Phathalocyanine Metal Complexes (M=Fe, Co, and Cu) Catalyzed Aerobic Oxidation of 2-Amino-benzyl Alcohols to Access Quinazolines and Quinolines

Liu, Zilin; Zhang, Xiaojie; Zhang, Heng; Jiang, Hui; Zhao, Xuemei; Shi, Linlin; Zhu, Xinju; Hao, Xin‐Qi; Song, Mao‐Ping

doi:10.6023/cjoc202003068

Cited by 7 publications

(1 citation statement)

References 4 publications

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“…酞菁(Phthalocyanine, Pc)是一类由四个异吲哚环通过氮原子首尾相连形成的大环共轭体系 [5][6] , 其中心具有直径约为 27 nm 的空腔, 可以与许多金属元素进行配位形成高度稳定的金属酞菁 (Metal-Phthalocyanine) (Figure 1) [7][8] . 无论是空腔酞菁还是金属酞菁配合物都具有丰富的电子结构及优异的光电性质, 它们在催化合成 [9][10][11] 、光电材料 [12][13] 和生物医学 [14][15] 等领域都得到了广泛应用. 因此研究者们希望通过修饰酞菁的母核结构促进酞菁领域的发展, 例如通过扩大母核结构得到超酞菁 [16][17] 或者缩小母核结构得到亚酞菁 [18] 、酞荭 [19] 等.…”

Section: 酞菁和亚酞菁简介unclassified

Research Progress in Synthesis, Properties and Application of Subphthalocyanine

Zhou,

Tu,

Gao

et al. 2023

Chinese Journal of Organic Chemistry

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Subphthalocyanine, as a typical contracted analogue of phthalocyanine, exhibits novel cone structure, excellent luminescent properties and high flexibility of modification, which enables it as a new type of fluorescent dye with great research prospects. It has been proved that simple modifications of the axial, peripheral or central ring structure of subphthalocyanine can effectively regulate its physical and chemical properties, such as solubility, absorption/fluorescence emission, fluorescence quantum yield and singlet oxygen yield, and these properties have attracted extensive attentions from chemists in recent years. This review introduces the structures, properties and research significance of subphthalocyanine. Then, the progress in the synthesis, the relationship between properties and molecular structure of subphthalocyanin, and their applications in the area of biochemistry, material chemistry and environmental chemistry are reviewed emphatically. Finally, the development status of subphthalocyanine is summarized, and the further development of subphthalocyanine is discussed and proposed. Keywords subphthalocyanine; structures; photoelectric properties; application 早在 20 世纪初, 日本著名化学家 Meller 和 Ossko [1] 在合成酞菁的过程中就偶然得到了亚酞菁. 随后科学家们通过 X 射线单晶衍射分析实验证实了亚酞菁的结构 [2] , 该发现为酞菁衍生物的发展开辟了新的研究方向. 与酞菁相比, 亚酞菁具有类似的共轭体系和光电性质, 在离子检测、有机太阳能电池、光敏剂、化学传感器、光动力治疗癌症等领域有广阔的应用前景 [3][4] , 因此本文主要综述了亚酞菁的研究进展.

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Section: 酞菁和亚酞菁简介unclassified

Research Progress in Synthesis, Properties and Application of Subphthalocyanine

Zhou,

Tu,

Gao

et al. 2023

Chinese Journal of Organic Chemistry

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Iron(III)‐Catalyzed Difluoroalkylation of Aryl Alkynes with Difluoroenol Silyl Ether in the Presence of Trimethylsilyl Chloride

et al. 2022

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The reaction of non‐fluorinated silyl enol ether with alkyne is useful for the synthesis of β,γ‐unsaturated carbonyl compounds. However, most of the existing methods for realizing such organic transformation usually employ stoichiometric amounts of relatively expensive Lewis acids/metallic salts. Herein, an iron(III)‐catalyzed difluoroalkylation of aryl alkynes with difluoroenol silyl ether was developed. The reactions proceeded smoothly in the presence of a catalytic amount of iron(III) chloride, stoichiometric amounts of trimethylsilyl chloride, and 4 Å molecular sieves in dichloroethane (DCE) to afford the corresponding α‐alkenyl‐α,α‐difluoroketones in modest to good yields. Remarkably, among the various metallic salts screened, cheap and less‐toxic iron(III) salt was found to be the most efficient Lewis acid catalyst for the present reaction. In addition, in the absence of iron(III) chloride or trimethylsilyl chloride, either no reaction occurred or considerably reduced reaction performance was observed. Moreover, the use of Brønsted acid to replace iron(III) chloride as reaction catalyst failed to promote the reaction. The reaction could be scaled up and the obtained difluoroalkylated carbonyl compound serves as a versatile building block which could be subjected to late‐stage diversification to be converted into useful organic molecules containing CF2H and CF2CF2 moieties. Deuterated experiments showed that the proton in the generated alkene product should originate from trace amounts of water present in the reaction system.

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Pharmacophore‐Based Modeling, Synthesis, and Biological Evaluation of Novel Quinazoline/Quinoline Derivatives: Discovery of EGFR Inhibitors with Low Nanomolar Activity

Evren,

Sağlik Özkan,

Akalin‐Çiftçi

et al. 2024

Advcd Theory and Sims

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The main aim of this study is to obtain novel molecules that are more selective on cancer cells compared to healthy cells. For this purpose, four hit molecules are identified using 11 new pharmacophore hypotheses followed by scanning the in‐house database. Then, based on those hit molecules, the synthesis and analysis of four different series (three quinazolines and one quinoline series) are carried out, and their anticancer activity is investigated. Finally, by using molecular docking and dynamics simulation methods, binding mode and structure–activity relationship are examined. Among the quinazolin‐4(3H)‐one derivatives, those containing halogen atom are found to be potentially effective, while the best epidermal growth factor receptor (EGFR) inhibition and apoptosis induction are displayed by compounds containing 4‐amino‐1,2,4‐triazole moiety. Notably, four compounds (4h, 8d, 8l, and 8m) show EGFR inhibition activity at 5.298 ± 0.164, 5.46 ± 0.221, 2.670 ± 0.124, and 2.191 ± 0.908 × 10−9 m, their inhibitory activity is similar to or stronger than gefitinib (IC50: 4.169 ± 0.156 × 10−9 m). In addition, EGFR inhibitor concentration of 4g, 8e, and 8o is determined as 27588 ± 6.945, 52.41 ± 2.312, and 33657 ± 8.512 × 10−9 m. These findings indicate that generated pharmacophore hypotheses successfully determine new EGFR inhibitors. In conclusion, four novel compounds, more active than gefitinib with fewer side effects, are reached, and the structure–activity relationships are clarified.

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Phathalocyanine Metal Complexes (M=Fe, Co, and Cu) Catalyzed Aerobic Oxidation of 2-Amino-benzyl Alcohols to Access Quinazolines and Quinolines

Cited by 7 publications

References 4 publications

Research Progress in Synthesis, Properties and Application of Subphthalocyanine

Research Progress in Synthesis, Properties and Application of Subphthalocyanine

Iron(III)‐Catalyzed Difluoroalkylation of Aryl Alkynes with Difluoroenol Silyl Ether in the Presence of Trimethylsilyl Chloride

Pharmacophore‐Based Modeling, Synthesis, and Biological Evaluation of Novel Quinazoline/Quinoline Derivatives: Discovery of EGFR Inhibitors with Low Nanomolar Activity

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