(+/-)-5-hydroxyl-1-(4'-hydroxyphenyl)-7-phenyl-3-heptanone | 105955-04-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (+/-)-5-hydroxyl-1-(4'-hydroxyphenyl)-7-phenyl-3-heptanone
• 英文别名: 5-hydroxy-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone；5-hydroxy-1-(4-hydroxy-phenyl)-7-phenyl-heptan-3-one；5-Hydroxy-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone (AO 2210)；5-hydroxy-1-(4-hydroxyphenyl)-7-phenylheptan-3-one
• CAS: 105955-04-2
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: NKSWRYBLSIGGIU-UHFFFAOYSA-N

物化性质

• 沸点：
  523.7±45.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-5-hydroxyl-1-(4'-hydroxyphenyl)-7-phenyl-3-heptanone 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 1.0h， 以12 mg的产率得到1-(4 hydroxyphenyl)-7-phenyl-hept-4-en-3-one
  参考文献：
  名称：

  Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation

  摘要：

  Three new diarylheptanoids, a 1: 2 mixture of (3S)- and (3R)-1-(4-methoxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (13a and 13b) and 1-(4-hydroxyphenyl)-7-phenyl-( 6E)-6-hepten-3- one ( 15), together with two synthetically known diarylheptanoids 1,7-diphenyl-(1E,3E,5E)-1,3,5-triene(9) and 1-(4-hydroxyphenyl)7-phenyl-(4E,6E)-4,6-heptadien-3- one ( 16), and nine known diarylheptanoids, 2, 8, 10 - 12, 14, a 3: 1 mixture of 17a and 17b, and 18, were isolated from the rhizomes of Curcuma comosa Roxb. The absolute stereochemistry of the isolated compounds has also been determined using the modified Mosher's method. The isolated compounds and the chemically modified analogues were evaluated for their estrogenic-like transcriptional activity using RT-PCR in HeLa cell line. Some of the isolated diarylheptanoids and their modified analogues exhibited estrogenic activity comparable to or higher than that of the phytoestrogen genistein. Based on the transcriptional activation of both estrogenic targets, Bcl-xL and ER beta gene expression, the structural features for a diarylheptanoid to exhibit high estrogenic activity are the presence of an phenolic function conjugated with the aromatic ring at the 7-position, a keto group at the 3-position, and a phenolic hydroxyl group at the p-position of the aromatic ring attached to the 1- position of the heptyl chain. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.051
• 作为产物：
  描述：

  覆盆子酮 在 水 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (+/-)-5-hydroxyl-1-(4'-hydroxyphenyl)-7-phenyl-3-heptanone
  参考文献：
  名称：

  摘要：

  (±)-5-羟基-1,7-双-(4'-羟基苯基)-3-庚酮 (2a)、(±)-5-羟基-1-(4'-羟基苯基)-7-苯基-3-庚酮 (2b)、(±)-5-羟基-7-(4'-羟基苯基)-1-苯基-3-庚酮 (2c) 和 (±)-5-羟基-1,7-双-(苯基)-3-庚酮 (2d) 已经被合成，用于研究在牛瘤胃液中体外消化抑制的结构-活性关系。这些化合物的活性与从 Betula pendula 分离出的具有手性 (S)-2a 及其苷 platyphylloside (1) 进行了比较。化合物 2a 的活性略低于 (S)-2a 和 platyphylloside，而 2b 和 2c 的活性更高，2d 的活性则低于 (S)-2a 和 platyphylloside。

  DOI：

  10.1023/a:1020847423427

文献信息

• Synthesis and biological evaluation of phenolic 4,5-dihydroisoxazoles and 3-hydroxy ketones as estrogen receptor α and β agonists
  作者：Pekka K. Poutiainen、Tuomas A. Venäläinen、Mikael Peräkylä、Juha M. Matilainen、Sami Väisänen、Paavo Honkakoski、Reino Laatikainen、Juha T. Pulkkinen

