pyridin-3-ylmethyl-carbamic acid tert-butyl ester | 1279817-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: pyridin-3-ylmethyl-carbamic acid tert-butyl ester
• 英文别名: tert-butyl 3-pyridinylmethylcarbamate；tert-butyl N-methyl-N-pyridin-3-ylcarbamate
• CAS: 1279817-03-6
• 化学式: C₁₁H₁₆N₂O₂
• 分子量: 208.26
• InChiKey: HLTOPPQESNNBDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  pyridin-3-ylmethyl-carbamic acid tert-butyl ester 在 platinum(IV) oxide 、 5% rhodium-on-charcoal 、 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 溶剂黄146 、 异丙醇 为溶剂， 60.0~70.0 ℃ 、1.38 MPa 条件下， 反应 8.0h， 生成 tert-butyl N-[1-(3-isothiocyanatopyridin-4-yl)piperidin-3-yl]-N-methylcarbamate
  参考文献：
  名称：

  Discovery of imidazopyridazines as potent Pim-1/2 kinase inhibitors

  摘要：

  High levels of Pim expression have been implicated in several hematopoietic and solid tumor cancers, suggesting that inhibition of Pim signaling could provide patients with therapeutic benefit. Herein, we describe our progress towards this goal using a screening hit (rac-1) as a starting point. Modification of the indazole ring resulted in the discovery of a series of imidazopyridazine-based Pim inhibitors exemplified by compound 22m, which was found to be a subnanomolar inhibitor of the Pim-1 and Pim-2 isoforms (IC50 values of 0.024 nM and 0.095 nM, respectively) and to potently inhibit the phosphorylation of BAD in a cell line that expresses high levels of all Pim isoforms, KMS-12-BM (IC50 = 28 nM). Profiling of Pim-1 and Pim-2 expression levels in a panel of multiple myeloma cell lines and correlation of these data with the potency of compound 22m in a proliferation assay suggests that Pim-2 inhibition would be advantageous for this indication. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.09.067
• 作为产物：
  描述：

  3-甲氨基吡啶 、 二碳酸二叔丁酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 pyridin-3-ylmethyl-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Discovery of imidazopyridazines as potent Pim-1/2 kinase inhibitors

  摘要：

  High levels of Pim expression have been implicated in several hematopoietic and solid tumor cancers, suggesting that inhibition of Pim signaling could provide patients with therapeutic benefit. Herein, we describe our progress towards this goal using a screening hit (rac-1) as a starting point. Modification of the indazole ring resulted in the discovery of a series of imidazopyridazine-based Pim inhibitors exemplified by compound 22m, which was found to be a subnanomolar inhibitor of the Pim-1 and Pim-2 isoforms (IC50 values of 0.024 nM and 0.095 nM, respectively) and to potently inhibit the phosphorylation of BAD in a cell line that expresses high levels of all Pim isoforms, KMS-12-BM (IC50 = 28 nM). Profiling of Pim-1 and Pim-2 expression levels in a panel of multiple myeloma cell lines and correlation of these data with the potency of compound 22m in a proliferation assay suggests that Pim-2 inhibition would be advantageous for this indication. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.09.067

文献信息

• ANTICANCER DERIVIATIVES, PREPARATION THEREOF, AND THERAPEUTIC USE THEREOF
  申请人：Arigon Jérôme

  公开号：US20120094986A1

  公开（公告）日：2012-04-19

  The invention relates to nicotinamide derivatives which can be used as anticancer drugs.

  这项发明涉及可用作抗癌药物的烟酰胺衍生物。
• Pyrimidine derivatives useful as inhibitors of PKC-theta
  申请人：Barbosa J.M. Antonio

  公开号：US20060025433A1

  公开（公告）日：2006-02-02

  Disclosed are novel compounds of formula (I): wherein X, Y, R 1 , R 2 and R 3 are as defined herein, which are useful as inhibitors of PKC-theta and are thus useful for treating a variety of diseases and disorders that are mediated or sustained through the activity of PKC-theta, including immunological disorders and type II diabetes. This invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

  披露了公式(I)的新颖化合物：其中X、Y、R1、R2和R3如本文所述定义，它们作为PKC-theta的抑制剂是有用的，因此可用于治疗通过PKC-theta活性介导或维持的多种疾病和失调，包括免疫失调和II型糖尿病。本发明还涉及包含这些化合物的药物组合物、使用这些化合物治疗各种疾病和失调的方法、制备这些化合物的方法以及在这些过程中有用的中间体。
• Antibacterial compounds
  申请人：Anderson D. David

  公开号：US20050159423A1

  公开（公告）日：2005-07-21

  Bacterial protein synthesis-inhibiting compounds having formula (I) and salts, prodrugs, and salts of prodrugs thereof, processes for making the compounds and intermediates in the processes, compositions containing the compounds, and methods of using the compounds are disclosed.

  抑制细菌蛋白质合成的化合物具有式(I)及其盐、前药、前药的盐，制备该化合物的方法和制备过程中的中间体，含有该化合物的组合物，以及使用该化合物的方法被披露。
• [EN] FUSED BICYCLIC COMPOUNDS AS INHIBITORS FOR PI3 KINASE<br/>[FR] COMPOSÉS BICYCLIQUES FUSIONNÉS UTILISÉS COMME INHIBITEURS DE LA PI3 KINASE
  申请人：MERCK SERONO SA

  公开号：WO2010100144A1

  公开（公告）日：2010-09-10

  The invention relates to compounds of formula (I) for the regulation of phosphoinositides 3-kinases activity and related diseases.

  该发明涉及用于调节磷脂酰肌醇3-激酶活性及相关疾病的化合物（I）的公式。
• Quinazolines useful as modulators of ion channels
  申请人：Wilson Dean

  公开号：US20060173018A1

  公开（公告）日：2006-08-03

  The present invention relates to compounds useful as inhibitors of voltage-gated sodium channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及作为电压门控钠通道抑制剂有用的化合物。本发明还提供了包括本发明化合物的药学上可接受的组合物，以及使用这些组合物治疗各种疾病的方法。