2-chloro-5-(pyridin-3-yl)pyrimidine | 1211588-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-chloro-5-(pyridin-3-yl)pyrimidine
• 英文别名: 2-chloro-5-pyridin-3-ylpyrimidine
• CAS: 1211588-38-3
• 化学式: C₉H₆ClN₃
• mdl: MFCD15475287
• 分子量: 191.62
• InChiKey: BBTYKBWCTGBYSG-UHFFFAOYSA-N

物化性质

• 沸点：
  401.3±28.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-5-(pyridin-3-yl)pyrimidine 在 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 1-(5-ethylthiophen-2-yl)-2-(5-(pyridin-3-yl)pyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Design and synthesis of furyl/thineyl pyrroloquinolones based on natural alkaloid perlolyrine, lead to the discovery of potent and selective PDE5 inhibitors

  摘要：

  Based on perlolyrine (1), a natural alkaloid with weak PDE5 potency from the traditional Chinese aphrodisiac plant Tribulus terrestris L., a series alpha-substituted tetrahydro-beta-carboline (TH beta C) derivatives were synthesized via T(+)BF4(-)-mediated oxidative C-H functionalization of N-aryl TH beta Cs with diverse potassium trifluoroborates. Following Winterfeldt oxidation afforded the corresponding furyl/thienyl pyrroloquinolones, of which 5-ethylthiophene/ethylfuran derivatives 20a-b were identified as the most potent and selective PDE5 inhibitors. Among the enantiomers, (S)-20a and (S)-20b (IC50 = 0.52 and 0.39 nM) were found to be more effective than their (R)-antipode, display favorable pharmacokinetic profiles, exert in vitro vasorelaxant effects on the isolated thoracic aorta, and exhibit in vivo efficacy in the anesthetized rabbit erectile model. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.039
• 作为产物：
  描述：

  3-吡啶硼酸 、 5-溴-2-氯嘧啶 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 0.5h， 生成 2-chloro-5-(pyridin-3-yl)pyrimidine
  参考文献：
  名称：

  Design and synthesis of furyl/thineyl pyrroloquinolones based on natural alkaloid perlolyrine, lead to the discovery of potent and selective PDE5 inhibitors

  摘要：

  Based on perlolyrine (1), a natural alkaloid with weak PDE5 potency from the traditional Chinese aphrodisiac plant Tribulus terrestris L., a series alpha-substituted tetrahydro-beta-carboline (TH beta C) derivatives were synthesized via T(+)BF4(-)-mediated oxidative C-H functionalization of N-aryl TH beta Cs with diverse potassium trifluoroborates. Following Winterfeldt oxidation afforded the corresponding furyl/thienyl pyrroloquinolones, of which 5-ethylthiophene/ethylfuran derivatives 20a-b were identified as the most potent and selective PDE5 inhibitors. Among the enantiomers, (S)-20a and (S)-20b (IC50 = 0.52 and 0.39 nM) were found to be more effective than their (R)-antipode, display favorable pharmacokinetic profiles, exert in vitro vasorelaxant effects on the isolated thoracic aorta, and exhibit in vivo efficacy in the anesthetized rabbit erectile model. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.039

文献信息

• NOVEL N-HYDROXY-BENZAMIDS FOR THE TREATMENT OF CANCER
  申请人：Guo Lei

  公开号：US20120065204A1

  公开（公告）日：2012-03-15

  The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt, ester or stereoisomer thereof, wherein R 1 to R 3 and X have the significances given herein. The present invention is also directed to processes for making said compounds and uses of said compounds, in particular their use as medicaments, more particularly their use as medicaments in the treatment of cancer.

  本发明提供了式（I）的化合物或其药学上可接受的盐、酯或立体异构体，其中R1至R3和X具有本文中给出的含义。本发明还涉及制备所述化合物的方法和所述化合物的用途，特别是它们作为药物的用途，更具体地说是它们作为治疗癌症的药物的用途。
• [EN] NOVEL N-HYDROXY-BENZAMIDES FOR THE TREATMENT OF CANCER<br/>[FR] NOUVEAUX N-HYDROXY-BENZAMIDES DESTINÉS AU TRAITEMENT DU CANCER
  申请人：HOFFMANN LA ROCHE

  公开号：WO2012031993A1

  公开（公告）日：2012-03-15

  The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt, ester or stereoisomer thereof, wherein R1 to R3 and X have the significances given herein. The present invention is also directed to processes for making said compounds and uses of said compounds, in particular their use as medicaments, more particularly their use as medicaments in the treatment of cancer.

  本发明提供了式（I）的化合物或其药用可接受的盐、酯或立体异构体，其中R1至R3和X具有本文中给出的含义。本发明还涉及制备所述化合物的方法和所述化合物的用途，特别是它们作为药物的用途，更具体地说是它们作为治疗癌症的药物的用途。
• N-hydroxy-benzamids for the treatment of cancer
  申请人：Guo Lei

  公开号：US08716285B2

  公开（公告）日：2014-05-06

  The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt, ester or stereoisomer thereof, wherein R1 to R3 and X have the significances given herein. The present invention is also directed to processes for making said compounds and uses of said compounds, in particular their use as medicaments, more particularly their use as medicaments in the treatment of cancer.

  本发明提供了化合物(I)的公式或其药学上可接受的盐、酯或立体异构体，其中R1至R3和X具有此处给出的含义。本发明还涉及制备所述化合物的过程以及所述化合物的用途，特别是作为药物的用途，更特别地作为治疗癌症的药物的用途。
• Amino acid compounds with unbranched linkers and methods of use
  申请人：Pliant Therapeutics, Inc.

  公开号：US11396506B2

  公开（公告）日：2022-07-26

  The invention relates to compounds of formula (A): or a salt thereof, wherein R1, R2, R5a, R5b, R6a, R6b, R7a, R7b, R8a, R8b, R9a, R9b, R10a, R10b, R11a, R11b, R21, n, and G are as described herein. Compounds of formula (I) and pharmaceutical compositions thereof are αVβ6 integrin inhibitors that are useful for treating fibrosis such as idiopathic pulmonary fibrosis (IPF) and nonspecific interstitial pneumonia (NSIP).

  本发明涉及式（A）化合物： 或其盐，其中 R1、R2、R5a、R5b、R6a、R6b、R7a、R7b、R8a、R8b、R9a、R9b、R10a、R10b、R11a、R11b、R21、n 和 G 如本文所述。式（I）化合物及其药物组合物是αVβ6整合素抑制剂，可用于治疗纤维化，如特发性肺纤维化（IPF）和非特异性间质性肺炎（NSIP）。
• NOVEL N-HYDROXY-BENZAMIDES FOR THE TREATMENT OF CANCER
  申请人：F.Hoffmann-La Roche AG

  公开号：EP2613775A1

  公开（公告）日：2013-07-17