3-(4-chlorophenyl)-1-(1H-indol-3-yl)prop-2-en-1-one | 34023-78-4

• 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: 3-(4-chlorophenyl)-1-(1H-indol-3-yl)prop-2-en-1-one
• 英文别名: 1-(3-Indolyl)-3-(4-chlorphenyl)-1-propenon；1-(3-Indolyl)-3-(4-chlorphenyl)-3-propenon；3-(4-chloro-phenyl)-1-indol-3-yl-propenone
• CAS: 34023-78-4
• 化学式: C₁₇H₁₂ClNO
• 分子量: 281.741
• InChiKey: BVWSVGRXDAGCKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 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：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-1-(1H-indol-3-yl)prop-2-en-1-one 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以66%的产率得到
  参考文献：
  名称：

  Pathak, Devender; Sharma, Gyanendra Kumar; Sharma, Vikas, Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 4, p. 401 - 402

  摘要：

  DOI：
• 作为产物：
  描述：

  3-乙酰吲哚 、 4-氯苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-(4-chlorophenyl)-1-(1H-indol-3-yl)prop-2-en-1-one
  参考文献：
  名称：

  取代螺氧吲哚衍生物通过抑制磷酸二酯酶作为有效的抗癌剂 1†

  摘要：

  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

  DOI：

  10.1039/c8ra02358a

文献信息

• Synthesis of New 3-Heteroarylindoles as Potential Anticancer Agents
  作者：Abdou Abdelhamid、Sobhi Gomha、Nadia Abdelriheem、Saher Kandeel

  DOI：10.3390/molecules21070929

  日期：——

  3-d]pyrimidin-4(1H)-ones, respectively. Also, hydrazonoyl halides were reacted with N’-(1-(1H-indol-3-yl)ethylidene)-2-cyanoacetohydrazide to afford 1,3,4-thiadiazole derivatives. Structures of the new synthesis were elucidated on the basis of elemental analysis, spectral data, and alternative synthetic routes whenever possible. Fifteen of the new compounds have been evaluated for their antitumor activity

  2-(3-(1H-Indol-3-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-取代-5-(取代二氮烯基)噻唑和2-(1H-indol-3-yl)-9-取代-4,7-二取代吡啶并[3,2-e][1,2,4]三唑并[4,3-a]嘧啶-5(7H) -ones 通过腙酰卤化物与 3-(1H-indol-2-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 和 7-(1H -indol-3-yl)-2-thioxo-5-取代的-2,3-二氢吡啶并[2,3-d]嘧啶-4(1H)-ones，分别。此外，腙酰卤与N'-(1-(1H-吲哚-3-基)亚乙基)-2-氰基乙酰肼反应得到1,3,4-噻二唑衍生物。新合成的结构是在元素分析、光谱数据和可能的替代合成路线的基础上阐明的。已经评估了 15 种新化合物对
• New 2-alkoxycyanopyridine derivatives as inhibitors of EGFR, HER2, and DHFR: Synthesis, anticancer evaluation, and molecular modeling studies
  作者：Samia S. Hawas、Selwan M. El-Sayed、Perihan A. Elzahhar、Mohamed A. Moustafa

  DOI：10.1016/j.bioorg.2023.106874

  日期：2023.12

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• 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.