hydrazinodemethoxycurcumin

• 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: hydrazinodemethoxycurcumin
• 英文别名: 4-[2-{3-[2-(4-hydroxyphenyl)ethenyl]-1H-pyrazol-5-yl}ethenyl]-2-methoxyphenol；4-[(E)-2-[5-[(E)-2-(4-hydroxyphenyl)ethenyl]-1H-pyrazol-3-yl]ethenyl]-2-methoxyphenol
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: BSYXTLLMKFYJQV-ZESFLVPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  脱甲氧姜黄 在 一水合肼 、 溶剂黄146 作用下， 以77%的产率得到hydrazinodemethoxycurcumin
  参考文献：
  名称：

  姜黄素的异恶唑类似物具有强效的多药耐药分枝杆菌活性

  摘要：

  姜黄素（1），去甲氧基姜黄素（2）和双去甲氧基姜黄素（3）（药用植物姜黄的姜黄素成分）已在结构上修饰为55个类似物，并已评估了其对结核分枝杆菌的抗分枝杆菌活性。在高活性姜黄素类化合物中，异恶唑类似物是活性最高的基团，单-O-甲基姜黄素异恶唑（53）是活性最高的化合物（MIC 0.09μg/ mL）。它的活性比母体化合物姜黄素（1）高1131倍，分别比标准药物卡那霉素和异烟肼高18倍和2倍。化合物53还显示出对耐多药结核分枝杆菌临床分离株的高活性，MIC值为0.195–3.125μg/ mL。姜黄素类似物表现出抗分枝杆菌活性的结构要求是在异戊基环上存在一个异恶唑环和两个不饱和键。紧密连接于异恶唑环的氮官能团的芳环上合适的对烷氧基的存在和另一个芳环上的游离对羟基的存在增强了生物活性。

  DOI：

  10.1016/j.ejmech.2010.07.003

文献信息

• Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents
  作者：C. Selvam、Sanjay M. Jachak、Ramasamy Thilagavathi、Asit. K. Chakraborti

  DOI：10.1016/j.bmcl.2005.02.039

  日期：2005.4

  pyrazole and isoxazole analogues were synthesized and evaluated for antioxidant, COX-1/COX-2 inhibitory and anti-inflammatory activities. The designed analogues significantly enhance COX-2/COX-1 selectivity and possess significant anti-inflammatory activity in carrageenan induced rat paw edema assay. Pyrazole, isoxazole analogues of curcumin (4 and 7) exhibited higher antioxidant activity than trolox

  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。
• Hydrazinocurcumin, a novel synthetic curcumin derivative, is a potent inhibitor of endothelial cell proliferation
  作者：Joong Sup Shim、Dong Hoon Kim、Hye Jin Jung、Jin Hee Kim、Dongyeol Lim、Seok-Ki Lee、Kyu-Won Kim、Jong Woong Ahn、Jong-Shin Yoo、Jung-Rae Rho、Jongheon Shin、Ho Jeong Kwon

  DOI：10.1016/s0968-0896(02)00129-3

  日期：2002.9

  Curcumin and some of its derivatives were known as in vivo inhibitors of angiogenesis. In present study. a novel curcumin derivative, named hydrazinocurcumin (HC) was synthesized and examined for its biological activities. HC potently inhibited the proliferation of bovine aortic endothelial cells (BAECs) at a nanomolar concentration (IC50 = 520 nM) without cytotoxicity. In vivo and in Nitro angiogenesis experiments showed HC Lis a new candidate for anti-angiogenic agent. (C) 2002 Published by Elsevier Science Ltd.
• 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.
• Hydrazinocurcumin, a novel synthetic curcumin derivative, Is a potent inhibitor of endothelial cell proliferation
  作者：Joong Sup Shim、Dong Hoon Kim、Hye Jin Jung、Jin Hee Kim、Dongyeol Lim、Seok-Ki Lee、Kyu-Won Kim、Jong Woong Ahn、Jong-Shin Yoo、Jung-Rae Rho、Jongheon Shin、Ho Jeong Kwon

  DOI：10.1016/s0968-0896(02)00116-5

  日期：2002.8

  Curcumin and some of its derivatives were known as in vivo inhibitors of angiogenesis. In present study, a novel curcumin derivative, named hydrazinocurcumin (HC) was synthesized and examined for its biological activities. HC potently inhibited the proliferation of bovine aortic endothelial cells (BAECs) at a nanomolar concentration (IC(50)=520 nM) without cytotoxicity. In vivo and in vitro angiogenesis experiments showed HC as a new candidate for anti-angiogenic agent.
• Antitumor Agents. Part 214:††For paper 213, see ref 1. Synthesis and Evaluation of Curcumin Analogues as Cytotoxic Agents
  作者：Junko Ishida、Hironori Ohtsu、Yoko Tachibana、Yuka Nakanishi、Kenneth F Bastow、Masahiro Nagai、Hui-Kang Wang、Hideji Itokawa、Kuo-Hsiung Lee

  DOI：10.1016/s0968-0896(02)00249-3

  日期：2002.11

  Fifty-eight curcumin analogues were prepared and evaluated for in vitro cytotoxicity against a panel of human tumor cell lines. Compound 50 was the most potent analogue against several cell lines, including HOS (bone cancer) and 1A9 (breast cancer), with ED50 values of 0.97 and <0.63 mug/mL, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.