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

• Substituted spirooxindole derivatives as potent anticancer agents through inhibition of phosphodiesterase 1
  作者：Assem Barakat、Mohammad Shahidul Islam、Hussien Mansur Ghawas、Abdullah Mohammed Al-Majid、Fardous F. El-Senduny、Farid A. Badria、Yaseen A. M. M. Elshaier、Hazem A. Ghabbour

  DOI：10.1039/c8ra02358a

  日期：——

  agent. Possible targets include cancers of the liver, prostate, lung, stomach, colon, and breast. Here, we demonstrate a one-pot three-component reaction via a [3 + 2] cycloaddition/ring contraction sequence of a dipolarophile (activated alkene) with in situ-generated azomethine ylide (1,3-dipoles) without the use of any catalyst. The reaction provides efficient access to synthetically useful and biologically

  螺氧吲哚是一种很有前景的化疗药物。可能的目标包括肝癌、前列腺癌、肺癌、胃癌、结肠癌和乳腺癌。在这里，我们展示了通过亲偶极体（活化烯烃）的 [3 + 2] 环加成/环收缩序列与原位生成的偶氮甲碱叶立德（1,3-偶极子）进行的一锅三组分反应，而无需使用任何催化剂。该反应以高产率（69-94%）和高非对映选择性提供了有效的合成有用和生物学上重要的螺羟吲哚的途径。使用结肠直肠癌 (HCT-116)、肝细胞癌 (HepG2) 和前列腺癌 (PC-3) 细胞对合成的化合物进行细胞毒性评估。化合物4i、4j和与顺铂相比，4k对 HCT-116 细胞显示出有效的细胞毒活性和高选择性。同时，与顺铂相比，化合物4d保留了对 HepG2 和 PC-3 细胞的高细胞毒活性和选择性。使用磷酸二酯酶 1 酶进一步研究了化合物4d的作用机制，显示出 74.2% 的抑制活性。使用 OpenEye 软件通过分子建模研究了化合物4d与
• 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