3-dimethylamino-2-pyridin-3-yl-acrylonitrile | 165404-42-2

• 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: 3-dimethylamino-2-pyridin-3-yl-acrylonitrile
• 英文别名: 3-(Dimethylamino)-2-(pyridin-3-yl)acrylonitrile；3-(dimethylamino)-2-pyridin-3-ylprop-2-enenitrile
• CAS: 165404-42-2
• 化学式: C₁₀H₁₁N₃
• 分子量: 173.217
• InChiKey: ABOJKLHOYVSECN-UHFFFAOYSA-N

物化性质

• 沸点：
  398.5±37.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-dimethylamino-2-pyridin-3-yl-acrylonitrile 在 氢溴酸肼 作用下， 以 乙醇 为溶剂， 生成 4-吡啶基-3-2H-吡唑-3-胺
  参考文献：
  名称：

  Development of a Reproducible and Scalable Method for the Synthesis of Biologically Active Pyrazolo[1,5-a]pyrimidine Derivatives

  摘要：

  摘要 为合成一系列 3,6 取代的吡唑并[1,5-a]嘧啶开发了一种可重复和可扩展的方法，该方法是合理设计 AMP 活化蛋白激酶选择性抑制剂的基础。关于新型碳骨架的形成，利用布赫瓦尔德配体在 5,7 二甲基取代的吡唑并[1,5-a]嘧啶的立体受阻位置 6 上形成 C-C 键的 Suzukii-Miyaura 交叉偶联的适用性已经得到证明。

  DOI：

  10.1134/s1070363223050043
• 作为产物：
  描述：

  3-吡啶甲醇 在 氯化亚砜 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 3-dimethylamino-2-pyridin-3-yl-acrylonitrile
  参考文献：
  名称：

  Development of a Reproducible and Scalable Method for the Synthesis of Biologically Active Pyrazolo[1,5-a]pyrimidine Derivatives

  摘要：

  摘要 为合成一系列 3,6 取代的吡唑并[1,5-a]嘧啶开发了一种可重复和可扩展的方法，该方法是合理设计 AMP 活化蛋白激酶选择性抑制剂的基础。关于新型碳骨架的形成，利用布赫瓦尔德配体在 5,7 二甲基取代的吡唑并[1,5-a]嘧啶的立体受阻位置 6 上形成 C-C 键的 Suzukii-Miyaura 交叉偶联的适用性已经得到证明。

  DOI：

  10.1134/s1070363223050043

文献信息

• HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
  申请人：McCall John M.

  公开号：US20120277224A1

  公开（公告）日：2012-11-01

  Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

  本文披露了新的杂环化合物和组合物，以及它们作为药物治疗疾病的应用。还提供了抑制PAS激酶（PASK）在人类或动物主体中活性的方法，用于治疗疾病，如糖尿病。
• 7-Aminopyrazolo[1,5-<i>a</i>]pyrimidines as Potent Multitargeted Receptor Tyrosine Kinase Inhibitors
  作者：Robin R. Frey、Michael L. Curtin、Daniel H. Albert、Keith B. Glaser、Lori J. Pease、Niru B. Soni、Jennifer J. Bouska、David Reuter、Kent D. Stewart、Patrick Marcotte、Gail Bukofzer、Junling Li、Steven K. Davidsen、Michael R. Michaelides

  DOI：10.1021/jm701397k

  日期：2008.7

  7-Aminopyrazolo[1,5-a]pyrimidine urea receptor tyrosine kinase inhibitors have been discovered. Investigation of structure-activity relationships of the pyrazolo[1,5-a]pyrimidine nucleus led to a series of 6-(4-N,N'-diphenyl)ureas that potently inhibited a panel of vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor (PDGFR) kinases. Several of these compounds, such as 34a, are potent inhibitors of kinase insert domain-containing receptor tyrosine kinase (KDR) both enzymatically (< 10 nM) and cellularly (< 10 nM). In addition, compound 34a possesses a favorable pharmacokinetic profile and demonstrates efficacy in the estradiol-induced murine uterine edema (UE) model (ED(50) = 1.4 mg/kg).
• Structure–activity relationship study of bone morphogenetic protein (BMP) signaling inhibitors
  作者：Gregory D. Cuny、Paul B. Yu、Joydev K. Laha、Xuechao Xing、Ji-Feng Liu、Carol S. Lai、Donna Y. Deng、Chetana Sachidanandan、Kenneth D. Bloch、Randall T. Peterson

