8-isopentyl-7-hydroxy-2H-chromen-2-one | 35129-52-3

• 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: 8-isopentyl-7-hydroxy-2H-chromen-2-one
• 英文别名: 7-hydroxy-8-(3-methyl-butyl)-chromen-2-one；7-hydroxy-8-isopentyl-coumarin；7-Hydroxy-8-isopentyl-cumarin；7-Hydroxy-8-(3-methylbutyl)chromen-2-one
• CAS: 35129-52-3
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: OPOVCOUIJWXXMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-isopentyl-7-hydroxy-2H-chromen-2-one 在 甲醇 、 18-冠醚-6 、 四丁基碘化铵 、 sodium hydride 、 lithium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-(8-isopentyl-2-oxo-2H-chromen-7-yloxy)pentanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of aliphatic-chain hydroxamates capped with osthole derivatives as histone deacetylase inhibitors

  摘要：

  Our previous studies have demonstrated that osthole, a Chinese herbal compound, could be incorporated into the hydroxycinnamide scaffold of LBH-589, a potent HDAC inhibitor, as an effective hydrophobic cap; the resulting compounds showed significant potency against several HDAC isoforms. Here, we presented a series of osthole derivatives fused with the aliphatic-hydroxamate core of suberoylanilide hydroxamic acid (SAHA), a clinically-approved HDAC inhibitor. Several compounds showed potent activity against nuclear HDACs. Further assays against individual HDAC isoforms revealed that some compounds showed not only SAHA-like activity towards HDAC1, -4 and -6, they inhibited HDAC8 by log difference than SAHA and thus exhibited a broader HDAC inhibition spectrum. Among them, compound 6g showed potent antiproliferative effect on several human cancer cell lines. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

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

  蛇床子提取物 在 三氯化铝 作用下， 以 氯苯 为溶剂， 反应 3.0h， 以26.3%的产率得到8-isopentyl-7-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  Banerji, J.; Bhaduri, N.; Rej, R. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 5, p. 341 - 345

  摘要：

  DOI：

文献信息

• Bottomley; White, Australian Journal of Scientific Research, Series A: Physical Sciences, 1951, vol. <A> 4, p. 112,114
  作者：Bottomley、White

  DOI：——

  日期：——
• Identification and structure-activity relationship studies of osthol, a cytotoxic principle from Cnidium monnieri
  作者：Yukio Hitotsuyanagi、Hiroshi Kojima、Hiroshi Ikuta、Koichi Takeya、Hideji Itokawa

  DOI：10.1016/0960-894x(96)00315-0

  日期：1996.8

  Osthol (1) was isolated from the fruit of Cnidium monnieri as a cytotoxic principle. Its structure-activity relationship study reveals that the 3,4-olefinic bond is essential for its cytotoxic activity, and the prenyl (C-5) unit attached at the 8 position enhances the cytotoxicity. Analogues 7 and 8 that have a longer alkoxy unit at the 7 position showed ten times higher cytotoxicity than 1. Copyright (C) 1996 Elsevier Science Ltd
• Discovery of novel osthole derivatives as potential anti-breast cancer treatment
  作者：Lisha You、Rui An、Xinhong Wang、Yimin Li

  DOI：10.1016/j.bmcl.2010.10.027

  日期：2010.12

  Osthole, an ingredient of Traditional Chinese Medicine (TCM) from natural product Cnidium monnieri (L.) Cusson, was used as a lead compound for structural modification. A series of osthole derivatives bearing aryl substituents at 3-position of coumarin, has been prepared and evaluated for their growth inhibitory activity against human breast cancer cell lines MCF-7 and MDA-MB-231. Interestingly, some derivatives exhibited good inhibition, among them compound 8e was found to be the most potent compound with IC50 values of 0.24 mu M, 0.31 mu M against MCF-7 and MDA-MB-231, respectively, which was improved more than 100-folds compared with its parent compound osthole. (C) 2010 Elsevier Ltd. All rights reserved.
• Injustice in forensic psychiatry: the Scott-Moncrieff hypothesis revisited
  作者：Philip Sugarman、Ashmesh Roychowdhury

  DOI：10.1080/09585180050142660

  日期：2000.1

  Scott-Moncrieff (1993) argued that key decision-making in forensic psychiatry may be biased against the individual by false or misleading information presented in reports. We examined this by comparing accounts of incidents and other problems in reports to the mental health review tribunal, with contemporaneous records. In a regional secure unit a significant discrepancy was found, particularly in the reporting of aggressive behaviour. The authors argue that reliance on verbal accounts and inadequate contemporaneous notekeeping are more likely explanations than true bias, but accept Scott-Moncrieff's recommendation of proper investigation of incidents in hospital.
• Synthesis of 8-Isoamyl-7-methoxycoumarin (Dihydro-osthol)
  作者：H. L. Haller、Fred Acree

  DOI：10.1021/ja01321a051

  日期：1934.6