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Synthesis and Antitumor Activity of Some New N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones 一些新的 N1-(8-氟-4-氧代喹啉-5-基)脒酮的合成和抗肿瘤活性
IF 1.8 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-01-17 DOI: 10.2174/0115701794282903231228055914
Hind M. A. Yahya, Jalal A. Zahra, Salim S. Sabri, Mustafa M. El-Abadelah, Sanaa Bardaweel
Background: Hydrazonoyl chloride, accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carboxylate, undergoes a reaction with sec-cyclic amines to generate N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. background: The hydrazonoyl chloride, accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carboxylate, underwent reaction with sec-cyclic amines to generate N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. Introduction: A novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates (7a-h) incorporating N-piperazines or related congeners was synthesized via interaction of the hy-drazonoyl chloride (6), accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carbox-ylate, with the appropriate sec-cyclic amine. These new compounds were characterized by 1H-NMR, 13C-NMR, and HRMS spectral data and screened for their anticancer activities. Aims: This study aimed at the synthesis of novel N1-( 4-oxoquinolin-5-yl)amidrazone carboxylate derivatives and investigated their potential as anticancer agents. Objective: The reaction of hydrazonoyl chloride with the appropriate sec-cyclic amine was applied to synthesize a novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5- yl)amidrazone carboxylates that incorporate N piperazines. Methods: A direct reaction of piperazines and related sec-cyclic amines with N-(4-oxoquinolin-5-yl)nitrile imine (1,3-dipole) was carried out for 8-10 h. conclusion: A novel set N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones were successfully synthesized. Several of these compounds showed moderate activity against three breast cancer cell lines (MCF-7, T47D, and MDA-MB-231) with IC50 values in the range =18-78µM compared to Doxorubicin Results: The 1,3-dipole, generated in situ from its hydrazonoyl chloride precursor in the presence of trimethylamine, is suitable for the facile synthesis of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. Conclusion: This study led to the successful synthesis of novel N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones. All the examined compounds showed moderate activity with reasonable IC50 values in the micromolar range compared to Doxorubicin.
背景:背景:从各自的 5-氨基-8-氟-4-氧代喹啉-3-羧酸酯中可获得的肼酰氯与仲环胺发生反应,生成 N1-(1-乙基-8-氟-4-氧代喹啉-5-基)脒酮羧酸酯:从相应的 5-氨基-8-氟-4-氧代喹啉-3-羧酸中获得的肼酰氯与仲环胺发生反应,生成 N1-(1-乙基-8-氟-4-氧代喹啉-5-基)脒腙羧酸盐。简介:通过从相应的 5-氨基-8-氟-4-氧代喹啉-3-羧酸酯中可获得的次氮酰氯(6)与适当的仲环胺的相互作用,合成了一组含有 N-哌嗪或相关同系物的新型 N1-(1-乙基-8-氟-4-氧代喹啉-5-基)脒腙羧酸酯(7a-h)。通过 1H-NMR、13C-NMR 和 HRMS 光谱数据对这些新化合物进行了表征,并对其抗癌活性进行了筛选。目的:本研究旨在合成新型 N1-( 4-oxoquinolin-5-yl)amidrazone 羧酸盐衍生物,并研究其作为抗癌剂的潜力。研究目的采用肼酰氯与适当的仲环胺反应的方法,合成一组含有 N-哌嗪的新型 N1-(1-乙基-8-氟-4-氧代喹啉-5-基)脒腙羧酸盐。方法:哌嗪和相关仲环胺与 N-(4-氧代喹啉-5-基)腈亚胺(1,3-二极)直接反应 8-10 小时:成功合成了一组新的 N1-(8-氟-4-氧代喹啉-5-基)脒酮。其中几个化合物对三种乳腺癌细胞系(MCF-7、T47D 和 MDA-MB-231)显示出中等程度的活性,与多柔比星结果相比,其 IC50 值范围为 =18-78µM:在三甲胺存在下,由其肼酰氯前体原位生成的 1,3-二极适用于简单合成 N1-(1-乙基-8-氟-4-氧代喹啉-5-基)脒腙羧酸盐。结论本研究成功合成了新型 N1-(8-氟-4-氧代喹啉-5-基)脒酮。与多柔比星相比,所有受检化合物均显示出中等活性,IC50 值在微摩尔范围内。
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引用次数: 0
A Brief Review on Recent Developments in Diels-Alder Reactions. Diels-Alder 反应最新发展简评。
IF 1.8 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-01-15 DOI: 10.2174/0115701794262102231214074336
Manish Chaudhary, Shareef Shaik, Muskan Magan, Sharwan Hudda, Mukta Gupta, Gurvinder Singh, Pankaj Wadhwa

The [4+2] Diels-Alder cycloaddition has been widely used for the synthesis of six-mem-ber scaffolds. In recent years, there have been significant developments in this area, including the discovery and design of novel dienes and dienophiles with improved reactivity and selectivity. These new building blocks can be used to develop diverse molecular structures with functional group compatibility. Additionally, there is the use of catalytic systems and metal-mediated reactions to enable asymmetric [4+2] cycloadditions, resulting in enantiomerically enriched products. Over-all, recent studies related to [4+2] Diels-Alder cycloaddition using numerous dienes, dienophiles, and catalysts in different reaction conditions have significantly improved the efficiency, selectivity, and versatility of the reaction, making it an increasingly important tool in the synthesis of complex organic molecules as presented in this review. These advancements offer exciting possibilities for the development of new methods and reagents for the construction of six-membered rings and the synthesis of bioactive compounds.

