Polycyclic Aromatic Compounds最新文献

英文中文

Computational Analysis on Molecular Stability and Binding Affinity of 3-(Aminothiazolyl)Quinolone Derivative as Multitargeting Antibacterial Agents through Ab Initio Methods and Molecular Docking 通过 Ab Initio 方法和分子对接计算分析 3-(氨基噻唑基)喹诺酮衍生物作为多靶点抗菌剂的分子稳定性和结合亲和力

IF 2.4 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2024-10-20 DOI: 10.1080/10406638.2023.2270123

The present study deals with the application of ab initio method using density functional theory (DFT) at M06-2X/6-311++G(d,p) to characterize the considered molecule completely. Though the anti-bacterial activity of the 3-(amino thiazolyl)quinolone derivatives was studied, the effects of intermolecular hydrogen bonding on chemical and biological processes remain unexplored or have not been thoroughly investigated so far. Investigations into non-covalent interactions were carried out using the reduced density gradient methodology and the quantum theory of atoms in molecules. An electron localization function was used to investigate the electronic vicinity of each atom in a molecule. Natural bond orbital analysis was used to determine the correlated stabilization energies for the intermolecular hydrogen bonds (H-bonds) that are responsible for the molecular stability of the dimer structure. The electrophilic and nucleophilic sites were predicted using the molecular electrostatic potential. The density of states and partial density of states were also used to represent the frontier molecular orbitals. The inhibitory activities of the compound with different classes of bacteria were also investigated using molecular docking simulation.

本研究采用 M06-2X/6-311++G(d,p)密度泛函理论 (DFT) 的 ab initio 方法，对所研究的分子进行了全面的表征。虽然对 3-(氨基噻唑基)喹诺酮衍生物的抗菌活性进行了研究，但分子间氢键对化学和生物过程的影响仍有待探索，或者说迄今为止尚未进行深入研究。对非共价相互作用的研究采用了还原密度梯度法和分子中原子的量子理论。利用电子定位功能研究了分子中每个原子的电子邻域。自然键轨道分析用于确定分子间氢键（H 键）的相关稳定能量，这些氢键是二聚体结构分子稳定性的原因。利用分子静电位预测了亲电和亲核位点。此外，还使用了状态密度和部分状态密度来表示前沿分子轨道。此外，还利用分子对接模拟研究了该化合物对不同种类细菌的抑制活性。

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引用次数: 0

Anticancer and anti-Inflammatory Activities of Garcinol and Its Analogs 加西诺及其类似物的抗癌和抗炎活性

IF 2.4 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2024-10-20 DOI: 10.1080/10406638.2023.2270116

Bioactive molecules have been significantly known for therapeutic potential. One such molecule, garcinol, is a naturally occurring benzophenone derived from medicinally applicable many species of garcinia family, more specifically Garcinia indica. Diverse therapeutic applications of garcinol and Garcinia indica have been studied and documented in the literature. This review covers our previous study on garcinol and its analogs as target-specific potential anti-cancer and anti-inflammatory agents. Also, it accomplishes recent reports on the medicinal significance and challenges of garcinol and its analogs to develop as therapeutics.

生物活性分子具有显著的治疗潜力。大蒜素醇就是这样一种分子，它是一种天然的二苯甲酮，从可药用的多种大蒜科植物，特别是印度大蒜中提取。文献中对加西诺和加西诺籼的各种治疗应用进行了研究和记录。这篇综述涵盖了我们之前关于甘牛素及其类似物作为靶向特异性潜在抗癌和抗炎药物的研究。此外，它还完成了有关甘薯醇及其类似物作为治疗药物的药用意义和挑战的最新报告。

引用次数: 0

Design, Synthesis, Spectral Analysis, Drug Likeness Prediction, and Molecular Docking Investigations of New Naphtho[2,1-b]Furan Encompassing Pyrimidines as Potential Antimicrobial Agents 作为潜在抗菌剂的新型萘并[2,1-b]呋喃嘧啶的设计、合成、光谱分析、药物相似性预测和分子对接研究

IF 2.4 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2024-10-20 DOI: 10.1080/10406638.2023.2272012

