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Synthesis, In Vitro and In Silico Investigations of 4-(1H-Indol-3-yl)-N′-[(E/Z)-(phenyl-substituted)methylidene] as Effective Inhibitors of α-Glucosidase 4-(1H-吲哚-3-基)-N′-[(E/Z)-(苯基取代)亚甲基]作为 α-葡萄糖苷酶有效抑制剂的合成、体外和硅学研究
IF 1.1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-09 DOI: 10.1134/S1068162024050157
M. Nazir, U. Khan, M. Jahangir

Objective: The study commenced with the conversion of 4-(1H-indol-3-yl)butanoic acid (I) into ethyl 4-(1H-indol-3-yl)butanoate (II), succeeded by the synthesis of the hydrazide nucleophile, 4-(1H-indol-3-yl)butanohydrazide (III). Methods: Following this, nucleophilic addition reactions of (III) with various electrophilic aldehydes (IVa–IVg) were conducted to yield the targeted derivatives (Va–Vg/Vʹa–Vʹg). The structural elucidation of all synthesized compounds relied on IR, 1H, 13C NMR, HMBC, and CHN analysis. Results and Discussion: Evaluation of the inhibitory effects of these heterocyclic butanohydrazides (Va–Vg/Vʹa–Vʹg) against the α-glucosidase enzyme revealed significant inhibition by compounds (Vg/Vʹg) compared to the standard. Conclusions: Hemolytic analysis indicated mild cytotoxicity towards red blood cell membranes, indicating the potential of these molecules as nontoxic medicinal scaffolds for skin pigmentation and related disorders.

研究目的本研究首先将 4-(1H-吲哚-3-基)丁酸 (I) 转化为 4-(1H-吲哚-3-基)丁酸乙酯 (II),然后合成亲核酰肼 4-(1H-吲哚-3-基)丁酰肼 (III)。方法:之后,(III)与各种亲电醛(IVA-IVg)发生亲核加成反应,得到目标衍生物(Va-Vg/Vʹa-Vʹg)。所有合成化合物的结构阐释均依赖于红外、1H、13C NMR、HMBC 和 CHN 分析。结果与讨论评估这些杂环丁酰肼(Va-Vg/Vʹa-Vʹg)对α-葡萄糖苷酶的抑制作用发现,与标准相比,化合物(Vg/Vʹg)具有显著的抑制作用。结论溶血分析表明这些化合物对红细胞膜有轻微的细胞毒性,这表明这些分子具有作为无毒药用支架治疗皮肤色素沉着及相关疾病的潜力。
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引用次数: 0
L-Proline Catalyzed Synthesis of Dihydropyrano[2,3-c]pyrazoles and Their Anti-Inflammatory Activity L-Proline 催化合成二氢吡喃并[2,3-c]吡唑及其抗炎活性
IF 1.1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-09 DOI: 10.1134/S1068162024050121
K. J. Pansuriya, I. J. Modasiya, G. G. Dubal

Objective: In the present work synthesis and characterization of new heterocyclic derivatives containing dihydropyrano[2,3-c]pyrazoles. Methods: Synthesis of compounds was done using the conventional method via multicomponent reaction using substituted aldehyde, hydrazine hydrate or phenyl hydrazine, malononitrile, and L-proline as a catalyst with good yield. Reaction optimization is also performed. Results and Discussion: All synthesized compounds were tested for their in vitro anti-inflammatory and a comparison was done against the standard drug Diclofenac sodium. Conclusions: Some of the newly synthesized compounds demonstrated good to moderate anti-inflammatory activity.

