Article
Chemistry, Multidisciplinary
Sonali Bera, Avishek Maji, Susanta Patra, Dibyendu Sekhar Mahanty, Shubhankar Samanta, Swarna Kamal Samanta, Biplab Biswas, Prasanta Patra
Summary: Both chromenone and pyrrolo[2,1-a]isoquinolines are important scaffolds in synthetic and medicinal chemistry, found in natural products and biomaterials. This review summarizes synthetic methodologies for the fusion of chromenones and pyrrolo[2,1-a]isoquinolines in various orientations, as well as their biological significance.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Denisa Dumitrescu, Sergiu Shova, Constantin Draghici, Marcel Mirel Popa, Florea Dumitrascu
Summary: 3-Arylsydnones bearing fluorine and bromine atoms on the benzene ring were synthesized and used in the synthesis of 1-(2-fluorophenyl)pyrazoles by 1,3-dipolar cycloaddition reaction. The sydnones were characterized as reaction intermediates using single crystal X-ray diffraction analysis, revealing halogen bonding as an important interaction in modeling the crystal structure.
Article
Chemistry, Organic
Kiran B. Manjappa, Jia-Wei Jhang, K. C. Seetha Lakshmi, Ding-Yah Yang
Summary: A novel synthetic method was developed for the synthesis of lamellarin D and its analogues, using a four-component reaction. Controlled demethylation of lamellarin D trimethyl ether yielded lamellarin analogues with different functional group positions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ekaterina A. Lystsova, Maksim V. Dmitriev, Andrey N. Maslivets, Ekaterina E. Khramtsova
Summary: A new synthetic approach to pyrrolobenzothiazoles is developed based on 1,4-thiazine ring contraction in 3-aroylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-triones under the action of nucleophiles. The proposed approach works well with alkanols, benzylamine, and arylamines. The synthesized pyrrolobenzothiazole derivatives represent an interest to pharmaceutics for targeted cancer therapy development.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Mark Molnar, Tamas John, Andras Dancso, Miklos Nyerges
Summary: 1,3-Dipolar cycloadditions of different azomethine ylides to 3-nitro-2(1H)-quinolinones resulted in the synthesis of 3a-nitro-4-oxo-1,2,3,3a,5,9b-hexahydropyrrolo[3,4-c]quinoline-4-one derivatives in satisfactory yield, mostly with excellent stereoselectivity. The structure and stereochemistry of the cycloadducts were extensively studied using X-ray and NMR spectroscopy methods.
Article
Chemistry, Organic
Xiao-Hui Chen, Yu-Yi Pan, Wei-Xun Wang, Hai-Lei Cui
Summary: An iron-catalyzed synthesis of pyrro-lo[2,1-a]isoquinoline derivatives has been developed, achieving highly functionalized products through a three-component cascade reaction. The obtained products can be easily modified to form structurally complex molecules with privileged frameworks.
Article
Chemistry, Organic
Mark Molnar, Tamas John, Andras Dancso, Miklos Nyerges
Summary: The 1,3-dipolar cycloaddition reactions between 3-nitro-2(1H)-quinolones and ester-stabilized azomethine ylides derived from sarcosine ester and various aromatic aldehydes have been extensively studied. The structure and stereochemistry of the cycloadducts were analyzed in detail using X-ray and NMR spectroscopy methods.
