Review
Cell Biology
Mariana Lucas, Marisa Freitas, Artur M. S. Silva, Eduarda Fernandes, Daniela Ribeiro
Summary: Styrylchromones (SC) are a group of oxygen-containing heterocyclic compounds, mainly obtained through chemical synthesis, with potential for drug development. Two types of SC are known: 2-styrylchromones and 3-styrylchromones, with 2-styrylchromones being the most common.
OXIDATIVE MEDICINE AND CELLULAR LONGEVITY
(2021)
Article
Chemistry, Medicinal
Meiyan Fan, Wei Yang, Min He, Yongjun Li, Zhiyun Peng, Guangcheng Wang
Summary: This review mainly focuses on the natural occurrence, chemical synthesis, and biological activities of 2-(2-phenylethyl)chromones (PECs) published up until 2020.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Hongyun Cai, Hari Datta Khanal, Yong Rok Lee
Summary: A mild base-promoted reaction between 3-substituted chromones and beta-keto esters is described for the easy access to various coumarins. The protocol provides highly functionalized 3-acyl-4-arylcoumarins in good-to-excellent yield via benzannulation and transesterification, with a proposed reaction mechanism involving Michael addition, 1,5-H shift, and intramolecular transesterification.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Martin-Louis Y. Riu, Wesley J. Transue, Jan M. Rall, Christopher C. Cummins
Summary: A novel diazene compound was synthesized in this study, which underwent a series of reactions to form corresponding cycloadducts. Structural data of the cycloadducts were obtained, and the thermolysis process of this compound along with its kinetic parameters were investigated.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Carlos F. M. Silva, Joao A. Pacheco, Diana C. G. A. Pinto, Artur M. S. Silva
Summary: Chromones, a naturally occurring class of compounds widely distributed in nature, have emerged as a privileged scaffold in medicinal chemistry due to their unique structural features, diverse biological activities, and pharmacological properties. Researchers have successfully synthesized 2-benzylchromones through both conventional and microwave-assisted methods.
Article
Chemistry, Organic
Ling Meng, Heyang Liu, Zhenyang Lin, Jun Wang
Summary: Highly efficient and straightforward access to enantioenriched five-membered ring-fused chromanones is achieved via [3+2]-cycloaddition. The reaction yields densely functionalized chiral cyclopenta[b]chromanones with high enantioselectivity and diastereoselectivity. The mechanism and selectivity of the reaction have been investigated.
Review
Chemistry, Applied
Seoung-Mi Choi, Ju Hyun Kim
Summary: This review summarizes the progress made in the synthesis of 2H-pyrroles since 2000, including methods such as dearomatization of 1H-pyrrole, oxidation of pyrrolines or pyrrolidines, ring construction via catalytic cycloaddition, and rearrangement of 3H-pyrroles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Biotechnology & Applied Microbiology
Upare Abhay Atmaram, Selvaraj Mohana Roopan
Summary: This review focuses on the pharmacological properties and structural modifications of the 5-membered heterocycles oxadiazole and thiadiazole, with a particular emphasis on the anti-tubercular and anticancer activities. These heterocycles exhibit important bioisosterism and can serve as replacements in drug design.
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
(2022)
Article
Chemistry, Medicinal
Mariana Lucas, Marisa Freitas, Marco Zanchetta, Artur M. S. Silva, Eduarda Fernandes, Daniela Ribeiro
Summary: This study evaluated the effects of 43 structurally related 2-styrylchromones (2-SC) on human neutrophils. It was found that most of the studied 2-SC did not affect neutrophil viability. Compounds with -OH or catechol groups were found to play a significant role in modulating neutrophil oxidative burst activity. These results highlight the potential of 2-SC's scaffold for developing new anti-inflammatory agents.