目的:本研究合成并表征了含有二氢吡喃并[2,3-c]吡唑的新杂环衍生物。方法:以取代醛、肼水合物或苯基肼、丙二腈和 L-脯氨酸为催化剂,通过多组分反应的传统方法合成了化合物,并取得了良好的收率。还对反应进行了优化。结果与讨论:对所有合成化合物进行了体外抗炎测试,并与标准药物双氯芬酸钠进行了比较。得出结论:一些新合成的化合物具有良好至中等程度的抗炎活性。
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引用次数: 0
Synthesis of Thioacetamide-Thiazoles as Anticholinesterase and Antioxidant Agents against Alzheimer’s Disease 作为抗胆碱酯酶和抗氧化剂防治阿尔茨海默病的硫代乙酰胺噻唑类化合物的合成
IF 1.1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-09 DOI: 10.1134/S1068162024050212
Arti Soni, Ashwani Kumar, Vivek Kumar

Objective: synthesize thioacetamide-thiazole as key pharmacophore possessing acetylcholinesterase (AChE) inhibitory activity. Methods: Thirteen compounds (IIIa–IIIm) were synthesized by preparing differently substituted aminothiazoles and subsequently evaluated for AChE inhibitory and antioxidant activity. Results and Discussion: Compound (IIIk) (IC50 = 1.99 µM) exhibits promising AChE inhibitory activity amongvarious derivatives of the series. The antioxidant potential of synthesized compounds were determined by DPPH assay (IC50 = 1.10 to 15.45 µM). Compound (IIIk) exhibited the utmost antioxidant activity with IC50 = 1.10 µM. Further molecular docking, drug-likeness, and ADMET predictions of all synthesized compounds were also assessed with computational methods. The results unequivocally supported the in vitro studies of all derivatives by displaying good docking score with binding pocket of PDB4EY7. Conclusions: The study concluded that compound (IIIk) emerged as potential lead compound as AChE inhibitor for the development of new compounds as anti-Alzheimer’s candidates.

目的:合成具有乙酰胆碱酯酶(AChE)抑制活性的硫代乙酰胺噻唑作为关键药源。方法:通过制备不同取代度的氨基噻唑,合成了 13 个化合物(IIIa-IIIm),随后对其 AChE 抑制和抗氧化活性进行了评估。结果与讨论:在该系列的各种衍生物中,化合物(IIIk)(IC50 = 1.99 µM)表现出良好的 AChE 抑制活性。DPPH 试验测定了合成化合物的抗氧化潜力(IC50 = 1.10 至 15.45 µM)。化合物 (IIIk) 的抗氧化活性最高,IC50 = 1.10 µM。此外,还通过计算方法对所有合成化合物的分子对接、药物相似性和 ADMET 预测进行了评估。结果显示,所有衍生物与 PDB4EY7 结合口袋的对接得分都很高,从而明确支持了体外研究的结果。结论研究认为,化合物 (IIIk) 有可能成为 AChE 抑制剂的先导化合物,用于开发抗阿尔茨海默氏症的新化合物。
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引用次数: 0
Synthesis and Study Anti-Inflammatory Activity of Nicotinic Acid Hydrazones 烟酸肼的合成与抗炎活性研究
IF 1.1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-09 DOI: 10.1134/S1068162024050376
О. А. Nurkenov, S. D. Fazylov, E. М. Satbayeva, Т. М. Seilkhanov, А. Zh. Mendibayeva, S. K. Kabiyeva, Sh. N. Tursymbek

Objective: The aim of this study is to produce novel of the new functionally substituted nicotinohydrazones, analyze their anti-inflammatory activity, and assess their toxicity. A promising avenue for the advancement of novel bioactive compounds is the pursuit of “hybrid molecules” that contain pharmacophore fragments within their structural composition, with a particular focus on the examination of these molecules for the discovery of novel biological activities. Methods: The synthesis of nicotinic acid hydrazones (II–VI) was performed by condensation of nicotinic acid hydrazide with various aldehydes in ethanol when refluxing the reaction mixture at 60–70°C. The anti-inflammatory activity was studied using the formalin paw edema method in non-linear white rats. The acute inflammatory reaction was reproduced by subplantar (i.e., underplantar or plantar aponeurosis) injection of 0.1 mL of a 2% formalin solution into the right paw using a conventional insulin syringe. Results and Discussion: The structure of the new functionally substituted nicotinohydrazones has been confirmed by a combination of the 1H and 13C NMR methods, and COSY (1H-1H), HMQC (1H–13C), and HMBC (1H–13C) two-dimensional NMR spectroscopy methods.1H, and 13C NMR spectroscopy were used to investigate all the prepared derivatives. The acute toxicity of the aforementioned compounds was preliminarily evaluated using a specially developed Toxicity Assessment Software Tool within the United States Environmental Protection Agency. The LD50 values for rats following oral administration of the compounds tested by the QSAR method. According to the projected toxicological effects, compounds (II), (III) can be classified into Class 4 in terms of toxicity. Compounds (IV), (V) and (VI) have low toxicity and very low toxicity, respectively. Conclusions: The anti-inflammatory activity of the synthesized hydrazones has been evaluated and it has been demonstrated that these compounds were ineffective in comparison with ibuprofen at a dosage of 100 mg/kg (p2 < 0.05). The low toxicity level of all the tested compounds was predicted by the computer modeling. The LD50 values of the compounds range from 445.461 to 1491.991 mg/kg. The studies on the model of formalin paw edema in nonlinear white rats indicate the absence of an anti-inflammatory effect of the tested compounds.

