11-oxo-11H-pyrido[2,1-b]quinazoline-8-carbonitrile | 65823-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 11-oxo-11H-pyrido[2,1-b]quinazoline-8-carbonitrile
• 英文别名: 11-Oxopyrido[2,1-b]quinazoline-8-carbonitrile
• CAS: 65823-05-4
• 化学式: C₁₃H₇N₃O
• 分子量: 221.218
• InChiKey: MHGGDZRZQPBZKY-UHFFFAOYSA-N

物化性质

• 沸点：
  397.1±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-oxo-11H-pyrido[2,1-b]quinazoline-8-carbonitrile 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 8-(1H-tetrazol-5-yl)-pyrido[2,1-b]quinazolin-11-one
  参考文献：
  名称：

  Alkaline phosphatase inhibition by a series of pyrido[2,1-b]quinazolines: a possible relationship with cromolyn-like antiallergy activity

  摘要：

  Several known antiallergic agents, including cromolyn sodium and a series of pyrido[2,1-b]quinazolines, inhibit human alkaline phosphatase (ALP), a membranal enzyme associated with calcium uptake in certain tissues. A comparison of ALP and rat passive cutaneous anaphylaxis (PCA) inhibition indicates that PCA inhibition may be associated with drug-ALP interaction, since ALP inhibition potency parallels PCA inhibitory activity. The unpredictability of the PCA test toward clinical efficacy could in part be related to the uncompetitive nature of these inhibitors. The results also suggest that alkaline phosphatase may be a component of membranal calcium channels.

  DOI：

  10.1021/jm00348a025
• 作为产物：
  描述：

  4-氯吡啶-3-羧胺 在 吡啶 、 盐酸 、 对甲苯磺酰氯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 11-oxo-11H-pyrido[2,1-b]quinazoline-8-carbonitrile
  参考文献：
  名称：

  Alkaline phosphatase inhibition by a series of pyrido[2,1-b]quinazolines: a possible relationship with cromolyn-like antiallergy activity

  摘要：

  Several known antiallergic agents, including cromolyn sodium and a series of pyrido[2,1-b]quinazolines, inhibit human alkaline phosphatase (ALP), a membranal enzyme associated with calcium uptake in certain tissues. A comparison of ALP and rat passive cutaneous anaphylaxis (PCA) inhibition indicates that PCA inhibition may be associated with drug-ALP interaction, since ALP inhibition potency parallels PCA inhibitory activity. The unpredictability of the PCA test toward clinical efficacy could in part be related to the uncompetitive nature of these inhibitors. The results also suggest that alkaline phosphatase may be a component of membranal calcium channels.

  DOI：

  10.1021/jm00348a025

文献信息

• Palladium‐Catalyzed Carbonylative Difunctionalization of C=N Bond of Azaarenes or Imines to Quinazolinones
  作者：Xibing Zhou、Yongzheng Ding、Hanmin Huang

  DOI：10.1002/asia.202000359

  日期：2020.6.2

  Supporting information for this article is given via a link at the end of the document. By intercepting the acylpalladium species with C=N bond of azaarenes or imines other than free amines or alcohols, the difunctionalization of C=N bond was established via palladium‐catalyzed carbonylation/nucleophilic addition sequence. This method is compatible with a diverse range of azaarenes and imines and allows

  本文末尾的链接提供了本文的支持信息。通过用氮杂芳烃或亚胺的C = N键（除游离胺或醇以外）拦截酰基铝物种，可通过钯催化的羰基化/亲核加成序列建立C = N键的双官能化。该方法与各种范围的氮杂芳烃和亚胺兼容，并允许有效合成范围广泛的喹唑啉酮及其衍生物。通过廉价的原料一步一步合成乙二胺及其类似物，已证明了其合成用途。
• Synthesis of Pyrido-Fused Quinazolinone Derivatives via Copper-Catalyzed Domino Reaction
  作者：Meilin Liu、Miaomiao Shu、Chaochao Yao、Guodong Yin、Dunjia Wang、Jinkun Huang

  DOI：10.1021/acs.orglett.6b00113

  日期：2016.2.19

  simple and efficient synthesis of 11H-pyrido[2,1-b]quinazolin-11-ones by Cu(OAc)2·H2O-catalyzed reaction of easily available substituted isatins and 2-bromopyridine derivatives has been developed. The reaction involves C–N/C–C bond cleavage and two C–N bond formations in a one-pot operation. This methodology is complementary to previously reported synthetic procedures, and two plausible reaction mechanisms

  通过Cu（OAc）2 ·H 2 O催化易得的取代的靛红与2-溴吡啶衍生物的反应，可以简单，有效地合成11 H-吡啶并[ 2,1 - b ]喹唑啉-11-酮。该反应在一锅操作中涉及C–N / CC键断裂和两个C–N键形成。该方法是对先前报道的合成方法的补充，并讨论了两个合理的反应机理。
• 一种制备喹唑啉酮衍生物的方法
  申请人：苏州大学

  公开号：CN108690015B

  公开（公告）日：2019-08-13

  本发明公开了一种制备喹唑啉酮衍生物的方法。本发明使用1‑吡啶基吲哚化合物为起始物在空气中即可反应制备产物，原料易得，种类广泛；利用本发明方法得到的产物类型多样，用途广泛，可用于合成各种药物；此外，本发明公开的方法步骤简单、反应条件温和、目标产物的收率高、污染小、反应操作和后处理过程简单，适合于工业化生产。
• Copper-Catalyzed Aerobic Oxidative Annulation and Carbon-Carbon Bond Cleavage of Arylacetamides: Domino Synthesis of Fused Quinazolinones
  作者：Jie Sun、Qitao Tan、Wusong Yang、Bingxin Liu、Bin Xu

  DOI：10.1002/adsc.201300818

  日期：2014.2.10

  AbstractAn efficient copper‐catalyzed tandem aerobic oxidative annulation and carbon‐carbon bond cleavage reaction was developed from easily accessible arylacetamides, which provides a direct approach for the domino synthesis of a vast array of tricyclic or tetracyclic fused quinazolinone alkaloid structures. A plausible reaction mechanism is proposed involving an aerobic benzylic oxidation/cyclization/decarbonylation cascade.magnified image
• SCHWENDER, C. F.;SUNDAY, B. R.;DECKER, V. L., J. MED. CHEM., 1982, 25, N 6, 742-745
  作者：SCHWENDER, C. F.、SUNDAY, B. R.、DECKER, V. L.

  DOI：——

  日期：——