatives for immunosuppression
  申请人：Ohlmeyer J. Michael

  公开号：US20070021443A1

  公开（公告）日：2007-01-25

  The present invention provides novel purine and imidazopyridine derivatives useful for the prevention and treatment of autoimmune diseases, inflammatory disease, mast cell mediated disease and transplant rejection. The compounds are of the general formulas:

  本发明提供了新型嘌呤和咪唑吡啶衍生物，可用于预防和治疗自身免疫性疾病、炎症性疾病、肥大细胞介导疾病和移植排斥。这些化合物的一般式如下：
• PURINE AND IMIDAZOPYRIDINE DERIVATIVES FOR IMMUNOSUPPRESSION
  申请人：Ohlmeyer Michael J.

  公开号：US20080287468A1

  公开（公告）日：2008-11-20

  The present invention provides novel purine and imidazopyridine derivatives useful for the prevention and treatment of autoimmune diseases, inflammatory disease, mast cell mediated disease and transplant rejection. The compounds are of the general formulas:

  本发明提供了新型嘌呤和咪唑吡啶衍生物，用于预防和治疗自身免疫性疾病、炎症性疾病、肥大细胞介导的疾病和移植排斥。这些化合物的一般式如下：
• Design and Synthesis of Potent Inhibitor of Apoptosis (IAP) Proteins Antagonists Bearing an Octahydropyrrolo[1,2-<i>a</i>]pyrazine Scaffold as a Novel Proline Mimetic
  作者：Kentaro Hashimoto、Bunnai Saito、Naoki Miyamoto、Yuya Oguro、Daisuke Tomita、Zenyu Shiokawa、Moriteru Asano、Hiroyuki Kakei、Naohiro Taya、Masanori Kawasaki、Hiroyuki Sumi、Masato Yabuki、Kenichi Iwai、Sei Yoshida、Mie Yoshimatsu、Kazunobu Aoyama、Yohei Kosugi、Takashi Kojima、Nao Morishita、Douglas R. Dougan、Gyorgy P. Snell、Shinichi Imamura、Tomoyasu Ishikawa

  DOI：10.1021/jm301674z

  日期：2013.2.14

  To develop novel inhibitor of apoptosis (IAP) proteins antagonists, we designed a bicyclic octahydropyrrolo-[1,2-a]pyrazine scaffold as a novel proline bioisostere. This design was based on the X-ray co-crystal structure of four N-terminal amino acid residues (AVPI) of the second mitochondria-derived activator of caspase (Smac) with the X-chromosome-linked IAP (XIAP) protein. Lead optimization of this scaffold to improve oral absorption yielded compound 45, which showed potent cellular IAP1 (cIAP1 IC50: 1.3 nM) and XIAP (IC50: 200 nM) inhibitory activity, in addition to potent tumor growth inhibitory activity (GI(50): 1.8 nM) in MDA-MB-231 breast cancer cells. X-ray crystallographic analysis of compound 45 bound to X1AP and to cIAPI was achieved, revealing the various key interactions that contribute to the higher cIAPI affinity of compound 45 over X1AP. Because of its potent IAP inhibitory activities, compound 45 (T-3256336) caused tumor regression in a MDA-MB-231 tumor xenograft model (T/C: -53% at 30 mg/kg).