tert-butyl methyl{trans-4-[(pyridin-4-ylmethyl)amino]-cyclohexyl}carbamate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: tert-butyl methyl{trans-4-[(pyridin-4-ylmethyl)amino]-cyclohexyl}carbamate
• 英文别名: tert-butyl N-methyl-N-[4-(pyridin-4-ylmethylamino)cyclohexyl]carbamate
• 化学式: C₁₈H₂₉N₃O₂
• 分子量: 319.447
• InChiKey: UUYHSKBTOKMCEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl methyl{trans-4-[(pyridin-4-ylmethyl)amino]-cyclohexyl}carbamate 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-[trans-4-(methylamino)cyclohexyl]-N-(pyridin-4-ylmethyl)benzo[b]-thiophene-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：

  trans-4-aminocyclohexan-1-ol 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 sodium azide 、 10% Pd/C 、 氢气 、 sodium methylate 、 magnesium sulfate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 68.25h， 生成 tert-butyl methyl{trans-4-[(pyridin-4-ylmethyl)amino]-cyclohexyl}carbamate
  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

• Potent small molecule Hedgehog agonists induce VEGF expression in vitro
  作者：Katrin Seifert、Anita Büttner、Stephan Rigol、Nicole Eilert、Elke Wandel、Athanassios Giannis

  DOI：10.1016/j.bmc.2012.08.026

  日期：2012.11

  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.