SYNTHETIC COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Asmaa Belabbes, Veronica Selva, Francisco Foubelo, M. De Gracia Retamosa, Jose M. Sansano
Summary: The synthesis of complex spiro{pyrrolidine-3,1'-pyrrolo[3,4-c]pyrrole} skeleton under mild conditions is presented, with the order of addition of a primary amine and two equivalents of corresponding maleimide being crucial for high yields. The mechanism was studied by simple tests, revealing the Michael type addition of the amine onto the maleimide as a key step. Interesting scaffold hybrids were prepared through sequential addition of two different maleimides, and a more intriguing architecture was obtained through a metathesis reaction between allylic residues in the molecule precursor.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Daohong Yu, Yungen Liu, Chi-Ming Che
Summary: A synthetic method for constructing trifluoromethyl-pyrrolo[2,1-a]isoquinolines via decarboxylation and photocatalytic reactions is described. This method exhibits broad substrate compatibility and enables facile access to pharmaceutically active derivatives.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Khalid Abdelmouna, Fatima Laghchioua, Filipe A. . A. . Paz, Ricardo F. Mendes, Nuno M. M. Moura, Maria A. F. Faustino, Jose A. S. Cavaleiro, Y. Kandri Rodi, El Mostapha Rakib, Maria G. P. M. S. Neves
Summary: This study reports a catalyst-less synthesis of new spiro[indoline-3,1'-pyrazolo[1,2-a]pyrazoles] with good yields, achieved via 1,3-dipolar cycloadditions. The synthesized cycloadducts were characterized through NMR spectroscopy and confirmed by single-crystal X-ray diffraction analysis.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Nikita A. Kaminskiy, Ekaterina E. Galenko, Mariya A. Kryukova, Mikhail S. Novikov, Alexander F. Khlebnikov
Summary: This study discovered that alpha-diazopyrroles selectively react with enamines at room temperature to produce organic compounds, which can be used for the synthesis of functionalized heterocycles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Ekaterina A. Lystsova, Alexander S. Novikov, Maksim V. Dmitriev, Andrey N. Maslivets, Ekaterina E. Khramtsova
Summary: Acyl(imidoyl)ketenes can be used to synthesize diverse drug-like heterocycles. By utilizing the [4+2]-cyclodimerization of acyl(1,3-benzothiazol-2-yl)ketenes, a new synthetic approach to pharmaceutically interesting pyrido[2,1-b][1,3]benzothiazol-1-ones has been developed. Thermal analysis and computational studies revealed the suitability of 3-aroylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-triones as a source of acyl(1,3-benzothiazol-2-yl)ketenes, and a novel mode of thermal transformation of [e]-fused 1H-pyrrole-2,3-diones was discovered. The synthesized pyrido[2,1-b][1,3]benzothiazol-1-ones are of interest due to their potential antiviral activity.
Article
Chemistry, Organic
Xiang Huang, Wan-Zhen Li, Shu-Chen Pei, Hai -Lei Cui
Summary: An iron-catalyzed oxidative dimerization reaction of pyrrolo[2,1-a]isoquinolines and pyrrolo[1,2-a] quinolines has been developed. Under mild reaction conditions using DTBP as oxidant and HFIP as solvent, a series of dimeric pyrrolo[2,1-a]isoquinolines and pyrrolo[1,2-a]quinolines were efficiently prepared (19 examples, 42-76% yield).
TETRAHEDRON LETTERS
(2023)
Article
Biochemistry & Molecular Biology
Beatrice-Cristina Ivan, Florea Dumitrascu, Adriana Iuliana Anghel, Robert Viorel Ancuceanu, Sergiu Shova, Denisa Dumitrescu, Constantin Draghici, Octavian Tudorel Olaru, George Mihai Nitulescu, Mihaela Dinu, Stefania-Felicia Barbuceanu
Summary: A series of new pyrrole derivatives were designed as chemical analogs of 1,4-dihydropyridines drugs to develop future new calcium channel blockers. The compounds showed minimal phytotoxicity on Triticum rootlets and induced moderate to high toxicity on Daphnia magna, similar to nifedipine. The newly synthesized pyrrole derivatives are promising molecules with biological activity and low acute toxicity.
Article
Chemistry, Organic
Jian-Bin Lu, Shu-Yuan Liang, Wu-Tao Gui, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: A relay catalytic protocol utilizing pyrrolidine and palladium catalysis has been developed for the asymmetric synthesis of 1,3-diamine derivatives from 3-substituted 1,3-dienes, sulfuric diamide, and aldehydes. This one-pot, three-component reaction offers the advantages of high atom step economy and operational simplicity, providing an efficient and straightforward access to valuable 1,3-diamines containing quaternary and tertiary stereogenic centers with moderate to good enantioselectivity.
