Recent Advances for the Synthesis of Selenium-containing Small Molecules as Potent Antitumor Agents

2018 ◽  
Vol 25 (17) ◽  
pp. 2009-2033 ◽  
Author(s):  
Qi Miao ◽  
Jinyi Xu ◽  
Aijun Lin ◽  
Xiaoming Wu ◽  
Liang Wu ◽  
...  

Selenium-containing small molecules have attracted considerable attention of chemical and medicinal researchers owing to their various biological activities, such as antitumor effects, cardiovascular protection, antibacterial or antiviral effects, immunoregulation and nerve protection, among which the most promising area is antineoplasm. In the past several decades, different kinds of organoselenium compounds, such as selenides, seleno(iso)cyanates, substituted selenoureas, selenious esters and Se-containing heterocycles have been reported as candidates of anti-cancer agents. Current reviews of Se-containing anticancer compounds mainly concerned about the investigation of their bioactivities, whereas, few attention has been addressed on their synthetic approaches. Herein, we summarized methodologies recently developed to synthesize organoselenium compounds with potent antineoplastic properties, which would be helpful for further design and synthesis of new bioactive Se-containing molecules with diverse structural features.

2020 ◽  
Vol 21 (3) ◽  
pp. 930
Author(s):  
Luis Fernando Méndez-López ◽  
Elvira Garza-González ◽  
María Yolanda Ríos ◽  
M. Ángeles Ramírez-Cisneros ◽  
Laura Alvarez ◽  
...  

Cissus trifoliata (L.) L belongs to the Vitaceae family and is an important medicinal plant used in Mexico for the management of infectious diseases and tumors. The present study aimed to evaluate the metabolic profile of the stems of C. trifoliata and to correlate the results with their antibacterial and cytotoxic activities. The hexane extract was analyzed using gas chromatography coupled with mass spectrometry (GC-MS) and the CHCl3-MeOH and aqueous extracts by ultraperformance liquid chromatography quadrupole time of fly mass spectrometry (UPLC-QTOF-MS). The antibacterial activity was determined by broth microdilution and the cytotoxicity was evaluated using MTS cell proliferation assay. Forty-six metabolites were putatively identified from the three extracts. Overall, terpenes, flavonoids and stilbenes characterize the metabolic profile. No antibacterial activity was found in any extract against the fifteen bacteria strains tested (MIC >500 µg/mL). However, high cytotoxic activity (IC50 ≤ 30 µg/mL) was found in the hexane and aqueous extracts against hepatocarcinoma and breast cancer cells (Hep3B, HepG2 and MCF7). This is the first report of the bioactive compounds of C. trifoliata stems and their antibacterial and cytotoxic properties. The metabolic profile rich in anticancer compounds correlate with the cytotoxic activity of the extracts from the stems of C. trifoliata. This study shows the antitumor effects of this plant used in the traditional medicine and justifies further research of its anticancer activity.


2019 ◽  
Vol 16 (6) ◽  
pp. 589-601 ◽  
Author(s):  
Iris Di Leo ◽  
Federica Messina ◽  
Vanessa Nascimento ◽  
Francesca G. Nacca ◽  
Donatella Pietrella ◽  
...  

In the recent years, an increasing attention has been given to the biological activities exerted by organoselenium compounds. In 1984, Sies reported for the first time the ability of ebselen to mimic the activity of glutathione peroxidase. From this milestone, several studies reported the pharmacological properties of selenium-containing compounds including their exploitation as antimicrobials. In this context, this minireview presents the most recent examples of seleno derivatives endowed with antimicrobial activities while discussing the most interesting and recent synthetic procedures used to obtain these compounds.