研究目的本研究的目的是制备新型功能取代烟酰肼,分析其抗炎活性并评估其毒性。开发新型生物活性化合物的一个前景广阔的途径是寻找在其结构组成中包含药源片段的 "混合分子",尤其是重点研究这些分子在发现新型生物活性方面的作用。研究方法烟酸酰肼与多种醛类在乙醇中缩合,反应混合物在 60-70°C 下回流,从而合成了烟酸酰肼(II-VI)。采用福尔马林爪水肿法对非线性白鼠进行了抗炎活性研究。用传统的胰岛素注射器向大鼠右爪下(即跖下或跖神经节下)注射 0.1 mL 2% 福尔马林溶液,再现急性炎症反应。结果与讨论:结合 1H 和 13C NMR 方法以及 COSY(1H-1H)、HMQC(1H-13C)和 HMBC(1H-13C)二维 NMR 光谱方法,证实了新的功能取代的烟酰肼的结构。利用美国环境保护局专门开发的毒性评估软件工具对上述化合物的急性毒性进行了初步评估。通过 QSAR 方法测试了大鼠口服化合物后的半数致死剂量。根据预测的毒理学效应,化合物(II)、(III)的毒性可归入第 4 类。化合物(IV)、(V)和(VI)分别具有低毒性和极低毒性。结论对合成的酰肼的抗炎活性进行了评估,结果表明,与布洛芬相比,这些化合物在 100 毫克/千克的剂量下无效(p2 <0.05)。计算机模型预测了所有测试化合物的低毒性水平。这些化合物的半数致死剂量范围为 445.461 至 1491.991 毫克/千克。对非线性白鼠福尔马林爪水肿模型的研究表明,受试化合物没有抗炎作用。
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引用次数: 0
Synthesis of SARS-CoV-2 Spike Glycoprotein Peptide Fragments and Study of Their Binding to Human Blood Cells SARS-CoV-2 穗状糖蛋白肽片段的合成及其与人类血细胞结合的研究
IF 1.1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-09 DOI: 10.1134/S1068162024050352
О. V. Gribovskaya, V. V. Yanchenko, A. M. Tsygankov, V. P. Martinovich

Objective: Тhe development of new proteins against COVID-19 is an urgent task. The goal of this work was the synthesis of the peptides Lys-Ile-Ala-Asp-Tyr-Asn-Tyr-Lys-Leu (417–425 aa) and Val-Arg-Gln-Ala-Pro-Asn-Gly- Gln-Thr (407–415 aa) – fragments of the surface glycoprotein Spike of SARS-CoV-2 – as potential components of a vaccine against COVID-19 and the study of their binding to human blood cells. Methods: The compounds were synthesized using peptide chemistry methods in solution. The effect of peptides on leukocytes was studied by flow cytometry using monoclonal antibodies against molecules expressed on leukocytes (CD45), that are responsible for the early activation of lymphocytes (CD69) and basophils (CD203c, CD63). The concentration of IFN-γ, which was secreted by lymphocytes in response to peptides, was determined by ELISA. Results and Discussion: It was established that peptides could bind to leukocytes, which indicates the universality of reactions to peptides, especially in innate immune cells. It was shown that the Lys-Ile-Ala-Asp-Tyr-Asn-Tyr-Lys-Leu peptide contacted the leukocytes activated the lymphocytes and basophils. It was confirmed by an increase in gamma interferon compared to the Val-Arg-Gln-Ala-Pro-Asn-Gly-Gln-Thr. Conclusions: A method that allows to evaluate the effect of short peptides on leukocytes was tested. It was shown that the obtained peptides interact with leukocytes, activating them, which was evidenced by secretion of IFN-γ. Our proposed method for evaluating the effect of short peptides on blood cells is the first step in the development of a new peptide-based vaccine against COVID-19.

