7-hydroxy-2-(2-thienyl)chromone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-hydroxy-2-(2-thienyl)chromone
• 英文别名: 7-hydroxy-2-(thiophene-2-yl)-4H-chromen-4-one；7-Hydroxy-2-(thiophen-2-yl)-4H-chromen-4-one；7-hydroxy-2-thiophen-2-ylchromen-4-one
• 化学式: C₁₃H₈O₃S
• 分子量: 244.271
• InChiKey: PTMPCXHWLVOQBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-hydroxy-2-(2-thienyl)chromone 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 (Z)-2-((7-hydroxy-4-oxo-2-(thiophen-2-yl)-4H-chromen-8-yl)methylene)hydrazine-1-carboxamide
  参考文献：
  名称：

  Flavonoid analogues as urease inhibitors: Synthesis, biological evaluation, molecular docking studies and in-silico ADME evaluation

  摘要：

  A series of novel flavonoid analogues were designed and synthesized. The aimed compounds for urease inhibitory activities were clearly superior to the control drug thiourea (more than 10 times). Among these compounds, L2 (IC₅₀ = 1.343 µM) and L12 (IC₅₀ = 1.207 µM) exhibited the most excellent urease inhibitory activity in vitro. The molecular dockings of L2, L12 and L22 into urease were performed to explore the binding modes and their structure-activity relationship. Furthermore, these aimed compounds showed good druggable properties.

  DOI：

  10.1016/j.bioorg.2020.104370
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 吡啶 、 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 66.0h， 生成 7-hydroxy-2-(2-thienyl)chromone
  参考文献：
  名称：

  黄酮8-乙酸的一些刚性类似物的合成和生物活性。

  摘要：

  描述了黄酮8-乙酸的一些刚性类似物。评估了合成化合物对四种肿瘤细胞系的直接体外毒性，并且还研究了这些化合物刺激培养物中小鼠腹膜巨噬细胞杀伤肿瘤的能力（间接毒性）。所有化合物仅在非常高的浓度下才能够诱导直接细胞毒性，但表现出显着的间接活性。特别地，化合物4d能够显着增加巨噬细胞的溶解特性，并且已经被选择用于进一步研究。

  DOI：

  10.1016/s0968-0896(99)00282-5

文献信息

• Synthesis and Biological Evaluation of (Thiophene-2-yl)-4H-Chromen-7-yl-Sulfonate Derivatives
  作者：Zhen Lv、Jialin Zang、Yushuang Xing、Jifang Yang、Ming Bu

  DOI：10.1134/s1068162021050368

  日期：2021.9

  the significant biological activity of our previously screened natural 4H-chromen, a series of novel (Thiophen-2-yl)-4H-chromen-7-yl-sulfonate derivatives (Va–Vi) were synthesized and investigated for their in vitro free radical scavenging potential as well as cytotoxic efficacies against selected cancer cell lines. The cytotoxicity of the 4H-chromen derivatives (Va–Vi) was evaluated according to three

  摘要 受我们先前筛选的天然 4 H-色烯显着生物活性的启发，合成了一系列新型 (Thiophen-2-yl)-4 H-色烯-7-基-磺酸盐衍生物 ( Va – Vi ) 并对其进行了研究。体外自由基清除能力以及对选定癌细胞系的细胞毒性作用。根据三种人类癌细胞系（HepG2、A549、HeLa），通过使用 MTT 测定来评估4 H-色烯衍生物 ( Va – Vi )的细胞毒性。因此，部分结果显示出比阳性对照（7-羟基-2-苯基-4 H -chromen-4-one, 4H -chromen-4-one 和芹菜素）。其中，化合物（Vc – Ve）对三种人类癌细胞系的阳性对照表现出更好的训练（IC 50 = 10.52 ± 0.39 μM 至 15.29 ± 0.35 μM）。此外，4 H-色烯衍生物 ( Va – Vi )的提取物对 2,2-diphenyl-1-picrylhydrazyl (DPPH)
• Synthesis and Antiproliferative Activity of Some Dihydro-1H-furo[2,3-c]pyrazole-Flavone Hybrids
  作者：Venkata Swamy Tangeti、D. Vasundhara、K.V.V.V. Satyanarayana、Kaja Srinivas Pavan Kumar

