curcumin 2 | 98886-27-2

• 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: curcumin 2
• 英文别名: 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,4,6-heptatrien-3-one；demethoxycurcumin；DMC
• CAS: 98886-27-2
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: NMRUIRRIQNAQEB-VEAXOGKZSA-N

物化性质

• 沸点：
  573.4±50.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  86.99
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  curcumin 2 在 一水合肼 、 溶剂黄146 作用下， 反应 7.0h， 以95 mg的产率得到hydrazinodemethoxycurcumin
  参考文献：
  名称：

  设计，合成，生物学评估和姜黄素类似物作为抗氧化剂，环氧合酶抑制剂和消炎剂的分子对接。

  摘要：

  从姜黄中分离姜黄素，合成其吡唑和异恶唑类似物并评估其抗氧化剂，COX-1 / COX-2的抑制和消炎活性。设计的类似物在角叉菜胶诱导的大鼠爪水肿测定中显着增强了COX-2 / COX-1的选择性，并具有显着的抗炎活性。姜黄素的吡唑，异恶唑类似物（4和7）显示出比trolox高的抗氧化活性。分子对接研究揭示了姜黄素类似物在COX活性位点的结合方向，从而有助于设计新型有效抑制剂。

  DOI：

  10.1016/j.bmcl.2005.02.039
• 作为产物：
  描述：

  香草醛 、 (3Z,5E)-4-hydroxy-6-(4-hydroxyphenyl)hexa-3,5-dien-2-one 在 boron trioxide 、 三丁基硼 、 正丁胺 作用下， 生成 curcumin 2
  参考文献：
  名称：

  Mann, Gerhard; Beyer, Lothar; Arrieta, Antonio, Zeitschrift fur Chemie, 1987, vol. 27, # 5, p. 172 - 173

  摘要：

  DOI：

文献信息

• Composition For The Prevention And Treatment Of Influenza Virus Infection And Composition For Suppressing Neuraminidase Activity Comprising Turmeric Extract
  申请人：Lee Woo-Song

  公开号：US20120107429A1

  公开（公告）日：2012-05-03

  Disclosed is a composition comprising a turmeric extract for preventing and treating influenza virus infection and for inhibiting neuraminidase activity. A turmeric extract, its fraction, and a curcuminoid-based compound separated therefrom may inhibit neuraminidase activity and have antiviral and cell degeneration inhibitory effects on influenza virus, and may be useful in preventing and treating influenza virus infection.

  本发明公开了一种包含姜黄提取物的组合物，用于预防和治疗流感病毒感染并抑制神经氨酸酶活性。姜黄提取物、其分离物以及从中分离出的以姜黄素为基础的化合物可以抑制神经氨酸酶活性，并对流感病毒具有抗病毒和细胞退化抑制作用，可用于预防和治疗流感病毒感染。
• Neuron activator
  申请人：Kinjirushi Co., Ltd.

  公开号：US11065288B2

  公开（公告）日：2021-07-20

  The present disclosure provides a neuron activator that activates neurons. The neuron activator includes at least one selected from the group consisting of a dopamine production promotor that promotes dopamine production of the neurons, a neuron extension promotor that promotes extension of the neurons, and an amyloid β resistance enhancer that enhances resistance of the neurons against amyloid β. The neuron activator includes 6-methylsulfinylhexyl isothiocyanates or glycosides thereof, and at least one selected from the group consisting of unsaturated fatty acid and polyphenol.

