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Unraveling the Anticancer Activity of Newly Synthesized Acylhydrazones and Hydrazones: In Vitro and Computational Insights 揭示新合成的酰基腙和腙的抗癌活性：体外和计算见解

IF 2.6 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2025-11-26 Epub Date: 2025-10-18 DOI: 10.1080/10406638.2025.2573682

Maha Salih Hussein (Conceptualization Investigation Methodology Project administration Resources Supervision Validation Writing – original draft Writing – review & editing) , Luay Ali Dhahi (Data curation Formal analysis Investigation Methodology Writing – original draft) , Hamid J. Mohammad (Data curation Formal analysis Investigation Methodology Writing – original draft) , Ghada F. Elmasry (Data curation Investigation Software Writing – original draft Writing – review & editing)

Over the past few decades, discovering new anticancer drugs was considered one of the biggest challenges for researchers. In this study, two series of acylhydrazones Z1-6 and hydrazones K1-6 were synthesized via reacting isoniazid or 2-hydrazinopyridine with some aromatic heterocyclic aldehydes under acidic conditions. The structures of all compounds were proven spectrophotometrically using proton nuclear magnetic resonance (¹HNMR) and carbon-13 NMR (¹³CNMR), in addition to liquid chromatography-mass (LCMS) spectra, infrared (IR) spectra, and elemental analyses. Our compounds were evaluated for their anticancer activity against three types of cancer cells: colon HCT-116, lung A-549, and MCF-7 breast Adenocarcinoma cancer cells by the SRB method. Compounds Z3 and K4 showed the highest inhibition against colon cancer cells with IC₅₀ values of 1.59 and <1 μM, respectively. Moreover, flowcytometric analysis revealed the ability of Z3 to cause cell cycle arrest at sub G1 phase and S phase in HCT-116 colon cancer cell line, in addition to prominent apoptotic effects. Subsequently, molecular docking was conducted to gain insight into the plausible mechanism of action for the most active compounds Z3 and K4 and it suggested Topoisomeras I as a potential biological target of the new counterparts. Absorption, Distribution, Metabolism Excretion, and Toxicity (ADMET) study predicted physicochemical and pharmacokinetic aspects. Furthermore, density functional theory (DFT) was carried out to better understand the structural properties, stability, and chemical reactivity of the most promising derivatives. In summary, this study offers new anticancer candidates with acylhyrazone/hydrazone scaffolds which may need further optimization.

在过去的几十年中，发现新的抗癌药物被认为是研究人员面临的最大挑战之一。在酸性条件下，通过异烟肼或2-肼吡啶与芳香族杂环醛反应，合成了两个酰基腙Z1-6和K1-6。采用质子核磁共振（1HNMR）和碳-13核磁共振（13CNMR），液相色谱-质谱（LCMS），红外（IR）光谱和元素分析等方法证实了所有化合物的结构。我们的化合物通过SRB方法对三种类型的癌细胞（结肠癌HCT-116、肺癌A-549和乳腺癌MCF-7）的抗癌活性进行了评估。化合物Z3和K4对结肠癌细胞的抑制作用最强，IC50值分别为1.59和1 μM。此外，流式细胞术分析显示，Z3在HCT-116结肠癌细胞系中除了显著的凋亡作用外，还能引起细胞周期阻滞在亚G1期和S期。随后，我们进行了分子对接，以深入了解Z3和K4最活性化合物的可能作用机制，并提出拓扑异构体I是新对应物的潜在生物学靶点。吸收，分布，代谢，排泄和毒性（ADMET）研究预测物理化学和药代动力学方面。此外，密度泛函理论（DFT）可以更好地理解最有前途的衍生物的结构性质、稳定性和化学反应性。综上所述，本研究提供了新的抗肿瘤候选酰基腙/腙支架，这些支架可能需要进一步优化。

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引用次数: 0

The Piloty-Robinson Reaction: A Versatile Tool for the Synthesis of 3,4-Disubstituted Pyrroles 皮洛特-罗宾逊反应：合成3,4-二取代吡咯的通用工具

IF 2.6 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2025-10-21 Epub Date: 2025-06-02 DOI: 10.1080/10406638.2025.2509695

