Pyrazoloquinazoline derivatives: Synthesis,reactions, and biological applications

This review deals with the synthesis, reactions and biological activity of pyrazoloquinazoline derivatives. Some of these reactions have been used successfully to the production of biologically importance compounds. The main purpose of this review is to present a survey of the literature on the chemistry of pyrazoloquinazolines and provides useful applications for these compounds.     

具有生物活性的色满衍生物不对称合成研究*

色满衍生物在自然界中广泛存在,并且大多数具有生物活性。这些具有生物活性的色满衍生物又大多具有手性,因此有关它们的不对称合成已经引起了有机合成工作者的广泛关注。合成色满衍生物的关键是构建含有手性中心的色满环。本文根据色满环构建方式的不同进行分类,概述了近十几年来合成手性色满衍生物的最新方法, 侧重讨论了各种合成方法在合成立体结构专一的色满环时的特点。     

Pharmacological evaluation of benzimidazole derivatives with potential antiviral and antitumor activity

In recent years the synthesis of benzimidazole and its derivatives has attracted the attention of many organic chemists because of the compounds’ interesting biological activity and the crucial importance of the benzimidazole unit in the function of these biologically important molecules. Benzimidazole-based polyheterocyclic compounds have several interesting biological properties. Simple synthetic strategies leading to benzimidazole-based fused polyheterocyclic systems and the antiviral and anticancer biological activity of the compounds are surveyed in this review article.     

Arylspiroboronate esters: from lithium batteries to wood preservatives to catalysis

The addition of catechol derivatives to boric acid affords a diverse family of compounds called arylspiroboronate esters. Due to boron's relatively low toxicity towards mammals, arylspiroboronate esters have several biological applications and are active for the treatment of wood against fungi and rot. These compounds are also finding increased use in organic synthesis and in catalysis. This critical review presents the synthesis, properties and applications of these remarkable compounds (149 references).     

Naproxen derivatives: Synthesis,reactions, and biological applications

This review describes the synthesis and reactions of naproxen derivatives and highlights the effects of compounds containing the naproxen moiety in important biological applications.     

The Chemistry of Acetylpyrazoles and Its Utility in Heterocyclic Synthesis

A literature survey revealed that a great deal of interest has been focused on the synthesis of functionalized pyrazole derivatives due to their synthetic and biological potentialities. The pharmacological activities that have been found for some pyrazole derivatives include selective enzyme inhibition, antiviral, estrogen receptor agonist, anti‐inflammatory, anticancer, antiobesity, and antitumor properties. Other activities such as potential inhibitors of HIV‐1, pesticides, fungicides, and antihypertensive agents were reported for other pyrazole derivatives. This review summarizes the synthetic methods and reactions of 3‐acetyl‐pyrazoles, 4‐acetyl‐pyrazoles, and 3,4‐di‐acetyl‐pyrazoles. Most reaction types have been successfully applied and used in the production of biologically active compounds. The aim of this review is to focus mainly on the utility of acetylpyrazole derivatives in the synthesis of heterocyclic compounds during the period 1990–2018.     

槲皮素衍生物的合成及生物活性研究进展

综述了槲皮素衍生物的合成及生物活性研究进展,介绍了国内外槲皮素氨基酸类、糖苷类、酯类、醚类衍生物及金属配合物的合成方法及其生物活性研究现状.指出槲皮素是一种从天然植物中提取的黄酮醇类化合物,具有抗氧化,抗菌,扩张血管,抗肿瘤及抗突变等多种生物学活性.然而,槲皮素具有水溶性差、生物利用度较低等缺点,临床应用受到限制.为此,国内外学者对其结构进行修饰改造,开发出了一系列具有新颖结构的槲皮素先导化合物,可望为新型槲皮素衍生物的设计合成提供参考.     

An overview on novel synthetic approaches and medicinal applications of benzimidazole compounds

Benzimidazole, a benzene-fused heterocyclic compound, has acquired significant attention in the field of contemporary medicinal chemistry because of its wide array of pharmacological activities. Nitrogen containing heterocyclic compounds are part of several therapeutically important agents with several recent patents shedding light on their worth. For these reasons, this review is concerned with different methods for synthesis of benzimidazole derivatives and their biological importance.     

