indolo[2,1-b]quinazolin-6(12H)-one | 113001-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: indolo[2,1-b]quinazolin-6(12H)-one
• 英文别名: 12H-indolo[2,1-b]quinazolin-6-one
• CAS: 113001-49-3
• 化学式: C₁₅H₁₀N₂O
• 分子量: 234.257
• InChiKey: VTMDQEHTVKDBHC-UHFFFAOYSA-N

物化性质

• 熔点：
  226-227 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  436.8±48.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯甲酰乙酸 、 indolo[2,1-b]quinazolin-6(12H)-one 在 copper(II) bis(trifluoromethanesulfonate) 、 (R,R)-2,2'-异亚丙基双(4-苯基-2-恶唑啉) 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以70%的产率得到2-(6-hydroxy-6,12-dihydroindolo[2,1-b]quinazolin-6-yl)-1-phenylethanone
  参考文献：
  名称：

  在铜催化的色氨酸与 β-酮酸的不对称脱羧醛醇反应中对映选择性的转换：意外的反阴离子效应

  摘要：

  开发了 Cu-双恶唑啉催化的色氨酸与芳基取代的β-酮酸的对映选择性脱羧醛醇反应，提供了一种直接的方法来提供一系列的苯菊酯 A 类似物。在单一手性配体存在下，通过简单地改变铜盐，可以以良好到高的对映选择性获得产物的两种对映异构体。基于手性 Cu(II)-双恶唑啉配合物的 X 射线晶体学分析，提出了初步的立体化学模型，以解释观察到的反阴离子诱导的对映选择性转换。

  DOI：

  10.1021/acs.orglett.1c01315
• 作为产物：
  描述：

  色胺酮 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 indolo[2,1-b]quinazolin-6(12H)-one
  参考文献：
  名称：

  室温下电化学氧化吲哚获得色胺酮

  摘要：

  据报道，在环境条件下吲哚核心的电氧化重建，导致色胺酮的构建。这种电化学策略通过使用市售的 NH-吲哚原料作为起始材料，简化了分子骨架跳跃。此外，这种骨骼重建的综合价值通过不同的进一步变换得到了证明。涉及控制实验和循环伏安研究的初步机理研究表明电的必要性以及氧气和 TEMPO 的重要性，从而揭示了可能的反应途径。

  DOI：

  10.1002/adsc.202301027

文献信息

• Design, Synthesis, and Structure–Activity Relationship Studies of Tryptanthrins As Antitubercular Agents
  作者：Jae-Min Hwang、Taegwon Oh、Takushi Kaneko、Anna M. Upton、Scott G. Franzblau、Zhenkun Ma、Sang-Nae Cho、Pilho Kim

  DOI：10.1021/np3007167

  日期：2013.3.22

  The natural product tryptanthrin (la) represents a potential lead for new tuberculosis (TB) drugs since tryptanthrin and its synthetic analogues possess potent in vitro activity against Mycobacterium tuberculosis (Mtb). However, in spite of their in vitro activity, none of these agents have been shown to be efficacious in vivo against animal models of TB. Described herein are syntheses of new tryptanthrin analogues together with a systematic investigation of their in vitro antitubercular activity and ADME properties followed by pharmacokinetic characterization in rodents for the most promising compounds. Those with the best potency and oral bioavailability were progressed to evaluations of efficacy against acute murine TB. The work aimed to prove the concept that this compound class can limit growth of Mtb during infection as well as to establish the SAR for in vitro activity against Mtb and the range of in vitro ADME parameters for this class of natural products. Novel C-11-deoxy (5b) and A-ring-saturated (6) tryptanthrin analogues were discovered that maintained activity against Mtb and showed improved solubility compared to tryptanthrin as well as evidence of oral bioavailability in rodents. However, neither 5b nor 6 demonstrated efficacy against acute murine TB following administration at doses up to 400 mg/kg daily for 4 weeks. Although 5b and 6 failed to inhibit replication or kill Mtb in vivo, they illuminate a path to new structural variations of the tryptanthrin scaffold that may maximize the potential of this class of compounds against TB.
• Baiocchi; Giannangeli; Rossi, Il Farmaco, 1993, vol. 48, # 4, p. 487 - 501
  作者：Baiocchi、Giannangeli、Rossi、Ambrogi、Grandolini、Perioli

  DOI：——

  日期：——
• Discovery of Tryptanthrins as Novel Antiviral and Anti-Phytopathogenic-Fungus Agents
  作者：Yanan Hao、Jincheng Guo、Ziwen Wang、Yuxiu Liu、Yongqiang Li、Dejun Ma、Qingmin Wang

  DOI：10.1021/acs.jafc.0c02101

  日期：2020.5.20

  Plant diseases seriously affect the yield and quality of crops and are difficult to control. Tryptanthrin and its derivatives (tryptanthrins) were synthesized and evaluated for their antiviral activities and fungicidal activities. We found that tryptanthrins have good antiviral activities against tobacco mosaic virus (TMV) for the first time. Most of the tryptanthrins showed higher anti-TMV activities than that of ribavirin (inhibitory rates of 40, 37, and 38% at 500 mu g/mL for inactivation, curative, and protection activities in vivo, respectively). Compound 3n (inhibitory rates of 52, 49, and 54% at 500 mu g/mL for inactivation, curative, and protection activities in vivo, respectively) and compound 14 (inhibitory rates of 51, 48, and 53% at 500 mu g/mL for inactivation, curative, and protection activities in vivo, respectively) emerged as new antiviral lead compounds with excellent antiviral activities. Compound 16 was selected for further antiviral mechanism research, which revealed that compound 16 could inhibit virus assembly by decomposing 20S coat protein (CP) disk. Molecular docking results showed that compounds 3n and 14, which have higher antiviral activities in vivo than that of compound 16, do show stronger interaction with TMV CP. Further fungicidal activity tests showed that tryptanthrins displayed broad-spectrum fungicidal activities, especially for compound 16. These compounds showed good selectivity to Physalospora piricola. In the current study, a small molecular library of tryptanthrin was constructed and the bioactivity spectrum of these compounds was broadened, which lays a foundation for their application in plant protection.
• Bergman, Jan; Tilstam, Ulf; Toernroos, Karl-Wilhelm, Journal of the Chemical Society. Perkin transactions I, 1987, p. 519 - 528
  作者：Bergman, Jan、Tilstam, Ulf、Toernroos, Karl-Wilhelm

  DOI：——

  日期：——
• BERGMAN J.; TILSTAM U.; TORNROOS K. -W., J. CHEM. SOC. PERKIN TRANS.,(1987) N 3, 519-527
  作者：BERGMAN J.、 TILSTAM U.、 TORNROOS K. -W.

  DOI：——

  日期：——