Rohit Kumar , Tahir Hussain Wani , Rashid Ali

In recent years, pyrrole and related compounds have engrossed a remarkable interest of the research community, as they have not only been a part of diverse natural and non-natural products but also played a vital role in molecular recognition, sensing, catalysis, and biological as well as material sciences, besides many more promising applications in other fields as well. In this minireview, we have for the first time disclosed the developments in the Piloty-Robinson pyrrole synthesis protocol, since its discovery in 1910 by O. Piloty and report in 1918 by G.M. Robinson and R. Robinson. Herein, we have tried to assemble all the reported pyrrole-based systems constructed by means of the Piloty-Robinson tactic. The authors believe that this specific and sole report for the preparation of substituted pyrroles via the Piloty-Robinson approach will provide a new avenue for the synthesis of a variety of valued pyrrole derivatives of specific interests.

近年来，吡咯及其相关化合物引起了研究界的极大兴趣，因为它们不仅是各种天然和非天然产物的一部分，而且在分子识别、传感、催化、生物和材料科学中发挥着重要作用，而且在其他领域也有更广阔的应用前景。在这篇小型综述中，我们首次披露了皮罗蒂-罗宾逊吡咯合成方案的进展，自1910年由O.皮罗蒂发现和1918年由G.M.罗宾逊和R.罗宾逊报告以来。在此，我们试图将所有已报道的以皮洛特-罗宾逊战术为基础的基于吡咯的系统组合起来。作者相信，这一专门的、唯一的用pilot - robinson方法制备取代吡咯的报道，将为合成各种有价值的吡咯衍生物提供一条新的途径。

引用次数: 0

Probing and Evaluating the Anion Binding Studies in Novel Coumarin Based Strapped Calix[4]Pyrrole 新型香豆素捆绑杯形吡咯阴离子结合研究的探讨与评价

IF 2.6 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2025-10-21 Epub Date: 2025-05-29 DOI: 10.1080/10406638.2025.2508250

Shafieq Ahmad Wagay , Rashid Ali

A novel coumarin-based strapped calix[4]pyrrole, C4P9, was synthesized through an acid cyclization reaction followed by the reaction of coumarin with dipyrromethane. The structure of C4P9 was confirmed using ¹H-NMR,¹³C-NMR, and mass spectrometry. Structural analysis revealed a pre-organized conformation for anion recognition, facilitated by intramolecular hydrogen bonding and the rigid strapping unit. An in-depth investigation of anion binding with various species such as F⁻, Br⁻, Cl⁻, I⁻, AcO⁻, NO₃⁻, HSO₄⁻, SCN⁻, and H₂PO₄⁻ was conducted using UV-vis and NMR spectroscopy. The anion binding studies were validated by comparing ¹H-NMR spectra of free receptor C4P9 with that of C4P9@F. The results from the online supramolecular Bindfit v0.5 program and Job’s plots indicated a 1:1 stoichiometry for the complexation between C4P9 and anions. The coumarin strap enhanced the binding ability and selectivity toward anions, as evidenced by calculations of binding constants. This was observed through interactions such as anion—π (involving aromatic moieties at the meso-position) and C–H—anion (involving the strapped linker and aromatic moiety) as well as N–H—anion interactions. This study demonstrates the potential of coumarin-based strapped calix[4]pyrrole as a versatile platform for developing functional anion receptors, particularly in anion/ion-pair coordination chemistry and supramolecular chemistry in general.

通过香豆素与二吡咯甲烷的酸环化反应，合成了一种新型的香豆素基杯状吡咯C4P9。C4P9的结构通过1H-NMR、13C-NMR和质谱分析得到了证实。结构分析显示，分子内氢键和刚性带单元促进了阴离子识别的预组织构象。利用紫外可见光谱和核磁共振光谱深入研究了阴离子与F−、Br−、Cl−、I−、AcO−、NO3−、HSO4−、SCN−和H2PO4−等多种物质的结合。通过比较游离受体C4P9与C4P9@F的1H-NMR谱，验证了阴离子结合的研究。在线超分子binfit v0.5程序和Job图的结果表明，C4P9与阴离子之间的络合反应呈1:1的化学计量。结合常数的计算表明，香豆素带增强了对阴离子的结合能力和选择性。这是通过阴离子-π（涉及中间位置的芳香族部分）和c - h阴离子（涉及绑定的连接剂和芳香族部分）以及n - h阴离子相互作用观察到的。本研究证明了香豆素基杯状吡咯作为开发功能性阴离子受体的多功能平台的潜力，特别是在阴离子/离子对配位化学和一般的超分子化学中。