2020 ◽  
Vol 13 (3) ◽  
pp. 37 ◽  
Author(s):  
Xunan Zheng ◽  
Zhengning Ma ◽  
Dawei Zhang

Imidazole and its derivatives are one of the most vital and universal heterocycles in medicinal chemistry. Owing to their special structural features, these compounds exhibit a widespread spectrum of significant pharmacological or biological activities, and are widely researched and applied by pharmaceutical companies for drug discovery. The van Leusen reaction based on tosylmethylisocyanides (TosMICs) is one of the most appropriate strategies to synthetize imidazole-based medicinal molecules, which has been increasingly developed on account of its advantages. In this review, we summarize the recent developments of the chemical synthesis and bioactivity of imidazole-containing medicinal small molecules, utilizing the van Leusen imidazole synthesis from 1977.


2021 ◽  
Vol 14 (12) ◽  
pp. 1267
Author(s):  
Cláudia Pinto ◽  
Honorina Cidade ◽  
Madalena Pinto ◽  
Maria Elizabeth Tiritan

Flavonoids are a group of natural products with a great structural diversity, widely distributed in plant kingdom. They play an important role in plant growth, development and defense against aggressors. Flavonoids show a huge variety of biological activities such as antioxidant, anti-inflammatory, anti-mutagenic, antimicrobial and antitumor, being able to modulate a large diversity of cellular enzymatic activities. Among natural flavonoids, some classes comprise chiral molecules including flavanones, flavan-3-ols, isoflavanones, and rotenoids, which have one or more stereogenic centers. Interestingly, in some cases, individual compounds of enantiomeric pairs have shown different antitumor activity. In nature, these compounds are mainly biosynthesized as pure enantiomers. Nevertheless, they are often isolated as racemates, being necessary to carry out their chiral separation to perform enantioselectivity studies. Synthetic chiral flavonoids with promising antitumor activity have also been obtained using diverse synthetic approaches. In fact, several new chiral bioactive flavonoids have been synthesized by enantioselective synthesis. Particularly, flavopiridol was the first cyclin-dependent kinase (CDK) inhibitor which entered clinical trials. The chiral pool approaches using amino acid as chiral building blocks have also been reported to achieve small libraries of chrysin derivatives with more potent in vitro growth inhibitory effect than chrysin, reinforcing the importance of the introduction of chiral moieties to improve antitumor activity. In this work, a literature review of natural and synthetic chiral flavonoids with antitumor activity is reported for the first time.


2020 ◽  
Vol 16 ◽  
Author(s):  
Amerah M. Al-Soliemy ◽  
Thoraya A. Farghaly ◽  
Eman M. H. Abbas ◽  
Mohamed R. Shaaban ◽  
Mohie E. M. Zayed ◽  
...  

Background: Morpholine and thiazole rings are two heterocycles which well-known with wide spectrum of different biological activities especially antitumor activity. Objective: The aim of the work is to design and synthesis hybrid heterocyclic compounds of morpholine and thiazole moieties via the reaction of morpholino-thiosemicarbazone derivatives with various αhalocarbonyl compounds and screening their antitumor activity against three tumor cell lines namely, TK-10, MCF-7 and UACC-62. Method: An efficient synthesis of a series of Nphenylmorpholine derivatives linked with thiazole moiety were accomplished. The reaction of Nsubistituted-2-(N-phenylmorpholine)ethylidene)hydrazine-1-carbothioamide (thiosemicarbazone derivative) with acetyl and ester-hydrazonoyl chlorides, α-chloroketones, or α-bromoesters afforded the corresponding thiazole derivatives pendent to N-phenylmorpholine moiety in good to excellent yields. Result: Mass, 1 H NMR, 13C NMR, and elemental analysis were used to confirm the structure of all the new derivatives. The antitumor activities of synthesized Nphenylmorpholine-thiazole derivatives were investigated against three tumor cells namely, TK-10, MCF-7 and UACC-62. The results of such investigation indicated that some derivatives showed good potential to inhibit the growth of the two cells of the tested tumor cells. Surprise, one of the tested compounds, N-methyl thiosemicarbazone derivative 7 revealed potent growth inhibition of all the three tumor cells. Conclusion: We have succeeded to synthesize a series of Nphenylmorpholine derivatives pendant to thiazole moiety as antitumor agents.