[4+2]Diels-Alder环化反应已被广泛用于合成六烯烃支架。近年来,这一领域取得了重大进展,包括发现和设计出反应性和选择性更强的新型二烯和二烯烃。这些新的结构单元可用于开发具有官能团兼容性的多种分子结构。此外,还利用催化系统和金属介导的反应来实现不对称[4+2]环化,从而产生对映体丰富的产品。总的来说,最近有关在不同反应条件下使用多种二烯、亲二烯化合物和催化剂进行 [4+2] Diels-Alder 环化反应的研究大大提高了该反应的效率、选择性和多功能性,使其成为本综述中介绍的合成复杂有机分子的日益重要的工具。这些进步为开发构建六元环和合成生物活性化合物的新方法和新试剂提供了令人兴奋的可能性。
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引用次数: 0
Organocatalytic Synthesis of (Hetero)arylidene Malononitriles Using a More Sustainable, Greener, and Scalable Strategy 使用更可持续、更绿色、更可扩展的策略有机催化合成(异)芳基丙二腈
IF 1.8 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-01-13 DOI: 10.2174/0115701794268766231108110816
Suzaimi Johari, Mohd Rafie Johan, Nader Ghaffari Khaligh
Aim and Objective: The establishment of a green and sustainable Knoevenagel con-densation reaction in organic chemistry is still crucial. This work aimed to provide a newly de-veloped metal-free and halogen-free catalytic methodology for the synthesis of CS and (het-ero-)arylidene malononitriles in the laboratory and industrial scale. The Knoevenagel condensa-tion reaction of various carbonyl groups with malononitrile was investigated in ethanol, an eco-friendly medium, in the presence of seven nitrogen-based organocatalysts. Materials and Methods: A comparative study was conducted using two as-obtained and four commercially available nitrogen-based organocatalysts in Knoevenagel condensation reactions. The synthesis of CS gas (2-chlorobenzylidene malononitrile) using a closed catalytic system was optimized based on their efficiency and greener approach. Results: The conversion of 100% and excellent yields were obtained in a short time. The products could be crystallized directly from the reaction mixture. After separating pure products, the resi-due solution was employed directly in the next run without any concentration, activation, purification, or separation. Furthermore, the synthesis of 2-chlorobenzylidenemahmonitrile (CS) was carried out on a large scale using imidazole as a selected nitrogen-based catalyst, afforded crys-talline products with 95±2% yield in five consecutive runs. Conclusion: Energy efficiency, cost saving, greener conditions, using only 5 mol% of organo-catalyst, high recyclability of catalyst, prevention of waste, recycling extractant by a rotary evaporator for non-crystallized products, demonstrated the potential commercial production of CS using imidazole in ethanol as an efficient and highly recyclable catalytic system
目的和目标:在有机化学中建立绿色和可持续的克诺文纳格尔缩合反应仍然至关重要。这项工作旨在提供一种新开发的无金属、无卤素催化方法,用于在实验室和工业规模上合成 CS 和(庚-烯)亚芳基丙二腈。在七种氮基有机催化剂存在下,研究了各种羰基与丙二腈在乙醇(一种环保介质)中发生的 Knoevenagel 缩合反应。材料和方法:在克诺文纳格尔缩合反应中使用了两种现成的氮基有机催化剂和四种市售的氮基有机催化剂进行了对比研究。根据其效率和绿色方法,对使用封闭催化系统合成 CS 气体(2-氯亚苄丙二腈)进行了优化。结果:在短时间内获得了 100% 的转化率和优异的产率。产物可直接从反应混合物中结晶出来。分离出纯净产物后,无需浓缩、活化、纯化或分离,即可直接用于下一次运行。此外,利用咪唑作为精选的氮基催化剂,大规模合成了 2-氯亚苄基马骝腈(CS),并连续五次获得了收率为 95±2% 的冰晶石产品。结论利用咪唑在乙醇中作为高效和高度可回收的催化系统,可实现 CS 的商业化生产。