  本公开提供了一种激活神经元的神经元激活剂。神经元激活剂包括至少一种选自由促进神经元产生多巴胺的多巴胺生成促进剂、促进神经元延伸的神经元延伸促进剂和增强神经元对淀粉样β抵抗力的淀粉样β抵抗力增强剂组成的组。
• Pedersen, Uffe; Rasmussen, Preben B.; Lawesson, Sven-Olov, Liebigs Annalen der Chemie, 1985, # 8, p. 1557 - 1569
  作者：Pedersen, Uffe、Rasmussen, Preben B.、Lawesson, Sven-Olov

  DOI：——

  日期：——
• Influence of side-chain changes on histone deacetylase inhibitory and cytotoxicity activities of curcuminoid derivatives
  作者：La-or Somsakeesit、Thanaset Senawong、Pakit Kumboonma、Somprasong Saenglee、Arunta Samankul、Gulsiri Senawong、Chavi Yenjai、Chanokbhorn Phaosiri

  DOI：10.1016/j.bmcl.2020.127171

  日期：2020.6

  Using curcuminoids as lead compounds, fifty-nine curcuminoid derivatives with different side chains at the phenolic moiety were synthesized. All compounds were investigated for their histone deacetylase (HDAC) inhibitory activities. The potent pan-HDAC inhibitors were further tested against three human cancer cell lines including Hela, HCT116 and MCF-7 with MTT-based assay. The bisethylamide 4z and the mono-sec-butyl derivative 5j manifested good antiproliferative activities against HCT116 cancer cells with the IC50 values as 14.60 +/- 1.19 mu g/mL and 7.33 +/- 0.98 mu g/mL, respectively. Molecular docking study of both compounds with Class I HDACs revealed that the compounds might bind tightly to the binding pocket of HDAC2. These findings suggested that these compounds can be putative candidates for the development of anticancer drugs via inhibiting HDACs.
• Antitumor Agents. 217. Curcumin Analogues as Novel Androgen Receptor Antagonists with Potential as Anti-Prostate Cancer Agents
  作者：Hironori Ohtsu、Zhiyan Xiao、Junko Ishida、Masahiro Nagai、Hui-Kang Wang、Hideji Itokawa、Ching-Yuan Su、Charles Shih、Tzuying Chiang、Eugene Chang、Lee、Meng-Yin Tsai、Chawnshang Chang、Kuo-Hsiung Lee

  DOI：10.1021/jm020200g

  日期：2002.11.1

  A number of curcumin analogues were prepared and evaluated as potential androgen receptor antagonists against two human prostate cancer cell lines, PC-3 and DU-145, in the presence of androgen receptor (AR) and androgen receptor coactivator, ARA70. Compounds 4 [5-hydroxy-1,7-bis(3,4-dimethoxyphenyl)-1,4,6-heptatrien-3-one], 20 [5-hydroxy-1,7-bis[3-methoxy-4-(meth-oxycarbonylmethoxy)phenyl]-1,4,6-heptatrien-3-one], 22 [7-(4-hydroxy-3-methoxyphenyl)-4-[3(4-hydroxy-3-methoxyphenyl)acryloyl]-5-oxohepta-4,6-dienoic acid ethyl ester], 23 [7-(4-hydroxy-3-methoxyphenyl)-4-[3-(4-hydroxy-3-methoxyphenyl)acryloyl]5-oxohepta-4,6-dienoic acid], and 39 [bis(3,4-dimethoxyphenyl)-1,3-propanedione] showed potent antiandrogenic activities and were superior to hydroxyflutamide, which is the currently available antiandrogen for the treatment of prostate cancer. Structure-activity relationship (SAR) studies indicated that the bis(3,4-dimethoxyphenyl) moieties, the conjugated beta-diketone moiety, and the intramolecular symmetry of the molecules seem to be important factors related to antiandrogenic activity. The data further suggest that the coplanarity of the beta-diketone moiety and the presence of a strong hydrogen bond donor group were also crucial for the antiandrogenic activity, which is consistent with previous SAR results for hydroxyflutamide analogues. When the pharmacophoric elements of dihydrotestosterone (DHT) and compound 4 are superposed, the resulting construct implies that the curcumin analogues may function as a 17alpha-substituted DHT. Compounds 4, 20, 22, 23, and 39 have been identified as a new class of antiandrogen agents, and these compounds or their new synthetic analogues could be developed into clinical trial candidates to control androgen receptor-mediated prostate cancer growth.

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