Article
Chemistry, Medicinal
Livio Racane, Katarina Zlatic, Maja Cindric, Emina Mehic, Grace Karminski-Zamola, Martin C. Taylor, John M. Kelly, Silvana Raic Malic, Marijana Radic Stojkovic, Marijeta Kralj, Marijana Hranjec
Summary: Novel benzo[b]thienyl and 2,2'-bithienyl-derived benzothiazoles and benzimidazoles were synthesized and tested for their antiproliferative and antitrypanosomal activities in vitro. The benzothiazole derivatives showed higher activity compared to the benzimidazole analogs. Among them, the 2,2'-bithienyl-substituted benzothiazoles with unsubstituted and 2-imidazolinyl amidine exhibited the most potent antitrypanosomal activity, while the benzimidazole derivatives bearing isopropyl, unsubstituted, and 2-imidazolinyl amidine showed the greatest selectivity. The 2,2'-bithiophene derivatives showed the most selective antiproliferative activity, with the benzothiazoles selectively active against lung carcinoma and the benzimidazoles selectively active against cervical carcinoma cells.
Article
Chemistry, Physical
Srishylam Penjarla, Paidi Yella Reddy, Santhosh Penta, Yogesh S. Sanghvi, Ludek Eyer, Michal Stefanik, Daniel Ruzek, Shyamapada Banerjee
Summary: An efficient synthetic approach leading to novel C-nucleosides containing oxadiazole or thiadiazole ring system is reported. This provides an ideal framework for the development of new antiviral and antitumor drugs. Two of the synthesized compounds showed mild anti-SARS-CoV-2 activity, with a decrease in viral titers by <1 log10 PFU/ml compared with controls. Mechanism for the formation of 5-substituted 1,3,4-thiadiazole ring is proposed and a structure-activity relationship is established with these C-nucleosides.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Correction
Chemistry, Multidisciplinary
Abdur Rehman Sheikh, Anam Arif, Md. Musawwer Khan
Summary: This article introduces the correction of using aryl glyoxal as a synthetic equivalent for multicomponent reactions in the design of oxygen heterocycles.
Review
Chemistry, Applied
Dimitris Matiadis
Summary: 2-Pyrazolines are important five-membered heterocycles with two adjacent nitrogen atoms. They have various functional groups and unique biological properties, and are used as building blocks. In recent years, there has been significant progress in the synthesis of 2-pyrazolines, with the development of novel strategies and improvements of existing protocols. This review summarizes the synthetic methodologies from 2012 to 2022, discussing the challenges, capabilities, scopes, and limitations of the reactions, as well as substitution patterns and mechanisms where applicable.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Biochemistry & Molecular Biology
Bagrat A. Shainyan, Larisa Zhilitskaya, Nina O. Yarosh
Summary: This review focuses on the synthesis, structural modification, reaction mechanisms, and potential pharmacological activity of C-2-substituted benzothiazoles, including traditional multistep reactions and one-pot atom economy processes using green chemistry principles.
Review
Biochemistry & Molecular Biology
Alicja K. Surowiak, Lucyna Balcerzak, Stanislaw Lochynski, Daniel J. Strub
Summary: Terpenoids with lactone moieties are known for their high bioactivity, with artemisinin being a well-known drug against malaria. New terpenoid lactones are considered potential active agents against various diseases.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Chemistry, Organic
Joana R. M. Ferreira, Mariana Alves, Barbara Sousa, Sandra I. Vieira, Artur M. S. Silva, Samuel Guieu, Angela Cunha, Raquel Nunes da Silva
Summary: Fluorescence imaging is widely used to study living organisms, but it is challenging to visualize fungi using this method due to their cell wall acting as a diffusion barrier and limited availability of synthetic organic dyes. To address this, a family of curcumin-based boron diketonate complexes was synthesized, allowing for visualization of fungi in different colors without noticeable toxicity. These probes readily entered cells and precisely localized in sub-cellular organelles.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Biochemistry & Molecular Biology
Carlos J. P. Monteiro, Maria G. P. M. S. Neves, Cristina Nativi, Adelaide Almeida, Maria Amparo F. Faustino
