7-hydroxy-4-methyl-2-oxo-2H-benzo[h]chromen-8,10-dicarbaldehyde | 933774-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 7-hydroxy-4-methyl-2-oxo-2H-benzo[h]chromen-8,10-dicarbaldehyde
• 英文别名: 7-hydroxy-4-methyl-2-oxo-benzo[h]chromene-8,10-dicarbaldehyde；7-hydroxy-4-methyl-2-oxo-2H-benzo[h]chromene-8,10-dicarbaldehyde；7-Hydroxy-4-methyl-2-oxobenzo[h]chromene-8,10-dicarbaldehyde
• CAS: 933774-89-1
• 化学式: C₁₆H₁₀O₅
• 分子量: 282.252
• InChiKey: LJBPKOBXLMKECX-UHFFFAOYSA-N

物化性质

• 熔点：
  204 °C
• 沸点：
  536.6±50.0 °C(predicted)
• 密度：
  1.478±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-hydroxy-4-methyl-2-oxo-2H-benzo[h]chromen-8,10-dicarbaldehyde 在 哌啶 、 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 5.5h， 生成 (E)-methyl 7-methyl-3,9-dioxo-11-(3-oxo-3-(thiophen-2-yl)prop-1-enyl)-3,9-dihydrochromeno[8,7-h]chromene-2-carboxylate
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of novel biscoumarin–chalcone hybrids

  摘要：

  A series of synthesized novel biscoumarin-chalcone hybrids were evaluated for their anti-inflammatory and antioxidant activity. The tested compounds significantly inhibit the carrageenin induced paw oedema in albino rats and also exhibit important scavenging activities. These compounds thus constitute an interesting template for the design of new therapeutic tools against inflammation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.002
• 作为产物：
  描述：

  4-methyl-2,7-dioxo-8-propylaminomethylene-7,8-dihydro-2H-benzo[h]chromene-10-carbaldehyde 在 sodium azide 、 N,N-二甲基甲酰胺 作用下， 反应 3.0h， 以72%的产率得到7-hydroxy-4-methyl-2-oxo-2H-benzo[h]chromen-8,10-dicarbaldehyde
  参考文献：
  名称：

  New Protocol for Masking and Unmasking Vicinal Hydroxyl and Formyl Groups in 6-Hydroxyarene-1,3-dicarboxaldehydes

  摘要：

  A simple and efficient protocol is revealed for the masking and unmasking of an -hydroxyl benzaldedyde group in aromatic dialdehydes by forming keto-enamine Schiff bases and subsequent unmasking using NaN3/DMF.

  DOI：

  10.1080/00397910802593096

文献信息

• Discovery and synthesis of novel substituted benzocoumarins as orally active lipid modulating agents
  作者：Koneni V. Sashidhara、Manoj Kumar、Ram K. Modukuri、Anuj Srivastava、Anju Puri

  DOI：10.1016/j.bmcl.2011.09.053

  日期：2011.11

  The synthesis of a series of benzocoumarin keto-enamine schiff bases is reported. The novel compounds were evaluated for their antihyperlipidemic activity in the hyperlipidemic hamster model. The compound 11 at a dose of 10 mg/kg body weight significantly lowered the plasma triglyceride levels (TG) by 70%, total cholesterol (TC) by 47%, accompanied by an increase in HDL-C/TC ratio by 80% in hyperlipidemic hamsters to a greater degree than the reference drugs atorvastatin and lovastatin. (C) 2011 Elsevier Ltd. All rights reserved.
• Highly efficient and regioselective synthesis of keto-enamine Schiff bases of 7-hydroxy-4-methyl-2-oxo-2H-benzo[h]chromene-8,10-dicarbaldehyde and 1-hydroxynaphthalene-2,4-dicarbaldehyde
  作者：Koneni V. Sashidhara、Jammikuntla N. Rosaiah、Tadigoppula Narender

  DOI：10.1016/j.tetlet.2007.01.044

  日期：2007.3

  A series of novel Schiff bases has been synthesized by reacting 7-hydroxy-4-methyl-2-oxo-2H-benzo[h]chromene-8,10-dicarbaldehyde 3 and 1-hydroxynaphthalene-2,4-dicarbaldehyde 8 with several primary alkylamines in ethyl alcohol at room temperature within 1-2 min. Schiff bases 4a-i and 9 were formed regioselectively by condensation with only one aldehyde, which is in chelation with a hydroxyl group. Extensive 2D NMR spectroscopic studies revealed that all the compounds 4a-i and 9 exist in the keto-enamine tautomeric form at room temperature. The high reactivity, regioselectivity and stable keto-enamine tautomeric form are due to the presence of an electron-withdrawing aldehyde group. (c) 2007 Elsevier Ltd. All rights reserved.
• Neo-tanshinlactone inspired synthesis, in vitro evaluation of novel substituted benzocoumarin derivatives as potent anti-breast cancer agents
  作者：Koneni V. Sashidhara、Jammikuntla N. Rosaiah、Manoj Kumar、Rishi Kumar Gara、Lakshma Vadithe Nayak、Kamini Srivastava、Hemant Kumar Bid、Rituraj Konwar

  DOI：10.1016/j.bmcl.2010.09.040

  日期：2010.12

  A small library of novel benzocoumarin derivatives based on naturally occurring neo-tanshinlactone scaffold was constructed and their antiproliferative activities against breast cancer cells MCF-7 and MDA-MB-231 were evaluated. A number of derivatives showed good anti-breast cancer activity, in some cases higher to that of the reference compound tamoxifen. In particular, benzocoumarins Bc-5, Bc-8 and Bc-9 strongly inhibited the proliferation of MCF-7 cancer cell line with the IC50 values of 3.8, 7.9 and 6.5 mu M, respectively. The compounds were capable of inducing nuclear fragmentation, cell cycle arrest and caspase dependent apoptosis in MCF-7 cell lines. In addition, these derivatives were devoid of cytotoxic effect against normal osteoblast cells. These synthetic benzocoumarins hold promises for developing safer alternative to the existing anti-breast cancer agents. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and anti-inflammatory activity of novel biscoumarin–chalcone hybrids
  作者：Koneni V. Sashidhara、Manoj Kumar、Ram K. Modukuri、Ravi Sonkar、Gitika Bhatia、A.K. Khanna、Shivika Rai、Rakesh Shukla

  DOI：10.1016/j.bmcl.2011.06.002

  日期：2011.8

  A series of synthesized novel biscoumarin-chalcone hybrids were evaluated for their anti-inflammatory and antioxidant activity. The tested compounds significantly inhibit the carrageenin induced paw oedema in albino rats and also exhibit important scavenging activities. These compounds thus constitute an interesting template for the design of new therapeutic tools against inflammation. (C) 2011 Elsevier Ltd. All rights reserved.
• New Protocol for Masking and Unmasking Vicinal Hydroxyl and Formyl Groups in 6-Hydroxyarene-1,3-dicarboxaldehydes
  作者：Koneni V. Sashidhara、Jammikuntla N. Rosaiah、Abdhesh Kumar

  DOI：10.1080/00397910802593096

  日期：2009.4.22

  A simple and efficient protocol is revealed for the masking and unmasking of an -hydroxyl benzaldedyde group in aromatic dialdehydes by forming keto-enamine Schiff bases and subsequent unmasking using NaN3/DMF.