5-(4-吡啶基)-2-嘧啶胺 | 96817-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-(4-吡啶基)-2-嘧啶胺
• 英文名称: 5-(pyridin-4-yl)pyrimidin-2-amine
• 英文别名: 5-pyridin-4-ylpyrimidin-2-ylamine；5-(4-pyridinyl)-2-pyrimidinamine；5-Pyridin-4-ylpyrimidin-2-amine
• CAS: 96817-88-8
• 化学式: C₉H₈N₄
• 分子量: 172.189
• InChiKey: FSHIOHCNOLTWBC-UHFFFAOYSA-N

物化性质

• 沸点：
  423.5±47.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-吡啶基)-2-嘧啶胺 在 吡啶 作用下， 以 氯仿 、 丙酸酐 为溶剂， 生成 N-[5(4-pyridinyl)-2-pyrimidinyl]-propanamide
  参考文献：
  名称：

  4(Or 5)-(pyridinyl)-2-pyrimidinamines and cardiotonic use thereof

  摘要：

  显示的是2-(NB)-4-PY-5-Q-嘧啶(I)和2-(NB')-5-PY-4-Q'-嘧啶(II)或其盐，其中PY是4-或3-吡啶基或带有一个或两个较低烷基取代基的4-或3-吡啶基，Q和Q'分别是氢或甲基，NB是二甲基氨基或N-(2-羟乙基)甲基氨基，NB'是氨基、二甲基氨基、乙酰氨基或丙酰氨基；其制备方法；以及它们的强心用途。

  公开号：

  US04512993A1
• 作为产物：
  描述：

  2-氨基-5-溴嘧啶 、 吡啶-4-硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 5-(4-吡啶基)-2-嘧啶胺
  参考文献：
  名称：

  Small Molecule that Reverses Dexamethasone Resistance in T-cell Acute Lymphoblastic Leukemia (T-ALL)

  摘要：

  Glucocorticoids are one of the most utilized and effective therapies in treating T-cell acute lymphoblastic leukemia. However, patients often develop resistance to glucocorticoids, rendering these therapies ineffective. We screened 9517 compounds, selected for their lead-like properties, chosen from among 3 372 615 compounds, against a dexamethasone-resistant T-ALL cell line to identify small molecules that reverse glucocorticoid resistance. We synthesized analogues of the most effective compound, termed J9, from the screen in order to define the scaffold's structure activity relationship. Active compounds restored sensitivity to glucocorticoids through upregulation of the glucocorticoid receptor. This compound and mechanism may provide a strategy for overcoming glucocorticoid resistance in patients with T-ALL.

  DOI：

  10.1021/ml500044g

文献信息

• [5(or 4)-(Pyridinyl)-2-pyrimidinyl]ureas and cardiotonic use thereof
  申请人：Sterling Drug Inc.

  公开号：US04504482A1

  公开（公告）日：1985-03-12

  N-R-N'-R'-N-[4(or 5)-PY-2-pyrimidinyl]ureas (I) or salts thereof, where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, R' is hydrogen or methyl and R is methyl or ethyl when PY is attached to the 4-position of the pyrimidine ring or R is hydrogen, ethyl or n-butyl when PY is attached to the 5-position of the pyrimidine ring are useful as cardiotonic agents. The preparations of I and their cardiotonic use are shown.

  N-R-N'-R'-N-[4(or 5)-PY-2-嘧啶基]脲类化合物（I）或其盐，其中PY是4-或3-吡啶基或带有一个或两个较低烷基取代基的4-或3-吡啶基，R'是氢或甲基，R是甲基或乙基（当PY连接到嘧啶环的4位时）或R是氢、乙基或正丁基（当PY连接到嘧啶环的5位时），可用作强心药物。所述化合物I的制备及其作为强心剂的用途已经展示。
• [EN] PYRIDINYL-2-PYRIMIDINAMINES USEFUL AS CARDIOTONICS AND PREPARATION THEREOF
  申请人：STERLING DRUG INC.

