5-(4-(2-bromoethoxy)phenyl)-3H-1,2-dithiole-3-thione | 1234493-46-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-(2-bromoethoxy)phenyl)-3H-1,2-dithiole-3-thione
• 英文别名: 5-[4-(2-Bromoethoxy)phenyl]dithiole-3-thione
• CAS: 1234493-46-9
• 化学式: C₁₁H₉BrOS₃
• 分子量: 333.294
• InChiKey: HWBYIPKEXQQINW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  91.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-(2-bromoethoxy)phenyl)-3H-1,2-dithiole-3-thione 在 盐酸 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 (±)-(E)-2-methoxy-4-(3-((6-(nitrooxy)hexyl)oxy)-3-oxoprop-1-en-1-yl)phenyl 2-(1-(2-(4-(2-(4-(3-thioxo-3H-1,2-dithiol-5-yl)phenoxy)ethyl)piperazin-1-yl)acetoxy)pentyl)benzoate
  参考文献：
  名称：

  发现带有供体NO / H 2 S的3-正丁基邻苯二甲酸酯的开环衍生物作为潜在的抗缺血性卒中剂

  摘要：

  为了寻找比已知药物3-n-丁基邻苯二甲酸酯（NBP）更高效力的新型抗缺血性中风药，NBP的一系列开环衍生物同时带有一氧化氮（NO）和硫化氢（H 2 S）-设计，合成和生物学评估供体部分（NO / H 2 S-NBP）（8a-8o）。活性最高的化合物8d在体外抑制ADP诱导的血小板凝集方面比NBP和相应的H 2 S-NBP 10或NO-NBP 13更有效。另外，8d产生中等水平的NO和H 2S，可能有益于改善心血管和脑循环。更重要的是，在短暂性局灶性脑缺血的大鼠模型中，口服治疗8d改善了神经行为功能，减小了梗塞的大脑大小和脑水含量，并增强了脑抗氧化剂SOD，GSH和GSH-Px的水平，但降低了水平氧化剂MDA。8d对缺血/再灌注（I / R）相关的脑损伤的保护作用大于NBP，这表明8d可能是有希望进行进一步研究的药物。

  DOI：

  10.1016/j.ejmech.2016.03.044
• 作为产物：
  描述：

  胆维他 在 吡啶盐酸盐 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.5h， 生成 5-(4-(2-bromoethoxy)phenyl)-3H-1,2-dithiole-3-thione
  参考文献：
  名称：

  设计，合成和生物评价3-正丁基邻苯二甲酸酯的硫化氢释放衍生物作为潜在的抗血小板和抗血栓形成剂。

  摘要：

  在本研究中，设计，合成和生物学评估了一系列的3-正丁基邻苯二甲酸酯（NBP）释放出硫化氢（H2S）的衍生物（8a-g和9a-f）。最有希望的化合物8e在体外显着抑制二磷酸腺苷（ADP）和花生四烯酸（AA）诱导的血小板凝集，优于NBP，盐酸噻氯匹定和阿司匹林。此外，8e可以在体外缓慢产生中等水平的H2S，这可能有益于改善心血管和脑循环。最重要的是，8e保护了小鼠免受胶原蛋白和肾上腺素诱导的血栓形成，并且在大鼠中显示出比NBP和阿司匹林更大的抗血栓形成活性。总体而言，8e值得进一步研究以治疗血栓形成相关的缺血性中风。

  DOI：

  10.1039/c4ob00830h

文献信息

• Synthesis and biological evaluation of novel hydrogen sulfide releasing glycyrrhetic acid derivatives
  作者：Heng Song、Yinxing Sun、Guanglin Xu、Bingbo Hou、Guizhen Ao

  DOI：10.3109/14756366.2016.1144596

  日期：2016.11.1

  exhibited the most potent inhibitory rate of 60.7%. Furthermore, preliminary structure-activity relationship studies demonstrated that 3-substituted GA derivatives had stronger anti-inflammatory activities than the corresponding 3-unsubstituted GA derivatives. In addition, anti-proliferative activities of compounds V1-9 were evaluated in three different human cancer cell lines. Compound V4 showed the most

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• Synthesis of melampomagnolide B derivatives as potential anti-Triple Negative Breast Cancer agents
  作者：Tianyang Chen、Xiaoping Chen、Lingling Liu、Quan Zhang、Yahui Ding

  DOI：10.1016/j.ejmech.2023.116024

  日期：2024.1

  Triple-negative breast cancer (TNBC) is the most malignant and aggressive subtype of breast cancer. Currently, the treatment options to TNBC are limited and the discovery of new drugs and novel therapeutic strategies for treatment of TNBC is urgently needed. In this study, a series of melampomagnolide B (MMB) derivatives were designed, synthesized, and evaluated for their anti-TNBC activities. Compound