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引用次数: 0
Regioselective Synthesis of Cycloalkane-fused pyrazolo[4,3-e]pyridines through Tandem Reaction of 5-aminopyrazoles, Cyclic Ketones and Electron-rich Olefins 通过 5-氨基吡唑、环酮和富电子烯烃的串联反应,实现环烷融合吡唑并[4,3-e]吡啶的区域选择性合成
IF 1.8 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-01-12 DOI: 10.2174/0115701794269765231204064930
Paola Cuervo-Prado, Fabián Orozco-López, Christian Becerra-Rivas, Diego Leon-Vargas, John Lozano-Oviedo, Justo Cobo
Background: Pyrazolopyridines are interesting fused heterocyclic pharmacophores that combine pyrazole and pyridine; two privileged nuclei extensively studied and with a wide range of applications. They can be obtained by a broad variety of synthetic methods among which multicomponent reactions have gained importance, especially from 5-aminopyrazoles and dielectrophilic reagents. However, the search for new approaches more in tune with sustainable chemistry and the use of unconventional heating in three-component synthesis are open and highly relevant study fields. Methods: A novel, practical and efficient three-component synthesis of cycloalkane-fused pyra-zolo[4,3-e]pyridines was developed through a tandem reaction of 5-aminopyrazoles, cyclic ke-tones and electron-rich olefins, using microwave induction in perfluorinated solvent and iodine as catalyst. objective: To apply the principles of sustainable chemistry through a microwave-induced synthesis in perfluorinated solvent to obtain novel cycloalkane-fused pyrazolo[4,3-e]pyridines, taking advantage of the versatility of electron-rich olefins in iodine-catalyzed cascade heterocyclizations. Results: The microwave-induced three-component approach applied in this work promoted the construction of 10 new pyrazolopyridines with high speed and excellent control of regioselec-tivity, favoring the linear product with good yields; where the versatility of electron-rich olefins in iodine-catalyzed cascade heterocyclizations, granted the additional benefit of easy isolation and the possibility to reuse the fluorous phase. Conclusions: Although pyrazolopyridines have been synthetically explored because of their structural and biological properties, most of the reported synthetic methods use common or even toxic organic solvents and conventional heating or multi-step processes. In contrast, this study applied a multicomponent methodology in a single step by microwave induction and with the versatility provided in this case by the use of perfluorinated solvent, which allowed easy isolation of the final product and recovery of the fluorous phase.