  公开号：WO1985000604A1

  公开（公告）日：1985-02-14

  (EN) 2-(NB)-4-PY-5-Q-pyrimidines (I) and 2-(NB')-5-PY-4-Q'-pyrimidines (II) or salts thereof, where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, Q and Q' are each hydrogen or methyl, NB is dimethylamino or N-(2-hydroxyethyl)methylamino and NB' is amino, dimethylamino, acetylamino or propionylamino; the preparation thereof; and their cardiotonic use. (FR) 2-(NB)-4-PY-5-Q-pyrimidines (I) et 2-(NB')-5-PY-4-Q'-pyrimidines (II) ou leurs sels, où PY est un 4- ou 3-pyridinyle ou un 4- ou 3-pyridinyle comportant un ou deux substituants d'alkyle inférieur, Q et Q' sont chacun de l'hydrogène ou du méthyle, NB est un diméthylamino ou un N-(2-hydroxyéthyl)méthylamino et NB' est un amino, un diméthylamino, un acétylamino ou un propionylamino. On décrit également leur préparation et leur utilisation en tant que cardiotoniques.

  （EN）2-(NB)-4-PY-5-Q-pyrimidines (I) 和 2-(NB')-5-PY-4-Q'-pyrimidines (II)，或它们的盐，其中 PY 为 4- 或 3-pyridinyl 或 4- 或 3-pyridinyl，具有一个或两个下部甲基取代基，Q 和 Q' 各自为氢或甲基，NB 为二甲氨基或 N-(2-羟基乙基)甲氨基，NB' 为氨基、二甲氨基、乙酰氨基或丙烯氨基；它们的制备；以及它们的利尿作用。 （FR）2-(NB)-4-PY-5-Q-pyrimidines (I) 和 2-(NB')-5-PY-4-Q'-pyrimidines (II) 或它们的盐，其中 PY 为 4- 或 3-pyridinyl 或 4- 或 3-pyridinyl，具有一个或两个下部甲基取代基，Q 和 Q' 分别为氢或甲基，NB 为二甲氨基或 N-(2-羟基乙基)甲氨基，NB' 为氨基、二甲氨基、乙酰氨基或丙烯氨基。我们也描述了它们的制备及其作为利尿药的用途。
• Rajitha, Ch.; Vineel, B. George; Venkataiah, Indian Journal of Heterocyclic Chemistry, 2015, vol. 24, # 3, p. 325 - 328
  作者：Rajitha, Ch.、Vineel, B. George、Venkataiah、Dubey

  DOI：——

  日期：——
• Discovery of (R)-5-((5-(1-methyl-1H-pyrazol-4-yl)-4-(methylamino)pyrimidin-2-yl)amino)-3-(piperidin-3-yloxy)picolinonitrile, a novel CHK1 inhibitor for hematologic malignancies
  作者：Lexian Tong、Pinrao Song、Kailong Jiang、Lei Xu、Tingting Jin、Peipei Wang、Xiaobei Hu、Sui Fang、Anhui Gao、Yubo Zhou、Tao Liu、Jia Li、Yongzhou Hu

  DOI：10.1016/j.ejmech.2019.03.062

  日期：2019.7

  Through virtual screening, we identified the lead compound MCL1020, which exhibited modest CHK1 inhibitory activity. Then a series of 5-(pyrimidin-2-ylamino)picolinonitrile derivatives as CHK1 inhibitors were discovered by further rational optimization. One promising molecule. (R)-17, whose potency was one of the best, had an IC50 of 0.4 nM with remarkable selectivity (>4300-fold CHK1 vs. CHK2). Compound (R)-17 effectively inhibited the growth of malignant hematopathy cell lines especially Z-138 (IC50: 0.013 mu M) and displayed low affinity for hERG (IC50> 40 mu M). Moreover, (R)-17 significantly suppressed the tumor growth in Z-138 cell inoculated xenograft model (20 mg/kg I.V., TGI = 90.29%) as a single agent with body weight unaffected. Taken together, our data demonstrated compound (R)-17 could be a promising drug candidate for the treatment of hematologic malignancies. (C) 2019 Published by Elsevier Masson SAS.
• LESHER, G. Y.;SINGH, BALDEV
  作者：LESHER, G. Y.、SINGH, BALDEV

  DOI：——

  日期：——