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引用次数: 0

A Click Chemistry Approach for the Synthesis of Triazole Linked Vanillin Scaffolds as Potent Pharmacophores: Anti-Diabetic, Anti-Inflammatory, Antioxidant, Molecular Docking and ADMET Investigations 点击化学方法合成三唑连接香兰素支架：抗糖尿病、抗炎、抗氧化、分子对接和ADMET研究

IF 2.6 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2025-10-21 Epub Date: 2025-05-26 DOI: 10.1080/10406638.2025.2507335

Vardhaman Babagond , Kariyappa Katagi , Mahesh Akki , Vinuta Kamat , Delicia Avilla Barretto , Ashwini Jaggal , Surekha Kademani , Arunkumar Shirahatti

In this study a series of triazole linked vanillin derivatives were synthesized via Click chemistry and characterized using FTIR,¹H NMR,¹³C NMR, and HRMS/MS. Among the synthesized compounds, 6k, 6f, and 6b showed strong α-amylase inhibitory activity (IC₅₀ = 50.70, 51.36, and 53.25 μg/mL, respectively) and α-glucosidase inhibitory activity (IC₅₀ = 36.85, 37.99, and 38.49 μg/mL), comparable to acarbose (IC₅₀ = 54.38 and 39.04 μg/mL). Compound 6e exhibited potent antibacterial activity (MIC = 0.5–2 μg/mL) against all tested strains, including S. aureus, S. pyogenes, S. typhi, and P. aeruginosa, comparable to streptomycin, while 6k also showed notable inhibition (MIC = 2–4 μg/mL). In antioxidant assays, 6a and 6j demonstrated IC₅₀ values (48.25 and 49.31 μg/mL) comparable to ascorbic acid (IC₅₀ = 49.18 μg/mL). Anti-inflammatory activity was significant for 6a and 6j (IC₅₀ = 36.66 and 37.21 μg/mL), surpassing diclofenac (IC₅₀ = 37.89 μg/mL). The compounds were nontoxic in cytotoxicity studies, with IC₅₀ values >120 μg/mL for Vero cells, significantly higher than cisplatin (35.15 μg/mL). Molecular docking supported the in vitro results, with active compounds showing strong binding affinities, and SwissADME analysis indicated favorable pharmacokinetic properties. These findings highlight the multifunctional therapeutic potential of the designed compounds as anti-diabetic, antibacterial, antioxidant, and anti-inflammatory agents.

本研究通过Click化学合成了一系列三唑类香兰素衍生物，并用FTIR、1H NMR、1³C NMR和HRMS/MS对其进行了表征。在所合成的化合物中，6k、6f和6b具有较强的α-淀粉酶抑制活性（IC50分别为50.70、51.36和53.25 μg/mL）和α-葡萄糖苷酶抑制活性（IC50分别为36.85、37.99和38.49 μg/mL），与阿卡波糖（IC50分别为54.38和39.04 μg/mL）相当。化合物6e对金黄色葡萄球菌、化脓性葡萄球菌、伤寒葡萄球菌和铜绿假单胞菌均表现出与链霉素相当的抑菌活性（MIC = 0.5 ~ 2 μg/mL），而化合物6k也表现出显著的抑菌活性（MIC = 2 ~ 4 μg/mL）。在抗氧化实验中，6a和6j的IC50值分别为48.25和49.31 μg/mL，与抗坏血酸的IC50值（49.18 μg/mL）相当。6a和6j的抗炎活性显著（IC50分别为36.66和37.21 μg/mL），超过双氯芬酸（IC50分别为37.89 μg/mL）。在细胞毒性研究中，化合物无毒，对Vero细胞的IC50值为120 μg/mL，显著高于顺铂（35.15 μg/mL）。分子对接支持体外结果，活性化合物显示出较强的结合亲和力，SwissADME分析显示出良好的药代动力学特性。这些发现突出了所设计的化合物作为抗糖尿病、抗菌、抗氧化和抗炎剂的多功能治疗潜力。

