4-hydroxy-5-propylisophthalaldehyde | 1357466-05-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-5-propylisophthalaldehyde
• 英文别名: 4-Hydroxy-5-propylbenzene-1,3-dicarbaldehyde；4-hydroxy-5-propylbenzene-1,3-dicarbaldehyde
• CAS: 1357466-05-7
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: DTWKNWFSKHKJET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  4-hydroxy-5-propylisophthalaldehyde 在 哌啶 、 ammonium acetate 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 9.0h， 生成 ethyl 4-(3-(ethoxycarbonyl)-2-oxo-8-propyl-2H-chromen-6-yl)-2-methyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of new coumarin–pyridine hybrids with promising anti-osteoporotic activities

  摘要：

  Anti-osteoporotic effects of the newly synthesized coumarin pyridine hybrids were evaluated in primary cultures of rat calvarial osteoblasts in vitro. Compounds 6a, i, j and k were potent in stimulating osteoblast differentiation and mineralization as assessed by the alkaline phosphatase production and alizarin red-S staining assay, respectively. These compounds were also found to be nontoxic in osteoblast cells as compared to the control group in an MTT assay. Furthermore, the effect of these compounds on the transcript levels of osteogenic genes revealed that the compound 6j robustly enhanced mineralization of the osteogenic genes in calvarial osteoblasts. In this context, compound 6j was selected as a potential lead for further structural optimization in the development of new anti-osteoporotic agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.060
• 作为产物：
  描述：

  2-正丙基苯酚 、 乌洛托品 在 三氟乙酸 、 硫酸 作用下， 以 水 为溶剂， 反应 6.0h， 生成 4-hydroxy-5-propylisophthalaldehyde
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new quinazolinone-benzopyran-indole hybrid compounds promoting osteogenesis through BMP2 upregulation

  摘要：

  DOI：

  10.1016/j.ejmech.2022.114813

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。
• 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.
• Hybrid benzofuran–bisindole derivatives: New prototypes with promising anti-hyperlipidemic activities
  作者：Koneni V. Sashidhara、Ram K. Modukuri、Ravi Sonkar、K. Bhaskara Rao、Gitika Bhatia

  DOI：10.1016/j.ejmech.2013.07.009

  日期：2013.10

  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.
• Synthesis and antifilarial activity of chalcone–thiazole derivatives against a human lymphatic filarial parasite, Brugia malayi
  作者：Koneni V. Sashidhara、K. Bhaskara Rao、Vikas Kushwaha、Ram K. Modukuri、Richa Verma、P.K. Murthy

  DOI：10.1016/j.ejmech.2014.05.029

  日期：2014.6

  Here we report the synthesis of novel chalcone thiazole compounds and their antifilarial activity. The antifilarial properties of these hybrids were assessed against microfilariae as well as adult worms of Brugia malayi. Among all the synthesized compounds, only two compounds, namely 4g and 4n were identified to be promising in vitro. These active compounds were tested in B. malayi-jird (Meriones unguiculatus) and B. malayi-Mastomys coucha models. Compound 4n showed 100% embryostatic effect and 49% macrofilaricidal in jirds and M. coucha models, respectively. This study provides a new structural clue for the development of novel antifilarial lead molecules. (C) 2014 Elsevier Masson SAS. All rights reserved.