8-溴-5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇 | 103845-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 8-溴-5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇
• 英文名称: 8-bromo-5H-[1,2,4]triazino[5,6-b]indole-3-thiol
• 英文别名: 8-Bromo-5H-[1,2,4]triazino[5,6-b]indole-3-thiol；8-bromo-2,5-dihydro-[1,2,4]triazino[5,6-b]indole-3-thione
• CAS: 103845-98-3
• 化学式: C₉H₅BrN₄S
• 分子量: 281.135
• InChiKey: QFJVRRZSQIPAMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 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：
  80.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-溴-5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇 在 一水合肼 、 溶剂黄146 作用下， 反应 2.0h， 生成 N-(benzylideneamino)-8-bromo-5H-[1,2,4]triazino[5,6-b]indol-3-amine
  参考文献：
  名称：

  Misra, Atma Ram; Tripathi, Maya Mani; Shahma, Abu, Oriental Journal of Chemistry, 2011, vol. 27, # 2, p. 783 - 788

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴靛红 在 氢氧化钾 作用下， 以 溶剂黄146 为溶剂， 反应 4.5h， 生成 8-溴-5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇
  参考文献：
  名称：

  Mohan, Jag; Ranjaneyulu, G. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 731 - 733

  摘要：

  DOI：

文献信息

• Further Studies on Triazinoindoles as Potential Novel Multitarget-Directed Anti-Alzheimer’s Agents
  作者：Dushyant V. Patel、Nirav R. Patel、Ashish M. Kanhed、Divya M. Teli、Kishan B. Patel、Pallav M. Gandhi、Sagar P. Patel、Bharat N. Chaudhary、Dharti B. Shah、Navnit K. Prajapati、Kirti V. Patel、Mange Ram Yadav

  DOI：10.1021/acschemneuro.0c00448

  日期：2020.11.4

  the development of multitarget-directed ligands as anti-AD agents. The experimental data indicated that some of these compounds exhibited significant anti-AD properties. Among them, 8-(piperidin-1-yl)-N-(6-(pyrrolidin-1-yl)hexyl)-5H-[1,2,4]triazino[5,6-b]indol-3-amine (60), the most potent cholinesterase inhibitor (AChE, IC50 value of 0.32 μM; BuChE, IC50 value of 0.21 μM), was also found to possess

  目前的抗阿尔茨海默氏病（AD）药物的临床疗效不足，以及它们对患者阿尔茨海默氏病进展的影响很小，已经将研究重点从单一靶标改为了多靶标定向配体。通过在吲哚环上引入各种取代基以开发多靶标配体作为抗AD剂，可获得一系列新的取代的三嗪并吲哚衍生物。实验数据表明这些化合物中的一些表现出显着的抗AD特性。其中，8-（哌啶-1-基） - ñ - （6-（吡咯烷-1-基）己基）-5- ħ - [1,2,4]三嗪并[5,6- b ]吲哚-3-胺（60），最有效的胆碱酯酶抑制剂（AChE，IC 50值为0.32μM; 还发现BuChE的IC 50值为0.21μM）具有显着的自我介导的Aβ1–42聚集抑制活性（在25μM浓度下为54％）。另外，化合物60显示出强的抗氧化剂活性。在PAMPA测定中，化合物60表现出血脑屏障穿透能力。在大鼠中进行的一项急性毒性研究表明，至多2000 mg / kg的剂量，均无毒性迹象
• 10.1007/s11030-024-10840-w
  作者：Li, He、Gao, Yali、Ni, Xin、Xiong, Yizu、Zhang, Peixi、Liu, Han、Wu, Xingye、Tong, Dandan、Wang, Cuifang、Ma, Junjie

  DOI：10.1007/s11030-024-10840-w

  日期：——

  The avidity of cancer cells for iron highlights the potential for iron chelators to be used in cancer therapy. Herein, we designed and synthesized a novel series of 5H-[1,2,4]triazino[5,6-b]indole derivatives bearing a pyridinocycloalkyl moiety using a ring-fusion strategy based on the structure of an iron chelator, VLX600. The antiproliferative activity evaluation against cancer cells and normal cells

  癌细胞对铁的渴望凸显了铁螯合剂用于癌症治疗的潜力。在此，我们使用基于铁螯合剂VLX600结构的环融合策略设计并合成了一系列带有吡啶环烷基部分的新型5 H -[1,2,4]三嗪[5,6- b ]吲哚衍生物。 。通过对癌细胞和正常细胞的抗增殖活性评估，鉴定出化合物3k ，其在体外对 A549、MCF-7、Hela 和 HepG-2 表现出最强的抗增殖活性，IC 50值为 0.59、0.86、1.31 和 0.92 μM，对 HEK293 的细胞毒性低于VLX600 。进一步的研究表明，与VLX600不同，化合物3k选择性地与亚铁离子结合，但不与三价铁离子结合，并且添加Fe 2+消除了3k的细胞毒性。流式细胞术检测表明， 3k将细胞周期阻滞在 G1 期，并以剂量​​和时间依赖性方式诱导 A549 细胞显着凋亡，这与 JC-1 染色检测结果相对应。 Bcl-2、Bax 和切割的 caspase-3
• Pal, Ram; Jain, Kiran; Gupta, G D, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 12, p. 1098 - 1103
  作者：Pal, Ram、Jain, Kiran、Gupta, G D、Handa, R N、Pujari, H K

  DOI：——

  日期：——
• Ligand-based virtual screening identifies a family of selective cannabinoid receptor 2 agonists
  作者：Matteo Gianella-Borradori、Ivy Christou、Carole J.R. Bataille、Rebecca L. Cross、Graham M. Wynne、David R. Greaves、Angela J. Russell

  DOI：10.1016/j.bmc.2014.11.002

  日期：2015.1

  The cannabinoid receptor 2 (CB2R) has been linked with the regulation of inflammation, and selective receptor activation has been proposed as a target for the treatment of a range of inflammatory diseases such as atherosclerosis and arthritis. In order to identify selective CB2R agonists with appropriate physicochemical and ADME properties for future evaluation in vivo, we first performed a ligand-based virtual screen. Subsequent medicinal chemistry optimisation studies led to the identification of a new class of selective CB2R agonists. Several examples showed high levels of activity (EC50 < 200 nM) and binding affinity (K-i < 200 nM) for the CB2R, and no detectable activity at the CB1R. The most promising example, DIAS2, also showed favourable in vitro metabolic stability and absorption properties along with a clean selectivity profile when evaluated against a panel of GPCRs and kinases. (C) 2014 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/3.0/).
• Triazino indole–quinoline hybrid: A novel approach to antileishmanial agents
  作者：Rashmi Sharma、Anand Kumar Pandey、Rahul Shivahare、Khushboo Srivastava、Suman Gupta、Prem M.S. Chauhan

  DOI：10.1016/j.bmcl.2013.11.018

  日期：2014.1

  A novel series of 1,2,4-triazino-[5,6b] indole-3-thione covalently linked to 7-chloro-4-aminoquinoline have been synthesized and evaluated for their in vitro activity against extracellular promastigote and intracellular amastigote form of Leishmania donovani. Among all tested compounds, compounds 7a and 7b were found to be the most active with IC50 values 1.11, 0.36 mu M and selectivity index (SI) values 67, >1111, respectively, against amastigote form of L. donovani which is several folds more potent than the standard drugs, miltefosine (IC50 = 8.10 mu M, SI = 7) and sodium stibo-gluconate (IC50 = 54.60 mu M, SI >= 7). (C) 2013 Published by Elsevier Ltd.