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引用次数: 0

Synthesis, Characterization, In Vitro Biological Evaluation, and Computational Studies of Pyrazole Derivatives as Promising Anticancer and Antibacterial Agents 吡唑类抗癌抗菌剂的合成、表征、体外生物学评价及计算研究

IF 2.6 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2025-10-21 Epub Date: 2025-10-06 DOI: 10.1080/10406638.2025.2563691

Ketan Vashisht (Data curation Formal analysis Writing – original draft) , Pooja Sethi (Data curation Formal analysis Investigation Writing – original draft) , Anshul Bansal (Data curation Formal analysis Investigation Writing – original draft) , Reena Kumari (Data curation Formal analysis Writing – original draft) , Manoj Singh (Data curation Formal analysis Investigation) , Ahmad Umar (Data curation Formal analysis Writing – review & editing) , Ahmed A. Ibrahim (Data curation Formal analysis Writing – review & editing) , Sotirios Baskoutas (Data curation Formal analysis Writing – review & editing)

A Series of newly designed pyrazole derivatives (3a–j) were synthesized through a condensation reaction between 3-(substituted phenylazo)-2,4-pentanedione (2) and 4-cyanophenyl hydrazine, yielding good results (70–85%). Their structural confirmations were carried out by using elemental analysis, mass spectrometry (MS), IR,¹H NMR and ¹³C NMR spectroscopy. The pyrazole series 3a–j were screened for their cytotoxicity against the SH-SY5Y neuroblastoma cancer cell line. Compound 3j exhibited the lowest IC₅₀ value of 19.18 µg/ml against the SH-SY5Y neuroblastoma cell line, demonstrating the highest effectiveness in inhibiting cell growth. Additionally, the compounds were evaluated for antibacterial activity against both Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Pseudomonas fluorescens and Escherichia coli). In addition, molecular docking analysis against 3V2B was performed, revealing that compound 3j exhibited a maximum binding affinity of −7.700 kcal/mol. The relative energies of compounds 3a–j were also determined through DFT studies utilizing the B3LYP methodology. This thorough analysis highlights the significant antibacterial and anticancer activities belonging to a new class of pyrazole derivatives, as well as their effective synthesis.

通过3-（取代苯偶氮）-2,4-戊二酮(2)与4-氰苯肼的缩合反应，合成了一系列新设计的吡唑衍生物（3a-j），收率为70-85%。采用元素分析、质谱（MS）、红外光谱（IR）、1H NMR和13C NMR对其结构进行了确证。筛选吡唑系列3a-j对SH-SY5Y神经母细胞瘤细胞系的细胞毒性。化合物3j对SH-SY5Y神经母细胞瘤细胞系的IC50值最低，为19.18µg/ml，显示出最高的抑制细胞生长的效果。此外，化合物对革兰氏阳性菌（枯草芽孢杆菌和金黄色葡萄球菌）和革兰氏阴性菌（荧光假单胞菌和大肠杆菌）的抗菌活性进行了评估。此外，对化合物3j与3V2B的分子对接分析表明，化合物3j的最大结合亲和力为−7.700 kcal/mol。化合物3a-j的相对能也通过使用B3LYP方法的DFT研究确定。这一深入的分析突出了一类新的吡唑衍生物的显著抗菌和抗癌活性，以及它们的有效合成。

