ethyl 8-sec-butyl-6-formyl-2-oxo-2H-chromene-3-carboxylate | 1257865-16-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: ethyl 8-sec-butyl-6-formyl-2-oxo-2H-chromene-3-carboxylate
• 英文别名: ethyl 8-butan-2-yl-6-formyl-2-oxochromene-3-carboxylate
• CAS: 1257865-16-9
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: FRPHYYLLKHLMOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 8-sec-butyl-6-formyl-2-oxo-2H-chromene-3-carboxylate 在 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 、 乙醇 为溶剂， 反应 9.0h， 生成 ethyl 4-(8-sec-butyl-3-(ethoxycarbonyl)-2-oxo-2H-chromen-6-yl)-2,7,7-trimethyl-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-仲丁基苯酚 在 哌啶 、 乌洛托品 作用下， 以 乙醇 为溶剂， 生成 ethyl 8-sec-butyl-6-formyl-2-oxo-2H-chromene-3-carboxylate
  参考文献：
  名称：

  香豆素-咪唑并[1,2- a ]吡啶衍生物的 设计，合成及体外评价抗癌性骨质疏松症†

  摘要：

  利用银（I）催化的Groebke-Blackburn-Bienayme多组分反应合成了一系列具有重要生物学意义的6-（咪唑并[1,2 - a ]吡啶-2-基）-2 H -chromen-2-one衍生物。通过碱性磷酸酶测定法和茜素红-S染色测定法在原发性颅盖骨成骨细胞中测试了合成的化合物的可能的骨保护特性。此外，通过qPCR测量活性化合物6h，6l和6o对成骨基因BMP2，RUNX2，COL1和OCN表达的影响。在三种有前途的化合物中，每升6升6a和6o通过线粒体去极化显着诱导了MDA-MB-231癌细胞的凋亡，而不影响正常细胞。在体外骨转移共培养模型中，我们研究了香豆素-咪唑并[1,2- a ]吡啶杂化物逆转MDA-MB-231癌细胞对成骨细胞分化的负面影响的能力。结果说明了设计的杂交体重建骨骼稳态的潜力。这些发现证明了新合成的杂种作为先导分子的重要性，既具有抗骨质疏松性又具有抗癌性，可

  DOI：

  10.1039/c6ra15674f
• 作为试剂：
  描述：

  5-sec-butyl-4-hydroxybenzene-1,3-dicarbaldehyde 、 丙二酸二乙酯 、 哌啶 在 水 、 氯仿 、 Sodium sulfate-III 、 silica gel 、 乙酸乙酯 、 正己烷 、 ethyl 8-sec-butyl-6-formyl-2-oxo-2H-chromene-3-carboxylate 作用下， 以 乙醇 为溶剂， 以provides ethyl 8-sec-butyl-6-formyl-2-oxo-2H-chromene-3-carboxylate (General Formula II)的产率得到ethyl 8-sec-butyl-6-formyl-2-oxo-2H-chromene-3-carboxylate
  参考文献：
  名称：

  Coumarin-chalcones as anticancer agents

  摘要：

  本发明涉及某些香豆素/查尔酮化合物或其药学上可接受的盐。本发明特别涉及香豆素/查尔酮化合物作为抗癌剂，用于治疗癌症。本发明还涉及所述化合物的制备方法。

  公开号：

  US08815940B2

文献信息

• Coumarin–trioxane hybrids: Synthesis and evaluation as a new class of antimalarial scaffolds
  作者：Koneni V. Sashidhara、Abdhesh Kumar、Ranga Prasad Dodda、Naikade Niraj Krishna、Pooja Agarwal、Kumkum Srivastava、S.K. Puri

  DOI：10.1016/j.bmcl.2012.04.100

  日期：2012.6

  First synthesis of novel coumarin–trioxane hybrids is reported. The synthesis was achieved via condensation of β-hydroxyhydroperoxides with coumarinic-aldehydes in presence of p-toluenesulfonic acid in good yields and the novel hybrids were evaluated for their antimalarial activity both in vitro and in vivo.

  据报道，首次合成了新型香豆素-三恶烷杂化物。在对甲苯磺酸的存在下，通过β-羟基氢过氧化物与香豆醛-醛的缩合可实现高收率，并在体外和体内评估了新型杂种的抗疟活性。
• [EN] COUMARIN-CHALCONES AS ANTICANCER AGENTS<br/>[FR] COUMARINE-CHALCONES EN TANT QU'AGENTS ANTICANCÉREUX
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2012017454A1

  公开（公告）日：2012-02-09

  The present invention relates to certain coumarin/chalcone compounds or a pharmaceutically acceptable salt thereof. The present invention particularly relates to the coumarin/chalcone compounds as anticancer agents useful for the treatment of cancer. The present invention also relates to the process of preparation of the said compounds.

  本发明涉及某些香豆素/香根素化合物或其药用可接受的盐。本发明特别涉及香豆素/香根素化合物作为抗癌剂，用于治疗癌症。本发明还涉及所述化合物的制备过程。
• COUMARIN-CHALCONES AS ANTICANCER AGENTS
  申请人：Sashidhara Koneni Venkata

  公开号：US20130210909A1

  公开（公告）日：2013-08-15

  The present invention relates to certain coumarin/chalcone compounds or a pharmaceutically acceptable salt thereof. The present invention particularly relates to the coumarin/chalcone compounds as anticancer agents useful for the treatment of cancer. The present invention also relates to the process of preparation of the said compounds.

  本发明涉及某些香豆素/香草醛化合物或其药用盐。本发明特别涉及香豆素/香草醛化合物作为抗癌药物，用于治疗癌症。本发明还涉及所述化合物的制备过程。
• Synthesis and antihyperlipidemic activity of novel coumarin bisindole derivatives
  作者：Koneni V. Sashidhara、Abdhesh Kumar、Manoj Kumar、Anuj Srivastava、Anju Puri

  DOI：10.1016/j.bmcl.2010.09.055

  日期：2010.11

  A series of novel coumarin bisindole heterocycles were synthesized following an uncommon method and evaluated for their antihyperlipidemic activity in hyperlipidemic hamster model. Among 12 compounds tested, the compound 5e showed potent antihyperlipidemic activity and was found to decrease the plasma triglyceride levels (TG) by 55%, total cholesterol (TC) by 20%, accompanied by an increase in HDL-C/TC ratio by 42% in hyperlipidemic rats to a greater degree than some of the reference statins. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and in vitro evaluation of novel coumarin–chalcone hybrids as potential anticancer agents
  作者：Koneni V. Sashidhara、Abdhesh Kumar、Manoj Kumar、Jayanta Sarkar、Sudhir Sinha

  DOI：10.1016/j.bmcl.2010.10.116

  日期：2010.12

  A series of coumarin-chalcone hybrids have been synthesized and evaluated for their in vitro cytotoxicity against a panel of four human cancer cell lines and normal fibroblasts (NIH3T3). Among 21 compounds screened, three compounds (23, 25 and 26) showed IC50 range from 3.59 to 8.12 mu M. The most promising compound 26 showed around 30-fold more selectivity towards C33A (cervical carcinoma) cells over normal fibroblast NIH3T3 cells with an IC50 value of 3.59 mu M. (C) 2010 Elsevier Ltd. All rights reserved.