In view of the extremely important biological and medicinal properties of napthofurans, the synthesis of these heterocycles has fascinated the interest of medicinal and organic chemists. Keeping this in mind, we herein report the synthesis and antimicrobial evaluation of 4-N-aryl-naphtho[2,1-b]furo[3,2-d] pyrimidines 5 (a–l). Structures of these synthesized compounds were confirmed by spectral analysis like IR, NMR, and Mass spectrometry. The in vitro antimicrobial activities were reported for all the compounds 5 (a–l). The compounds 5e and 5f exhibited excellent antibacterial, antifungal, and antidermatophytic activities against tested pathogens at MIC 3.125, and 3.125 µg/mL, respectively. Furthermore, molecular docking studies of these compounds against S. aureus tyrosyl-tRNA synthetase (PDB ID: 1JIJ), S. aureus Gyrase (PDB ID: 2XCT), and SARS-CoV-2 Omicron (PDB ID: 7TOB), revealed the potential binding mode of the ligands to the site of the appropriate targets. Finally, drug-likeness and structure-activity relationship studies were also disclosed.

鉴于萘呋喃具有极其重要的生物和药用特性，这些杂环的合成引起了医药和有机化学家的兴趣。有鉴于此，我们在此报告 4-N-芳基萘并[2,1-b]呋喃并[3,2-d]嘧啶 5（a-l）的合成和抗菌评价。通过红外光谱、核磁共振和质谱等光谱分析确认了这些合成化合物的结构。报告了所有化合物 5（a-l）的体外抗菌活性。化合物 5e 和 5f 在 MIC 值分别为 3.125 微克/毫升和 3.125 微克/毫升的情况下，对测试病原体表现出卓越的抗菌、抗真菌和抗皮肤癣菌活性。此外，这些化合物针对金黄色葡萄球菌酪氨酰-tRNA 合成酶（PDB ID：1JIJ）、金黄色葡萄球菌回旋酶（PDB ID：2XCT）和 SARS-CoV-2 Omicron（PDB ID：7TOB）的分子对接研究揭示了配体与相应靶点的潜在结合模式。最后，还披露了药物相似性和结构-活性关系研究。

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引用次数: 0

Synthesis, Anti-Proliferative Activity, DFT and Docking Studies of Some Novel Chloroquinoline-Based Heterocycles 一些新型氯喹啉基杂环的合成、抗增殖活性、DFT 和 Docking 研究

IF 2.4 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2024-10-20 DOI: 10.1080/10406638.2023.2271112

Cancer is one of the leading causes of death. Quinoline is well known as one of the most potent pharmaceutically active scaffolds with remarkable pharmacological properties. So, in this article, we focused our efforts on the utility of the key scaffold N′-(1-(4-((7-chloroquinolin-4-yl)amino)phenyl)ethylidene)-2-cyanoacetohydrazide (5) in the synthesis of their novel heterocyclic compounds with potential as anticancer agents. Based on these preliminary screening results against four different human cancer cell lines (HepG2, MCF-7, HCT-116, and PC-3). Gratifyingly, compounds 9 and 16 showed the highest anticancer activity. Adenosine A2B receptor (A2BAR) was found to be the probable cellular target for both promising candidate compounds 9 and 16. The docking study of tested compounds 9 and 16 revealed that they bind more strongly to the A2BAR as compared to that of its co-crystalized ligand, suggesting that the anticancer activities of the tested compounds may be related to their ability to block the A2BAR receptor signaling in cancer cells, leading to cell death. Computational studies and countersurfaces of the novel compounds helped us clarify and interpret the compounds that have high and low anticancer activity. Noteworthy, the results of these studies are approximately compatible with what was done in vitro.

癌症是导致死亡的主要原因之一。众所周知，喹啉是最有效的药物活性支架之一，具有显著的药理特性。因此，在本文中，我们重点研究了关键支架 N′-(1-(4-((7-氯喹啉-4-基)氨基)苯基)亚乙基)-2-氰基乙酰肼 (5) 在合成具有抗癌潜力的新型杂环化合物中的应用。令人欣慰的是，化合物 9 和 16 显示出了最高的抗癌活性。研究发现，腺苷 A2B 受体（A2BAR）可能是 9 号和 16 号候选化合物的细胞靶点。对受试化合物 9 和 16 的对接研究表明，与共晶体配体相比，它们与 A2BAR 的结合力更强，这表明受试化合物的抗癌活性可能与其阻断癌细胞中 A2BAR 受体信号转导、导致细胞死亡的能力有关。新型化合物的计算研究和反面研究帮助我们澄清和解释了抗癌活性高和低的化合物。值得注意的是，这些研究结果与体外研究结果基本一致。

