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Novel pyrano[2,3-c]pyrazolopyrimidines as promising anticancer agents: Design, synthesis, and cell cycle arrest of HepG2 cells at S phase 新型吡喃并[2,3-c]吡唑嘧啶作为有前途的抗癌剂:设计、合成和抑制 S 期 HepG2 细胞的细胞周期
IF 2.1 3区 化学 Q3 Chemistry Pub Date : 2024-04-17 DOI: 10.1080/00397911.2024.2327047
David S. A. Haneen , Mohamed H. Hekal , Wael S. I. Abou-Elmagd , Wael M. El-Sayed

The poor selectivity, significant toxicity, high cost, and emergence of resistance of conventional chemotherapies are driving motive for the ongoing search for novel anticancer agents. New pyrano[2,3-c]pyrazolopyrimidines were synthesized and examined as antiproliferative agents, and the possible molecular mechanism(s) of action were explored. The mass and elemental analyses, alongside the IR,1H, and 13C NMR spectra, confirmed the proposed structures of the obtained compounds. Derivatives 4 and 7 demonstrated the best antiproliferative profile against HepG2 cancer cells at 4 µM, with a high selectivity index of ∼7–9 folds. They increased the S phase cell population by 51% and 40% and caused a 5- and 11-fold increase in the p21 protein. Compound 7 was superior in inhibiting HepG2 cell migration and delayed wound healing, reducing migration rates by 55% and 90%, respectively. Future studies on the pharmacokinetics, pharmacodynamics, antimetastatic, and antitumor activities in animal models would be a robust advance.

传统化疗药物选择性差、毒性大、成本高、抗药性强,这些都是目前寻找新型抗癌药物的动力。新型吡喃并[2...
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引用次数: 0
Review of synthesis process of benzimidazole-heterocycle hybrid compounds 苯并咪唑杂环化合物合成工艺综述
IF 2.1 3区 化学 Q3 Chemistry Pub Date : 2024-04-17 DOI: 10.1080/00397911.2024.2316718
Abouelhaoul El Alami , Hamid Sdassi , Said Bouzikri

Over the last few years, benzimidazole-heterocycle hybrid compounds have received considerable attention due to the wide spectrum of their biological property and many important chemical and pharmacological applications. These compounds have revealed antibacterial, antimicrobial, anticoagulant, antidiabetic and other activities, and they have been used as drugs in the market to treat several diseases. Furthermore, hybrid heterocyclic compounds possessing a benzimidazole skeleton exhibit significant complexing and anticorrosive properties. All of these applications have favored the development of a large number of synthetic strategies to prepare these heterocyclic systems in different reaction conditions. Many research articles on the synthesis of benzimidazole-heterocycle hybrid compounds have been reported in the literature. In this review, we present and discuss the synthetic routes of several benzimidazole-heterocycle hybrid compounds.

在过去几年中,苯并咪唑-杂环杂化化合物因其广泛的生物特性和许多重要的化学和医药用途而受到广泛关注。
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引用次数: 0
The Lacunae identified in processing, analyzing and finding means of catalyst free Oxone mediated through C-3 oxidation of N-alkyl quinoxalin-2(1h)-one 在处理、分析和寻找通过 C-3 氧化 N-烷基喹喔啉-2(1h)-酮介导的无催化剂 Oxone 的方法过程中发现的缺陷
IF 2.1 3区 化学 Q3 Chemistry Pub Date : 2024-04-17 DOI: 10.1080/00397911.2024.2329245
Vikas S. Patil , Gayathri Chunduri , Balaram Kiran Avasarala , Gangaiah L , Pasham Yoganand , Kola Srinivas , Murali Koparala , Nagaraju Devunuri

A catalyst free oxone mediated synthesizing N-alkyl 1, 4-dihydroquinoxaline-2,3-dione has been developed by oxidation of the N-alkyl quinoxalin-2(1H)-one. The developed method is a novel, safest, cost-effective, industrially viable method and applicable for N-substituted and without substitution of 1,4-dihydroquinoxaline-2,3-dione. Consequently, the process is applicable to a broad spectrum of functionality. The reaction can be performed in all organic solvents without any further heating with an extended time and without generating side products. This novel synthetic methodology using Oxone is believed to be the shortest and most efficient to prepare various key intermediates which can be used for further derivatization to make the different biologically active molecules, the key feature of this methodology is not solvent specific, all organic solvents giving the optimum purity and quality using the same reaction condition.