目标开发针对 COVID-19 的新蛋白质是一项紧迫任务。这项工作的目标是合成 SARS-CoV-2 表面糖蛋白 Spike 的多肽 Lys-Ile-Ala-Asp-Tyr-Asn-Tyr-Lys-Leu (417-425 aa) 和 Val-Arg-Gln-Ala-Pro-Asn-Gly-Gln-Thr (407-415 aa),作为 COVID-19 疫苗的潜在成分,并研究它们与人血细胞的结合情况。研究方法这些化合物是用多肽化学方法在溶液中合成的。使用针对白细胞上表达的分子(CD45)、淋巴细胞早期活化分子(CD69)和嗜碱性粒细胞分子(CD203c、CD63)的单克隆抗体,通过流式细胞术研究肽对白细胞的影响。用酶联免疫吸附法测定了淋巴细胞对多肽反应分泌的 IFN-γ 的浓度。结果与讨论:研究证实肽能与白细胞结合,这表明肽反应的普遍性,尤其是先天性免疫细胞。研究表明,Lys-Ile-Ala-Asp-Tyr-Asn-Tyr-Lys-Leu 多肽与白细胞接触后可激活淋巴细胞和嗜碱性粒细胞。与 Val-Arg-Gln-Ala-Pro-Asn-Gly-Gln-Thr 相比,γ 干扰素的增加证实了这一点。结论我们测试了一种评估短肽对白细胞影响的方法。结果表明,获得的短肽能与白细胞相互作用,激活白细胞,并通过分泌 IFN-γ 证明了这一点。我们提出的评估短肽对血细胞影响的方法是开发基于短肽的新型 COVID-19 疫苗的第一步。
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引用次数: 0
Erratum to: Histopathological, Antioxidant, and Enzyme Activity of Boronic Incorporated Catechin Compound: Screening of Bioactivity with Molecular Docking Studies 勘误:硼酸结合儿茶素化合物的组织病理学、抗氧化和酶活性:通过分子对接研究筛选生物活性
IF 1.1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-09 DOI: 10.1134/S1068162024050418
Salih Paşa, Metin Atlan, Hamdi Temel, Burçin Türkmenoğlu, Abdulselam Ertaş, Aslı Okan, Seher Yilmaz, Şükrü Ateş
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引用次数: 0
Boc/Bzl Solid-Phase Synthesis of Deltorphin II and Its Analogs without the Utilization of Anhydrous Hydrogen Fluoride 不使用无水氟化氢的 Boc/Bzl 固相合成德尔托啡 II 及其类似物
IF 1.1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-09 DOI: 10.1134/S1068162024050297
V. N. Azev, L. G. Mustaeva, E. Yu. Gorbunova, L. K. Baidakova, A. N. Chulin, L. N. Maslov, A. V. Mukhomedzyanov, М. В. Molchanov, A. I. Miroshnikov