{"title":"Synthesis, Characterization, In Vitro Biological Evaluation, and Computational Studies of Pyrazole Derivatives as Promising Anticancer and Antibacterial Agents","authors":"Ketan Vashisht (Data curation Formal analysis Writing – original draft) , Pooja Sethi (Data curation Formal analysis Investigation Writing – original draft) , Anshul Bansal (Data curation Formal analysis Investigation Writing – original draft) , Reena Kumari (Data curation Formal analysis Writing – original draft) , Manoj Singh (Data curation Formal analysis Investigation) , Ahmad Umar (Data curation Formal analysis Writing – review & editing) , Ahmed A. Ibrahim (Data curation Formal analysis Writing – review & editing) , Sotirios Baskoutas (Data curation Formal analysis Writing – review & editing)","doi":"10.1080/10406638.2025.2563691","DOIUrl":"10.1080/10406638.2025.2563691","url":null,"abstract":"<div><div>A Series of newly designed pyrazole derivatives (3a–j) were synthesized through a condensation reaction between 3-(substituted phenylazo)-2,4-pentanedione (2) and 4-cyanophenyl hydrazine, yielding good results (70–85%). Their structural confirmations were carried out by using elemental analysis, mass spectrometry (MS), IR,1H NMR and 13C NMR spectroscopy. The pyrazole series 3a–j were screened for their cytotoxicity against the SH-SY5Y neuroblastoma cancer cell line. Compound 3j exhibited the lowest IC50 value of 19.18 µg/ml against the SH-SY5Y neuroblastoma cell line, demonstrating the highest effectiveness in inhibiting cell growth. Additionally, the compounds were evaluated for antibacterial activity against both Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Pseudomonas fluorescens and Escherichia coli). In addition, molecular docking analysis against 3V2B was performed, revealing that compound 3j exhibited a maximum binding affinity of −7.700 kcal/mol. The relative energies of compounds 3a–j were also determined through DFT studies utilizing the B3LYP methodology. This thorough analysis highlights the significant antibacterial and anticancer activities belonging to a new class of pyrazole derivatives, as well as their effective synthesis.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 9","pages":"Pages 1741-1758"},"PeriodicalIF":2.6,"publicationDate":"2025-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145475877","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

A Novel Phenoxyquinoline-Pyrimidine Hybrids: Synthesis, In Silico ADME Studies, Molecular Docking and in Vitro Cytotoxic Activity 一种新型苯氧喹啉-嘧啶杂合体：合成、硅ADME研究、分子对接和体外细胞毒活性

IF 2.6 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2025-10-21 Epub Date: 2025-08-08 DOI: 10.1080/10406638.2025.2538877

Vadlamani Nagarjuna (Investigation) , Suresh Maddila (Supervision Writing – original draft) , Ravikumar Kapavarapu (Software) , Lalu Venigalla (Methodology) , Badampudi Santosh Kumar (Resources) , Amal F. Seliem (Writing – original draft) , Mohamed A. Nassan (Conceptualization) , Mahmoud M. Hessien (Writing – review & editing)

This study designed and synthesized novel phenoxyquinoline-pyrimidine hybrids (7a-k) as potential EGFR inhibitors, with 7a and 7k exhibiting superior cytotoxicity (IC₅₀ = 2.13 ± 0.18 µM and 1.01 ± 0.10 µM against A549 and MCF-7 cancer cell lines, respectively) compared to Gefitinib. Molecular docking revealed strong binding to EGFR-TKD (−9.4 kcal/mol for 7a), supported by key interactions with MET793 and LEU844, while SAR analysis highlighted methoxy groups as critical for activity. These findings introduce a new class of hybrid anticancer agents with validated mechanistic insights, offering a foundation for targeted therapy development.

本研究设计并合成了新型苯氧喹啉-嘧啶杂合体（7a-k）作为潜在的EGFR抑制剂，与吉非替尼相比，7a和7k对A549和MCF-7癌细胞的IC50分别为2.13±0.18µM和1.01±0.10µM，具有更强的细胞毒性。分子对接显示与EGFR-TKD的强结合（7a为- 9.4 kcal/mol），与MET793和LEU844的关键相互作用支持，而SAR分析强调甲氧基是活性的关键。这些发现介绍了一类新的混合抗癌药物，具有有效的机制见解，为靶向治疗的发展提供了基础。

引用次数: 0

Green Synthesis of Novel Benzo[a][1,3]Oxazino[6,5-c]Phenazin-3-One Derivatives Under Solvent-Free Conditions Using Acetic Acid as an Efficient Catalyst via Microwave Irradiation 微波辐射乙酸催化下无溶剂条件下新型苯并[a][1,3]恶氮基[6,5-c]吩那辛-3- 1衍生物的绿色合成

IF 2.6 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2025-10-21 Epub Date: 2025-09-23 DOI: 10.1080/10406638.2025.2556798