Synthesis ◽  
2017 ◽  
Vol 50 (04) ◽  
pp. 685-699 ◽  
Author(s):  
Shunsuke Chiba ◽  
Atsushi Kaga

Cylindricines, lepadiformines, and fasicularin are tricyclic marine alkaloids bearing perhydropyrrolo- and pyrido[2,1-j] frameworks having divergent chemical functionalities. They have been isolated from marine tunicates over the last two decades and found to have a range of cytotoxicity such as DNA-alkylating ability. Recently, polycitorols have emerged as a new member of this alkaloid family. Their unique structural features and biological activities have intrigued many researchers and challenged them in their synthesis. This review describes recent syntheses of the tricyclic alkaloids based on key synthetic approaches.1 Introduction2 Total and Formal Syntheses2.1 Overview of Synthetic Strategies2.2 Azaspirocycle (BC Ring) Approaches2.3 Indolizidine (AC Ring) Approaches2.4 Azadecalin (AB Ring) Approaches2.5 Tandem Cyclization Approaches3 Summary and Future Perspective


2020 ◽  
Vol 20 (19) ◽  
pp. 2019-2035
Author(s):  
Esmaeil Sheikh Ahmadi ◽  
Amir Tajbakhsh ◽  
Milad Iranshahy ◽  
Javad Asili ◽  
Nadine Kretschmer ◽  
...  

Naturally occurring naphthoquinones (NQs) comprising highly reactive small molecules are the subject of increasing attention due to their promising biological activities such as antioxidant, antimicrobial, apoptosis-inducing activities, and especially anticancer activity. Lapachol, lapachone, and napabucasin belong to the NQs and are in phase II clinical trials for the treatment of many cancers. This review aims to provide a comprehensive and updated overview on the biological activities of several new NQs isolated from different species of plants reported from January 2013 to January 2020, their potential therapeutic applications and their clinical significance.


2019 ◽  
Vol 16 (3) ◽  
pp. 342-368 ◽  
Author(s):  
Ramandeep Kaur ◽  
Yagyesh Kapoor ◽  
Sundeep K. Manjal ◽  
Ravindra K. Rawal ◽  
Kapil Kumar

The furo [2,3-b] indoline ring system is one of the most important structural units in various natural products. It has been known to have inherent biological activities and is utilized as a synthetic target for a number of natural compounds; therefore, this has contributed to a great demand for the growth of synthetic methods for this ring system. Most important compounds with furoindoline ring system are physovenine, madindoline A and B and makomotindoline etc. These compounds are well known to exhibit biological activity against different diseases such as glaucoma, cancer, cachexia, Castleman’s disease, rheumatoid arthritis, etc. The current article focuses on various synthetic approaches for furoindoline containing compounds and essential furoindoline moiety, such as oxindole-5-O-tetrahydropyranyl ether route etc., and various other diastereoand enantio- controlled approach in a very concise way.


Marine Drugs ◽  
2021 ◽  
Vol 19 (6) ◽  
pp. 330
Author(s):  
Timofey V. Malyarenko ◽  
Alla A. Kicha ◽  
Valentin A. Stonik ◽  
Natalia V. Ivanchina

Sphingolipids are complex lipids widespread in nature as structural components of biomembranes. Commonly, the sphingolipids of marine organisms differ from those of terrestrial animals and plants. The gangliosides are the most complex sphingolipids characteristic of vertebrates that have been found in only the Echinodermata (echinoderms) phylum of invertebrates. Sphingolipids of the representatives of the Asteroidea and Holothuroidea classes are the most studied among all echinoderms. In this review, we have summarized the data on sphingolipids of these two classes of marine invertebrates over the past two decades. Recently established structures, properties, and peculiarities of biogenesis of ceramides, cerebrosides, and gangliosides from starfishes and holothurians are discussed. The purpose of this review is to provide the most complete information on the chemical structures, structural features, and biological activities of sphingolipids of the Asteroidea and Holothuroidea classes.


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