通过氧化 N-烷基喹喔啉-2(1H)-酮,开发了一种无催化剂氧化酮介导合成 N-烷基 1,4-二氢喹喔啉-2,3-二酮的方法。所开发的方法是一种新颖、安全、简便的合成方法。
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引用次数: 0
KHSO4 promoted practical synthesis of quinazolin-4(3H)-ones and benzothiadiazine 1,1-dioxides KHSO4 促进喹唑啉-4(3H)-酮和苯并噻二嗪 1,1-二氧化物的实用合成
IF 2.1 3区 化学 Q3 Chemistry Pub Date : 2024-04-04 DOI: 10.1080/00397911.2024.2335638
Jiecheng Zheng , Feng Gong , Wei Wang , Yue Wu , Dezhang Zhao , Tianyuan Zhang , WenWen Yang , Zongjie Gan

A broad scope of quinazolin-4(3H)-ones or benzothiadiazine 1,1-dioxides was obtained via a transition-metal free and convenient method. This approach involving KHSO4 promoted cyclization and dehydration between diverse functionalized 2-aminobenzamides or 2-aminobenzenesulfonamides and N, N-dimethylformamide derivatives. The protocol offers moderate to excellent yields (45%-93%) under mild condition in a short of reaction time of 6 hours. The use of an environment-friendly and less expensive catalyst KHSO4 also makes this protocol more attractive.

通过一种不含过渡金属的便捷方法,获得了范围广泛的喹唑啉-4(3H)-酮或苯并噻二嗪-1,1-二氧杂环。这种方法涉及 KHSO4,促进了多种官能化 2-氨基苯甲酰胺或 2-氨基苯磺酰胺与 N,N-二甲基甲酰胺衍生物之间的环化和脱水。该方案在温和的条件下,只需 6 小时的反应时间,就能获得中等到极好的产率(45%-93%)。使用环保且价格较低的催化剂 KHSO4 也使该方案更具吸引力。
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引用次数: 0
Synthesis of 2-aryl quinoxaline derivatives and their in silico investigation for breast cancer medication 2- 芳基喹喔啉衍生物的合成及其用于乳腺癌药物治疗的硅学研究
IF 2.1 3区 化学 Q3 Chemistry Pub Date : 2024-04-01 DOI: 10.1080/00397911.2024.2333014
Barkha Darra Wadhwani , Deepak Mali , Lokesh Kumar Agarwal , Pooja Kumawat , Pooja Vyas , Rashmy Nair , Tarun Kumar , Poonam Khandelwal

The main objective of the present work is to synthesize and identify the potential breast cancer medication of 2-aryl quinoxaline ­derivatives via in silico investigations. Synthesis of 2-aryl quinoxaline derivatives have been achieved via the reaction of 3-aroylmethylene-2H-indol-2-ones 1 with various 1,2-diamines. Good yields were obtained at 60 °C in methanol by using graphene oxide (GO) as catalyst, however, the regio selectivity in case of unsymmetrically substituted diamines were low to moderated. This is the first report of the oxidative cleavage of C = C bond during the course of the reaction. Molecular docking study of these synthesized compounds were employed to calculate the binding affinity with human epidermal growth factor receptor 2 (HER2). 6-Bromo-3-phenylpyrido[2,3-b]pyrazine 3k showed highest binding energy of −7.70 kcal/mol depicting the potential inhibitor of HER2 receptor protein. However, this study needs to be supported by in vitro and in vivo studies.

本研究的主要目的是通过硅学研究合成和鉴定 2-芳基喹喔啉衍生物的潜在乳腺癌治疗药物。2- 芳基喹喔啉衍生物是通过 3- 芳基亚甲基-2H-吲哚-2-酮 1 与各种 1,2-二胺反应合成的。使用氧化石墨烯(GO)作为催化剂,在 60 °C甲醇条件下获得了良好的产率,然而,对于不对称取代的二胺,其区域选择性较低。这是首次报道 C = C 键在反应过程中发生氧化裂解。通过对这些合成化合物进行分子对接研究,计算了它们与人表皮生长因子受体 2(HER2)的结合亲和力。6- 溴-3-苯基吡啶并[2,3-b]吡嗪 3k 的结合能最高,为 -7.70 kcal/mol,表明它是 HER2 受体蛋白的潜在抑制剂。不过,这项研究还需要体外和体内研究的支持。
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引用次数: 0
Magnetic nanomaterials as green and recoverable nanocatalysts: Research on synthesis of benzimidazole derivatives 作为绿色可回收纳米催化剂的磁性纳米材料:苯并咪唑衍生物的合成研究
IF 2.1 3区 化学 Q3 Chemistry Pub Date : 2024-03-28 DOI: 10.1080/00397911.2024.2325786
Khalid Mujasam Batoo , Mohammed Kadhem Abid , Abdul-Hameed M. Hamoody , Ola Kamal A. Alkadir , Sajjad Hussain , Ahmed Alawadi , Ali Alsalamy

