trans-3-(1H-indol-3-yl)-1-(2''-chlorophenyl)-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: trans-3-(1H-indol-3-yl)-1-(2''-chlorophenyl)-2-propen-1-one
• 英文别名: (E)-1-(2-chlorophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
• 化学式: C₁₇H₁₂ClNO
• 分子量: 281.741
• InChiKey: IMIAMDVGGBIMCB-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：

  丙二腈 、 trans-3-(1H-indol-3-yl)-1-(2''-chlorophenyl)-2-propen-1-one 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以9%的产率得到2-Amino-6-(2-chloro-phenyl)-4-(1H-indol-3-yl)-nicotinonitrile
  参考文献：
  名称：

  Anti-inflammatory, analgesic and antipyretic 4,6-disubstituted 3-cyano-2-aminopyridines

  摘要：

  4,6-diaryl and 4,6-aryl-indolyl substituted 3-cyano-2-aminopyridines were synthesized and submitted to evaluation for their anti-inflammatory, analgesic and antipyretic activity. The electronegativity of the substituents and their displacement on the 4- or 6-aryl ring of the 4,6-diaryl-3-cyano-2-aminopyridine nucleus (3a-q) influenced the anti-inflammatory activity which was higher in the presence of electron-realising groups. The introduction of the indol-3-yl substituent in the 4-position of the 3-cyano-2-aminopyridine nucleus (6a-x) increased the anti-inflammatory and analgesic power, but there was no evidence of the relationship among the electronic characteristic of the substituents, their displacement on the 6-phenyl ring and the activity. Conversely, the displacement of the 2-hydroxyphenyl group in the 4-position (4a-e) and of the indol-3-yl group in the 6-position (8h-w) decreased the anti-inflammatory activity. All derivatives did not show any significative antipyretic activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80057-9
• 作为产物：
  描述：

  3-吲哚甲醛 、 邻氯苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以85%的产率得到trans-3-(1H-indol-3-yl)-1-(2''-chlorophenyl)-2-propen-1-one
  参考文献：
  名称：

  取代的查尔酮衍生物与诺氟沙星对耐甲氧西林的金黄色葡萄球菌的体外和体内协同相互作用

  摘要：

  通过碱催化的克莱森·施密特缩合反应合成了三十种查尔酮衍生物，并单独或与诺氟沙星组合评估了它们的抗甲氧西林抗金黄色葡萄球菌（MRSA）活性。其中5个衍生物，即反式-3-（1 H-吲哚-3-基）-1-（4'-苄氧基苯基）-2-丙烯-1-酮（2），1-（4″-联苯）- 3-（3'4'-二羟基苯基）-2-丙烯-1-酮（11），1-（4''-羟基-3''-甲基苯基）3-（4'-羟基苯基）-2-丙烯-1-一（14），3-（4'-氯苯基）-1-（4''-羟苯基）2-丙烯-1-酮（17）和LTG-肟（27）在MIC 12.5–50 µg时显示出显着的抗菌活性。毫升-1。在组合研究中，衍生物2和14显著诺氟沙星高达16倍（FICI <0.5）降低了MIC，而衍生物11， 17和27减少了它由多达八个倍（FICI≤0.5）。流式细胞仪分析结果清楚地表明，衍生物2和14显着促进了Et-Br外排的积累和抑制，这通

  DOI：

  10.1039/c4ra10842f

文献信息

• In vitro and in vivo synergistic interaction of substituted chalcone derivatives with norfloxacin against methicillin resistant Staphylococcus aureus
  作者：Rashmi Gaur、Vivek Kumar Gupta、Anirban Pal、Mahendra Padurang Darokar、Rajendra Singh Bhakuni、Brijesh Kumar

  DOI：10.1039/c4ra10842f

  日期：——

  Thirty chalcone derivatives were synthesized via a base catalyzed Claisen Schmidt condensation and evaluated for their anti-methicillin-resistant Staphylococcus aureus (MRSA) activity alone and in combination with norfloxacin. Among these, 5 derivatives namely trans-3-(1H-indol-3-yl)-1-(4′-benzyloxyphenyl)-2-propen-1-one (2), 1-(4″-biphenyl)-3-(3′4′-dihydroxyphenyl)-2-propen-1-one (11), 1-(4″-hydroxy-3

  通过碱催化的克莱森·施密特缩合反应合成了三十种查尔酮衍生物，并单独或与诺氟沙星组合评估了它们的抗甲氧西林抗金黄色葡萄球菌（MRSA）活性。其中5个衍生物，即反式-3-（1 H-吲哚-3-基）-1-（4'-苄氧基苯基）-2-丙烯-1-酮（2），1-（4″-联苯）- 3-（3'4'-二羟基苯基）-2-丙烯-1-酮（11），1-（4''-羟基-3''-甲基苯基）3-（4'-羟基苯基）-2-丙烯-1-一（14），3-（4'-氯苯基）-1-（4''-羟苯基）2-丙烯-1-酮（17）和LTG-肟（27）在MIC 12.5–50 µg时显示出显着的抗菌活性。毫升-1。在组合研究中，衍生物2和14显著诺氟沙星高达16倍（FICI <0.5）降低了MIC，而衍生物11， 17和27减少了它由多达八个倍（FICI≤0.5）。流式细胞仪分析结果清楚地表明，衍生物2和14显着促进了Et-Br外排的积累和抑制，这通
• Chemical synthesis, docking studies and biological effects of functionalized 1,3-diaryl-2-propen-1-ones on human colon cancer cells
  作者：Guo-Min Zhu、Guo-Dong Huang