  DOI：10.1016/j.bmc.2010.04.007

  日期：2010.5

  In this work, 52 diphenyl-4,5-dihydroisoxazoles and -3-hydroxy ketones were prepared and their estrogen receptor alpha (ER alpha) and estrogen receptor beta (ER beta) activities were explored in order to systematize and maximize their biological activity. The biological activity was firstly screened by using ERE reporter assay to find out how aromatic hydroxylation and methylation of the chiral centers of the compounds affect the ability of ER to mediate biological responses. For selected 19 compounds, the relative binding affinities (RBA, relative to 3,17 beta-estradiol) and ability to induce transcription of primary E2 target gene pS2 in human MCF-7 breast cancer cells were determined. In the reporter assay, many compounds showed even stronger activity than E2 and some of them showed RBA larger than 1%. The highest RBAs were determined for the enantiomers of 1-hydroxy-6-(4-hydroxy-phenyl)-1-phenyl-hexan-3-one (50a and 50b). Isomer 50a showed high binding affinity both to ER alpha (with RBA similar to 200%) and ERb (with RBA similar to 60%), while the RBAs of 50b were ca. 40% of those. Some of the other compounds (with RBA similar to 1-16%) showed also notable ERa binding selectivity. When four most promising ligands (50a, 50b, 45a, and 45b) were studied with respect to their ability to induce the transcription of primary E2 target gene pS2, the compounds acted as agonists or partial agonists. Computer modeling was used to predict receptor binding conformations and to rationalize the RBA differences of the compounds. (C) 2010 Elsevier Ltd. All rights reserved.
• ——
  作者：Katharina Bratt、Kerstin Sunnerheim

  DOI：10.1023/a:1020847423427

  日期：——

  (+/-)-5-Hydroxy-1,7-bis-(4'-hydroxyphenyl)-3-heptanone (2a), (+/-)-5-hydroxyl-1-(4'-hydroxyphenyl)-7-phenyl-3-heptanone (2b), (+/-)-5-hydroxy-7-(4'-hydroxyphenyl)-1-phenyl-3-heptanone (2c), and (+/-)-5-hydroxy-1,7-bis-(phenyl)-3-heptanone (2d) have been synthesized to study the structure-activity relationship regarding digestibility inhibition in vitro in cow rumen fluid. The activities were compared with the activity of chiral (S)-2a and its glucoside platyphylloside (1), isolated from Betula pendula. Compound 2a was slightly less active, 2b and 2c were more active, and 2d was less active than (S)-2a and platyphylloside.

  (±)-5-羟基-1,7-双-(4'-羟基苯基)-3-庚酮 (2a)、(±)-5-羟基-1-(4'-羟基苯基)-7-苯基-3-庚酮 (2b)、(±)-5-羟基-7-(4'-羟基苯基)-1-苯基-3-庚酮 (2c) 和 (±)-5-羟基-1,7-双-(苯基)-3-庚酮 (2d) 已经被合成，用于研究在牛瘤胃液中体外消化抑制的结构-活性关系。这些化合物的活性与从 Betula pendula 分离出的具有手性 (S)-2a 及其苷 platyphylloside (1) 进行了比较。化合物 2a 的活性略低于 (S)-2a 和 platyphylloside，而 2b 和 2c 的活性更高，2d 的活性则低于 (S)-2a 和 platyphylloside。
• Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation
  作者：Apichart Suksamrarn、Mathurose Ponglikitmongkol、Kanjana Wongkrajang、Anon Chindaduang、Suthadta Kittidanairak、Aroon Jankam、Boon-ek Yingyongnarongkul、Narin Kittipanumat、Ratchanaporn Chokchaisiri、Pichit Khetkam、Pawinee Piyachaturawat

  DOI：10.1016/j.bmc.2008.05.051

  日期：2008.7

  Three new diarylheptanoids, a 1: 2 mixture of (3S)- and (3R)-1-(4-methoxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (13a and 13b) and 1-(4-hydroxyphenyl)-7-phenyl-( 6E)-6-hepten-3- one ( 15), together with two synthetically known diarylheptanoids 1,7-diphenyl-(1E,3E,5E)-1,3,5-triene(9) and 1-(4-hydroxyphenyl)7-phenyl-(4E,6E)-4,6-heptadien-3- one ( 16), and nine known diarylheptanoids, 2, 8, 10 - 12, 14, a 3: 1 mixture of 17a and 17b, and 18, were isolated from the rhizomes of Curcuma comosa Roxb. The absolute stereochemistry of the isolated compounds has also been determined using the modified Mosher's method. The isolated compounds and the chemically modified analogues were evaluated for their estrogenic-like transcriptional activity using RT-PCR in HeLa cell line. Some of the isolated diarylheptanoids and their modified analogues exhibited estrogenic activity comparable to or higher than that of the phytoestrogen genistein. Based on the transcriptional activation of both estrogenic targets, Bcl-xL and ER beta gene expression, the structural features for a diarylheptanoid to exhibit high estrogenic activity are the presence of an phenolic function conjugated with the aromatic ring at the 7-position, a keto group at the 3-position, and a phenolic hydroxyl group at the p-position of the aromatic ring attached to the 1- position of the heptyl chain. (c) 2008 Elsevier Ltd. All rights reserved.