6-hydroxy-6-(2-oxo-2-phenylethyl)indolo[2,1-b]quinazolin-12(6H)-one | 1032057-21-8

• 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: 6-hydroxy-6-(2-oxo-2-phenylethyl)indolo[2,1-b]quinazolin-12(6H)-one
• 英文别名: 6-Hydroxy-6-phenacyl-indolo[2,1-b]quinazolin-12-one；6-hydroxy-6-phenacylindolo[2,1-b]quinazolin-12-one
• CAS: 1032057-21-8
• 化学式: C₂₃H₁₆N₂O₃
• 分子量: 368.392
• InChiKey: HWQHXQCQIRAPKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-hydroxy-6-(2-oxo-2-phenylethyl)indolo[2,1-b]quinazolin-12(6H)-one 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以20%的产率得到色胺酮
  参考文献：
  名称：

  Synthesis of (±)-Cephalanthrin A Using Baeyer-Villiger Oxidation

  摘要：

  Indoloquinazoline alkaloid (+/-)-cephalanthrin A was synthesized through the Baeyer-Villiger oxidation of the phenyl ketone derived from aldol reaction of tryptanthrin and acetophenone.

  DOI：

  10.3987/com-16-s(s)5
• 作为产物：
  描述：

  靛红酸酐 在 N-乙基哌啶 、 二甲胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 吡啶 为溶剂， 生成 6-hydroxy-6-(2-oxo-2-phenylethyl)indolo[2,1-b]quinazolin-12(6H)-one
  参考文献：
  名称：

  费坦素同类药物作为抗分枝杆菌药物的合成及生物学评价

  摘要：

  发现天然生物碱类胰蛋白酶（吲哚并[2,1 - b ]喹唑啉-6,12-二酮）及其类似物具有抗MDR-TB的有效抗结核活性。已经合成了一类新型的吲哚[2，1- b ]喹唑啉酮来评估其抗分枝杆菌活性。结核分枝杆菌的烯丙基酰基载体蛋白还原酶（InhA）是关键酶之一，已被证实是有效的抗微生物靶标。在计算机分子对接研究中表明，合成的化合物对结核分枝杆菌显示出高亲和力药物目标InhA。费坦素是一种天然产物，属于色胺素家族，除了在第6位外，还显示出结构相似性。色胺素衍生物是通过修饰色胺素的酮官能团制备的。发现这些类紫杉醇同源物显示出有希望的抗结核活性。

  DOI：

  10.1016/j.bmcl.2015.07.057

文献信息

• Isolation, Structure Elucidation, and Synthesis of Cytotoxic Tryptanthrin Analogues from <i>Phaius mishmensis</i>
  作者：Chen-Wei Jao、Wei-Chih Lin、Yao-Ting Wu、Pei-Lin Wu

  DOI：10.1021/np800064w

  日期：2008.7.1

  Bioassay-guided chromatographic separation of the cytotoxic MeOH extract of Phaius mishmensis led to the isolation of two known and six new indoloquinazolinones, phaitanthrins A-E (1-5) and methylisatoid (6). The structures of the new compounds were elucidated by spectroscopic analysis. Phaitanthrin A (1) and tryptanthrin (7) showed moderate cytotoxicity against MCF-7, NCI-H460, and SF-268 cell lines

  生物测定引导的色谱法对米氏海葵的细胞毒性甲醇提取物进行了色谱分离，从而分离出了两种已知的和六种新的吲哚并喹唑啉酮类，泛坦霉素AE（1-5）和甲基isatoid（6）。通过光谱分析阐明了新化合物的结构。Phaitanthrin A（1）和tryptanthrin（7）对MCF-7，NCI-H460和SF-268细胞系显示中等程度的细胞毒性。制备一系列色胺酮的酮加合物，并初步测试了其体外抗MCF-7，NCI-H460和SF-268人癌细胞系的抗癌活性。3-戊酮加合物13显示出类似于色胺酮的活性。
• Electrochemical Oxidation of Indoles to Access Tryptanthrins at Room Temperature
  作者：Ziyi Guo、Yi Liu、Hang Li、Jiaping Wu、Meihua Xie、Jitan Zhang

  DOI：10.1002/adsc.202301027

  日期：2024.1.30

  An electrooxidative reconstruction of the indole core under ambient conditions is reported, resulting in the construction of tryptanthrins. This electrochemical strategy simplifies molecular skeleton-hopping by employing commercially available NH-indole feedstock as the starting materials. Furthermore, the synthetic value of this skeletal reconstruction was demonstrated by divergent further transformations

  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。
• 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.
• Synthesis and biological evaluation of phaitanthrin congeners as anti-mycobacterial agents
  作者：Ahmed Kamal、B.V. Subba Reddy、B. Sridevi、A. Ravikumar、A. Venkateswarlu、G. Sravanthi、J. Padma Sridevi、P. Yogeeswari、D. Sriram

  DOI：10.1016/j.bmcl.2015.07.057

  日期：2015.9

  Natural alkaloid, tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione) and its analogues are found to exhibit potent anti-tubercular activity against MDR-TB. A novel class of indolo[2,1-b]quinazolinones have been synthesized to evaluate their anti-mycobacterial activity. Enoyl-acyl carrier protein reductase (InhA) of Mycobacterium tuberculosis is one of the key enzymes and has been validated as an effective

  发现天然生物碱类胰蛋白酶（吲哚并[2,1 - b ]喹唑啉-6,12-二酮）及其类似物具有抗MDR-TB的有效抗结核活性。已经合成了一类新型的吲哚[2，1- b ]喹唑啉酮来评估其抗分枝杆菌活性。结核分枝杆菌的烯丙基酰基载体蛋白还原酶（InhA）是关键酶之一，已被证实是有效的抗微生物靶标。在计算机分子对接研究中表明，合成的化合物对结核分枝杆菌显示出高亲和力药物目标InhA。费坦素是一种天然产物，属于色胺素家族，除了在第6位外，还显示出结构相似性。色胺素衍生物是通过修饰色胺素的酮官能团制备的。发现这些类紫杉醇同源物显示出有希望的抗结核活性。
• Synthesis of (±)-Cephalanthrin A Using Baeyer-Villiger Oxidation
  作者：Minoru Ishikura、Tomoki Itoh、Takumi Abe、Tominari Choshi、Takashi Nishiyama

  DOI：10.3987/com-16-s(s)5

  日期：——

  Indoloquinazoline alkaloid (+/-)-cephalanthrin A was synthesized through the Baeyer-Villiger oxidation of the phenyl ketone derived from aldol reaction of tryptanthrin and acetophenone.