3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-4H-1-benzopyran-4-one

• 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: 3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-4H-1-benzopyran-4-one
• 英文别名: 3-(5-methyl-1,3,4-thiadiazol-2-ylthio)-4H-chromen-4-one；3-[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]chromen-4-one
• 化学式: C₁₂H₈N₂O₂S₂
• 分子量: 276.34
• InChiKey: NFTAEOPPZXFATP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-氨基咪唑 、 3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-4H-1-benzopyran-4-one 在 sodium methylate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以78%的产率得到2-{6-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]imidazo[1,2-a]pyrimidin-5-yl}phenol
  参考文献：
  名称：

  含硫醚和芳基部分的新型双取代吡唑并[1,5-a]嘧啶，咪唑并[1,2-a]嘧啶和嘧啶并[1,2-a]苯并咪唑的合成

  摘要：

  一系列新颖的6-[（（1,3,4-噻二唑-2-基）硫烷基] -7-苯基吡唑并[1,5- a ]嘧啶，5-苯基-6-[（1,3,4-噻二唑）吡啶-2-基）硫基]咪唑并[1,2一]嘧啶，和2-苯基-3 - [（1,3,4-噻二唑-2-基）硫基]嘧啶并[1,2一]苯并咪唑有从2-羟基苯乙酮开始的四步合成。中间体3 [[（1,3,4-噻二唑-2-基）硫烷基] -4 H -1-苯并吡喃-4-酮与吡唑-3-胺，5-甲基吡唑-3-胺和1 H反应咪唑-2-胺，1 H苯并咪唑-2-胺通过在MeONa作为碱的存在下，经环缩合得到标题化合物。该方法以可接受的到良好的产率提供目标化合物。这些新化合物的IR，NMR和HR质谱图进行了表征。

  DOI：

  10.1002/hlca.201100495
• 作为产物：
  描述：

  1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone 在 potassium tert-butylate 、 碘 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-4H-1-benzopyran-4-one
  参考文献：
  名称：

  含硫醚和芳基部分的新型双取代吡唑并[1,5-a]嘧啶，咪唑并[1,2-a]嘧啶和嘧啶并[1,2-a]苯并咪唑的合成

  摘要：

  一系列新颖的6-[（（1,3,4-噻二唑-2-基）硫烷基] -7-苯基吡唑并[1,5- a ]嘧啶，5-苯基-6-[（1,3,4-噻二唑）吡啶-2-基）硫基]咪唑并[1,2一]嘧啶，和2-苯基-3 - [（1,3,4-噻二唑-2-基）硫基]嘧啶并[1,2一]苯并咪唑有从2-羟基苯乙酮开始的四步合成。中间体3 [[（1,3,4-噻二唑-2-基）硫烷基] -4 H -1-苯并吡喃-4-酮与吡唑-3-胺，5-甲基吡唑-3-胺和1 H反应咪唑-2-胺，1 H苯并咪唑-2-胺通过在MeONa作为碱的存在下，经环缩合得到标题化合物。该方法以可接受的到良好的产率提供目标化合物。这些新化合物的IR，NMR和HR质谱图进行了表征。

  DOI：

  10.1002/hlca.201100495

文献信息

• Design, syntheses, and antitumor activity of novel chromone and aurone derivatives
  作者：Wei Huang、Ming-Zhen Liu、Yan Li、Ying Tan、Guang-Fu Yang

  DOI：10.1016/j.bmc.2007.05.022

  日期：2007.8

  A series of new chromone analogues bearing heterocyclic thioether moiety and aurone analogues bearing cyclic tertiary amine moiety were designed and synthesized under microwave irradiation. The synthetic protocol was found to present many advantages, such as higher yields, shorter reaction time (10-20 min), mild condition, and readily isolation of the products. The synthesized compounds were assayed for their antitumor activity against four kinds of human solid tumor cell lines including HCCLM-7, Hep-2, MDA-MB-435S, and SW-480. Two compounds, (Z)-2-((4-benzyl-piperazin-1-yl)methylene)benzofuran-3(2H)-one 5e and (Z)-2-((4-(bis(4-fluorophenyl)methylene)piperazin-1-yl)methylene)benzofuran-3(2H)-one 5f, were identified as the most promising candidates with the IC50 values in the range of 4.1-13.1 mu M. Further cell cycle studies revealed that compounds 5e and 5f arrest the cell cycle in G(0)/G(1) phase and displayed apoptosis-inducing effect on Hep-2 cells. (c) 2007 Elsevier Ltd. All rights reserved.
• Efficient synthesis and antiproliferative activity of novel thioether-substituted flavonoids
  作者：Wei Huang、Qiong Chen、Wen-Chao Yang、Guang-Fu Yang

  DOI：10.1016/j.ejmech.2013.05.037

  日期：2013.8

  As widely occurring natural products, flavonoids are an important source for drug discovery, due to their structural diversity and broad-spectrum biological activity. In this work, a library of novel, thioether-substituted flavonoids with diverse heterocyclic groups was synthesized via a microwave-assisted procedure with the advantages of good yields, short times, mild conditions and ready isolation of the products. Their antiproliferative activities were evaluated against six cancer cell lines, HCCLM-7, Hela, MDA-MB-435S, SW-480, Hep-2, and MCF-7 by the MU-based assay. Compared with the positive control 5-fluorouracil, three compounds, 6a, 6b and 6j were successfully identified as the most promising candidates, due to their higher potency and broad-spectrum bioactivity with IC50 values in the range of 0.43 mu M-6.7 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis of Novel Disubstituted Pyrazolo[1,5-a]pyrimidines, Imidazo[1,2-a]pyrimidines, and Pyrimido[1,2-a]benzimidazoles Containing Thioether and Aryl Moieties
  作者：Gang Li、Zun-Ting Zhang、Li-Yan Dai、Yin-Li Du、Dong Xue

  DOI：10.1002/hlca.201100495

  日期：2012.6

  A series of novel 6‐[(1,3,4‐thiadiazol‐2‐yl)sulfanyl]‐7‐phenylpyrazolo[1,5‐a]pyrimidines, 5‐phenyl‐6‐[(1,3,4‐thiadiazol‐2‐yl)sulfanyl]imidazo[1,2‐a]pyrimidines, and 2‐phenyl‐3‐[(1,3,4‐thiadiazol‐2‐yl)sulfanyl]pyrimido[1,2‐a]benzimidazoles have been synthesized in four steps starting with 2‐hydroxyacetophenone. The intermediate 3‐[(1,3,4‐thiadiazol‐2‐yl)sulfanyl]‐4H‐1‐benzopyran‐4‐ones reacted with

  一系列新颖的6-[（（1,3,4-噻二唑-2-基）硫烷基] -7-苯基吡唑并[1,5- a ]嘧啶，5-苯基-6-[（1,3,4-噻二唑）吡啶-2-基）硫基]咪唑并[1,2一]嘧啶，和2-苯基-3 - [（1,3,4-噻二唑-2-基）硫基]嘧啶并[1,2一]苯并咪唑有从2-羟基苯乙酮开始的四步合成。中间体3 [[（1,3,4-噻二唑-2-基）硫烷基] -4 H -1-苯并吡喃-4-酮与吡唑-3-胺，5-甲基吡唑-3-胺和1 H反应咪唑-2-胺，1 H苯并咪唑-2-胺通过在MeONa作为碱的存在下，经环缩合得到标题化合物。该方法以可接受的到良好的产率提供目标化合物。这些新化合物的IR，NMR和HR质谱图进行了表征。