2-pyrrolidin-1-yl-5H-chromeno[4,3-d]pyrimidin-5-ol | 61466-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-pyrrolidin-1-yl-5H-chromeno[4,3-d]pyrimidin-5-ol
• 英文别名: 2-(Pyrrolidin-1-yl)-5H-[1]benzopyrano[4,3-d]pyrimidin-5-ol；2-pyrrolidin-1-yl-5H-chromeno[4,3-d]pyrimidin-5-ol
• CAS: 61466-27-1
• 化学式: C₁₅H₁₅N₃O₂
• 分子量: 269.303
• InChiKey: JXCDCKABQVAALQ-UHFFFAOYSA-N

物化性质

• 熔点：
  203-204 °C (decomp)
• 沸点：
  551.1±60.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-pyrrolidin-1-yl-5H-chromeno[4,3-d]pyrimidin-5-ol 在 sodium hydroxide 、 potassium permanganate 作用下， 反应 0.5h， 生成 2-pyrrolidino-5H-[1]benzopyrano[4,3-d]pyrimidin-5-one
  参考文献：
  名称：

  Petersen,U.; Heitzer,H., Justus Liebigs Annalen der Chemie, 1976, p. 1663 - 1673

  摘要：

  DOI：
• 作为产物：
  描述：

  pyrrolidine-1-carboxamidine hydrochloride 、 色酮-3-甲醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以97%的产率得到2-pyrrolidin-1-yl-5H-chromeno[4,3-d]pyrimidin-5-ol
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 2,5-cycloamino-5H-[1]benzopyrano[4,3-d]pyrimidines endowed with in vitro antiplatelet activity

  摘要：

  A series of new 2,5-cycloamino-5H-[1]benzopyrano[4,3-d]pyrimidines 3a-i have been synthesized and tested in vivo for the anti-inflammatory/analgesic/antipyretic effects and in vitro to evaluate the antiplatelet activity on guinea-pig platelet-rich plasma aggregated by collagen, adenosine-5'-diphosphate (ADP) and arachidonic acid (AA). Title compounds were ineffective in vivo; however, the pyrrolidino derivatives 3a and 3c exhibited an antiplatelet activity against all the aggregants differing from that of acetylsalicylic acid (ASA) while the 5-morpholino derivatives 3g-i showed the most potent ASA-like antiplatelet activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00221-9

文献信息

• Petersen,U.; Heitzer,H., Justus Liebigs Annalen der Chemie, 1976, p. 1663 - 1673
  作者：Petersen,U.、Heitzer,H.

  DOI：——

  日期：——
• PETERSEN U.; HEITZER H., J. LIEBIGS ANN. CHEM. <JLAC-BF>, 1976, NO 9, 1663-1673
  作者：PETERSEN U.、 HEITZER H.

  DOI：——

  日期：——
• Synthesis, antiplatelet and antithrombotic activities of new 2-substituted benzopyrano[4,3-d]pyrimidin-4-cycloamines and 4-amino/cycloamino-benzopyrano[4,3-d]pyrimidin-5-ones
  作者：Olga Bruno、Chiara Brullo、Silvia Schenone、Francesco Bondavalli、Angelo Ranise、Massimiliano Tognolini、Mariannina Impicciatore、Vigilio Ballabeni、Elisabetta Barocelli

  DOI：10.1016/j.bmc.2005.07.066

  日期：2006.1

  Atherothrombotic coronary artery disease, associated with deep vein thrombosis, is one of the most common causes of death worldwide. Recently, antiplatelet combination therapy using agents with different mechanisms of action, Such as aspirin, dipyridamole, and thienopyridines, seems to be an attractive preventive approach. Moreover, several large, randomized clinical trials support combination therapy with aspirin plus warfarin in high-risk patients with atherosclerotic heart disease. Our research on the benzopyrano[4,3-d]pyrimidine system gave rise to the synthesis of a large number of Compounds endowed with in vitro anti-aggregating activity. Several SAR considerations Suggest that the benzopyranopyrimidine system is an appropriate scaffold to obtain molecules that are able to act simultaneously in different pathways of aggregation. Now, we report the synthesis of new 2-substituted benzopyrano[4,3-d]pyrimidin-4-cycloamines and 4-amino/cycloamino-benzopyrano[4,3-d]pyrimidin-5-ones and the results of the pharmacological study on haemostasis. Some tested compounds showed a large-spectrum antiplatelet activity in vitro, and are more potent than aspirin as antithrombotics in vivo but, at variance with aspirin, they do not increase bleeding. This paper describes novel antithrombotic Compounds with an interesting pharmacological profile and a potentially attractive benefit/risk ratio, with their mechanism of action generally, but not exclusively, dependent on antiplatelet activity, deserving further investigations. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and pharmacological evaluation of 2,5-cycloamino-5H-[1]benzopyrano[4,3-d]pyrimidines endowed with in vitro antiplatelet activity
  作者：O Bruno、C Brullo、A Ranise、S Schenone、F Bondavalli、E Barocelli、V Ballabeni、M Chiavarini、M Tognolini、M Impicciatore

  DOI：10.1016/s0960-894x(01)00221-9

  日期：2001.6

  A series of new 2,5-cycloamino-5H-[1]benzopyrano[4,3-d]pyrimidines 3a-i have been synthesized and tested in vivo for the anti-inflammatory/analgesic/antipyretic effects and in vitro to evaluate the antiplatelet activity on guinea-pig platelet-rich plasma aggregated by collagen, adenosine-5'-diphosphate (ADP) and arachidonic acid (AA). Title compounds were ineffective in vivo; however, the pyrrolidino derivatives 3a and 3c exhibited an antiplatelet activity against all the aggregants differing from that of acetylsalicylic acid (ASA) while the 5-morpholino derivatives 3g-i showed the most potent ASA-like antiplatelet activity. (C) 2001 Elsevier Science Ltd. All rights reserved.