Research on benzimidazole derivatives is always an attractive challenge among synthetic chemists because benzimidazole derivatives are very key and important components in the structure of many drugs, biological active molecules, and natural products. Benzimidazole derivatives are very interesting because of their valuable biological and medicinal activities, such as anti-bacterial, anti-cancer, anti-tuberculosis, anti-fungal, pain killer, and anti-HIV activities. During the last decade, most reports in the field of catalysts have been related to magnetic nanocatalysts, which shows the high popularity and remarkable efficiency of this type of catalyst in performing chemical reactions. Magnetic nanocatalysts are ideal catalysts both from the point of view of green chemistry and economically because they are easily separated from the reaction mixture and have significant catalytic activity. In this review article, we have summarized the methods presented on the synthesis of various benzimidazole derivatives based on the use of magnetic nanomaterials as green recoverable catalysts.

由于苯并咪唑衍生物是许多药物、生物活性分子和天然产物结构中非常关键和重要的组成部分,因此对苯并咪唑衍生物的研究一直是合成化学家们面临的一项极具吸引力的挑战。苯并咪唑衍生物具有重要的生物和医药活性,如抗菌、抗癌、抗结核、抗真菌、止痛和抗艾滋病毒等活性,因此非常引人关注。在过去的十年中,催化剂领域的大多数报道都与磁性纳米催化剂有关,这表明这类催化剂在进行化学反应时非常受欢迎,而且具有显著的效率。从绿色化学和经济角度来看,磁性纳米催化剂都是理想的催化剂,因为它们很容易从反应混合物中分离出来,而且具有显著的催化活性。在这篇综述文章中,我们总结了利用磁性纳米材料作为绿色可回收催化剂合成各种苯并咪唑衍生物的方法。
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引用次数: 0
Synthetic strategies and anticancer evaluation for the novel 3-(6-heteroaryltriazolo[3,4-b][1,3,4]thiadiazol-3-yl)chromeno [2,3-b]pyridines 新型 3-(6-杂芳基三唑并[3,4-b][1,3,4]噻二唑-3-基)色烯并[2,3-b]吡啶的合成策略和抗癌评估
IF 2.1 3区 化学 Q3 Chemistry Pub Date : 2024-03-16 DOI: 10.1080/00397911.2024.2330617
Najla A. Alshaye , Magdy A. Ibrahim

The novel chromonyltriazolo[3,4-b][1,3,4]thiadiazole derivative 5 was efficiently synthesized and utilized as key intermediate for construction of a diversity of heterocyclic rings; through reactions with binucleophilic reagents. Treating electron deficient substrate 5 with hydrazine hydrate, phenylhydrazine and hydroxylamine furnished pyrazolyl/isoxazolyltriazolo[3,4-b][1,3,4]thiadiazoles 6-8. Also, reacting substrate 5 with guanidine, cyanoguanidine and thiourea provided pyrimidinyltriazolo[3,4-b][1,3,4]thiadiazoles 9-11. Reaction of substrate 5 with ethylenediamine and o-phenylenediamine afforded diazepine derivatives 12 and 13. Reaction of substrate 5 with malononitrile, ethyl cyanoacetate and cyanoacetamide afforded pyrans 14, 15 and pyridine 16 linked triazolo[3,4-b][1,3,4]thiadiazolyl chromeno[2,3-b]pyridines. The anticancer efficiency of the current compounds presented diverse inhibitory action against certain cancer cell lines. On the basis of analytical and spectral findings, the structures of the synthesized products were confirmed.

