tert-butyl 4-((4-cyanobenzyl)amino)piperidine-1-carboxylate | 888944-30-7

• 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-((4-cyanobenzyl)amino)piperidine-1-carboxylate
• 英文别名: tert-Butyl 4-(4-cyanobenzylamino)piperidine-1-carboxylate；tert-butyl 4-[(4-cyanophenyl)methylamino]piperidine-1-carboxylate
• CAS: 888944-30-7
• 化学式: C₁₈H₂₅N₃O₂
• 分子量: 315.415
• InChiKey: NKVCRRZNDRSVDX-UHFFFAOYSA-N

物化性质

• 沸点：
  457.7±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-((4-cyanobenzyl)amino)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-[(4-cyanophenyl)methyl]-6-fluoro-N-piperidin-4-yl-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-((4-cyanobenzyl)amino)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

• Novel 4-Aminopiperidine Derivatives
  申请人：Boss Christoph

  公开号：US20080076762A1

  公开（公告）日：2008-03-27

  Novel substituted 4-aminopiperidine derivatives of the formula I: wherein n, R 1 , Y, and are as defined in claim 1, and optically pure enantiomers, mixtures of enantiomers, racemates, diastereomers, mixtures of diastereomers, diastereomeric racemates, mixtures of diastereomeric racemates and meso-forms, as well as salts and solvent complexes of such compounds, and morphological forms, that exhibit useful parasite aspartic proteases inhibiting properties and can thus be used in the form of pharmaceutical compositions as antimalarial medicines.

  新型替代4-氨基哌啶衍生物的化学式I： 其中n，R1，Y和如权利要求1中定义的是光学纯对映体，对映体混合物，外消旋体，二对映异构体，对映异构体混合物，对映异构体外消旋体，对映异构体外消旋体混合物和中间体形式，以及这些化合物的盐和溶剂络合物，以及表现出有用的寄生虫天冬氨酸蛋白酶抑制特性的形态形式，因此可以作为抗疟药物的药用组合物的形式使用。
• Identification of novel aminopiperidine derivatives for antibacterial activity against Gram-positive bacteria
  作者：Hee-Yeol Lee、Kyung-Mi An、Juyoung Jung、Je-Min Koo、Jeong-Geun Kim、Jong-Min Yoon、Myong-Jae Lee、HyeonSoo Jang、Hong-Sub Lee、Soobong Park、Jae-Hoon Kang

  DOI：10.1016/j.bmcl.2016.04.086

  日期：2016.7

  inhibitor and evaluated its antibacterial activity against Gram-positive bacteria, but poor pharmacokinetic profiles have resulted in low efficacy in in vivo mouse models. In order to overcome these weaknesses, we newly synthesized aminopiperidine derivatives with remarkable antimicrobial properties and oral bioavailability, and also identified their in vivo efficacy against methicillin-resistant Staphylococcus

  我们以前曾报道过酰氨基哌啶衍生物作为一种新型肽去甲酰基化酶（PDF）抑制剂，并评估了其对革兰氏阳性细菌的抗菌活性，但是不良的药代动力学特性导致体内小鼠模型的功效低下。为了克服这些弱点，我们新合成了具有显着抗菌特性和口服生物利用度的氨基哌啶衍生物，并且还确定了它们对甲氧西林抗性金黄色葡萄球菌（MRSA），耐万古霉素肠球菌（VRE）和耐青霉素的肺炎链球菌的体内功效（PRSP）。
• Accessing Aliphatic Amines in C–C Cross-Couplings by Visible Light/Nickel Dual Catalysis
  作者：Weizhe Dong、Shorouk O. Badir、Xuange Zhang、Gary A. Molander

  DOI：10.1021/acs.orglett.1c01207

  日期：2021.6.4

  desilylation of α-silylamines upon single-electron transfer (SET) facilitated by carbonate, α-amino radicals are generated regioselectively, which then engage in nickel-mediated C–C coupling. The reaction displays high chemoselectivity for C–C over C–N bond formation. Highly functionalized pharmacophores and peptides are also amenable.

  开发了芳基卤化物的一般氨基烷基化，克服了镍介导的 C-C 偶联中游离胺的不耐受性。这种转化具有广泛的官能团耐受性和高效率。利用碳酸盐促进的单电子转移（SET）时α-甲硅烷胺的快速脱甲硅烷基化，区域选择性地产生α-氨基自由基，然后参与镍介导的C-C偶联。该反应对 C-C 的化学选择性高于 C-N 键的形成。高度功能化的药效团和肽也是适用的。
• [EN] NOVEL 4-AMINOPIPERIDINE DERIVATIVES<br/>[FR] NOUVEAUX DERIVES DE 4-AMINOPIPERIDINE
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2006056930A2

  公开（公告）日：2006-06-01

  [EN] Novel substituted 4-aminopiperidine derivatives of the formula I: wherein n, R¹ , Y, (A) , and (B) are as defined in claim 1 and optically pure enantiomers, mixtures of enantiomers, racemates, diastereomers, mixtures of diastereomers, diastereomeric racemates, mixtures of diastereomeric racemates and meso-forms, as well as salts and solvent complexes of such compounds, and morphological forms, that exhibit useful parasite aspartic proteases inhibiting properties and can thus be used in the form of pharmaceutical compositions as antimalarial medicines.
  [FR] L'invention concerne de nouveaux dérivés de 4-aminopipéridine substitués de formule I, dans laquelle n, R¹, Y, (A) et (B) sont tels que définis dans la revendication 1, ainsi que des énantiomères optiquement purs, des mélanges d'énantiomères, des racémates, des diastéréomères, des mélanges de diastéréomères, des racémates diastéréomériques, des mélanges de racémates diastéréomériques et des formes méso, ainsi que des sels et des complexes de solvants desdits composés, et des formes morphologiques, présentant des propriétés utiles inhibitrices de protéases aspartiques parasitaires et pouvant ainsi être utilisés sous la forme de compositions pharmaceutiques en tant qu'antipaludiques.
• 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.