Bahareh Ghasemi Meimandi (Data curation Investigation Methodology) , Razieh Mohebat (Conceptualization Data curation Formal analysis Funding acquisition Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing) , Alireza Hassanabadi (Writing – review & editing)

A simple, one-pot method for the synthesis of benzo[a][1,3]oxazino[6,5-c]phenazin-3-one derivatives has been reported via reactions of 4-hydroxy-1,2-naphthoquinone, benzene-1,2-diamine, methyl carbamate, and aromatic aldehydes in the presence of acetic acid as a catalyst under solvent-free conditions using microwave irradiation. Compared with other synthetic methods, this method has the advantages such as faster heating with higher energy efficiency, and less initial heating time, faster heating, higher energy efficiency, less space, more precise process control, mild reaction conditions, short reaction time, easy work-up, high yields of products, and selective heating can be mentioned.

报道了在无溶剂条件下，以乙酸为催化剂，微波辐射，以4-羟基-1,2-萘醌、苯-1,2-二胺、氨基甲酸甲酯和芳香醛为原料，用一锅法合成苯并[A][1,3]恶氮基[6,5-c]苯那津-3-酮衍生物。与其他合成方法相比，该方法具有加热速度快、能效高、初加热时间短、加热速度快、能效高、占用空间少、工艺控制精确、反应条件温和、反应时间短、易于加工、产品收率高、可选择性加热等优点。

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引用次数: 0

Synthesis of Betti Bases via Multicomponent Mannich-Type Reaction Using Pd-MMZ as a Reusable Lewis Acid Catalyst Pd-MMZ作为可重复使用的Lewis酸催化剂，多组分曼尼型反应合成Betti碱

IF 2.6 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2025-10-21 Epub Date: 2025-09-30 DOI: 10.1080/10406638.2025.2566309

Ilaamirthamani Simsonrubarathinam (Formal analysis) , Kumarraja Mayilvasagam (Formal analysis)

A simple multicomponent approach has been developed for the synthesis of a broad range of 1-(α-aminoalkyl)-2-naphthol derivatives known as Betti bases, using a novel Pd-MMZ catalyst. Morphology of the modified framework of catalyst was characterized by electron microscopy and the loading level of Pd was determined by EDAX methods. The catalytic efficiency of MMZ framework over the other porous materials and the influence of various metal ions and solvents in the yield of products were also studied well. Most of the experiments did not require further purification work. The recyclability of catalyst was also tested for four times. Green chemistry matrix is calculated for all the 18 products. The role of Lewis acid Pd(II) ions, acidity of phenolic OH group and the framework of MMZ on determining the yield of products (18 examples) are well described by a suitable mechanism. Merits of the present catalytic system are compared with other reported methods and the details are highlighted.

采用一种新型Pd-MMZ催化剂，开发了一种简单的多组分方法，用于合成广泛的1-（α-氨基烷基）-2-萘酚衍生物，称为Betti碱。用电子显微镜对改性后催化剂骨架的形貌进行了表征，并用EDAX法测定了钯的负载水平。研究了MMZ骨架对其他多孔材料的催化效率，以及各种金属离子和溶剂对产物收率的影响。大多数实验不需要进一步的净化工作。对催化剂的可回收性进行了四次试验。对所有18种产品计算绿色化学矩阵。用合适的机理描述了Lewis酸Pd（II）离子、酚羟基酸度和MMZ结构对产物收率的影响（18个例子）。将本催化体系的优点与其他已报道的方法进行了比较，并重点介绍了细节。

引用次数: 0

Synthesis, Anticancer Activity, ADMET, DFT, Molecular Docking and Molecular Dynamics Study of Pyrazole-Incorporated Monocarbonyl Curcumin Analogues 吡唑单羰基姜黄素类似物的合成、抗癌活性、ADMET、DFT、分子对接及分子动力学研究

IF 2.6 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2025-10-21 Epub Date: 2025-06-18 DOI: 10.1080/10406638.2025.2519010

Uday V. Baviskar , Rizwan Ali , Sanket Rathod , Shatha Algheribe , Mubarak H. Shaikh , Abdullah H. Alanazi , Somdatta Chaudhari , Prafulla Choudhari , Bapurao B. Shingate , Yasinalli Tamboli , Amol A. Nagargoje

Curcumin holds promise as an anticancer agent but is hindered by limited stability and bioavailability. To overcome these challenges, a series of monocarbonyl curcumin analogues featuring a pyrazole scaffold were synthesized and evaluated for their anticancer potential. The analogues 5 m and 5o exhibited superior cytotoxicity against breast cancer cells compared to curcumin. Furthermore, apoptosis induction was validated through advanced imaging techniques, and computational studies offered insights into their pharmacokinetic and pharmacodynamic profiles. These findings identify synthesized analogues as a promising lead compounds for further optimization in anticancer drug development.