Advances in the Chemistry of 4-Azatricyclo[4.3.1.13,8]undecane (4-Azahomoadamantane) Derivatives

The review summarizes published data on the synthesis, physical and chemical properties, and biological activity of 4-azatricyclo[4.3.1.1^{3 8}]undecane derivatives and some related tricyclic compounds, tricycloundecane homologs and diadamantane derivatives.     

Reactions of 3-formylchromone with active methylene and methyl compounds and some subsequent reactions of the resulting condensation products

This review presents a survey of the condensations of 3-formylchromone with various active methylene and methyl compounds, e.g. malonic or barbituric acid derivatives, five-membered heterocycles, etc. The utilisation of the condensation products for the synthesis of different heterocyclic systems, which is based on the ability of the gamma-pyrone ring to be opened by the nucleophilic attack is also reviewed. Finally, the applications of microwave irradiation as an unconventional method of reaction activation in the synthesis of condensation products is described and the biological activity of some chromone derivatives is noted.     

Synthesis and biological action of novel 4-position-modified derivatives of D-myo-inositol 1,4,5-trisphosphate

The design of a range of 4-position-modified D-myo-inositol 1,4,5-trisphosphate derivatives is described. The enantioselective synthesis of these compounds is reported, along with initial biological analysis, which indicates that these compounds do not act as D-myo-inositol 1,4,5-trisphosphate receptor agonists or antagonists.     

含二茂铁的β-内酰胺的研究进展

β-内酰胺类抗生素是目前最具应用价值的抗生素, 其结构特征具有β-内酰胺环的基元结构, 该类化合物的设计、合成和立体化学研究一直是有机合成化学研究的前沿和热点领域. 二茂铁凭借其独特的结构和多样的性质, 在生物和医药方面均有广泛的应用价值. 因此, 二茂铁修饰的β-内酰胺是一类结构新颖且具有潜在生物活性的化合物. 对该类化合物的深入研究, 将对新型抗生素的研发提供重要的指导意义. 综述了近年来青霉烷类和头孢烯类β-内酰胺及单环类β-内酰胺这两大类含二茂铁取代的β-内酰胺衍生物的合成与生物活性的研究进展.     

Recent advances in the synthesis,biological activities and various applications of ferrocene derivatives

Ferrocene derivatives constitute an important class of organometallic compounds with not only an extensive range of biological activities but also diverse industrial as well as material science applications. These stimulating features of ferrocene derivatives spurred us to review the recent advances in synthesis methods and biological and other applications reported in the latest literature. An effort has been made to summarize the recent developments in synthetic methods providing access to ferrocene scaffolds and the useful medicinal and material applications, including agricultural, catalytic, polymer, conducting, redox mediating, ferrocenyl stationary phase, rocket propellant and ion sensing applications. Ferrocene‐based bulky metallocenes are also discussed.     

Metal‐Catalyzed C−H Bond Activation of 5‐Membered Carbocyclic Rings: A Powerful Access to Azulene,Acenaphthylene and Fulvene Derivatives

Azulene, acenaphthylene and fulvene derivatives exhibit important physical properties useful in materials chemistry as well as valuable biological properties. Since about two decades ago, the metal‐catalyzed functionalization of such compounds, via C?H bond activation of their 5‐membered carbocyclic ring, proved to be a very convenient method for the synthesis of a wide variety of azulene, acenaphthylene and fulvene derivatives. For such reactions, there is no need to prefunctionalize the 5‐membered carbocyclic rings. In this review, the progress in the synthesis of azulene, acenaphthylene and fulvene derivatives via metal‐catalyzed C?H bond activation of their 5‐membered carbocyclic ring are summarized.     

Chemistry and Applications of Functionalized 2,4-Thiazolidinediones

Thiazolidinedione (TZD) is one of the privileged heterocyclic rings and has shown many biological applications in medicinal chemistry and drug discovery. This review covers the synthetic approaches of TZD and its derivatives, different synthetic techniques for affording the desired regioselectivity and stereoselectivity, and the techniques that would enhance reaction conditions such as microwave, one-pot, or ultrasound synthesis. It focuses on synthetic challenges of glitazones and the transformation of other heterocycles to TZD. Moreover, the chemical and biological behavior of TZD through the substitution in the N3 position, modification of the C5 position, annealing in complex heterocyclic systems, and hybridization with other pharmacologically attractive moieties are discussed. All reactions mentioned are provided as possible with different reaction conditions, mechanisms, derivatives scope, yield and clarified by applications of such reactions in the construction of potential medicinal agents. The review also answers questions about rapid racemization of glitazones, their toxicity, considering TZD as pan-assay interference compounds (PAINS) or not, and the influence of saturation of 5-position of TZD in their biological activities. This review is a comprehensive guide to make informed decisions for construction of TZD derivatives with biological potentials.     