Objective: The disadvantages of the published methods for the preparation of peptide deltorphin II and its analogues hamper thorough biological investigations of this class of molecules. Aiming to develop a more productive synthetic method we investigated an approach where Boc/Bzl solid phase peptide synthesis technique was employed without the utilization of anhydrous hydrogen fluoride. Deltorphin II and its analogues were prepared in high yields and purity using the developed method and trifluoromethane sulfonic acid as a deprotection regent. Methods: Boc/Bzl solid phase peptide synthesis using accelerated and classical coulpling protocols was employed. A few strong Lewis acids were used in the final deprotection synthesis step. Results and Discussion: The toxicity and aggressive nature of hydrogen fluoride have resulted in the development of alternative strong Lewis acid-based reagents for the final deprotection and cleavage steps in Boc/Bzl peptide synthesis. Unlike hydrogen fluoride, these acids have high boiling points; however, the favorable physicochemical properties of most peptides allow them to be quite easily isolated from the cleavage cocktails by precipitation with ether. We found that this simple procedure is not suitable for the isolation of deltorphin II peptide and its analogs and developed and successfully implemented alternative methods of synthesis, isolation, and purification of these peptides. Conclusions: The use of strong Lewis acids as an alternative to anhydrous hydrogen fluoride may complicate the isolation of hydrophobic peptides by the standard techniques. An alternative method was proposed and successfully employed in the preparation of peptide deltorphin II and its three analogs. The developed procedures can be used to purify other hydrophobic peptides.

研究目的已公布的多肽 deltorphin II 及其类似物的制备方法存在很多缺点,妨碍了对这类分子进行深入的生物学研究。为了开发一种更有效的合成方法,我们研究了一种不使用无水氟化氢的 Boc/Bzl 固相肽合成技术。使用所开发的方法和三氟甲烷磺酸作为脱保护剂,制备出了高产率和高纯度的 Deltorphin II 及其类似物。制备方法采用 Boc/Bzl 固相多肽合成法,使用加速和经典耦合方案。在最后的脱保护合成步骤中使用了一些强路易斯酸。结果与讨论:由于氟化氢的毒性和侵蚀性,人们开发了基于强路易斯酸的替代试剂,用于 Boc/Bzl 多肽合成的最后脱保护和裂解步骤。与氟化氢不同,这些酸的沸点较高;不过,由于大多数肽具有良好的物理化学特性,因此很容易通过乙醚沉淀将它们从裂解鸡尾酒中分离出来。我们发现这种简单的方法并不适用于分离 deltorphin II 肽及其类似物,因此开发并成功实施了合成、分离和纯化这些肽的替代方法。结论使用强路易斯酸替代无水氟化氢可能会使标准技术分离疏水性多肽的过程复杂化。我们提出了一种替代方法,并成功用于制备多肽 deltorphin II 及其三种类似物。所开发的程序可用于纯化其他疏水性多肽。
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引用次数: 0
Discovering the DPPH Free Radical Scavenging Activity of Azine Derivatives Bearing Ethyl Phenyl Ketone Moiety 发现含有乙基苯基酮分子的偶氮衍生物的 DPPH 自由基清除活性
IF 1.1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-09 DOI: 10.1134/S1068162024050029
Munir Ur Rehman, Aftab Alam, Syed Adnan Ali Shah, Abid Ali, Qaisar Ali, Abdullah F. AlAsmari, Fawaz Alasmari, Momin Khan

Objective: The aim of this study was to synthesize azine analogues of 1,2-diphenylethan-1-one while assessing their ability to scavenge free radicals with DPPH. In order to explore these compounds’ potential as novel antioxidant agents with possible applications in the pharmaceutical, neutraceutical, and other industries, we synthesized them. Methods: The initial steps involved reacting 1,2-diphenylethan-1-one and additional amount of hydrated hydrazine in an ethanol solvent to produce the needed hydrazone, which paved the way for a two-step reaction that produced azine derivatives. Ultimately, a number of substituted aldehydes that are aromatic were heated by reflux condition, catalyzed by acetic acid with the obtained hydrazone to produce the azine derivatives in high yields. Results: These synthetic derivatives were screened for their anti-oxidant activity, compound (IIe) (IC50 = 24.13 ± 0.27 µM), (IIf) (IC50 = 29.11 ± 0.41 µM), and (IIg) (IC50 = 31.12 ± 0.44 µM) attributed the most excellent activity, however compound (IIc) and (IId) were found as significant DPPH free radical scavenging agents with IC50 values 46.21 ± 0.12 and 49.23 ± 0.54 µM, respectively while compound (IIa) and (IIb) displayed less anti-oxidant effect with IC50 values 55.11 ± 0.24 and 66.21 ± 0.12 µM. Conclusions: The study shows that the azine derivatives under investigation have promising potential as synthetic antioxidants due to their significant DPPH radical scavenging action. Furthermore, compounds containing electron-donating groups exhibit antioxidant activity comparable to that of ascorbic acid, an antioxidant that occurs naturally. These findings highlight the antioxidant qualities of the synthetic azine derivatives and suggest potential applications as medical treatments for oxidative stress-related illnesses.