背景:吡唑并吡啶是结合了吡唑和吡啶的有趣的融合杂环类药物。它们可以通过多种合成方法获得,其中多组分反应的重要性日益凸显,尤其是从 5-氨基吡唑和亲电试剂中获得。然而,寻找更符合可持续化学的新方法,以及在三组分合成中使用非常规加热,都是开放且高度相关的研究领域。方法:以碘为催化剂,在全氟溶剂中进行微波诱导,通过 5-氨基吡唑、环烯酮和富电子烯烃的串联反应,开发了一种新型、实用和高效的环烷烃融合吡唑并[4,3-e]吡啶的三组分合成方法:利用富电子烯烃在碘催化级联杂环反应中的多功能性,通过全氟溶剂中的微波诱导合成,应用可持续化学原理获得新型环烷融合吡唑并[4,3-e]吡啶。结果:这项工作中采用的微波诱导三组分方法促进了 10 种新吡唑并吡啶的构建,这种方法速度快,对区域电导率的控制极佳,有利于获得线性产物,且收率高;富电子烯烃在碘催化级联杂环反应中的多功能性带来了额外的好处,即易于分离,且可以重复使用流相。结论:尽管吡唑并吡啶因其结构和生物特性已被用于合成研究,但大多数报道的合成方法都使用普通甚至有毒的有机溶剂和传统的加热或多步骤工艺。相比之下,本研究采用了多组分方法,通过微波诱导一步完成,并且使用全氟溶剂提供了多功能性,可以轻松分离最终产物并回收氟相。
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引用次数: 0
Reactions and Biological Activities of Hydrazonoyl Halides 肼酰卤的反应和生物活性
IF 1.8 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-01-11 DOI: 10.2174/0115701794268313231127110713
Munirah Alarbash, Yasir Al-Faiyz, Jeffery Wiggins, Abdelwahed Sayed
: This review covers the literature information on the chemistry of hydrazonoyl halides with different substrates to give heterocyclic compounds. From the foregoing survey, it seems this provides a useful and convenient strategy for the synthesis of numerous heterocyclic derivatives. The subject of such reactions is still ongoing and undoubtedly will provide new fused functionalized compounds of both industrial and biological interest. A literature survey revealed that a great deal of interest has been focused on the synthesis of functionalized heterocyclic compounds due to their wide range of biological activities, such as contact dermatitis, anthelmintic, antiviral, antimicrobial, herbicidal, and anti-cancer. On the other hand, hydrazonoyl halides are interesting synthons for valuable bioactive heterocyclic compounds. The reaction of hydrazonoyl halides with various types of substrates gave a huge number of different heterocyclic systems. In this review, we collected all reactions of hydrazonoyl halides with different moieties and classified them as aryl diazo of monoheterocycles, aryldiazo of 5,5-bis-heterocycles, aryldiazo of 5,6-bis-heterocycles, aryldiazo of 6,6-bis-heterocycles, aryldiazo of 5,5,6-tri-heterocycles, aryldiazo of 5,6,6-tri-heterocycles, aryldiazo of 6,6,6-tri-heterocycles, hetero annulation of bisheterocycles, hetero annulation of tri-heterocycles, hetero-annulation of tetra-heterocycles, synthesis of spiro-heterocycles, heterocyclic ring transformations, and 1,3-dipolar cycloaddition reactions catalyzed by transition metals using hydrazonoyl halides as substrates. Most reaction types have been successfully applied and used in the production of biologically active compounds. The aim of the present survey is to consider in the reader the opportunity interactions and biological activities of hydrazonoyl halides. The information of several artificial paths and varied physics-chemical factors of such heterocycles made a special consideration of chemists in different fields to yield a combinatorial library and carry out thorough efforts in the search for hydrazonoyl halides
:本综述涵盖了有关肼酰卤与不同底物生成杂环化合物的化学文献信息。从上述调查来看,这似乎为合成多种杂环衍生物提供了一种有用而方便的策略。此类反应的研究课题仍在进行中,无疑将为工业和生物领域提供新的融合功能化化合物。文献调查显示,由于功能化杂环化合物具有广泛的生物活性,如接触性皮炎、驱虫、抗病毒、抗菌、除草和抗癌等,人们对其合成产生了极大的兴趣。另一方面,肼酰卤也是具有重要生物活性的杂环化合物的有趣合成物。肼酰卤与各种类型的底物反应产生了大量不同的杂环系统。在本综述中,我们收集了所有肼酰卤与不同分子的反应,并将其分为单杂环的芳基重氮、5,5-双杂环的芳基重氮、5,6-双杂环的芳基重氮、6,6-双杂环的芳基重氮、5,5,6-三杂环的芳基重氮、5,6,6-三杂环的芳基重氮、双杂环的杂环化、三杂环的杂环化、四杂环的杂环化、螺三环的合成、杂环环转化,以及过渡金属催化的以肼酰卤为底物的 1,3-二极环加成反应。大多数反应类型已成功应用于生物活性化合物的生产。本调查旨在向读者介绍肼酰卤的相互作用机会和生物活性。关于此类杂环的几种人工途径和各种物理化学因素的信息,使不同领域的化学家特别考虑建立一个组合库,并在寻找肼酰卤化物方面进行了深入的努力。
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引用次数: 0
Recent progress in free radical transformations of allenamides 烯酰胺自由基转化的最新进展
IF 1.8 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-01-04 DOI: 10.2174/0115701794269961231027054854
Yongchun Liu, Zimin Wang, Rui Li, Yinhai Yao, Zhichuan Shi, Qin Sun, Guowei Deng
: Allenamides are special allenes, and the unique reactivity, selectivity (both stereoselective and regionally selective) and stability of allenamides have been widely studied. In this review, the development of the free radical transformation of allenamides over the last few years will be summarized. This review discusses in detail in three parts: intermolecular radical addition to C- X (X = N, S, O, Se) bonds, metal salt mediated cyclization of allenamides, and photocatalytic cyclization of allenamides. In addition, reasonable details of the mechanisms are provided for the vast majority of these transformations.