姜黄素有望成为抗癌药物，但其稳定性和生物利用度有限。为了克服这些挑战，我们合成了一系列具有吡唑支架的单羰基姜黄素类似物，并对其抗癌潜力进行了评估。与姜黄素相比，类似物5m和50对乳腺癌细胞具有更强的细胞毒性。此外，通过先进的成像技术验证了细胞凋亡诱导，计算研究提供了对其药代动力学和药效学概况的见解。这些发现确定了合成类似物作为抗癌药物开发中进一步优化的有前途的先导化合物。

引用次数: 0

Gram-Scalable One-Pot Synthesis of Dihydro-Pyrano[3,2-c]Chromenes Using Magnetic Salicylaldehyde-Melamine Copper Complex 磁性水杨醛-三聚氰胺铜配合物一锅法合成二氢吡喃[3,2-c]铬

IF 2.6 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2025-10-21 Epub Date: 2025-06-20 DOI: 10.1080/10406638.2025.2519001

Afsaneh Zonouzi , Neda Ghasemi

The present study reports the synthesis of a nanomagnetic heterogeneous catalyst, namely, Fe₃O₄@SiO₂@Si(CH₂)₃@melamine@salicylicaldehyde@Cu. This synthesis occurred through intermolecular forces, covalent and dative bonds. After synthesis of the catalyst, its structure was confirmed through different characterization techniques, including FTIR, FESEM, TEM, EDX, VSM, and TGA. In sequence, the activity of the as-synthesized catalyst was evaluated using 4-hydroxycoumarin, malononitrile, and various benzaldehydes as a multi-component model reaction. Then, the reaction condition was optimized to find the solvent type, catalyst amount, and temperature corresponding to ethanol, 0.03 g of catalyst, and reflux conditions. Finally, various derivatives of dihydro-pyrano[3,2-c]chromenes were synthesized using aryl and heterocyclic aldehydes. To evaluate the reuse of the as-synthesized catalyst, it was recovered using an external magnet and used in five cycles. The results showed that the catalyst could be recovered and reused without significant leaching and loss in efficiency. Various characterization techniques confirmed the stability of the used catalyst. Since the magnetic properties of the catalyst allow for easy separation and recycling, maintaining considerable yield for at least five cycles, probably due to the presence of melamine, which plays a vital role in stability and reusability. The present procedure can be done in gram-scale amounts, which can be a candidate for further scaling up.

本研究报道了一种纳米磁性非均相催化剂Fe3O4@SiO2@ si (CH2)3@melamine@salicylicaldehyde@Cu的合成。这种合成是通过分子间作用力、共价键和负键进行的。催化剂合成后，通过FTIR、FESEM、TEM、EDX、VSM、TGA等不同表征技术对其结构进行了确认。随后，以4-羟基香豆素、丙二腈和各种苯甲醛为多组分模型反应，对合成催化剂的活性进行了评价。然后对反应条件进行优化，确定溶剂类型、催化剂用量、乙醇对应温度、催化剂用量0.03 g、回流条件。最后，利用芳基醛和杂环醛合成了多种二氢吡喃[3,2-c]铬衍生物。为了评价合成催化剂的再利用性，采用外部磁铁回收，并进行了五个循环。结果表明，该催化剂可回收再利用，且无明显的浸出和效率损失。各种表征技术证实了所用催化剂的稳定性。由于催化剂的磁性使其易于分离和回收，因此至少在五个循环中保持相当大的产量，这可能是由于三聚氰胺的存在，三聚氰胺在稳定性和可重用性中起着至关重要的作用。目前的程序可以以克为单位进行，这可以作为进一步扩大规模的候选。

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引用次数: 0