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引用次数: 0

Design, Characterization and Antimicrobial Efficiency of Novel Annulated Furo[3'',2'':6',7']Chromeno[3',4':4,5]Furo [3,2-b]Pyridines 新型环状呋喃并[3'',2'':6',7']色并[3',4':4,5]呋喃并[3,2-b]吡啶的设计、表征和抗菌效率

IF 2.4 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2024-10-20 DOI: 10.1080/10406638.2023.2270119

The principle approach of the present study is directed to find an appropriate technique to create a new category of multi-fused compounds including furo[3,2-g]chromenes. The novel 2-acetyl-3-amino-6,10-dimethoxy-4-oxo-4H-difuro[3,2-c:3′,2′-g]chromene (3) was efficiently synthesized and utilized as a key intermediate to build a new class of multi-fused compounds namely furo[3′′,2′′:6′,7′]chromeno[3′,4′:4,5]furo[3,2-b]pyridines. Reaction of precursor 3 with active methylene nitriles yielded 2-amino-3-substituted furo[3′′,2′′:6′,7′]chromeno[3′,4′:4,5]furo[3,2-b]pyridines 4–9. Also, Friedländer's reaction of precursor 3 with active methylene ketones produced hetero-annulated furochromenofuropyridines 10–13. The synthesized compounds showed high inhibition action when tested in vitro against fungal strains, whereas compounds 3 and 8 showed good inhibitory effects against all types of tested microorganisms. The structures of the novel annulated compounds were inferred using spectral and analytical results.

本研究的主要方法是寻找一种适当的技术，以创造出包括呋喃并[3,2-g]色烯在内的新型多融合化合物。The novel 2-acetyl-3-amino-6,10-dimethoxy-4-oxo-4H-difuro[3,2-c:3′,2′-g]色烯（3）的高效合成，并将其作为一种关键的中间体来构建一类新的多融合化合物，即呋喃并[3′′,2′′:6′,7′′]色烯并[3′,4′:4,5]呋喃并[3,2-b]吡啶。前体 3 与活性亚甲基腈反应生成 2-氨基-3-取代的呋喃并[3′′,2′′:6′,7′]色烯并[3′′,4′′:4,5]呋喃并[3,2-b]吡啶 4-9。此外，前体 3 与活性亚甲基酮的弗里德兰德反应生成了杂环呋喃苯并吡啶 10-13。在体外测试中，合成的化合物对真菌菌株有很强的抑制作用，而化合物 3 和 8 则对所有类型的微生物都有很好的抑制作用。利用光谱和分析结果推断了这些新型环化化合物的结构。

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引用次数: 0

A Catalyst-Free One-Pot Multicomponent Green Strategy for the Synthesis of Spiroindene-1,3dione-Benzochromene/ Thio-Chromene Derivatives under Neat/Aqueous Conditions 在洁净/水溶液条件下合成螺茚-1,3-二酮-苯并铬烯/硫代铬烯衍生物的无催化剂单锅多组分绿色策略

IF 2.4 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2024-10-20 DOI: 10.1080/10406638.2023.2270126

An efficient, facile, and catalyst-free one-pot multicomponent green strategy under neat or aqueous conditions has been developed to synthesize a series of spiro compounds that contain two biologically active pharmacophores, benzochromenes/thio-chromenes and indan-1,3-dione, in a single molecular framework. The desired Spiroindene-1,3dione-benzochromene/thio-chromene derivatives were yielded through a one-pot, three-component reaction between ninhydrin, substituted 1,3-dicarbonyls, and 2-naphthol/2-naphthalene thiol via the Knoevenagel–Michael cascade. The advances of this strategy include high product yields (94–82%), the formation of a new asymmetric center, cost-effectiveness, atom economy, and a straightforward workup procedure that does not require any additional purification steps.

