5-ethyl-4-hydroxyisophthalaldehyde | 125895-96-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-ethyl-4-hydroxyisophthalaldehyde
• 英文别名: 5-Ethyl-4-hydroxybenzene-1,3-dicarbaldehyde；5-ethyl-4-hydroxybenzene-1,3-dicarbaldehyde
• CAS: 125895-96-7
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: SCFASGCYLVWYOU-UHFFFAOYSA-N

物化性质

• 沸点：
  288.5±40.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-ethyl-4-hydroxyisophthalaldehyde 在 碘 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.5h， 生成 (5-(bis(5-methoxy-1H-indol-3-yl)methyl)-7-ethylbenzofuran-2-yl)(4-methoxyphenyl)methanone
  参考文献：
  名称：

  Hybrid benzofuran–bisindole derivatives: New prototypes with promising anti-hyperlipidemic activities

  摘要：

  A series of different benzofuran bisindole hybrids were synthesized and evaluated in vitro for their antioxidant and in vivo for antidyslipidemic activity in triton WR-1339 induced hyperlipidemic rats. Among the series, compounds 4a, 4c, 4h and 4j showed significant decrease in plasma levels of total cholesterol (TC), phospholipids (PL) and triglycerides (TG) followed by increase in post heparin lipolytic activity (PHLA). In addition, the active hybrids possessed moderate antioxidant properties and increased the plasma lecithin cholesterol acyltransferase (LCAT) activity, which plays a key role in lipoprotein metabolism contributing to an increased level of HDL-C in serum. These results indicate that these hybrids constitute novel prototypes for the management of dyslipidemia. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.009
• 作为产物：
  描述：

  乙基苯酚 、 乌洛托品 在 三氟乙酸 、 硫酸 作用下， 反应 6.0h， 以69%的产率得到5-ethyl-4-hydroxyisophthalaldehyde
  参考文献：
  名称：

  苯并呋喃-二氢吡啶杂化物：一类新的潜在的骨合成代谢剂

  摘要：

  通过分子杂交方法设计了一系列新颖的苯并呋喃-二氢吡啶杂化物，并对其骨合成代谢活性进行了评估。在筛选的文库中，乙基4-（7-（仲丁基）-2-（4-甲基苯甲酰基）苯并呋喃-5-基）-2-甲基-5-氧代-1,4,5,6,7,8 -六氢喹啉-3-羧酸盐（化合物21）显着增强了ALP的产生和矿化的结节形成，这是体外成骨过程中的首要条件。以10 mg.kg -1 天-1的剂量口服化合物21持续两周，可通过显着增加BV / TV和Tb.N来恢复钻孔骨折模型中的小梁骨微结构。此外，组织学和分子研究表明21通过增加BMP表达在钻孔缺损部位触发新的骨再生。此外，进行了分子建模研究以深入了解结合方法，该研究表明苯并呋喃和二氢吡啶部分对于显示相似的结合相互作用以适应成骨剂的重要靶点BMP2受体的活性位点都是必不可少的。我们的结果表明，化合物21刺激成骨细胞中BMP2的合成，从而促进骨折部位新骨的形成（约40％），从而有助于缩短愈合时间。

  DOI：

  10.1016/j.bmc.2017.10.018

文献信息

• One-Pot Regioselective Synthesis of Imidazole and 2,3-Dihydroquinazolinone Derivatives - An Easy Access to ‘Nature-Like Molecules'; Part XIII in the Series: ‘Studies on Novel Synthetic Methodologies'
  作者：Koneni Sashidhara、Gopala Palnati、Ranga Dodda、Srinivasa Avula、Priyanka Swami

  DOI：10.1055/s-0033-1339466

  日期：——

  A mild and highly practical regioselective synthesis of imidazole and 2,3-dihydroquinazolinone derivatives from 5-alkyl-4-hydroxyisophthalaldehydes with suitable substrates in acetic acid is reported. Further exploration of the molecular diversity of 2,3-dihydroquinazolinone is demonstrated by the synthesis of diverse pharmacologically relevant natural-product-like scaffolds.

