7-羟基-4-丙基-2H-色烯-2-酮 | 19225-02-6

• 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
• 中文名称: 7-羟基-4-丙基-2H-色烯-2-酮
• 英文名称: 4-propyl-umbelliferone
• 英文别名: 7-hydroxy-4-propyl-2H-chromen-2-one；7-hydroxy-4-propylcoumarin；7-hydroxy-4-propyl-2H-1-benzopyran-2-one；7-hydroxy-4-propylchromen-2-one
• CAS: 19225-02-6
• 化学式: C₁₂H₁₂O₃
• mdl: MFCD00052608
• 分子量: 204.225
• InChiKey: GQJVOVBBBZRUBH-UHFFFAOYSA-N

物化性质

• 熔点：
  135-137°C
• 沸点：
  390.9±37.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  7-羟基-4-丙基-2H-色烯-2-酮 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 7-(4-(4-(6-fluorobenzoisoxazol-3-yl)-1-piperidyl)-n-butoxy)-4-n-propyl-2H-benzopyran-2-one
  参考文献：
  名称：

  Synthesis and Biological Investigation of Coumarin Piperazine (Piperidine) Derivatives as Potential Multireceptor Atypical Antipsychotics

  摘要：

  The discovery and synthesis of potential and novel antipsychotic coumarin derivatives, associated with potent dopamine 132, D3, and serotonin S-HT1A and S-HT2A, receptor properties, are the focus of the present article. The most-promising derivative was 7-(4-(4-(6-fluorobenzo[d]-isoxazol-3-yl)-piperidin-1-yl)butoxy)-4-methyl-8-chloro-2H- chromen-2-one (17m). This derivative possesses unique pharmacological features, including high affinity for dopamine D-2 and D-3 and serotonin S-HT1A and 5-HT2A receptors. Moreover, it possesses low affinity for S-HT2C and H-1 receptors (to reduce the risk of obesity associated with chronic treatment) and hERG channels (to reduce the incidence of torsade des pointes). In animal models, compound 17m inhibited apomorphine-induced climbing behavior, MK-801-induced hyperactivity, and the conditioned avoidance response without observable catalepsy at the highest dose tested. Further, fewer preclinical adverse events were noted with 17m compared with risperidone in assays that measured prolactin secretion and weight gain. Acceptable pharmacokinetic properties were also noted with 17m. Taken together, 17m may constitute a novel class of drugs for the treatment of schizophrenia.

  DOI：

  10.1021/jm400408r
• 作为产物：
  描述：

  丁酰乙酸乙酯 生成 7-羟基-4-丙基-2H-色烯-2-酮
  参考文献：
  名称：

  Compound

  摘要：

  描述了一种化合物。具体来说，描述了一种非甾体磺酸酯化合物。该化合物适用于用作雌二醇磺酸酯酶的抑制剂。该化合物具有一般式(A)，其中R1-R6分别选自H、卤素、羟基、磺酸酯、烷基和其取代体或盐，但至少其中一个是磺酸酯基团；X是S、NH、取代的N、CH2或取代的C中的任意一个。

  公开号：

  US06921776B1

文献信息

• Synthesis of dipeptide derivatives of 3,4-substituted 7-hydroxycoumarins
  作者：S. V. Shilin、M. M. Garazd、V. P. Khilya

  DOI：10.1007/s10600-008-9047-6

  日期：2008.5

  Coumarins modified with dipeptides were prepared by condensation of N-hydroxysuccinimide esters of 2-(3,4,8-substituted-2-oxo-2H-7-chromenyloxy)-and 2-(3,4-substituted-7-methyl-2-oxo-2H-5-chromenyloxy)acetic and-propionic acids with amino acids and dipeptides.

  通过将2-(3,4,8-取代-2-氧代-2H-7-色烯氧基)-和2-(3,4-取代-7-甲基-2-氧代-2H-5-色烯氧基)乙酸和丙酸的N-羟基琥珀酰亚胺酯与氨基酸和二肽缩合，制备了经二肽修饰的香豆素。
• 7-(2-Oxoalkoxy)coumarins: Synthesis and Anti-Inflammatory Activity of a Series of Substituted Coumarins
  作者：Juri Timonen、Katriina Vuolteenaho、Tiina Leppänen、Riina Nieminen、Eeva Moilanen、Paula Aulaskari、Janne Jänis

  DOI：10.1002/jhet.2173

  日期：2015.9

  A series of 7‐(2‐oxoalkoxy)coumarins have been synthesized by conjugating substituted 7‐hydroxycoumarins with different chloroketones. The anti‐inflammatory properties of 7‐(2‐oxoalkoxy)coumarins were studied in LPS‐induced inflammatory response in J774 macrophages. Western blot was used to determine the expression of iNOS and COX‐2, NO was determined by measuring its metabolite nitrite by Griess reaction