Review
Chemistry, Organic
Debora Procopio, Carlo Siciliano, Sonia Trombino, Denisa Elena Dumitrescu, Felicia Suciu, Maria Luisa Di Gioia
Summary: This review discusses literature from the past decade on strategies for reducing and replacing hazardous solvents, focusing on the use of biobased and neoteric solvents, such as ionic liquids and deep eutectic solvents, as greener alternatives for amide bond formation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Benita Barton, Mino R. Caira, Daniel Jooste, Eric C. Hosten
Summary: The host ability of four compounds based on xanthenyl- and thioxanthenyl-fused tricyclic systems was evaluated and compared with three alkylaromatic solvents. The 1,2 analogues showed lower selectivity in guest/guest competition experiments compared to the 1,4 analogues, which exhibited higher selectivity under certain conditions.
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Benita Barton, Mino R. Caira, Ulrich Senekal, Eric C. Hosten
Summary: This study evaluated the selectivity behavior of a roof-shaped host compound, H1, in different anisole mixtures. The results showed that H1 exhibited remarkable selectivities for ANI or mMANI when oMANI or pMANI was also present. Additionally, high selectivities were noted for ANI and mMANI in ternary experiments with ANI/oMANI/pMANI and oMANI/mMANI/pMANI solutions.
CRYSTAL GROWTH & DESIGN
(2022)
Article
Chemistry, Organic
Alexios I. Vicatos, Zakiena Hoossen, Mino R. Caira
Summary: This study addresses the poor solubility of two potent steroid hormones by complexing them with water-soluble cyclodextrins. The structures and stoichiometries of the complexes were determined using various analysis methods. The aqueous solubilities of the complexes were significantly improved compared to the pure hormones.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Benita Barton, Mino R. Caira, Ulrich Senekal, Eric C. Hosten
Summary: In this study, the compound DED was found to have a strong affinity for 4-BA when recrystallized from mixtures containing this guest species. This host selectivity was observed even at low concentrations of 4-BA. Single crystal X-ray diffraction analyses showed that 4-BA had short intermolecular contacts with the host molecule, while ANI and 2-BA were accommodated in open channels. Thermal analyses confirmed the stability of DED with 4-BA and its ability to separate 4-BA-containing mixtures.
CRYSTAL GROWTH & DESIGN
(2023)
Article
Chemistry, Multidisciplinary
Marcel Mirel Popa, Sergiu Shova, Mihaela Dascalu, Mino R. R. Caira, Florea Dumitrascu
Summary: Single crystal X-ray diffraction analysis and Hirshfeld analysis were used in this study to investigate the supramolecular properties of five 5-brominated pyrazoles. The results revealed the formation of Br·O or Br·Br type halogen contacts in these compounds. Structural analysis showed the isostructurality of compounds 2 and 3, while compound 5 was found to be isostructural with its iodo-analogue, indicating the importance of halogen contacts in these compounds.
Article
Chemistry, Multidisciplinary
Felicia Suciu, Iuliana Stoicescu, Elena Carmen Lupu, Antoanela Popescu, Adrian Cosmin Rosca, Florentina Nicoleta Roncea, Denisa-Elena Dumitrescu, Victoria Badea, Florin Ciprian Badea
Summary: The aim of this study was to evaluate the antibacterial and antifungal properties of extracts from Lysimachia nummularia L. for pharmaceutical product development in the treatment of infectious and antifungal oral diseases. Different extracts from the plant were obtained and chemically characterized. The extracts exhibited antimicrobial activity against Gram-positive bacteria, but had weaker effects on Gram-negative bacteria and no antifungal effects on Candida albicans. The aerial parts of the plant had the highest concentration of polyphenols and showed the best antibacterial results.
APPLIED SCIENCES-BASEL
(2023)
Article
Chemistry, Medicinal
Sebastian Mihai, Denisa Elena Dumitrescu, Antoanela Popescu, Iuliana Stoicescu, Nadia Matroud, Ana-Madalina Raducanu, Magdalena Mititelu
Summary: This study evaluates the potential of a bio-adhesive patch loaded with Semperivium ruthenicum Koch extract, rich in polyphenols, as a novel oral antioxidant delivery system for reducing oxidative stress in periodontitis. The patches demonstrated satisfactory technical characteristics and release kinetics, and may effectively scavenge free radicals and regulate cytokine activity.