:烯酰胺是一种特殊的烯烃,人们对烯酰胺独特的反应性、选择性(立体选择性和区域选择性)和稳定性进行了广泛的研究。在本综述中,将总结过去几年来烯酰胺自由基转化的发展情况。本综述将分三个部分进行详细讨论:C- X(X = N、S、O、Se)键的分子间自由基加成、金属盐介导的烯酰胺环化以及烯酰胺的光催化环化。此外,还提供了绝大多数转化过程的合理机制细节。
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引用次数: 0
Heteroaromatization of Coumarin Part I: Design, Synthesis, Reactions, Antitumor Activities of Novel Pyridine and Naphthyridine Derivatives 香豆素的异芳香化第一部分:新型吡啶和萘啶衍生物的设计、合成、反应和抗肿瘤活性
IF 1.8 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-01-02 DOI: 10.2174/0115701794265924230920061222
Rita Mohammed Ahmed Borik, Ashraf Hassan Fekry Abd El-Wahab
: A novel series of chromen-3-yl-pyridine moieties were synthesized. IR, NMR, and MS spectroscopy were used to confirm the structure of these novel compounds and study antitumor activity of these compounds. The structure-activity relationship investigation demonstrated that 2,4-diamino-5-(3- methoxyphenyl)-7-(2-oxo-2H-chromen-3-yl)-1,8-naphthyridine-3-carbonitrile (16), naphthyridine-3- carbonitrile derivatives 17, 18 and pyrido[2,3-d]pyrimidine derivative 12 were found to be more effective, while compounds 5a,b, 9c, 11, 13 and 14 showed moderate activity for antitumor activities. Objectives: The objective was to design a series of new chromen-3-yl-pyridine and pyrido[2,3-d]pyrimidine derivatives and study the antitumor of these compounds. Materials and Methods: The condensation reaction of 3-acetyl-2H-chromen-2-one with 3-methoxy benzaldehyde and malononitrile or ethyl cyanoacetate in the presence of ammonium acetate and acetic acid under reflux to give the corresponding chromen-3-yl pyridine-3-carbonitrile derivatives. Results: In this study, the antitumor activity of the synthesized compounds chromen-3-yl-pyridine derivatives has been determined for the broad spectrum of cytotoxic activity toward the investigated three cell lines and 5-Fluorouracil, as reference drugs. Conclusion: A series of new chromen-3-yl-pyridine and pyrido[2,3-d]pyrimidine derivatives were synthesized in this work. All compounds were evaluated for cytotoxic activity.
:合成了一系列新型色烯-3-基吡啶分子。利用红外光谱、核磁共振光谱和质谱光谱确认了这些新型化合物的结构,并研究了这些化合物的抗肿瘤活性。结构-活性关系研究表明,2,4-二氨基-5-(3-甲氧基苯基)-7-(2-氧代-2H-苯并吡喃-3-基)-1,8-萘啶-3-甲腈(16)、萘啶-3-甲腈衍生物 17、18 和吡啶并[2,3-d]嘧啶衍生物 12 的抗肿瘤活性较高,而化合物 5a、b、9c、11、13 和 14 的抗肿瘤活性一般。目标:目的是设计一系列新的色烯-3-基吡啶和吡啶并[2,3-d]嘧啶衍生物,并研究这些化合物的抗肿瘤活性。材料和方法:在乙酸铵和乙酸存在下,3-乙酰基-2H-苯并吡喃-2-酮与 3-甲氧基苯甲醛和丙二腈或氰基乙酸乙酯在回流条件下发生缩合反应,得到相应的色烯-3-基吡啶-3-甲腈衍生物。研究结果本研究测定了合成化合物铬烯-3-基吡啶衍生物对所研究的三种细胞系和作为参考药物的 5-氟尿嘧啶的广谱细胞毒性活性。结论本研究合成了一系列新的铬-3-基吡啶和吡啶并[2,3-d]嘧啶衍生物。对所有化合物的细胞毒性活性进行了评估。
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引用次数: 0
Sustainable Green Synthesis of Pyrimidine Derivatives: Review on Multicomponent Synthesis, Catalysts and Techniques. 嘧啶衍生物的可持续绿色合成:多组分合成、催化剂和技术综述。
IF 1.8 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-01-01 DOI: 10.2174/1570179420666230330081211
Elshimaa Mohmed Eid

"The founder of green chemistry explains how chemicals manufacturing must change to support a sustainable future." In this review, Green chemistry is considered in the synthesis of heterocycles compounds containing Pyrimidine nuclei using different catalyzes, solvents, and techniques for the synthesis of pyrimidine derivatives that achieve sustainability. The mentioned fused heterocycles are classified according to the type of ring system. The yield of the target molecules reported in the review is given in the reaction's last step.

