Tert-butyl 4-(thiophen-2-ylmethylamino)piperidine-1-carboxylate | 1154101-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: Tert-butyl 4-(thiophen-2-ylmethylamino)piperidine-1-carboxylate
• CAS: 1154101-60-6
• 化学式: C₁₅H₂₄N₂O₂S
• 分子量: 296.434
• InChiKey: OIHLIKLFFIBZNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Tert-butyl 4-(thiophen-2-ylmethylamino)piperidine-1-carboxylate 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-chloro-N-piperidin-4-yl-N-(thiophen-2-ylmethyl)-1-benzothiophene-2-carboxamide
  参考文献：
  名称：

  Potent small molecule Hedgehog agonists induce VEGF expression in vitro

  摘要：

  Here, we describe the synthesis, SAR studies as well as biological investigations of the known Hedgehog signaling agonist SAG and a small library of its analogues. The SAG and its derivatives were analyzed for their potency to activate the expression of the Hh target gene Gli1 in a reporter gene assay. By analyzing SAR important molecular descriptors for Gill activation have been identified. SAG as well as compound 10c proven to be potent activators of VEGF expression in cultivated dermal fibroblasts. Importantly and in contrast to SAG, derivative 10c displayed no toxicity in concentrations up to 250 mu m. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.026
• 作为产物：
  描述：

  4-(benzylidene-amino)-piperidine-1-carboxylic acid tert-butyl ester 在 sodium tetrahydroborate 、 potassium hydrogensulfate 、 水 、 magnesium sulfate 作用下， 以 乙醇 、 甲基叔丁基醚 为溶剂， 反应 26.0h， 生成 Tert-butyl 4-(thiophen-2-ylmethylamino)piperidine-1-carboxylate
  参考文献：
  名称：

  Potent small molecule Hedgehog agonists induce VEGF expression in vitro

  摘要：

  Here, we describe the synthesis, SAR studies as well as biological investigations of the known Hedgehog signaling agonist SAG and a small library of its analogues. The SAG and its derivatives were analyzed for their potency to activate the expression of the Hh target gene Gli1 in a reporter gene assay. By analyzing SAR important molecular descriptors for Gill activation have been identified. SAG as well as compound 10c proven to be potent activators of VEGF expression in cultivated dermal fibroblasts. Importantly and in contrast to SAG, derivative 10c displayed no toxicity in concentrations up to 250 mu m. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.026

文献信息

• Tetrahydroquinoline sulfonamides as vasopressin 1b receptor anatgonists
  作者：Jack D. Scott、Michael W. Miller、Sarah W. Li、Sue-Ing Lin、Henry A. Vaccaro、Liwu Hong、Deborra E. Mullins、Mario Guzzi、Jay Weinstein、Robert A. Hodgson、Geoffrey B. Varty、Andrew W. Stamford、Tin-Yau Chan、Brian A. McKittrick、William J. Greenlee、Tony Priestley、Eric M. Parker

  DOI：10.1016/j.bmcl.2009.09.050

  日期：2009.11

  Vasopressin 1b (V1b) antagonists have been postulated as possible treatments for depression and anxiety. A novel series of potent and selective V1b antagonists has been identified starting from an in-house screen hit. The incorporation of a sulfonamide linker between a tetrahydroisoquinoline core and amino piperidine lead to the identification of a V1b antagonist with similar affinity for human and rat receptors. Further optimization of the right hand portion afforded potent V1b antagonists that possessed moderate to high selectivity over other receptors. (C) 2009 Elsevier Ltd. All rights reserved.