  三阴性乳腺癌（TNBC）是乳腺癌中最恶性和最具侵袭性的亚型。目前，TNBC的治疗选择有限，迫切需要发现治疗TNBC的新药和新的治疗策略。在本研究中，设计、合成了一系列 melampomagnolide B (MMB) 衍生物，并评估了其抗 TNBC 活性。化合物7和13a对不同的TNBC细胞表现出高效的活性，IC 50值范围为0.37 μM至1.52 μM，与母体化合物MMB相比，活性提高了3.6至54倍。表型效应表明化合物7和13a可以抑制TNBC细胞的转移、诱导细胞凋亡并阻滞细胞周期分布。此外，机制研究表明化合物7和13a结合IKKβ并抑制IKKβ介导的IκB和p65磷酸化，进而抑制p65的核转位，最终在NF-κB控制下调节与转移、凋亡和细胞周期相关的基因。此外，化合物7在体内抑制肿瘤生长，脾脏和肝脏的重量也较对照组减轻，表明化合物7可以抑制体内TNBC的转移。这些发现表明化合物7可作
• 一类多甲氧基取代的查尔酮衍生物、制备方法和医药用途
  申请人：泰州学院

  公开号：CN117683015A

  公开（公告）日：2024-03-12

  本发明公开了一类多甲氧基取代的查尔酮衍生物、制备方法和医药用途。本发明提供了式Ⅰ或式Ⅱ所示的多甲氧基查尔酮衍生物，并提供了其制备方法。药理结果显示，该类化合物对ADP诱导或者AA诱导的血小板凝集抑制活性均优于各自的母体化合物；与临床上常用的具有抗凝作用的药物相比，该类化合物对ADP诱导的血小板聚集的抑制活性与阳性药噻氯吡嗪相当，对AA诱导的血小板聚集的抑制活性明显优于阳性对照药物阿司匹林。因此，该类多甲氧基取代的查尔酮衍生物具有开发成抗血小板聚集的药物的前景。#imgabs0#
• Antiproliferative hydrogen sulfide releasing evodiamine derivatives and their apoptosis inducing properties
  作者：Xu Hu、Runwei Jiao、Haonan Li、Xianhua Wang、Haoda Lyu、Xiang Gao、Fanxing Xu、Zhanlin Li、Huiming Hua、Dahong Li

  DOI：10.1016/j.ejmech.2018.04.009

  日期：2018.5

  To explore antitumor agents with high efficiency and selectivity, two series of 16 H2S donating evodiamine derivatives 8-12 were synthesized and characterized by H-1 NMR, C-13 NMR and HRMS. Their antiproliferative activities were tested against five cancer cell lines (Bel-7402, MCF-7, SGC-7901, Caco-2 and HL-60) and human normal peripheral blood mononuclear cells. Among them, compound 12c showed the most potent inhibitory activities against human leukemia HL-60 and epithelial colorectal adenocarcinoma Caco-2 cells with IC50 values of 0.58 and 2.02 mu M, respectively. Additionally, high selectivity was also observed between human normal peripheral blood mononuclear cells and human leukemia HL-60 cells. Further mechanism studies confirmed that 12c could induce apoptosis, arrest cell cycle at the G2/M phase and lead to mitochondrial dysfunction in HL-60 cells. Furthermore, western blot assay demonstrated that 12c induced the intrinsic apoptotic mitochondrial pathway by upregulating protein expression of Bax, cytochrome c, caspase-3,-9 and p53, and downregulating the relative levels of Bcl-2. The levels of cell cycle related proteins cyclin B1 and cdc2 were also downregulated in which G(2)/M phase arrest was confirmed. Overall, 12c possessed immense potential for the discovery of antitumor candidates with high efficiency and selectivity. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Design, synthesis, and pharmacological evaluation of the aqueous prodrugs of desmethyl anethole trithione with hepatoprotective activity
  作者：Pei Chen、Yu Luo、Li Hai、Shan Qian、Yong Wu

  DOI：10.1016/j.ejmech.2010.03.029

  日期：2010.7

  A metabolite-based prodrug strategy to increase the solubility of anethole trithione was reported to facilitate the clinical application of this hepatoprotective agent. Water-soluble analogs of anethole trithione were synthesized via substituting the methyl group of anethole trithione with the simple hydrophilic alkylamino group, and subjected to physiochemical, pharmacological and metabolic studies. The prodrugs displayed increased solubility as well as other physiochemical properties favorable for parenteral use. Among the analogs synthesized, the compound 5a exhibited best hepatoprotective activity at the dose of 2.0 mg/kg in mice equal to that of anethole trithione. The in vivo metabolic investigation demonstrated that the straight-side chain prodrug 5a could convert to desmethyl anethole trithione in vivo, while the ring-side chain prodrug 5d could not. The hepatoprotective activity of the prodrugs might result from the active metabolite desmethyl anethole trithione. (c) 2010 Elsevier Masson SAS. All rights reserved.