“绿色化学的创始人解释了化学品制造必须如何改变以支持可持续发展的未来。”在这篇综述中,绿色化学考虑了在合成含有嘧啶核的杂环化合物中使用不同的催化剂,溶剂和技术来合成具有可持续性的嘧啶衍生物。上述熔融杂环按环系类型分类。本文报道的目标分子的产率是在反应的最后一步给出的。
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引用次数: 0
Thematic Issue: Emerging Aspects of Click Chemistry. 专题:点击化学的新兴方面。
IF 1.8 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-01-01 DOI: 10.2174/157017942104240218204834
Vinod K Tiwari, Diganta Sarma
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引用次数: 0
Green Approach Toward Triazole Forming Reactions for Developing Anticancer Drugs. 开发抗癌药物的三唑形成反应绿色方法
IF 1.8 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-01-01 DOI: 10.2174/1570179420666230508125144
Shiva K Rastogi, Veronica C Ciliberto, Monica Z Trevino, Brooke A Campbell, William J Brittain

Compounds containing triazole have many significant applications in the dye and ink industry, corrosion inhibitors, polymers, and pharmaceutical industries. These compounds possess many antimicrobial, antioxidant, anticancer, antiviral, anti-HIV, antitubercular, and anticancer activities. Several synthetic methods have been reported for reducing time, minimizing synthetic steps, and utilizing less hazardous and toxic solvents and reagents to improve the yield of triazoles and their analogues synthesis. Among the improvement in methods, green approaches towards triazole forming biologically active compounds, especially anticancer compounds, would be very important for pharmaceutical industries as well as global research community. In this article, we have reviewed the last five years of green chemistry approaches on click reaction between alkyl azide and alkynes to install 1,2,3-triazole moiety in natural products and synthetic drug-like molecules, such as in colchicine, flavanone cardanol, bisphosphonates, thiabendazoles, piperazine, prostanoid, flavonoid, quinoxalines, C-azanucleoside, dibenzylamine, and aryl-azotriazole. The cytotoxicity of triazole hybrid analogues was evaluated against a panel of cancer cell lines, including multidrug-resistant cell lines.

含三唑的化合物在染料和油墨行业、腐蚀抑制剂、聚合物和制药行业有许多重要应用。这些化合物具有多种抗菌、抗氧化、抗癌、抗病毒、抗艾滋病毒、抗结核和抗癌活性。为了缩短三唑及其类似物的合成时间、减少合成步骤、利用危险性和毒性较低的溶剂和试剂来提高合成产量,已有多种合成方法被报道。在这些方法的改进中,绿色方法对制药业和全球研究界来说非常重要,因为这些方法可以生产出具有生物活性的三唑化合物,尤其是抗癌化合物。在本文中,我们回顾了近五年来有关烷基叠氮化物和炔烃通过点击反应在天然产物和合成药物样分子中安装 1,2,3- 三唑分子的绿色化学方法,如秋水仙碱、黄酮贲醇、双磷酸盐、噻苯达唑、哌嗪、类前列腺素、类黄酮、喹喔啉、C-氮核苷、二苄胺和芳基-氮杂三唑。评估了三唑混合类似物对一组癌细胞株(包括耐多药细胞株)的细胞毒性。
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引用次数: 0
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Current organic synthesis
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