  DOI：10.1016/j.bmcl.2008.06.052

  日期：2008.8

  A structure-activity relationship study of dorsomorphin, a previously identified inhibitor of SMAD 1/5/8 phosphorylation by bone morphogenetic protein (BMP) type 1 receptors ALK2, 3, and 6, revealed that increased inhibitory activity could be accomplished by replacing the pendent 4-pyridine ring with 4-quinoline. The activity contributions of various nitrogen atoms in the core pyrazolo[1,5-a]pyrimidine ring were also examined by preparing and evaluating pyrrolo[1,2-a] pyrimidine and pyrazolo[1,5-a] pyridine derivatives. In addition, increased mouse liver microsome stability was achieved by replacing the ether substituent on the pendent phenyl ring with piperazine. Finally, an optimized compound 13 (LDN-193189 or DM-3189) demonstrated moderate pharmacokinetic characteristics (e.g., plasma t(1/2) = 1.6 h) following intraperitoneal administration in mice. These studies provide useful molecular probes for examining the in vivo pharmacology of BMP signaling inhibition. (c) 2008 Elsevier Ltd. All rights reserved.
• 3-(5-Alkylamino-4-isoxazolyl)-1,2,5,6-tetrahydropyridines: a novel class of central nicotinic receptor ligands
  作者：Preben H. Olesen、Michael D.B. Swedberg、Karin Rimvall

  DOI：10.1016/s0968-0896(98)00101-1

  日期：1998.9

  A novel class of central nicotinic acetylcholine receptor ligands, 3-(5-alkylamino-4-isoxazolyl)-1,2,5,6-tetrahydropyridine 4a-f, was synthesized. Several of the compounds showed high affinity for central nicotinic receptors (4c: IC50 = 50 nM), with more than a 100-fold selectivity for nicotinic over muscarinic receptors. The compounds showed up to a 10-fold selectivity for the central nicotinic subtype combination alpha 4 beta 2 (4c: IC50 = 4.6 nM), as compared to the major ganglionic subtype composed of alpha 3 containing subunits (4c: IC50 = 48 nM). The compounds were further evaluated in a dopamine release assay in vitro, and in a drug discrimination assay in vivo. Compound 4a is an effective nicotinic agonist with a potency 50-100 times lower than nicotine. Extending the alkylamino chain beyond one, compound (4b-f), changed the pharmacological profile of the compounds in an antagonistic direction. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Development of a Reproducible and Scalable Method for the Synthesis of Biologically Active Pyrazolo[1,5-a]pyrimidine Derivatives
  作者：D. S. Novikova、F. Darwish、T. A. Grigoreva、V. G. Tribulovich

  DOI：10.1134/s1070363223050043

  日期：2023.5

  A reproducible and scalable method has been developed for the synthesis of a series of 3,6-substituted pyrazolo[1,5-a]pyrimidines, which are the basis for the rational design of selective inhibitors of AMP-activated protein kinase. Regarding the formation of new types of the carbon skeleton, the applicability of the Suzuki–Miyaura cross-coupling using the Buchwald ligands to form C–C bond in the sterically hindered position 6 of 5,7-dimethyl-substituted pyrazolo[1,5-a]pyrimidine has been shown.

  摘要 为合成一系列 3,6 取代的吡唑并[1,5-a]嘧啶开发了一种可重复和可扩展的方法，该方法是合理设计 AMP 活化蛋白激酶选择性抑制剂的基础。关于新型碳骨架的形成，利用布赫瓦尔德配体在 5,7 二甲基取代的吡唑并[1,5-a]嘧啶的立体受阻位置 6 上形成 C-C 键的 Suzukii-Miyaura 交叉偶联的适用性已经得到证明。