5,6-diphenyl-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitrile | 1379792-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5,6-diphenyl-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitrile
• 英文别名: 5,6-Diphenylpyrrolo[2,3-b]pyrazine-2,3-dicarbonitrile；5,6-diphenylpyrrolo[2,3-b]pyrazine-2,3-dicarbonitrile
• CAS: 1379792-80-9
• 化学式: C₂₀H₁₁N₅
• 分子量: 321.341
• InChiKey: OZUHOAFYMFURCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,6-二氯-2,3-二氰基吡嗪 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium dodecyl-sulfate 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 5,6-diphenyl-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitrile
  参考文献：
  名称：

  通过一锅钯催化的水中偶联反应/环化反应，高效合成5,6-二取代-5 H-吡咯并[2,3 - b ]吡嗪-2,3-二腈

  摘要：

  提出了高效的一锅法合成5,6-二取代-5 H-吡咯并[2,3 - b ]吡嗪-2,3-二碳腈。在水中存在表面活性剂SDS的情况下，在Pd-Cu催化下，5-（烷基-芳基氨基）-6-氯吡嗪-2,3-二腈与苯乙炔的反应可制得所需的产品。高产。

  DOI：

  10.1016/j.tetlet.2012.04.016

文献信息

• COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH APJ RECEPTOR ACTIVITY
  申请人：Annapurna Bio, Inc.

  公开号：US20220125787A1

  公开（公告）日：2022-04-28

  This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt and/or hydrate and/or prodrug of the compound) that modulate (e.g., agonize) the apelin receptor (also referred to herein as the APJ receptor; gene symbol APLNR). This disclosure also features compositions containing the same as well as other methods of using and making the same. The chemical entities are useful, e.g., for treating a subject (e.g., a human) having a disease, disorder, or condition in which a decrease in APJ receptor activity (e.g., repressed or impaired APJ receptor signaling; e.g., repressed or impaired apelin-APJ receptor signaling) or downregulation of endogenous apelin contributes to the pathology and/or symptoms and/or progression of the disease, disorder, or condition. Non-limiting examples of such diseases, disorders, or conditions include: (i) cardiovascular disease; (ii) metabolic disorders; (iii) diseases, disorders, and conditions associated with vascular pathology; and (iv) organ failure; (v) diseases, disorders, and conditions associated with infections (e.g., microbial infections); and (vi) diseases, disorders, or conditions that are sequela or comorbid with any of the foregoing or any disclosed herein. More particular non-limiting examples of such diseases, disorders, or conditions include pulmonary hypertension (e.g., PAH); heart failure; type II diabetes; renal failure; sepsis; and systemic hypertension.
• [EN] COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH APJ RECEPTOR ACTIVITY<br/>[FR] COMPOSÉS ET COMPOSITIONS DESTINÉS AU TRAITEMENT D'ÉTATS PATHOLOGIQUES ASSOCIÉS À UNE ACTIVITÉ DU RÉCEPTEUR DE L'APJ
  申请人：ANNAPURNA BIO INC

  公开号：WO2020073011A1

  公开（公告）日：2020-04-09

  This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt and/or hydrate and/or prodrug of the compound) that modulate (e.g., agonize) the apelin receptor (also referred to herein as the APJ receptor; gene symbol APLNR). This disclosure also features compositions containing the same as well as other methods of using and making the same. The chemical entities are useful, e.g., for treating a subject (e.g., a human) having a disease, disorder, or condition in which a decrease in APJ receptor activity (e.g., repressed or impaired APJ receptor signaling; e.g., repressed or impaired apelin-APJ receptor signaling) or downregulation of endogenous apelin contributes to the pathology and/or symptoms and/or progression of the disease, disorder, or condition. Non-limiting examples of such diseases, disorders, or conditions include: (i) cardiovascular disease; (ii) metabolic disorders; (iii) diseases, disorders, and conditions associated with vascular pathology; and (iv) organ failure; (v) diseases, disorders, and conditions associated with infections (e.g., microbial infections); and (vi) diseases, disorders, or conditions that are sequela or comorbid with any of the foregoing or any disclosed herein. More particular non-limiting examples of such diseases, disorders, or conditions include pulmonary hypertension (e.g., PAH); heart failure; type II diabetes; renal failure; sepsis; and systemic hypertension.
• Highly efficient synthesis of 5,6-disubstituted-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitriles through a one-pot palladium-catalyzed coupling reaction/cyclization in water
  作者：Ali Keivanloo、Mohammad Bakherad、Hossein Nasr-Isfahani、Somayeh Esmaily

  DOI：10.1016/j.tetlet.2012.04.016

  日期：2012.6

  A highly efficient one-pot synthesis of 5,6-disubstituted-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitriles is presented. The reaction of 5-(alkyl-arylamino)-6-chloropyrazine-2,3-dicarbonitriles with phenylacetylene, catalyzed by Pd–Cu, in the presence of SDS as the surfactant in water, leads to the desired products in good-to-high yields.

  提出了高效的一锅法合成5,6-二取代-5 H-吡咯并[2,3 - b ]吡嗪-2,3-二碳腈。在水中存在表面活性剂SDS的情况下，在Pd-Cu催化下，5-（烷基-芳基氨基）-6-氯吡嗪-2,3-二腈与苯乙炔的反应可制得所需的产品。高产。