研究目的本研究旨在合成 1,2-二苯基乙烷-1-酮的叠氮类似物,同时评估它们用 DPPH 清除自由基的能力。为了探索这些化合物作为新型抗氧化剂的潜力,并将其应用于制药、中性药物和其他行业,我们合成了这些化合物。合成方法最初的步骤包括在乙醇溶剂中使 1,2-二苯基乙烷-1-酮和大量的水合肼反应生成所需的腙,这为生成叠氮衍生物的两步反应铺平了道路。最后,在回流条件下加热一些芳香的取代醛,在乙酸的催化下与得到的腙反应,以高产率生产出嗪衍生物。结果:对这些合成衍生物的抗氧化活性进行了筛选,化合物(IIe)(IC50 = 24.13 ± 0.27 µM)、(IIf)(IC50 = 29.11 ± 0.41 µM)和(IIg)(IC50 = 31.12 ± 0.然而,化合物(IIc)和(IId)被发现是重要的 DPPH 自由基清除剂,IC50 值分别为 46.21 ± 0.12 和 49.23 ± 0.54 µM,而化合物(IIa)和(IIb)的抗氧化效果较差,IC50 值分别为 55.11 ± 0.24 和 66.21 ± 0.12 µM。结论研究表明,所研究的叠氮衍生物具有显著的 DPPH 自由基清除作用,因此有望成为合成抗氧化剂。此外,含有电子供能基团的化合物所表现出的抗氧化活性可与天然抗氧化剂抗坏血酸相媲美。这些发现凸显了合成叠氮衍生物的抗氧化性,并表明它们有可能应用于治疗与氧化应激有关的疾病。
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引用次数: 0
Design, Synthesis, and Biological Evaluation of Novel Apigenin Derivatives as Potential Antitumor Agents 作为潜在抗肿瘤药物的新型芹菜素衍生物的设计、合成和生物学评价
IF 1.1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-09 DOI: 10.1134/S1068162024050091
Bei-Qiao He, Xiao-Xiao Fan, Tian-Yu Zheng, Ya-Ting Gao, Xu Chen, Yong-Gang Liu, Yuan-Yuan Zhang

Objective: The objective of this study was to design and synthesize novel apigenin derivatives and evaluate their antitumor activities against NSCLC cells. Methods: A series of apigenin derivatives were synthesized and their antiproliferative effects were evaluated against the NSCLC cell line A549. The most promising compounds were identified based on their antitumor activities. Their safety was confirmed by testing them on the normal human lung cell line Beas-2B. The mechanisms of their antitumor activities were investigated by inducing apoptosis in A549 cells and inhibiting Akt protein phosphorylation. The physicochemical and ADME properties of these compounds were also predicted to evaluate their potential as PI3K inhibitors for NSCLC therapy. Results and Discussion: Compounds (Va) and (VIa) exhibited suitable antitumor activities against A549 cells, with no significant toxicity towards Beas-2B cells. They were capable of inducing apoptosis in A549 cells and inhibiting Akt protein phosphorylation, which preliminarily revealed their mechanisms for antitumor activities in vitro. The predictions of physicochemical and ADME properties showed that compound (VIa) would be a potent PI3K inhibitor for NSCLC therapy in the future. Conclusions: This study has successfully designed and synthesized apigenin derivatives with antitumor activities for NSCLC therapy. Compounds (Va) and (VIa) exhibited suitable antitumor activities with low toxicity and promising mechanisms of action. The physicochemical and ADME properties of compound (VIa) suggest its potential as a potent PI3K inhibitor for NSCLC therapy in the future. These findings provide valuable insights for the development of novel therapeutic agents against NSCLC.