Summary: Cellulose is a versatile starting material for developing sustainable materials, and its combination with photoactive dyes enables selective microorganism killing in antimicrobial photodynamic therapy. This review focuses on porphyrinic photosensitizers supported on cellulose materials and their synthetic routes for effective photoinactivation. The efficiency of cellulose-based photoactive dyes for cancer treatment using photodynamic therapy is also discussed.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Rita Ferro, Nuno Viduedo, A. Sofia Santos, Artur M. S. Silva, Beatriz Royo, M. Manuel B. Marques
Summary: A bimetallic synthesis method for 2-arylindoles from alcohols and anilines is presented, involving the dehydrogenation or oxidation of secondary alcohols using Ni or Mn catalysts, followed by conversion of the formed ketone into an imine intermediate and subsequent Pd-catalyzed oxidative cyclization to obtain the desired 2-arylindole. The intermediates generated were not isolated, allowing for the preparation of a series of 2-arylindoles. The compatibility of catalysts was explored, and the optimized protocol enables the integration of Earth-abundant metals and palladium complexes, enhancing the sustainability of N-heterocycle synthesis.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Physical
Carlos F. R. A. C. Lima, Marco A. L. Lima, J. Ricardo M. Pinto, M. Gabriela T. C. Ribeiro, Artur M. S. Silva, Luis M. N. B. F. Santos
Summary: A systematic synthetic study was conducted to explain the common trend of selectivity towards multi-coupling over mono-coupling in Suzuki-Miyaura reactions. This preference was observed under various reaction conditions, including different halobenzenes, substituents on the boronic acid, and changes in catalyst and temperature. Additionally, it was found that the reaction selectivity increased for more reactive systems and more diluted media. The results provide experimental evidence that the formation of totally substituted coupling product is kinetically favored by the proximity of the regenerated catalyst and the newly formed coupling intermediate.
Article
Pharmacology & Pharmacy
Ana Teresa Rufino, Mariana Lucas, Artur M. S. Silva, Daniela Ribeiro, Eduarda Fernandes
Summary: The study found that 2-SC can reduce oxidative stress and inflammation in rheumatoid arthritis by inhibiting the NF-kappa B pathway. However, one of the 2-SC also has the ability to suppress the NF-kappa B pathway, further reducing the expression of inflammatory factors. These results suggest that 2-SC may be potential drugs for new therapeutic strategies for rheumatoid arthritis.
Article
Pharmacology & Pharmacy
Carlos F. M. Silva, Teresa Leao, Filipa Dias, Ana M. Tomas, Diana C. G. A. Pinto, Eduardo F. T. Oliveira, Ana Oliveira, Pedro A. Fernandes, Artur M. S. Silva
Summary: Leishmaniasis is a neglected disease mainly affecting people in developing countries, with approximately 350 million people at risk. The lack of vaccines and chemotherapy has led to an increase in the incidence of the disease. A computational study focusing on a specific enzyme of the parasite has identified potential inhibitors, indicating the promise of using these compounds for developing novel antileishmanial drugs.
Article
Agriculture, Dairy & Animal Science
Rita Silva-Reis, Ana I. I. Faustino-Rocha, Jessica Silva, Abigael Valada, Tiago Azevedo, Lara Anjos, Lio Goncalves, Maria de Lurdes Pinto, Rita Ferreira, Artur M. S. Silva, Susana M. M. Cardoso, Paula A. A. Oliveira
Summary: This study assessed a humane endpoint scoring system to detect animal suffering in a rat model of type 2 diabetes. Results showed that weight loss, polyuria, polyphagia, abnormal posture, abdominal distension, and abnormal stool appearance were the most effective parameters to evaluate humane endpoints in this rat model. This study is important for defining humane endpoints in a rat model of type 2 diabetes.
Review
Biochemistry & Molecular Biology
Rita Silva-Reis, Artur M. S. Silva, Paula A. Oliveira, Susana M. Cardoso
Summary: Cannabis sativa has been used in medicine for centuries and recent research has focused on its bioactive compounds, particularly cannabinoids and terpenes. These compounds have shown antitumor effects in colorectal cancer (CRC) through various mechanisms such as apoptosis, proliferation, metastasis, inflammation, angiogenesis, oxidative stress, and autophagy. Terpenes like β-caryophyllene, limonene, and myrcene also have potential antitumor effects on CRC through apoptosis induction, inhibition of cell proliferation, and angiogenesis. The synergy between cannabinoids and terpenes is believed to be important in CRC treatment. Further research is needed to fully understand the mechanisms of action and safety of these compounds.