我们开发了一种高效、简便、无催化剂的单锅多组分绿色策略，可在纯水或水溶液条件下合成一系列螺类化合物，这些化合物在单个分子框架中包含两种具有生物活性的发色团（苯并二氢吡喃/硫代二氢吡喃和茚-1,3-二酮）。通过 Knoevenagel-Michael 级联反应，茚三酮、取代的 1,3-二羰基和 2-萘酚/2-萘硫醇在一锅三组分反应中生成了所需的螺茚-1,3-二酮-苯并二氢吡喃/硫代二氢吡喃衍生物。该策略的优点包括：产品收率高（94%-82%）、可形成新的不对称中心、成本效益高、原子经济以及无需任何额外纯化步骤的简便操作程序。

引用次数: 0

The Merrifield–Simmons Index of the Fullerene Derivative Hexagonal System 富勒烯衍生物六方体系的梅里菲尔德-西蒙斯指数

IF 2.4 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2024-10-20 DOI: 10.1080/10406638.2023.2274476

The fullerene derivative hexagonal system is obtained from fullerene C_n and hexagonal system sticked by a common edge. The Merrifield–Simmons index of a graph G is defined as the total number of the independent sets of G. In this paper, we give the lower and larger bound of Merrifield–Simmons index of the fullerene derivative hexagonal system. Furthermore, we give two formulas of the Merrifield–Simmons index of the fullerene derivative hexagonal system C₂₀ ⊗ l(n) and C₂₀ ⊗ (l(n₁), l(n₂)).

富勒烯衍生六边形系统是由富勒烯 Cn 和六边形系统通过一条公共边粘连而成。本文给出了富勒烯衍生六方体系的 Merrifield-Simmons 指数的下界和大界。此外，我们还给出了富勒烯衍生六边形系统的梅里菲尔德-西蒙斯指数 C20 ⊗ l(n) 和 C20 ⊗ (l(n1), l(n2)) 的两个公式。

引用次数: 0

Synthesis, Cytotoxic, and Antioxidant Activity of Some Benzoquinoline-Based Heterocycles 一些苯并喹啉基杂环化合物的合成、细胞毒性和抗氧化活性

IF 2.4 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2024-10-20 DOI: 10.1080/10406638.2023.2270767

A series of benzoquinoline-based heterocycles was synthesized using 2-((3-chlorobenzo[f]quinolin-2-yl)methylene)hydrazine-1-carbothioamide as a key material via condensation of 3-chlorobenzo[f]quinoline-2-carbaldehyde with thiosemicarbazide. The titled thiosemicarbazone scaffold was conducted with some carbon electrophilic reagents such as acetic anhydride, chloroacetyl chloride, chloroacetic acid, 2-bromo-1-(3-nitrophenyl)ethan-1-one, 2-chloro-N-phenylacetamide, and dimethyl but-2-ynedioate to obtain triazole thione, imidazolone, thiazolidinone, and thiazole derivatives. On the other hand, hydrazinolysis of thiosemicarbazone did not proceed as expected but it gave the azine derivative. The in vitro antitumor and antioxidant activity of the synthesized compounds were screened and revealed that triazole thione and thiazole derivatives were the most potent.

以 2-((3-氯苯并[f]喹啉-2-基)亚甲基)肼-1-硫代甲酰胺为关键材料，通过 3-氯苯并[f]喹啉-2-甲醛与硫代氨基脲的缩合，合成了一系列苯并喹啉基杂环。以硫代氨基甲酰肼为关键材料，通过 3-氯苯并[f]喹啉-2-甲醛与硫代氨基甲酰肼的缩合，得到硫代氨基甲酰肼支架，并与一些碳亲电试剂如乙酸酐、氯乙酰氯、氯乙酸、2-溴-1-(3-硝基苯基)乙-1-酮、2-氯-N-苯基乙酰胺和丁-2-炔二酸二甲酯进行反应，得到三唑硫酮、咪唑啉酮、噻唑啉酮和噻唑衍生物。另一方面，硫代氨基甲酸肼的肼解过程并不像预期的那样，但却得到了叠氮衍生物。对合成化合物的体外抗肿瘤和抗氧化活性进行了筛选，结果表明三唑硫酮和噻唑衍生物的抗肿瘤和抗氧化活性最强。

引用次数: 0

Design, Synthesis, and Biological Testing of Pyrazoline Derivatives of Combretastatin-A4: A Quest for Anticancer, Anti-Inflammatory, and Antioxidant Agents 联合他汀-A4 的吡唑啉衍生物的设计、合成和生物测试：抗癌、抗炎和抗氧化剂的探索

IF 2.4 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2024-10-20 DOI: 10.1080/10406638.2023.2271113

