1-(4-hydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-one | 1062082-72-7

• 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: 1-(4-hydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-one
• 英文别名: 1-(4-hydroxyphenyl)-7-phenyl-(6E)-hept-6-en-3-one；(E)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one
• CAS: 1062082-72-7
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: HLXPZGZUVCDNGK-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以94%的产率得到1-(4-hydroxyphenyl)-7-phenyl-3-heptanone
  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：

  (3S)-1-(4-hydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以65%的产率得到1-(4-hydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-one
  参考文献：
  名称：

  在体外和体内发现具有抗炎活性的巨噬细胞中激活α7 nAchR-JAK2-STAT3信号的二芳基庚烷

  摘要：

  脓毒症等急性炎症性疾病是危及生命的疾病。调节 α7 烟碱型乙酰胆碱受体 (α7 nAchR) 介导的信号传导可能是治疗败血症的有希望的策略。早就发现二芳基庚烷具有抗炎特性。然而，很少研究二芳基庚烷的可能机制。在这项研究中，我们分离并合成了 49 种二芳基庚烷和类似物，并评估了它们的抗炎活性。其中，化合物28和40显着阻断了脂多糖 (LPS) 诱导的小鼠 RAW264.7 细胞中一氧化氮 (NO)、白细胞介素 1β (IL-1β) 和白细胞介素 6 的产生。此外，化合物28和40还有效减弱 LPS 诱导的脓毒症、急性肺损伤和体内细胞因子释放。从机制上讲，化合物28和40显着诱导 janus 激酶 2/信号转导和转录激活因子 3 (JAK2/STAT3) 信号传导和核因子-κB (NF-κB) 通路的抑制。此外，阻断 α7 nAchR 可以有效地消除化合物28和40介导的 JAK2-STAT3

  DOI：

  10.1016/j.bmc.2022.116811

文献信息

• 二芳基庚烷类化合物
  申请人：中国科学院成都生物研究所

  公开号：CN106831383B

  公开（公告）日：2021-03-30

  本发明公开了一种式(A)所示的二芳基庚烷类化合物。本发明化合物可以显著地抑制iNOS、IL‑1β、IL‑6的转录和蛋白表达以及IκB蛋白的磷酸化水平，可以用于炎症及其他多种疾病的治疗，包括治疗败血症和治疗阿尔茨海默病。
• 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.
• Discovery of diarylheptanoids that activate α7 nAchR-JAK2-STAT3 signaling in macrophages with anti-inflammatory activity in vitro and in vivo
  作者：Yuan Lin、Kanjana Wongkrajang、Xiaofei Shen、Ping Wang、Zongyuan Zhou、Thipphawan Chuprajob、Nilubon Sornkaew、Na Yang、Lijuan Yang、Xiaoxia Lu、Ratchanaporn Chokchaisiri、Apichart Suksamrarn、Guolin Zhang、Fei Wang

  DOI：10.1016/j.bmc.2022.116811

  日期：2022.7

  anti-inflammatory properties. However, the possible mechanism of diarylheptanoids has rarely been investigated. In this study, we isolated and synthesized 49 diarylheptanoids and analogues and evaluated their anti-inflammatory activities. Among them, compounds 28 and 40 markedly blocked lipopolysaccharide (LPS)-induced production of nitric oxide (NO), interleukin-1β (IL-1β) and interleukin-6 in murine RAW264.7 cells

  脓毒症等急性炎症性疾病是危及生命的疾病。调节 α7 烟碱型乙酰胆碱受体 (α7 nAchR) 介导的信号传导可能是治疗败血症的有希望的策略。早就发现二芳基庚烷具有抗炎特性。然而，很少研究二芳基庚烷的可能机制。在这项研究中，我们分离并合成了 49 种二芳基庚烷和类似物，并评估了它们的抗炎活性。其中，化合物28和40显着阻断了脂多糖 (LPS) 诱导的小鼠 RAW264.7 细胞中一氧化氮 (NO)、白细胞介素 1β (IL-1β) 和白细胞介素 6 的产生。此外，化合物28和40还有效减弱 LPS 诱导的脓毒症、急性肺损伤和体内细胞因子释放。从机制上讲，化合物28和40显着诱导 janus 激酶 2/信号转导和转录激活因子 3 (JAK2/STAT3) 信号传导和核因子-κB (NF-κB) 通路的抑制。此外，阻断 α7 nAchR 可以有效地消除化合物28和40介导的 JAK2-STAT3