Article
Chemistry, Organic
Daniela Malafaia, Joana L. C. Sousa, Artur M. S. Silva, Helio M. T. Albuquerque
Summary: We report a new 2-SC derivative, 2,2'-[(1E,1'E)-{[hexa-2,4-diyne-1,6-diylbis(oxy)] bis(2,1-phenylene)} bis(ethene-2,1-diyl)] bis(4H-chromen-4-one), which is a dimeric compound formed by linking two units of 2-SC through a 1,3-diyne moiety. The compound was obtained with excellent yield (96%) through the copper-catalyzed homocoupling of two molecules of O-propargyl-2-SC. Its structure was characterized by 1D (H-1 and C-13) and 2D (HSQC and HMBC) NMR techniques as well as HRMS.
Article
Chemistry, Organic
Joana L. C. Sousa, Helio M. T. Albuquerque, Artur M. S. Silva
Summary: A new VN derivative, VN-CHO, was synthesized through photoredox-catalyzed hydroxymethylation reaction followed by oxidation. The introduction of a formyl group in VN structure offers a promising site for further functionalization.
Article
Pharmacology & Pharmacy
Sonia N. Pedro, Ana T. P. C. Gomes, Carla Vilela, Carla Vitorino, Rosa Fernandes, Adelaide Almeida, Maria Helena Amaral, Mara G. Freire, Armando J. D. Silvestre, Carmen S. R. Freire
Summary: A new type of microemulsion based on deep eutectic solvent (DES) has been developed to improve the efficacy of antibiotics in ocular infections. By using betaine-based DES aqueous solutions, the water solubility of the antibiotic chloramphenicol can be increased up to 140-fold. These DES solutions are applied as water phases in stable water-in-oil-in-water (w/o/w) microemulsions, achieving sustained-release and higher permeation through the cornea. Compared to commercialized eye drops, these microemulsions show higher antimicrobial activity and faster action against methicillin-resistant Staphylococcus aureus (MRSA) infections.
ADVANCED THERAPEUTICS
(2023)
Article
Chemistry, Applied
Paloma Lopes, A. Sofia M. Joaquinito, Artur Ribeiro, Nuno M. M. Moura, Ana T. P. Gomes, Susana G. Guerreiro, M. Amparo F. Faustino, Adelaide Almeida, Paula Ferreira, Manuel A. Coimbra, M. Graca P. M. S. Neves, Idalina Goncalves
Summary: This study explores the feasibility of incorporating cationic TMPyP into starch-based films to enhance their physicochemical, mechanical, antimicrobial, and wound healing abilities. The results showed that TMPyP not only gave the films a reddish color but also increased their hydrophobicity and the mobility of starch polymeric chains. The films effectively photoinactivated Escherichia coli and facilitated the wound healing process. Thus, the incorporation of TMPyP into starch-based formulations is a promising strategy for developing water tolerant and photosensitive biomaterials that can act as multitarget antimicrobial medical dressings and carriers of active compounds for effective wound healing.
CARBOHYDRATE POLYMERS
(2023)
Editorial Material
Biochemistry & Molecular Biology
Vera L. M. Silva, Artur M. S. Silva
Article
Chemistry, Organic
Sara M. Tome, Raquel G. Soengas, Artur M. S. Silva
Summary: The potential of the Heck reaction for the C-glycosylation of phenolic compounds was investigated, and an efficient and general methodology was developed. This methodology was successfully applied to the synthesis of previously unreported C-glycosylated compounds with potential biological relevance.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Applied
Sara R. D. Gamelas, Maria Bartolomeu, Thierry J. Gomes, Maria A. F. Faustino, Joao P. C. Tome, Augusto C. Tome, Adelaide Almeida, Ana T. P. C. Gomes, Leandro M. O. Lourenco
Summary: Viruses, especially RNA viruses, have a high mutation rate which leads to their resistance to traditional antivirals. Photodynamic treatment is a potential method that does not promote the development of resistance. In this study, new cationic ZnPcs were synthesized and successfully used for the photodynamic inactivation of a RNA-virus model.