  通过将取代的7-羟基香豆素与不同的氯酮缀合，可以合成一系列7-（2-氧代烷氧基）香豆素。在L774诱导的J774巨噬细胞的炎症反应中研究了7-（2-氧代烷氧基）香豆素的抗炎特性。用Western印迹法测定iNOS和COX-2的表达，通过Griess反应测定其代谢产物亚硝酸盐测定NO，通过ELISA测定IL-6。在100μM的浓度下，有17种被研究的化合物抑制NO和IL-6的产生超过50％。最佳抑制剂的IC 50值对于化合物12为21μM/ 24μM（NO / IL-6），对于化合物20为30μM/ 10μM（NO / IL-6）。主要结果是，被7-（2-氧代烷氧基）取代可改善大多数研究的7-羟基香豆素的抗炎特性。
• Synthesis of Substituted Coumarins via Brønsted Acid Mediated Condensation of Allenes with Substituted Phenols or Anisoles
  作者：Sundae Kim、Dongjin Kang、Chang-Hee Lee、Phil Ho Lee

  DOI：10.1021/jo301086k

  日期：2012.8.3

  Coumarins were obtained from the condensation of electron-rich arenes with allenes in the presence of TfOH in good yield. Depending on the substituent pattern of allenes employed, the general synthetic method of 4-substituted and 3,4-disubstituted 3-arylcoumarins has been developed. Readily available allenes were employed as the three-carbon atom sources constituting the coumarin skeleton.

  在TfOH存在下，富电子芳烃与丙二烯的缩合可得到香豆素。根据所用的烯的取代基样式，已经开发了4-取代和3，4-二取代的3-芳基香豆素的一般合成方法。使用现成的丙二烯作为构成香豆素骨架的三碳原子源。
• Antidiabetic agents
  申请人：Merck & Co., Inc.

  公开号：US05859051A1

  公开（公告）日：1999-01-12

  The instant invention is concerned with acetylphenols which are useful as antiobesity and antidiabetic compounds. Compositions and methods for the use of the compounds in the treatment of diabetes and obesity and for lowering or modulating triglyceride levels and cholesterol levels or raising high density lipoprotein levels or for increasing gut motility or for treating atherosclerosis are also disclosed.

  该发明涉及乙酰苯酚，可用作抗肥胖和抗糖尿病化合物。还公开了在治疗糖尿病和肥胖中使用这些化合物的组合物和方法，以及降低或调节甘油三酯水平和胆固醇水平，或提高高密度脂蛋白水平，或增加肠道蠕动或治疗动脉粥样硬化的方法。
• Investigation of the cytotoxicity of bioinspired coumarin analogues towards human breast cancer cells
  作者：Leonidas Gkionis、Eleni Kavetsou、Alexandros Kalospyros、Dimitris Manousakis、Miguel Garzon Sanz、Sam Butterworth、Anastasia Detsi、Annalisa Tirella

  DOI：10.1007/s11030-020-10082-6

  日期：2021.2

  Coumarins possess a wide array of therapeutic capabilities, but often with unclear mechanism of action. We tested a small library of 18 coumarin derivatives against human invasive breast ductal carcinoma cells with the capacity of each compound to inhibit cell proliferation scored, and the most potent coumarin analogues selected for further studies. Interestingly, the presence of two prenyloxy groups (5,7-diprenyloxy-4-methyl-coumarin,4g) or the presence of octyloxy substituent (coumarin4d) was found to increase the potency of compounds in breast cancer cells, but not against healthy human fibroblasts. The activity of potent compounds on breast cancer cells cultured more similarly to the conditions of the tumour microenvironment was also investigated, and increased toxicity was observed. Results suggest that tested coumarin derivatives could potentially reduce the growth of tumour mass. Moreover, their use as (combination) therapy in cancer treatment might have the potential of causing limited side effects.

  摘要：香豆素具有广泛的治疗能力，但其作用机制通常不清楚。我们对18种香豆素衍生物进行了测试，针对具有抑制细胞增殖能力的每种化合物进行评分，选择了最有效的香豆素类似物进行进一步研究。有趣的是，在乳腺癌细胞中发现了两个异戊氧基基团（5,7-二异戊氧基-4-甲基香豆素，4g）或辛氧基取代基（香豆素4d）的存在可以增加化合物在乳腺癌细胞中的活性，但对健康的人类成纤维细胞没有影响。还研究了强有效化合物在培养条件更类似于肿瘤微环境的乳腺癌细胞上的活性，并观察到了增加的毒性。结果表明，测试的香豆素衍生物可能有潜力减少肿瘤质量的增长。此外，在癌症治疗中将它们用作（联合）疗法可能会导致有限的副作用。