新颖的铬基三唑并[3,4-b][1,3,4]噻二唑衍生物 5 被高效合成,并用作构建多种杂环的关键中间体;通过反应...
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引用次数: 0
Sustainable synthesis of imidazoles using a catalyst-free approach and ethyl lactate as a bio-based green solvent in the Debus-Japp-Radziszewski reaction 在 Debus-Japp-Radziszewski 反应中使用无催化剂方法和作为生物基绿色溶剂的乳酸乙酯可持续合成咪唑类化合物
IF 2.1 3区 化学 Q3 Chemistry Pub Date : 2024-03-07 DOI: 10.1080/00397911.2024.2323999
Flavia Martins da Silva , Joel Jones Junior , July A. Hernández Muñoz , Priscila Nogueira de Azevedo

A highly substituted family of imidazoles is effectively obtained through the Debus-Japp-Radziszewski reaction. In this process, benzil, ammonium acetate, and various benzaldehydes react in a particularly notable solvent: ethyl lactate (EL). This bio-based solvent, derived from biomass fermentation, stands out not only for its sustainable origin but also for its remarkable properties. Ethyl lactate is biodegradable, health-risk-free, is easily recyclable, and is non-corrosive, categorizing it as an exemplary green solvent. The multicomponent reaction, carried out under these conditions, eliminates the need for a catalyst, resulting in products with good yields. The isolation of the products is very simple, requiring only filtration, as they are insoluble in the solvent. In this way, this methodology aligns with various principles of green chemistry, emphasizing the strategic choice of ethyl lactate. This choice has a positive impact on the synthesis of imidazoles, well-known for their pharmacological properties.

通过 Debus-Japp-Radziszewski 反应可以有效地获得高度取代的咪唑系列。在这一过程中,苯齐尔、醋酸铵和各种苯甲醛会发生部分反应。
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引用次数: 0
Design, synthesis and antibacterial assessment of novel 4H-chromene analogues 新型 4H-chromene 类似物的设计、合成和抗菌评估
IF 2.1 3区 化学 Q3 Chemistry Pub Date : 2024-02-29 DOI: 10.1080/00397911.2024.2324009
Safaa S. M. Shaban , David S. A. Haneen , Mohsen M. Abou-El-Regal , Souad A. El-Metwally

The significant medicinal and pharmacological facts about chromenes (benzopyran) nucleus prompted us to focus on constructing unique chromenes with biological value. New chromene derivatives 2–15 were synthesized, and their antibacterial effectiveness was studied. The reaction of the 2-amino-4H-chromene derivative 1 with a variety of reagents such as acetic anhydride, formic acid, chloroacetyl chloride, cyclopentanone, ethyl acetoacetate, diethyl malonate, aldehydes, and isatin produced derivatives 213. Compound 1 was also treated with aromatic amines such as p-toluidine and/or benzene-1,4-diamine with formaldehyde, yielding derivatives 14 and 15, respectively; spectral techniques were used to confirm the predicted structures of all compounds. The antibacterial activity of the recently synthesized compounds was assessed against two types of bacteria, Bacillus subtilis and Escherichia coli. There is encouraging antibacterial activity in compounds 5 and 7.

关于铬烯(苯并吡喃)核的重要药用和药理学事实促使我们专注于构建具有生物学价值的独特铬烯。新的苯并二氢吡喃衍生物2-15具有...
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引用次数: 0
An efficient four-component protocol for synthesis of poly-substituted pyridines with SiO2 as a robust recyclable catalyst 以二氧化硅为强效可回收催化剂合成多取代吡啶的高效四组分方案
IF 2.1 3区 化学 Q3 Chemistry Pub Date : 2024-02-28 DOI: 10.1080/00397911.2024.2320398
V. N. Chandra Sekhar , Gorle Simhachalam , L. Vaikunta Rao , A. V. Dhanunjaya Rao , Madhavaram Shankar , Akula Raghunadh

A four-component protocol for the development of poly-substituted pyridines derivatives by using SiO2 as a recycle catalyst. The protocol offers good to excellent yields (85%-95%) under milder conditions in a short reaction time of 2-3 hours. The use of a less expensive catalyst makes this protocol more convenient. SiO2 has been identified as a convenient catalyst for the synthesis and can be reused for up to three cycles.

利用 SiO2 作为循环催化剂,开发出一种四组分的多取代吡啶衍生物。在较温和的条件下,该方案可提供良好至卓越的产率(85%-95%)。
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引用次数: 0
期刊
Synthetic Communications
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