4-[6-(4-hydroxy-phenoxy)-hexyl]-heptane-3,5-dione | 56219-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-[6-(4-hydroxy-phenoxy)-hexyl]-heptane-3,5-dione
• 英文别名: 4-[6-(4-hydroxyphenoxy)hexyl]-3,5-heptanedione；4-[6-(4-Hydroxyphenoxy)hexyl]heptane-3,5-dione
• CAS: 56219-67-1
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: HFSBLVPMZPDDRF-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  499.8±40.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[6-(4-hydroxy-phenoxy)-hexyl]-heptane-3,5-dione 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以73%的产率得到3,5-diethyl-4-[6-(4-hydroxyphenoxy)hexyl]isoxazole
  参考文献：
  名称：

  Ellipticine derivatives with an affinity to the estrogen receptor. An approach to develop intercalating drugs with a specific effect on the hormone-dependent breast cancer

  摘要：

  In order to obtain breast tumor directed agents, we have prepared mixed compounds using estradiol or (E)-clomiphene as specific vectors of the breast tissue and a DNA intercalator from the ellipticine series as the cytotoxic agent. Among the newly synthesized ellipticine derivatives, only the 2-[3-aza-5-(3,17 beta-dihydroxy-1,3,5-estratrien-17 alpha-yl)-4-oxopentamethylene]ellipticinium bromide shows the desired properties, DNA intercalation and affinity for estrogen receptor. Competition experiments with estradiol on the hormone-dependent human MCF-7 breast cancer cell line demonstrate that a transport by the estrogen receptor system is not involved in the antitumor activity of derivative 24.

  DOI：

  10.1021/jm00383a011
• 作为产物：
  描述：

  3,5-庚烷二酮 在 palladium on activated charcoal 乙醇 、 氢气 作用下， 生成 4-[6-(4-hydroxy-phenoxy)-hexyl]-heptane-3,5-dione
  参考文献：
  名称：

  Antiviral activity of some .beta.-diketones. 1. Aryl alkyl diketones. In vitro activity against both RNA and DNA viruses

  摘要：

  The discovery that 4-[3-ethyl-6-[(3,4-methylenedioxy)phenyl]-3-hexenyl]-3,5-heptanedione (40) exhibited an in vitro inhibitory effect against equine rhinovirus led to a structure--activity study to establish the criteria for optimum activity. Modification of the bridge included removal of the ethyl group and reduction of the double bond. The heptanedione was replaced with hexanedione and pentanedione with a minimal effect. The effect of replacing the heptanedione with beta-keto esters and monoketones was also investigated. Maintaining the hexamethylene bridge and heptanedione, the methylenedioxy group was replaced with various substitutents. In general, most substituents did not adversely affect activity particularly against equine rhinovirus although there was some variation in activity against herpesvirus. Strongly hydrophilic groups significantly reduced activity. Finally, the effect of varying the length of the alkyl bridge was examined in the 4-hydroxyphenyl series, where peak activity was attained with n = 8.

  DOI：

  10.1021/jm00216a003

文献信息

• DIANA, G. D.;MCKINLAY, M. A.;BRISSON, C. J.;ZALAY, E. S.;MIRALLES, J. V.;+, J. MED. CHEM., 1985, 28, N 6, 748-752
  作者：DIANA, G. D.、MCKINLAY, M. A.、BRISSON, C. J.、ZALAY, E. S.、MIRALLES, J. V.、+

  DOI：——

  日期：——
• DIANA H. D.; SALVADOR U. J.; ZALAY E. S.; CARABATEAS P. M.; WILLIAMS G. L+, J. MED. CHEM. <JMCM-AR>, 1977, 20, NO 6, 757-761
  作者：DIANA H. D.、 SALVADOR U. J.、 ZALAY E. S.、 CARABATEAS P. M.、 WILLIAMS G. L+

  DOI：——

  日期：——
• US4182761A
  申请人：——

  公开号：US4182761A

  公开（公告）日：1980-01-08
• US4198436A
  申请人：——

  公开号：US4198436A

  公开（公告）日：1980-04-15
• US4268678A
  申请人：——

  公开号：US4268678A

  公开（公告）日：1981-05-19