  报道了一种温和且高度实用的区域选择性合成咪唑和 2,3-二氢喹唑啉酮衍生物，由 5-烷基-4-羟基间苯二醛与合适的底物在乙酸中合成。2,3-二氢喹唑啉酮的分子多样性的进一步探索通过多种药理学相关的天然产物样支架的合成得到证明。
• Benzofuran-pyran hybrids: A new class of potential bone anabolic agents
  作者：Sampa Gupta、Sulekha Adhikary、Ram K. Modukuri、Dharmendra Choudhary、Ritu Trivedi、Koneni V. Sashidhara

  DOI：10.1016/j.bmcl.2018.04.041

  日期：2018.6

  analysis of these compounds on osteoblast cells revealed that compound 22 up-regulated the expression of osteogenic genes RUNX2, BMP-2, COL-1, thus substantiating that compound 22 having two geminal methyl groups in its R3 position is a potent osteogenic agent. Additionally, compound 22 enhanced the ability of bone marrow stromal cells to differentiate towards osteoblast lineage and therefore can be

  苯并呋喃部分是一种重要的药效团，对骨骼健康具有积极作用。在本研究中，合成了十六种苯并呋喃-吡喃杂化物，并评估了它们对从颅盖分离的原代成骨细胞的成骨作用。如通过碱性磷酸酶活性所评估的，发现化合物22和24在刺激成骨细胞分化方面是有效的。与MTT测定中的对照细胞相比，还发现这些化合物对成骨细胞无毒。此外，用于可视化钙结节的茜素红-S染色证实了化合物22和34在增强成骨细胞中的矿化作用方面发挥了积极作用。此外，这些化合物在成骨细胞上的转录分析表明，化合物22上调了成骨基因RUNX2，BMP-2，COL-1的表达，因此证实了在其R 3位具有两个双甲基的化合物22是有效的。成骨剂。另外，化合物22增强了骨髓基质细胞向成骨细胞谱系分化的能力，因此可以在体内在骨丢失模型中进行进一步研究。
• Synthesis and study of benzofuran-pyran analogs as BMP-2 targeted osteogenic agents
  作者：Pragati Kushwaha、Ashish Kumar Tripathi、Sampa Gupta、Priyanka Kothari、Akanksha Upadhyay、Naseer Ahmad、Tanuj Sharma、M.I. Siddiqi、Ritu Trivedi、Koneni V. Sashidhara

  DOI：10.1016/j.ejmech.2018.06.062

  日期：2018.8

  rat calvarial osteoblasts in vitro. Among all the compounds screened for the alkaline phosphatase activity, three compounds 4e, 4j and 4k showed potent activity at picomolar concentrations in osteoblast differentiating stimulation. Additionally, these compounds were found effective in mineralization, assessed by alizarin red-S staining assay. Compounds were again validated through a series of other in vitro

  二十四新颖苯并呋喃吡喃衍生物的合成和评价大鼠颅骨成骨细胞的初级培养物及其抗骨质疏松活性体外。在所有筛选出的碱性磷酸酶活性的化合物中，三种化合物4e，4j和4k在皮摩尔浓度下在成骨细胞分化刺激中均显示出有效的活性。另外，通过茜素红-S染色测定法评估发现这些化合物对矿化有效。化合物再次通过一系列其他体外验证实验。此外，分子动力学模拟表明，苯并呋喃和吡喃部分都必须适合BMP-2受体的活性位点，而BMP-2受体是成骨剂的关键靶标。所获得的结果有力地证明了化合物4e是合成系列中潜在的骨合成代谢剂，其可以作为治疗骨质疏松症的药物先导而进一步探索。
• Discovery of coumarin-dihydroquinazolinone analogs as niacin receptor 1 agonist with in-vivo anti-obesity efficacy
  作者：L. Ravithej Singh、Ajeet Kumar、Akanksha Upadhyay、Sampa Gupta、Gopala Reddy Palanati、Kamakshi Sikka、Mohammad Imran Siddiqi、Prem N. Yadav、Koneni V. Sashidhara

  DOI：10.1016/j.ejmech.2018.04.037

  日期：2018.5

  In this study, we presented rational designing and synthesis of coumarin-dihydroquinazolinone conjugates to evaluate their agonist activity at GPR109a receptor. Among the synthesized small molecule library, compound 10c displayed robust agonist action at GPR109a with EC50 < 11 nM. Homology model of human GPR109a protein was generated to realize the binding interaction of the active molecule with the active site of GPR109a. Further, the efficacy of active compound 10c was supported by in -vivo experiments which showed reduced body weight in diet induced obese mice model. Interestingly, compound 10c reduced leptin in blood plasma and total serum cholesterol. These results suggest that the coumarin-dihydroquinazolinone conjugate is a suitable scaffold to further expand the chemical diversity and make them potential niacin receptor 1 agonist. (C) 2018 Elsevier Masson SAS. All rights reserved.
• A new iodine catalyzed regioselective synthesis of xanthene synthons
  作者：Koneni V. Sashidhara、Abdhesh Kumar、Ranga Prasad Dodda、Bikash Kumar

  DOI：10.1016/j.tetlet.2012.04.061

  日期：2012.6

  This Letter describes the iodine catalyzed one-pot regioselective synthesis of p-condensed xanthenes as our key point of transformation, which provides an efficient access to five skeletally diverse scaffolds in excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.