研究目的本研究旨在设计和合成新型芹菜素衍生物,并评估其对 NSCLC 细胞的抗肿瘤活性。方法: 合成一系列芹菜素衍生物,并评估其对 NSCLC 细胞的抗肿瘤活性:合成了一系列芹菜素衍生物,并评估了它们对 NSCLC 细胞株 A549 的抗增殖作用。根据其抗肿瘤活性,确定了最有前景的化合物。通过对正常人肺细胞株 Beas-2B 的测试,证实了这些化合物的安全性。通过诱导 A549 细胞凋亡和抑制 Akt 蛋白磷酸化,研究了这些化合物的抗肿瘤机制。此外,还预测了这些化合物的理化和 ADME 特性,以评估它们作为 PI3K 抑制剂治疗 NSCLC 的潜力。结果与讨论:化合物(Va)和(VIa)对 A549 细胞具有适当的抗肿瘤活性,对 Beas-2B 细胞无明显毒性。它们能够诱导 A549 细胞凋亡并抑制 Akt 蛋白磷酸化,初步揭示了其体外抗肿瘤活性机制。化合物(VIa)的理化和 ADME 特性预测表明,它将是一种有效的 PI3K 抑制剂,未来可用于 NSCLC 治疗。结论本研究成功设计并合成了具有抗肿瘤活性的芹菜素衍生物,用于 NSCLC 治疗。化合物(Va)和(VIa)具有合适的抗肿瘤活性、低毒性和良好的作用机制。化合物(VIa)的理化和 ADME 特性表明,它将来有可能成为治疗 NSCLC 的强效 PI3K 抑制剂。这些发现为开发新型 NSCLC 治疗药物提供了宝贵的启示。
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引用次数: 0
Design, Synthesis, and Anticancer Activities of Bakuchiol-1,3,5-triazine Derivatives 白屈菜-1,3,5-三嗪衍生物的设计、合成和抗癌活性
IF 1.1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-09 DOI: 10.1134/S1068162024050066
Rui Li, Ya-Min Ding, Tian Qin, Xuan-Yi Xue, Wei-Wei Liu, Rong-Bin Wei, Yuan-Fen Zhai, Gang Ding, Da-Hua Shi

Objective: In search of the better anticancer agents, fifteen bakuchiol-1,3,5-triazine derivatives were designed and synthesized through nucleophilic substitution reaction. Methods: The newly synthesized derivatives were evaluated for their in vitro cytotoxic activity against Panc-1, MDA-MB-231, A549, and UM-UC-3 using the MTT assay. Results and Discussion: The data revealed that all of the bakuchiol-1,3,5-triazine derivatives could inhibit the proliferation of Panc-1 cells. Four compounds exhibited better antiproliferative activities than that of bakuchiol. Among them, compound (IVj) displayed potent antiproliferative activity with IC50 values of 21.83 μM. Compound (IVj) also showed potent inhibitory activity against the proliferation of MDA-MB-231, A549, and UM-UC-3 cells when compared with bakuchiol. Additionally, compound (IVj) exhibited strong inhibitory effects on the migration, invasion, and adhesion of Panc-1 cells. Conclusions: The results showed that, compound (IVj) could be a promising candidate agent for the treatment of cancer.

目的:为寻找更好的抗癌药物,设计并通过亲核取代反应合成了 15 种百超-1,3,5-三嗪衍生物。方法:通过亲核取代反应设计并合成了十五种巴枯焦-1,3,5-三嗪衍生物:采用 MTT 法评估了新合成的衍生物对 Panc-1、MDA-MB-231、A549 和 UM-UC-3 的体外细胞毒性活性。结果与讨论:数据显示,所有的百部-1,3,5-三嗪衍生物都能抑制 Panc-1 细胞的增殖。四个化合物的抗增殖活性优于巴枯焦。其中,化合物(IVj)具有强效的抗增殖活性,其 IC50 值为 21.83 μM。与巴枯焦相比,化合物(IVj)对 MDA-MB-231、A549 和 UM-UC-3 细胞的增殖也有很强的抑制作用。此外,化合物(IVj)对 Panc-1 细胞的迁移、侵袭和粘附也有很强的抑制作用。结论结果表明,化合物(IVj)可能是一种治疗癌症的有前途的候选药物。
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Russian Journal of Bioorganic Chemistry
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