(E)-1-(2,5-dihydroxyphenyl)-3-(indol-3-yl)-2-propen-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-1-(2,5-dihydroxyphenyl)-3-(indol-3-yl)-2-propen-1-one
• 英文别名: (E)-1-(2,5-dihydroxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: JJBSLPGXLFUYBY-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 pyridium para-toluenesulfonate 、 barium hydroxide octahydrate 、 对甲苯磺酸 作用下， 生成 (E)-1-(2,5-dihydroxyphenyl)-3-(indol-3-yl)-2-propen-1-one
  参考文献：
  名称：

  合成查耳酮可作为潜在的抗炎药和癌症化学预防剂。

  摘要：

  为了开发有效的抗炎药和癌症化学预防剂，通过适当的苯乙酮与适当的芳族醛的克莱森-施密特缩合反应制备了一系列查耳酮，或通过与适当的烷基溴反应的适当的二氢查耳酮制备了一系列查耳酮，或通过一锅法制备通过在碱性氧化铝上超声搅拌获得苯乙酮和方便的芳香醛。测试了合成产物对肥大细胞，嗜中性粒细胞，巨噬细胞和小胶质细胞活化的抑制作用。进一步评估了巨噬细胞和小胶质细胞中NO产生的有效抑制剂对几种人类癌细胞系的体外细胞毒性作用。2'-羟基查耳酮1-3和2'，5' -二羟基查耳酮7对用甲酰-Met-Leu-Phe（fMLP）/细胞松弛素B（CB）刺激的大鼠嗜中性粒细胞释放β-葡萄糖醛酸苷酶或溶菌酶具有有效的抑制作用。响应fMLP / CB，两个2'-羟基查耳酮（1和3）对大鼠中性粒细胞中超氧阴离子的生成具有有效的抑制作用。先前报道的查耳酮5、6和12在脂多糖（LPS）/干扰素-γ（IFN-γ）激活的N9小胶质细胞或LPS激活的RAW

  DOI：

  10.1016/j.ejmech.2004.09.006

文献信息

• MODIFIED CHALCONE COMPOUNDS AS ANTIMITOTIC AGENTS
  申请人：ROSE Seth D.

  公开号：US20070265317A1

  公开（公告）日：2007-11-15

  Antimitotic agents comprising a modified chalcone or modified chalcone derivative are disclosed. The modified chalcone or modified chalcone derivative compounds are of the general formula CHAL-LIN—COV, wherein CHAL is a chalcone or chalcone derivative portion, LIN is an optional linker portion, and COV is a covalent bonding portion (e.g., an α,β-unsaturated thiol ester group). The modified chalcone or modified chalcone derivative compounds provide an improved method of interference with tubulin polymerization, for example by covalent (and essentially irreversible) bonding between tubulin and the covalent bonding portion, potentially resulting in a decrease in tumor size and/or disappearance of the cancer, to the benefit of cancer patients.

  本发明涉及一种包含改性查尔酮或改性查尔酮衍生物的抗有丝分裂剂。改性查尔酮或改性查尔酮衍生物化合物的一般式为CHAL-LIN-COV，其中，CHAL是查尔酮或查尔酮衍生物部分，LIN是可选的连接部分，COV是共价键合部分（例如α，β-不饱和硫酯酯基）。改性查尔酮或改性查尔酮衍生物化合物提供了一种改进的干扰微管聚合的方法，例如通过微管和共价键合部分之间的共价键合（基本上是不可逆的），可能导致肿瘤大小减小和/或癌症消失，从而使癌症患者受益。
• Modified chalcone compounds as antimitotic agents
  申请人：Arizona Biomedical Research Commission

  公开号：EP2447248A2

  公开（公告）日：2012-05-02

  Antimitotic agents comprising a modified chalcone or modified chalcone derivative are disclosed. The modified chalcone or modified chalcone derivative compounds are of the general formula CHAL-LIN-COV, wherein CHAL is a chalcone or chalcone derivative portion, LIN is an optional linker portion, and COV is a covalent bonding portion (e.g., an a,ss-unsaturated thiol ester group). The modified chalcone or modified chalcone derivative compounds provide an improved method of interference with tubulin polymerization, for example by covalent (and essentially irreversible) bonding between tubulin and the covalent bonding portion, potentially resulting in a decrease in tumor size and/or disappearance of the cancer, to the benefit of cancer patients.

  本发明公开了包含改性查尔酮或改性查尔酮衍生物的抗硝化剂。改性查尔酮或改性查尔酮衍生物化合物的通式为 CHAL-LIN-COV，其中 CHAL 为查尔酮或查尔酮衍生物部分，LIN 为任选连接部分，COV 为共价键部分（例如，a,s-不饱和硫醇酯基）。改性查尔酮或改性查尔酮衍生物化合物提供了一种改进的干扰小管蛋白聚合的方法，例如通过小管蛋白与共价键部分之间的共价键（且基本上不可逆），可能导致肿瘤体积减小和/或癌症消失，从而使癌症患者受益。
• Cytotoxic 2′,5′-dihydroxychalcones with unexpected antiangiogenic activity
  作者：Nguyen-Hai Nam、Yong Kim、Young-Jae You、Dong-Ho Hong、Hwan-Mook Kim、Byung-Zun Ahn

  DOI：10.1016/s0223-5234(02)01443-5

  日期：2003.2

  A series of 2',5'-dihydroxychalcones were synthesized and evaluated for cytotoxicity against tumor cell lines and human umbilical venous endothelial cells (HUVEC). It was found that chalcones with electron-withdrawing substituents on the B ring exhibited potent cytotoxicity against a variety of tumor cell lines while compounds with electron-releasing groups ere less potent in general. Those compounds with B ring replaced by extended or heteroaromatic rings exhibited significant bioactivity. Several compounds were shown to have marked cytotoxic selectivity towards HUVECs. Especially, among the synthesized compounds. 2-chloro-2'.5'dihydroxychalcone (2-3) showed the highest selectivity index up to 66 in comparison to HCT 116 cells. This Compound also exhibited strong inhibitory effects on the HUVEC tube formation in an in vitro model. When administered into BDF1 mice bearing Lewis lung carcinoma cells at 50 mg kg(-1) day (-1), 2-3 was found to inhibit the growth of tumor mass by 60.5%. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Modified Chalcone Compounds as Antimitotic Agents
  申请人：Rose Seth D.

  公开号：US20100222380A1

  公开（公告）日：2010-09-02

  Antimitotic agents comprising a modified chalcone or modified chalcone derivative are disclosed. The modified chalcone or modified chalcone derivative compounds are of the general formula CHAL-LIN-COV, wherein CHAL is a chalcone or chalcone derivative portion, LIN is an optional linker portion, and COV is a covalent bonding portion (e.g., an α,β-unsaturated thiol ester group). The modified chalcone or modified chalcone derivative compounds provide an improved method of interference with tubulin polymerization, for example by covalent (and essentially irreversible) bonding between tubulin and the covalent bonding portion, potentially resulting in a decrease in tumor size and/or disappearance of the cancer, to the benefit of cancer patients.
• US7714025B2
  申请人：——

  公开号：US7714025B2

  公开（公告）日：2010-05-11