  DOI：10.14233/ajchem.2017.20550

  日期：——

  A new series of dihydro-1H-furo[2,3-c]pyrazole-flavone hybrids were synthesized from one-pot four-component reaction of b-keto ester (1), hydrazine (2), 7-hydroxy 8-formyl flavones (3), pyridiniumylide (4) in presence of NEt3 as catalyst under ethanol reflux conditions and their antiproliferative properties were evaluated against human cancer cell lines, namely, laryngeal carcinoma (Hep2), lung adenocarcinoma (A549) and cervical cancer (HeLa). The best among them, furo[2,3-c]pyrazole-flavone with C4-methoxy substitution was selected for further structure activity relationship (SAR) studies. Among the derivatives, (4S,5S)-ethyl 4-(7-hydroxy-5-methoxy-4-oxo-2-(2,4,6-trimethoxyphenyl)-4H-chromen-8-yl)-3-methyl-4,5-dihydro-1H-furo[2,3-c]pyrazole-5-carboxylate (8r) showed most potent cytotoxic activity against all three cancer cell lines. Toxicity studies revealed that the dihydro-1H-furo[2,3-c]pyrazole-flavones are specifically target the cancer cell lines.

  一系列二氢-1H-呋喃[2,3-c]吡唑-黄酮杂合物通过一锅四组分反应合成，反应物包括β-酮酯（1）、肼（2）、7-羟基-8-醛黄酮（3）和吡啶亚胺（4），在三乙胺（NEt3）催化下于乙醇回流条件下进行。随后评估了这些化合物对人类癌细胞系的抗增殖活性，包括喉癌（Hep2）、肺腺癌（A549）和宫颈癌（HeLa）。在这些化合物中，C4-取代的甲氧基二氢-1H-呋喃[2,3-c]吡唑-黄酮被选为进一步结构-活性关系（SAR）研究的对象。在这些衍生物中，(4S,5S)-乙基4-(7-羟基-5-甲氧基-4-氧基-2-(2,4,6-三甲氧基苯基)-4H-香豆烯-8-基)-3-甲基-4,5-二氢-1H-呋喃[2,3-c]吡唑-5-羧酸酯（8r）对所有三种癌细胞系表现出最强的细胞毒活性。毒性研究表明，二氢-1H-呋喃[2,3-c]吡唑-黄酮特别靶向癌细胞系。
• Synthesis and biological activity of some rigid analogues of flavone-8-acetic acid
  作者：Piero Valenti、Alessandra Bisi、Angela Rampa、Federica Belluti、Silvia Gobbi、Antonella Zampiron、Maria Carrara

  DOI：10.1016/s0968-0896(99)00282-5

  日期：2000.1

  Some rigid analogues of flavone-8-acetic acid are described. Direct in vitro toxicity of the synthesised compounds was evaluated towards four tumoral cell lines and the ability of these compounds to stimulate mouse peritoneal macrophages in culture to become tumoricidal (indirect toxicity) was also studied. All compounds were able to induce direct cytotoxicity only at very high concentrations but showed

  描述了黄酮8-乙酸的一些刚性类似物。评估了合成化合物对四种肿瘤细胞系的直接体外毒性，并且还研究了这些化合物刺激培养物中小鼠腹膜巨噬细胞杀伤肿瘤的能力（间接毒性）。所有化合物仅在非常高的浓度下才能够诱导直接细胞毒性，但表现出显着的间接活性。特别地，化合物4d能够显着增加巨噬细胞的溶解特性，并且已经被选择用于进一步研究。
• Flavonoid analogues as urease inhibitors: Synthesis, biological evaluation, molecular docking studies and in-silico ADME evaluation
  作者：Honghui Liu、Yan Wang、Mingxia Lv、Yi Luo、Bu-Ming Liu、Yan Huang、Mian Wang、Jianyi Wang

  DOI：10.1016/j.bioorg.2020.104370

  日期：2020.12

  A series of novel flavonoid analogues were designed and synthesized. The aimed compounds for urease inhibitory activities were clearly superior to the control drug thiourea (more than 10 times). Among these compounds, L2 (IC₅₀ = 1.343 µM) and L12 (IC₅₀ = 1.207 µM) exhibited the most excellent urease inhibitory activity in vitro. The molecular dockings of L2, L12 and L22 into urease were performed to explore the binding modes and their structure-activity relationship. Furthermore, these aimed compounds showed good druggable properties.