4-hydroxy-5,7-dimethoxy-2H-chromene-2-thione | 154114-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4-hydroxy-5,7-dimethoxy-2H-chromene-2-thione
• 英文别名: 4-hydroxy-5,7-dimethoxychromene-2-thion
• CAS: 154114-02-0
• 化学式: C₁₁H₁₀O₄S
• 分子量: 238.264
• InChiKey: SZYASTVHQIBCNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5,7-dimethoxy-2H-chromene-2-thione 在 potassium carbonate 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 29.0h， 生成 2-(4-benzylpiperazin-1-yl)-5,7-dimethoxy-4H-chromen-4-one
  参考文献：
  名称：

  Flavonoid derivatives as selective ABCC1 modulators: Synthesis and functional characterization

  摘要：

  A series of chromones, bearing substituted amino groups or N-substituted carboxamide moieties in position 2, was synthesized and characterized in cellular assays for modulation of the ABC transporters ABCC1 (MDCKII-MRP1 cells), ABCB1 (Kb-V1 cells) and ABCG2 (MCF-7/Topo cells). The most potent ABCC1 modulators identified among these flavonoid-type compounds were comparable to the reference compound reversan regarding potency, but superior in terms of selectivity concerning ABCB1 and ABCG2 (2-[4-(Benzo[c][1,2,5]oxadiazol-5-ylmethyl)piperazin-1-yl]-5,7-dimethoxy-4H-chromen-4-one (51): ABCC1, IC50 11.3 mu M; inactive at ABCB1 and ABCG2). Compound 51 was as effective as reversan in reverting ABCC1-mediated resistance to cytostatics in MDCKII-MRP1 cells and proved to be stable in mouse plasma and cell culture medium. Modulators, such as compound 51, are of potential value as pharmacological tools for the investigation of the (patho)physiological role of ABCC1. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.010
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 potassium tert-butylate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 16.0h， 生成 4-hydroxy-5,7-dimethoxy-2H-chromene-2-thione
  参考文献：
  名称：

  Flavonoid derivatives as selective ABCC1 modulators: Synthesis and functional characterization

  摘要：

  A series of chromones, bearing substituted amino groups or N-substituted carboxamide moieties in position 2, was synthesized and characterized in cellular assays for modulation of the ABC transporters ABCC1 (MDCKII-MRP1 cells), ABCB1 (Kb-V1 cells) and ABCG2 (MCF-7/Topo cells). The most potent ABCC1 modulators identified among these flavonoid-type compounds were comparable to the reference compound reversan regarding potency, but superior in terms of selectivity concerning ABCB1 and ABCG2 (2-[4-(Benzo[c][1,2,5]oxadiazol-5-ylmethyl)piperazin-1-yl]-5,7-dimethoxy-4H-chromen-4-one (51): ABCC1, IC50 11.3 mu M; inactive at ABCB1 and ABCG2). Compound 51 was as effective as reversan in reverting ABCC1-mediated resistance to cytostatics in MDCKII-MRP1 cells and proved to be stable in mouse plasma and cell culture medium. Modulators, such as compound 51, are of potential value as pharmacological tools for the investigation of the (patho)physiological role of ABCC1. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.010
• 作为试剂：
  描述：

  potassium tert-butylate 、 2-羟基-4,6-二甲氧基苯乙酮 、 carbon monosulfide 、 4-hydroxy-5,7-dimethoxy-2H-chromene-2-thione 、 potassium carbonate 、 碘甲烷 在 ice 、 甲苯 、 硫酸 、 水 、 4-hydroxy-5,7-dimethoxy-2H-chromene-2-thione 作用下， 以 甲苯 、 水 为溶剂， 反应 115.5h， 以under reduced pressure, whereby crude 5,7-dimethoxy-2-methylthiochromone, 146.8 g, was obtained的产率得到5,7-Dimethoxy-2-methylthiochromone
  参考文献：
  名称：

  Chromone derivative, and aldose reductase inhibitor comprising said

  摘要：

  本发明涉及一种染色酮衍生物和一种包含该化合物作为有效成分的醛还原酶抑制剂，其由以下公式表示：##STR1## 其中R.sub.1和R.sub.2分别表示较低的烷基等，R.sub.3表示氧原子、硫原子等，R.sub.7表示取代或未取代的苯基等，R表示氢原子或较低的烷氧基。该化合物表现出优异的醛还原酶抑制作用，可用于治疗糖尿病的各种并发症，如白内障、视网膜病变、角膜病变、肾病和神经病变。

  公开号：

  US05627204A1

文献信息

• CHROMONE DERIVATIVE AND ALDOSE REDUCTASE INHIBITOR CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：TSUMURA & CO.

  公开号：EP0516860A1

  公开（公告）日：1992-12-09

  A chromone derivative represented by general formula (I) and an aldose reductase inhibitor containing the same as the active ingredient wherein R₁ and R₂ represent each lower alkyl, etc.; R₃ represents oxygen, sulfur, etc.; R₇ represents (un)substituted phenyl, etc.; and R₄ represents hydrogen or lower alkoxy. This compound is excellent in the inhibition of aldose reductase and is useful for treating various complications accompanying diabetes.

  一种由通式(I)代表的铬酮衍生物和一种以其为活性成分的醛糖还原酶抑制剂，其中 R₁ 和 R₂ 分别代表低级烷基等；R₃ 代表氧、硫等；R₇ 代表（未）取代的苯基等；R₄ 代表氢或低级烷氧基。这种化合物对醛糖还原酶有很好的抑制作用，可用于治疗糖尿病的各种并发症。
• US5455267A
  申请人：——

  公开号：US5455267A

  公开（公告）日：1995-10-03
• US5521216A
  申请人：——

  公开号：US5521216A

  公开（公告）日：1996-05-28
• US5627204A
  申请人：——

  公开号：US5627204A

  公开（公告）日：1997-05-06
• US5675023A
  申请人：——

  公开号：US5675023A

  公开（公告）日：1997-10-07