Three groups of novel analogs of combretastatin-A4 (CA-4), viz., the N¹-phenyl-pyrazoline (5a–e), N¹-alkyl acetylated pyrazoline (6a–c), and N¹-phenyl acetylated pyrazoline (7a–g) were designed, and synthesized in good yield. The structure of the compounds was confirmed by spectroscopic techniques. All the compounds were evaluated for their in vitro anticancer (MCF-7 cell line), antioxidant (DPPH, NO, SOR, and H₂O₂), and anti-inflammatory activity. Compounds 5d, 7g, 7f, 7e, 7c, 5b, 6a, 7b, and 7a showed excellent potency with GI₅₀ ranging from 0.1 to 10.9 µM against the MCF-7 cell line. Compounds 7f, 7g, 5c, 5d, 5b, 7e, and 6a exhibited good anti-inflammatory activity. Encouraged by these results, all the compounds were also tested for their antioxidant potency. Compounds 6a, 6c, 7b, 7c, 7f, and 7g were found to be excellent scavengers of all four free radicals (DPPH, NO, SOR, and H₂O₂).

研究人员设计了三组新的考布他丁-A4（CA-4）类似物，即N1-苯基吡唑啉（5a-e）、N1-烷基乙酰化吡唑啉（6a-c）和N1-苯基乙酰化吡唑啉（7a-g）。

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引用次数: 0

Comparative Analysis of Reverse Degree and Entropy Topological Indices for Drug Molecules in Blood Cancer Treatment through QSPR Regression Models 通过 QSPR 回归模型比较分析血癌治疗药物分子的反向度和熵拓扑指标

IF 2.4 3区化学 Q2 CHEMISTRY, ORGANIC

Polycyclic Aromatic Compounds

Pub Date : 2024-10-20 DOI: 10.1080/10406638.2023.2271648

The topological indices provide quantitative structural characteristics of drug molecules that can be utilized to predict or establish correlations with the biological activity, physicochemical properties, and toxicity of the molecules. Such studies play a crucial role in the initial stages of drug development by aiding in the identification and optimization of potential drug candidates and providing cost-effective techniques for experimental studies. Cancer, a multifaceted disease, can originate in any part of the body due to various factors, including genetic mutations, environmental toxins, and lifestyle choices. Blood cancer, encompassing malignancies affecting the blood, bone marrow, and lymphatic systems, is the focus of this research paper. The current study investigates a comprehensive set of drugs employed in blood cancer treatment, including clofarabine, mercaptopurine, olutasidenib, glasdegib, gliteritinib, zanubrutinib, chlorambucil, ibrutinib, bosutinib, hydroxyurea, cyclophosphamide, doxorubicin, daunorubicin, ivosidenib, prednisone, busulfan, omacetaxine mepesuccinate, and asciminib. By conducting a thorough analysis of these drugs, we acquire valuable insights into their molecular properties, which are crucial for predicting their behavior and efficacy in blood cancer treatment. We have devised QSPR models by leveraging the reverse degree and entropy topological indices. Our proposed QSPR models are compared with existing degree-based models, emphasizing the superior effectiveness of our approach.

拓扑指数提供了药物分子的定量结构特征，可用于预测或建立药物分子与生物活性、理化性质和毒性之间的相关性。此类研究在药物开发的初始阶段发挥着至关重要的作用，有助于识别和优化潜在的候选药物，并为实验研究提供具有成本效益的技术。癌症是一种多发性疾病，可因基因突变、环境毒素和生活方式选择等各种因素而起源于身体的任何部位。血癌包括影响血液、骨髓和淋巴系统的恶性肿瘤，是本研究论文的重点。本研究调查了用于血癌治疗的一整套药物，包括氯法拉滨、巯嘌呤、奥鲁替尼、格拉斯替吉、格列替尼、扎鲁替尼、氯布嘧啶、伊布替尼、博苏替尼、羟基脲、环磷酰胺、多柔比星、达乌诺比星、伊维替尼、泼尼松、丁螺环素、甲磺酸奥美沙星和阿西米尼。通过对这些药物进行全面分析，我们对其分子特性有了宝贵的了解，这对预测它们在血癌治疗中的行为和疗效至关重要。我们利用反向度和熵拓扑指数设计了 QSPR 模型。我们提出的 QSPR 模型与现有的基于度数的模型进行了比较，强调了我们方法的优越性。

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