Toward high-throughput synthesis of complex natural product-like compounds in the genomics and proteomics age

In the age of high-throughput biology, novel genes and proteins are emerging quickly. The need for developing organic synthesis-derived methods that allow rapid access to polyfunctional, complex natural product-like compounds is growing constantly, largely because these small-molecule-based compounds serve as smart, powerful tools both in understanding the roles and functions of emerging biological targets and in validating their biological responses. Developing asymmetric synthesis-derived organic reactions on solid phase allows the synthesis of complex natural product-like compounds in a high-throughput manner. Solid phase organic synthesis is now commonly utilized in the library synthesis of rather simple compounds (i.e., compounds with no multiple stereogenic centers). With few exceptions, the synthesis of complex natural product-like derivatives is still in its infancy. Some recent efforts made in this area indicate opportunities yet to be explored.     

Synthesis of a library of 3-oxopiperazinium and perhydro-3-oxo-1,4-diazepinium derivatives and identification of bioactive compounds

The design and synthesis of a library of novel families of 3-oxopiperazinium and perhydro-3-oxo-1,4-diazepinium derivatives is reported. The library was composed of 44 3-oxopiperazinium derivatives (11 of these compounds had a spiranic skeleton) and 22 perhydro-3-oxo-1,4-diazepinium compounds. The synthetic procedure involved a 6-step sequence carried out in solution, along with the use of solid-phase linked scavengers and microwave activation for the rapid removal of the excess of amine reagents. A final cyclization step performed under mild conditions led to the charged heterocyclic moiety. Screening of this library in two biological assays identified active compounds that inhibit the activity of the vanilloid receptor TRPV1 and modulators of the multidrug resistance phenomenon. Thus, this synthetic sequence represents a facile and convenient entry to unprecedented libraries of this sort of tetraalkylammonium derivatives that may be of use for identification of novel scaffolds of diverse biological activity.     

SYNTHESIS,REACTIONS AND BIOLOGICAL ACTIVITY OF PHOSPHORUS-CONTAINING DERIVATIVES OF CHROMONE AND COUMARIN

Chromone and coumarin derivatives exhibit a wide spectrum of biological activity, including spasmolytic, antiarrhythmic, cardiothonic, antiviral, and anticancer properties. Phosphorus-containing chromone and coumarin derivatives form a novel group of compounds, possessing remarkable cytotoxicity and alkylating and anticancer activity against selected tumor cell lines. Derivatives containing a phosphorus atom at position 2 of a γ-pyrone ring are known to be efficient antibacterial agents.

This review presents methods developed for the synthesis of derivatives of chromone and coumarin that contain a phosphonate moiety. Among them, the reaction of derivatives of 2-hydroxyacetophenone with phosphonic compounds is the one most frequently used. Some analogues were characterized by X-ray crystallography.     

New dimensions in triazolo[4,3-a]pyrazine derivatives: The land of opportunity in organic and medicinal chemistry

Synthesis of novel and potent hit molecules have endless demand. The triazolo[4,3-a]pyrazine scaffold is used as an essential building block/scaffold in organic synthesis, which works as a key template for the development of various therapeutic agents. It displays a wide spectrum of potential biological activities that have been progressively studied in recent years on account of their versatile structure and the diverse derivatives that can be synthesized from it to ensure functional motifs. This review article gives an inclusive account of the synthetic utility of triazolo[4,3-a] pyrazine derivatives employed in the design and synthesis of different types of compounds containing various active heterocyclic rings with greater emphasis in recent literature.     

Benzoxaboroles - Old compounds with new applications

This comprehensive review covers the structure, methods of synthesis, properties and fields of application of benzoxaboroles - derivatives of phenylboronic acids. Some of the title compounds were described over 50 years ago, however most of them have been investigated only recently due to their exceptional properties and wide applications. In addition to their usage as building blocks and protecting groups in organic synthesis, certain benzoxaboroles display biological activity and are under clinical trials. They also bind hydroxyl compounds and thus can be applied as molecular receptors for sugars and glycoconjugates.