8-bromo-6-hydrazonoindolo[2,1-b]quinazolin-12(6H)-one | 1421232-19-0

• 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: 8-bromo-6-hydrazonoindolo[2,1-b]quinazolin-12(6H)-one
• 英文别名: 8-bromo-6-hydrazinylideneindolo[2,1-b]quinazolin-12-one
• CAS: 1421232-19-0
• 化学式: C₁₅H₉BrN₄O
• 分子量: 341.167
• InChiKey: NRMSJXCDGXJCFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.27
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  8-bromo-6-hydrazonoindolo[2,1-b]quinazolin-12(6H)-one 在 sodium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.25h， 生成
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 8-substituted-6-hydrazonoindolo[2,1- b ]quinazolin-12(6 H )-one scaffolds as potential cytotoxic agents: IDO-1 targeting molecular docking studies

  摘要：

  Herein, we have reported the synthesis of 18 novel 8-substituted tryptanthrin analogues based on our earlier work. All these tryptanthrin analogues were well characterized by H-1 & C-13 NMR, FT-IR, Mass Spectrometry and Elemental Analysis. All these 8-substituted analogues were screened for their anti-oxidant activity by DPPH radical scavenging assay. Out of all the tested compounds, T-11, T-12,T-17 and T-18 showed potent anti-oxidant activity. The anti-cancer activity have been performed by using MTT assay protocol and their results depicts that compounds having the 4-pyridyl or 4-carboxyphenyl substituents at the 8th position of the tryptanthrin framework are found to be the most promising cytotoxic agent against A549, MCF-7 and HeLa human cancer cell lines compared to others as well as with the standard drug cisplatin. Moreover, the comparative molecular docking studies against the three protein receptors IDO1, EGFR and HER2 strongly suggested that IDO1 is the best target protein, which exhibits lowest binding energies of -11.73 and -11.61 kcal mol(-1) for T-11 and T-12 scaffolds, respectively towards the in vitro anti-cancer activity. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.08.064
• 作为产物：
  描述：

  8-bromoindolo[2,1-b]quinazoline-6,12-dione 在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以74%的产率得到8-bromo-6-hydrazonoindolo[2,1-b]quinazolin-12(6H)-one
  参考文献：
  名称：

  作为细胞抑制剂的新型取代腙吲哚[2,1-b]喹唑啉-6,12-二酮类似物：合成、晶体结构、生物学评价和分子对接研究。

  摘要：

  已经合成了一系列新型取代腙吲哚 [2,1-b] 喹唑啉-6,12-二酮类似物，并筛选了它们的体外细胞毒性和抗菌活性。在所有目标化合物中，3c对三种癌细胞系MCF-7、A549、HeLa表现出最强的抑制活性，IC50值分别为07.14±1.285μM、09.18±0.968μM和10.57±0.581μM，同时对非细胞系保持低毒性-癌症起源的细胞系，HEK-293。通过使用对接模拟完成了与可能的靶蛋白吲哚胺 2,3-双加氧酶 (IDO1) 的分子相互作用的详细研究。对接模型的结果与实验体外细胞毒活性结论一致，即3c 显示出最高结合能-11.25kcal/mol。此外，

  DOI：

  10.1016/j.bmcl.2016.10.006

文献信息

• Design, synthesis and biological evaluation of 8-substituted-6-hydrazonoindolo[2,1- b ]quinazolin-12(6 H )-one scaffolds as potential cytotoxic agents: IDO-1 targeting molecular docking studies
  作者：Ramu Guda、Rajashekar Korra、Siripireddy Balaji、Rambabu Palabindela、Rakesh Eerla、Harikiran Lingabathula、Narsimha Reddy Yellu、Girijesh Kumar、Mamatha Kasula

  DOI：10.1016/j.bmcl.2017.08.064

  日期：2017.10

  Herein, we have reported the synthesis of 18 novel 8-substituted tryptanthrin analogues based on our earlier work. All these tryptanthrin analogues were well characterized by H-1 & C-13 NMR, FT-IR, Mass Spectrometry and Elemental Analysis. All these 8-substituted analogues were screened for their anti-oxidant activity by DPPH radical scavenging assay. Out of all the tested compounds, T-11, T-12,T-17 and T-18 showed potent anti-oxidant activity. The anti-cancer activity have been performed by using MTT assay protocol and their results depicts that compounds having the 4-pyridyl or 4-carboxyphenyl substituents at the 8th position of the tryptanthrin framework are found to be the most promising cytotoxic agent against A549, MCF-7 and HeLa human cancer cell lines compared to others as well as with the standard drug cisplatin. Moreover, the comparative molecular docking studies against the three protein receptors IDO1, EGFR and HER2 strongly suggested that IDO1 is the best target protein, which exhibits lowest binding energies of -11.73 and -11.61 kcal mol(-1) for T-11 and T-12 scaffolds, respectively towards the in vitro anti-cancer activity. (C) 2017 Elsevier Ltd. All rights reserved.
• Novel substituted hydrazono indolo[2,1- b ]quinazoline-6,12-dione analogues as cytostatic agents: Synthesis, crystal structure, biological evaluation and molecular docking studies
  作者：Ramu Guda、Sirassu Narsimha、Ramavath Babu、Srujana Muthadi、Harikiran Lingabathula、Rambabu Palabindela、Narsimha Reddy Yellu、Girijesh Kumar、Mamatha Kasula

  DOI：10.1016/j.bmcl.2016.10.006

  日期：2016.11

  A series of novel substituted hydrazono indolo[2,1-b]quinazoline-6,12-dione analogues have been synthesized and screened for their in vitro cytotoxic and antimicrobial activities. Among all the target compounds, 3c exhibited the most potent inhibitory activity against three cancer cell lines MCF-7, A549, HeLa with IC50 values 07.14±1.285μM, 09.18±0.968μM and 10.57±0.581μM respectively, while maintaining

  已经合成了一系列新型取代腙吲哚 [2,1-b] 喹唑啉-6,12-二酮类似物，并筛选了它们的体外细胞毒性和抗菌活性。在所有目标化合物中，3c对三种癌细胞系MCF-7、A549、HeLa表现出最强的抑制活性，IC50值分别为07.14±1.285μM、09.18±0.968μM和10.57±0.581μM，同时对非细胞系保持低毒性-癌症起源的细胞系，HEK-293。通过使用对接模拟完成了与可能的靶蛋白吲哚胺 2,3-双加氧酶 (IDO1) 的分子相互作用的详细研究。对接模型的结果与实验体外细胞毒活性结论一致，即3c 显示出最高结合能-11.25kcal/mol。此外，