Article
Chemistry, Multidisciplinary
Felicia Suciu, Iuliana Stoicescu, Elena Carmen Lupu, Adina Magdalena Musuc, Antoanela Popescu, Magdalena Mititelu, Adrian Cosmin Rosca, Denisa-Elena Dumitrescu, Florin Ciprian Badea, Aureliana Caraiane, Victoria Badea
Summary: The phenolic compounds from different parts of Lysimachia nummularia L. plant were analyzed using HPLC technique. The extracts from root, aerial part, and flowers were obtained through ethanol extraction and their polyphenol content and antioxidant activity were evaluated. The hydroethanolic extract from flowers showed the highest content of total polyphenols (22.10 +/- 1.48 mg/g gallic acid) and exhibited remarkable antioxidant activity.
APPLIED SCIENCES-BASEL
(2023)
Article
Pharmacology & Pharmacy
Magdalena Mititelu, Calin Pavel Cobelschi, Emma Gheorghe, Sorinel Marius Neacsu, Costin-Teodor Streba, Andreea Mihai, Adina Magdalena Musuc, Ovidiu Tafuni, Angelica Caunii, Gabriel Olteanu, Stefan Sebastian Busnatu, Denisa-Elena Dumitrescu, Manuela Ghica
Summary: This cross-sectional observational study based on a questionnaire evaluated the adherence of the Romanian population to a balanced diet and a healthy lifestyle, as well as the correlation between nutritional imbalances and the respondents' health status. Only a small percentage of the respondents (4.3%) followed a balanced diet, with the majority being middle-aged women. Overweight was prevalent among male respondents (43.7%). Unhealthy eating habits and lifestyle issues were found among a significant proportion of the respondents.
Article
Chemistry, Multidisciplinary
Dauda K. Tolulop, Graham E. Jackson, Mino R. Caira, Ahmed N. Hammouda
Summary: This study investigated the effects of copper, nickel, and zinc complexes on the permeability and bioavailability of isoniazid. The results showed that the incorporation of a metal ion improved the hydrophilicity of the drug, leading to enhanced permeation through an artificial membrane.
SOUTH AFRICAN JOURNAL OF CHEMISTRY-SUID-AFRIKAANSE TYDSKRIF VIR CHEMIE
(2022)
Article
Chemistry, Multidisciplinary
Florea Dumitrascu, Emilian Georgescu, Mino R. Caira, Constantin Draghici, Florentina Georgescu, Marcel M. Popa, Stefania-Felicia Barbuceanu, Beatrice-Cristina Ivan
Summary: New highly substituted pyrroles with fluorine atoms in their structure were synthesized through an improved two-step procedure. The structures of the fluorine-substituted pyrroles were confirmed by IR and NMR spectroscopy and X-Ray analysis.
REVUE ROUMAINE DE CHIMIE
(2022)
Review
Nutrition & Dietetics
Corina-Bianca Ionita-Mindrican, Khaled Ziani, Magdalena Mititelu, Eliza Oprea, Sorinel Marius Neacsu, Elena Morosan, Denisa-Elena Dumitrescu, Adrian Cosmin Rosca, Doina Draganescu, Carolina Negrei
Summary: Fiber intake plays a crucial role in health and high-fiber foods have been shown to reduce the risk of disease. This article provides information on global fiber consumption, fiber metabolism, and the various health benefits associated with fiber intake.
Article
Chemistry, Multidisciplinary
Benita Barton, Mino R. Caira, Ulrich Senekal, Eric C. Hosten
Summary: In this study, the host behavior of a compound H1 in different pyridine compounds was assessed, and it was found that H1 exhibited high selectivity for 2MP and 3MP. The analysis of the solid samples revealed that the complexes formed between H1 and 2MP or 3MP were actually salts, and the host preference for 2MP and 3MP was not only due to guest enclathration but also strong charge-assisted hydrogen bonding. Additionally, the thermal stabilities of the complexes were consistent with the preferences of the guests.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
