5,7-bis(benzyloxy)-4-oxo-4H-chromene-3-carbaldehyde | 1227277-42-0

• 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: 5,7-bis(benzyloxy)-4-oxo-4H-chromene-3-carbaldehyde
• 英文别名: 4-Oxo-5,7-bis(phenylmethoxy)chromene-3-carbaldehyde
• CAS: 1227277-42-0
• 化学式: C₂₄H₁₈O₅
• 分子量: 386.404
• InChiKey: AZHOHGXOQXNFBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7-bis(benzyloxy)-4-oxo-4H-chromene-3-carbaldehyde 在 aluminum oxide 作用下， 以 异丙醇 为溶剂， 反应 4.0h， 以68%的产率得到5,7-bis(benzyloxy)-3-(hydroxymethyl)-4H-chromen-4-one
  参考文献：
  名称：

  一系列新型的双酚色酮衍生物作为LPS活化的RAW264.7巨噬细胞中NO生成的抑制剂的合成

  摘要：

  合成了一系列新的双酚色酮衍生物，并分别通过LPS激活的鼠巨噬细胞RAW264.7测定和MTT方法评估了它们对一氧化氮（NO）产生的抑制活性和细胞毒性。在这些化合物中，（5,7-二羟基-4-氧代-4 H-铬烯-3-基）甲基酯（6b，6c，6f，6g和6h）具有很强的抑制活性，IC 50值为2.20，分别为3.48、0.35、0.80和0.61μM。MTT结果表明，在有效浓度下，所有活性化合物均未显示出细胞毒性。最有效化合物的初步机理（6b，基于RT-PCR结果进一步检查了6c，6f，6g和6h），并且化合物6f，6g和6h通过以剂量依赖性方式抑制iNOS mRNA的表达来抑制NO产生。此外，对理化参数的计算分析表明，大多数化合物具有类似药物的特性。

  DOI：

  10.1016/j.bmc.2010.03.020
• 作为产物：
  描述：

  氯化苄 在 六甲基磷酰三胺 、 potassium carbonate 、 三氯氧磷 作用下， 反应 3.0h， 生成 5,7-bis(benzyloxy)-4-oxo-4H-chromene-3-carbaldehyde
  参考文献：
  名称：

  Neochromine S5 improves contact hypersensitivity through a selective effect on activated T lymphocytes

  摘要：

  Strategy on activated T cells is an effective treatment for T cell mediated diseases. By using a synthesized chromone derivative, we examined its effects on the activated T cells. This compound, (Z)-1,3-dihydroxy-9-methyl-1,3H-benzo[b]chromeno[3,2-f][1,4]oxazepin-13-one (neochromine S5), exhibited immunosuppressive activity in vitro and in vivo. Interestingly, neochromine S5 selectively inhibited proliferation and induced apoptosis in T lymphocytes activated by concanavalin A (Con A) in a dose-dependent manner but not in naive T lymphocytes, distinct from quercetin. This compound triggered mitochondrial apoptotic pathway including cleavage of caspase 3, caspase 9 and PARP, downregulation of bc1-2 and release of cytochrome c in activated T cells, but did not affect ER stress or Fas signals. In addition, neochromine S5 downregulated the expression of CD25 and CD69 and the production of inflammatory cytokines, including TNF alpha, IFN-gamma and IL-2, improved ear swelling in mice with contact hypersensitivity, reduced CD4(+) T cells infiltration, and increased apoptosis of isolated T lymphocytes from peripheral lymph nodes. Moreover, neochromine S5 showed no effect on the weight of mice and their immune organs, while dexamethasone caused a significant weight loss. Taken together, our results suggest that neochromine S5 exerts a unique anti-inflammatory activity mainly through a selective effect on.activated T cells, which.is different from the current immunosuppressant, dexamethasone. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2014.08.032