N-(环丁基甲基)丙烷-1-胺 | 741698-32-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(环丁基甲基)丙烷-1-胺
• 英文名称: N-(cyclobutylmethyl)propan-1-amine
• CAS: 741698-32-8
• 化学式: C₈H₁₇N
• 分子量: 127.23
• InChiKey: VGOOQTQNDFDKKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(环丁基甲基)丙烷-1-胺 在 dimethylaminomethyl-polystyrene resin 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-(cyclobutylmethyl)-3-[3-(diaminomethylideneamino)oxypropoxy]-5-methyl-N-propylbenzamide
  参考文献：
  名称：

  Oxyguanidines. Part 2: Discovery of a novel orally active thrombin inhibitor through structure-based drug design and parallel synthesis

  摘要：

  Through structure-based drug design and parallel synthesis, we have discovered a novel series of nonpeptidic phenyl-based thrombin inhibitors using oxyguanidines as guanidine bioisosteres. These compounds have been found to be highly potent, highly selective, and orally bioavailable. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.002

文献信息

• An orally active corticotropin releasing factor 1 receptor antagonist from 8-aryl-1,3a,7,8-tetraaza-cyclopenta[a]indenes
  作者：Xiaojun Han、Rita Civiello、Sokhom S. Pin、Kevin Burris、Lynn A. Balanda、Jay Knipe、Shelly Ren、Tracey Fiedler、Kaitlin E. Browman、Robert Macci、Matthew T. Taber、Jie Zhang、Gene M. Dubowchik

  DOI：10.1016/j.bmcl.2007.01.008

  日期：2007.4

  8-Aryl-1,3a,7,8-tetraaza-cyclopenta[a]indenes represent a novel series of high-affinity corticotropin-releasing factor-1 receptor (CRF1R) antagonists. Herein we report the synthesis and SAR around the tricyclic core and the anxiolytic activity of an orally dosed exemplary compound 9d (K(i)=8.0 nM) in a mouse canopy model.

  8-芳基-1,3a，7,8-四氮杂-环戊[a]茚代表一系列新的高亲和性促肾上腺皮质激素释放因子-1受体（CRF1R）拮抗剂。在此，我们报道了在小鼠冠层模型中三环核心周围的合成和SAR，以及口服剂量的示例性化合物9d（K（i）= 8.0 nM）的抗焦虑活性。
• Discovery of 6-chloro-2-trifluoromethyl-7-aryl-7H-imidazo[1,2-a]imidazol-3-ylmethylamines, a novel class of corticotropin-releasing factor receptor type 1 (CRF1R) antagonists
  作者：Dmitry Zuev、Vivekananda M. Vrudhula、Jodi A. Michne、Bireshwar Dasgupta、Sokhom S. Pin、Xiaohua Stella Huang、Dedong Wu、Qi Gao、Jie Zhang、Matthew T. Taber、John E. Macor、Gene M. Dubowchik

  DOI：10.1016/j.bmcl.2010.04.094

  日期：2010.6

  A novel series of [6-chloro-2-trifluoromethyl-7-aryl-7H-imidazo[1,2-a]imidazol-3-ylmethyl]-dialkylamines was discovered as potent CRF1R antagonists. The optimization of binding affinity in the series by the parallel reaction approach is discussed herein. (c) 2010 Elsevier Ltd. All rights reserved.
• Synthesis, Structure−Activity Relationships, and in Vivo Properties of 3,4-Dihydro-1<i>H</i>-pyrido[2,3-<i>b</i>]pyrazin-2-ones as Corticotropin-Releasing Factor-1 Receptor Antagonists
  作者：Carolyn D. Dzierba、Amy G. Takvorian、Maria Rafalski、Padmaja Kasireddy-Polam、Harvey Wong、Thaddeus F. Molski、Ge Zhang、Yu-Wen Li、Snjezana Lelas、Yong Peng、John F. McElroy、Robert C. Zaczek、Rebecca A. Taub、Andrew P. Combs、Paul J. Gilligan、George L. Trainor

  DOI：10.1021/jm049737f

  日期：2004.11.1

  Corticotropin releasing factor (CRF) is the primary regulator of the hypothalamus-pituitary-adrenal (HPA) axis, coordinating the endocrine, behavioral, and autonomic responses to stress. It has been postulated that small molecules that can antagonize the binding of CRF, to its receptor may serve as a treatment for anxiety-related and/or affective disorders. Members within a series of 3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-ones, exemplified by compound 2 (IC50 = 0.70 nM), were found to be very potent antagonists of CRF1. Compound 8w showed high CRF1 receptor binding affinity and was examined further in vivo. The compound was efficacious in a defensive withdrawal model of anxiety in rats and had a long half-life and reasonable oral bioavailability in dog pharmacokinetic studies.
• Optimization of CRF1R binding affinity of 2-(2,4,6-trichlorophenyl)-4-trifluoromethyl-5-aminomethylthiazoles through rapid and selective parallel synthesis
  作者：Dmitry Zuev、Jodi A. Michne、Sokhom S. Pin、Jie Zhang、Matthew T. Taber、Gene M. Dubowchik

  DOI：10.1016/j.bmcl.2004.10.055

  日期：2005.1

  An efficient approach was developed to synthesize 2-(2,4,6-trichlorophenylamino)-4-trifluoromethyl-5-aminomethylthiazoles, corticotropin-releasing factor type 1 receptor (CRF1R) antagonists, by monoalkylation of amines with chloromethyl intermediate 5. The effect of variations in aminomethyl side chain of 6 on binding affinity is discussed. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and structure–activity relationship of imidazo[1,2-a]benzimidazoles as corticotropin-releasing factor 1 receptor antagonists
  作者：Xiaojun Han、Sokhom S. Pin、Kevin Burris、Lawrence K. Fung、Stella Huang、Matthew T. Taber、Jie Zhang、Gene M. Dubowchik

  DOI：10.1016/j.bmcl.2005.06.028

  日期：2005.9

  8-Aryl-1,3a,8-triaza-cyclopenta[a]indenes represent a novel series of high binding affinity corticotropin-releasing factor 1 receptor antagonists. Here, we report their synthesis, SAR, and pharmacokinetic properties of compound 8e (K-i = 23 nM). (c) 2005 Elsevier Ltd. All rights reserved.