1-(3-Indolyl)-3-(4-anisyl)-2-propen-3-on | 27664-01-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(3-Indolyl)-3-(4-anisyl)-2-propen-3-on
• 英文别名: 3-<3-(4-Methoxyphenyl)-acryloyl>-indol；1-indol-3-yl-3-(4-methoxy-phenyl)-propenone；1-(1H-indol-3-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 27664-01-3
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: BXMDCXQVPHEZKY-UHFFFAOYSA-N

物化性质

• 熔点：
  200 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  510.6±50.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-Indolyl)-3-(4-anisyl)-2-propen-3-on 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 [4-(1H-indol-3-yl)-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzoxazepin-3-yl]-(2-methoxyphenyl)diazene
  参考文献：
  名称：

  Bajaj, Kiran; Szivastava; Lata, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 7, p. 1723 - 1728

  摘要：

  DOI：
• 作为产物：
  描述：

  3-乙酰吲哚 、 4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以55%的产率得到1-(3-Indolyl)-3-(4-anisyl)-2-propen-3-on
  参考文献：
  名称：

  杂环吲哚衍生物的合成和抗炎活性。

  摘要：

  吲哚1-5的查尔酮及其相应产品；合成吡唑啉6-10和偶氮化合物11-15，并评估口服剂量50 mg x kg（-1）的白化病大鼠对角叉菜胶诱发的水肿的抗炎活性。化合物的结构通过IR，（1）H-NMR和质谱数据确认。该系列的所有化合物均显示出有希望的抗炎活性。该系列中活性最高的化合物是3- [1-乙酰基-5-（对羟基苯基）-2-吡唑啉-3-基]吲哚（7）最有效，已显示出较高的抑制率。与标准药物苯基丁氮酮相比，具有明显的水肿性，较低的致溃疡作用和急性毒性。

  DOI：

  10.1016/j.ejmech.2003.11.002

文献信息

• Synthesis and antiinflammatory activity of heterocyclic indole derivatives
  作者：Preeti Rani、V.K. Srivastava、Ashok Kumar

  DOI：10.1016/j.ejmech.2003.11.002

  日期：2004.5

  of indole 1-5 and their corresponding products; pyrazolines 6-10 and azo compounds 11-15 were synthesised and evaluated for their antiinflammatory activity against carrageenan induced oedema in albino rats at a dose of 50 mg x kg(-1) oral. The structure of compounds was confirmed by IR, (1)H-NMR and mass spectral data. All the compounds of this series showed promising antiinflammatory activity. The

  吲哚1-5的查尔酮及其相应产品；合成吡唑啉6-10和偶氮化合物11-15，并评估口服剂量50 mg x kg（-1）的白化病大鼠对角叉菜胶诱发的水肿的抗炎活性。化合物的结构通过IR，（1）H-NMR和质谱数据确认。该系列的所有化合物均显示出有希望的抗炎活性。该系列中活性最高的化合物是3- [1-乙酰基-5-（对羟基苯基）-2-吡唑啉-3-基]吲哚（7）最有效，已显示出较高的抑制率。与标准药物苯基丁氮酮相比，具有明显的水肿性，较低的致溃疡作用和急性毒性。
• Synthesis and biological evaluation of indolyl chalcones as antitumor agents
  作者：Dalip Kumar、N. Maruthi Kumar、Kanako Akamatsu、Eriko Kusaka、Hiroshi Harada、Takeo Ito

  DOI：10.1016/j.bmcl.2010.05.016

  日期：2010.7

  A series of indolyl chalcones were synthesized and evaluated in vitro for their anticancer activity against three human cancer cell lines. Compounds 3b-d, 3h, 3j, 3l, 3m, 4g, and 4j showed significant cytotoxicity, particularly, indolyl chalcones 3l and 3m were identified as the most potent and selective anticancer agents with IC50 values 0.03 and 0.09 mu M, against PaCa-2 cell line, respectively. (c) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of new thiazolo-pyrrolidine–(spirooxindole) tethered to 3-acylindole as anticancer agents
  作者：Mohammad Shahidul Islam、Hussien Mansur Ghawas、Fardous F. El-Senduny、Abdullah Mohammed Al-Majid、Yaseen A.M.M. Elshaier、Farid A. Badria、Assem Barakat

  DOI：10.1016/j.bioorg.2018.10.036

  日期：2019.2

  Anticancer therapeutics with profiles of high potency, low toxicity, and low resistance is of considerable interest. A new series of functionalized spirooxindole linked with 3-acylindole scaffold is reported, starting from chalcones derived from 3-acetyl indole with isatin, and l-4-thiazolidinecarboxylic acid. The reactions proceeded regioselectivity, stereoselectivity, without side products in high yield (71-89%). The new spirooxindole hybrids have been evaluated in vitro for their antiproliferative effects against colon cancer (HCT-116), hepatocellular carcinoma (HepG2) and prostate cancer (PC-3). The selectivity of their activity was evaluated. Some of the synthesized compounds showed considerable anticancer activities. Compound 4k proved to retain a high cytotoxic activity and selectivity against colon cancer cells HCT-116 (IC50 = 7 +/- 0.27 mu M, SI: 3.7), and HepG2 (IC50 = 5.5 +/- 0.2 mu M, SI: 4.7) in comparison to (IC50 = 12.6 +/- 0.5, SI: 0.4 and 5.5 +/- 0.3 mu M, SI: 0.9, respectively). Compound 4k was less active (IC50 = 6 +/- 0.3 mu M, SI: 4.3) than cisplatin (IC50 = 5 +/- 0.56 mu M, SI: 1.0) but showed greater selectivity towards prostate cancer cells PC-3 in comparison to cisplatin. The details of the binding mode of the active compounds were clarified by molecular docking. Ligand Efficiency (LE) and Ligand Lipophilic Efficiency (LLE) were evaluated and revealed that compound 4k had acceptable value.
• INDOLE DERIVATIVES AS TESTOSTERONE 5 ALPHA-REDUCTASE INHIBITORS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0648208A1

  公开（公告）日：1995-04-19
• US5530019A
  申请人：——

  公开号：US5530019A

  公开（公告）日：1996-06-25