  DOI：10.3329/bjp.v10i1.21699

  日期：——

  A series of 1, 3-diaryl-2-propen-1-ones was synthesised in order to obtain a new type of anticancer drug, designed with hybrid features to inhibit colon cancer activated receptor. Based on computational modelling and docking studies, potential inhibitors were synthesised and their biological activity evaluated. The structures of newly synthesized compounds were confirmed by 1HNMR, 13CNMR and Mass spectrometry. All analogues were evaluated for in vitro cytotoxicity against human colon (caco-2) cancer cell lines. Compounds 1b, 1f-1h, and 2i showed significant cytotoxicity. Chalcones 1b, 1f and 1g were identified as the most potent and selective anticancer agents with IC50 values <1 µg/mL and 1.5 µg/mL, against caco-2 cell line, respectively. In conclusion, this finding confirms the suitability of indolyl chalcone analogues as candidates for further investigation towards the management of colon cancer related diseases.

  为了获得一种新型抗癌药物，我们合成了一系列 1，3-二芳基-2-丙烯-1-酮，其设计具有抑制结肠癌活化受体的混合特征。在计算建模和对接研究的基础上，合成了潜在的抑制剂，并对其生物活性进行了评估。新合成化合物的结构通过 1HNMR、13CNMR 和质谱进行了确认。评估了所有类似物对人结肠癌（caco-2）细胞系的体外细胞毒性。化合物 1b、1f-1h 和 2i 显示出显著的细胞毒性。查耳酮 1b、1f 和 1g 被确定为最有效的选择性抗癌剂，对 caco-2 细胞系的 IC50 值分别为 1 µg/mL 和 1.5 µg/mL。总之，这一发现证实了吲哚基查尔酮类似物适合作为进一步研究结肠癌相关疾病治疗的候选药物。
• Anti-inflammatory, analgesic and antipyretic 4,6-disubstituted 3-cyano-2-aminopyridines
  作者：Fedele Manna、Franco Chimenti、Adriana Bolasco、Bruna Bizzarri、Walter Filippelli、Amelia Filippelli、Luigi Gagliardi

  DOI：10.1016/s0223-5234(99)80057-9

  日期：1999.3

  4,6-diaryl and 4,6-aryl-indolyl substituted 3-cyano-2-aminopyridines were synthesized and submitted to evaluation for their anti-inflammatory, analgesic and antipyretic activity. The electronegativity of the substituents and their displacement on the 4- or 6-aryl ring of the 4,6-diaryl-3-cyano-2-aminopyridine nucleus (3a-q) influenced the anti-inflammatory activity which was higher in the presence of electron-realising groups. The introduction of the indol-3-yl substituent in the 4-position of the 3-cyano-2-aminopyridine nucleus (6a-x) increased the anti-inflammatory and analgesic power, but there was no evidence of the relationship among the electronic characteristic of the substituents, their displacement on the 6-phenyl ring and the activity. Conversely, the displacement of the 2-hydroxyphenyl group in the 4-position (4a-e) and of the indol-3-yl group in the 6-position (8h-w) decreased the anti-inflammatory activity. All derivatives did not show any significative antipyretic activity. (C) Elsevier, Paris.
• Synthesis, molecular modelling studies of indolyl chalcone derivatives and their antimalarial activity evaluation
  作者：Jyoti、Rashmi Gaur、Yogesh Kumar、Harveer Singh Cheema、Deepak Singh Kapkoti、Mahendra P. Darokar、Feroz Khan、Rajendra Singh Bhakuni

  DOI：10.1080/14786419.2019.1696788

  日期：2021.10.2

  of terrestrial plants, precursors for the biosynthesis of flavonoids and exhibit various biological activities. Antiplasmodial IC50 (half-maximal inhibitory concentration) activity of a compound against malaria parasites in vitro provides a good first screen for identifying the antimalarial potential of the compound. The most active compound was Trans-3-(1H-indol-3-yl)-1-(2’-hydroxyphenyl)-2-propen-1-one

  摘要 使用 Claisen-Schmidt 缩合合成了 21 种查尔酮衍生物，测定了它们对恶性疟原虫的抗疟活性，并建立了定量构效关系 (QSAR)。取代苯乙酮与各种芳香醛在室温下缩合得到 75-96% 产率的查耳酮。查耳酮是陆生植物的次生代谢产物，是类黄酮生物合成的前体，具有多种生物活性。化合物在体外抗疟原虫的抗疟原虫IC 50（半数最大抑制浓度）活性为鉴定该化合物的抗疟潜力提供了良好的初步筛选。最活跃的化合物是Trans-3-(1H-indol-3-yl)-1-(2'-hydroxyphenyl)-2-propen-1-one (1b)，IC 50为 2.1 µM/L。通过对活性化合物的计算机对接和 ADMET 研究探索了分子机制。