Article
Chemistry, Organic
Andrey N. Komogortsev, Boris V. Lichitsky, Turan T. Karibov, Valeriya G. Melekhina
Summary: This study presents an efficient one-step approach for the preparation of substituted 2-aminooxazoles containing 3-hydroxy-4H-pyran-4-one moiety. The method involves multicomponent condensation of allomaltol derivatives with alpha-ketoaldehydes and cyanamide. The proposed protocol offers advantages such as readily available starting materials, mild reaction conditions, atom economy, and easy workup procedure.
Article
Chemistry, Organic
Guo-Sheng Zhu, Pei-Jun Yang, Chen-Xue Ma, Gaosheng Yang, Zhuo Chai
Summary: In this study, Hantzsch esters (HEs) were used as two-carbon partners in a copper(I)-catalyzed enantioselective [3 + 2] annulation with racemic 2-(hetero)aryl-N-sulfonyl aziridines via kinetic resolution to provide pyrrolo[2,3-b]tetrahydropyridines containing multiple contiguous stereogenic centers. The reactions yielded products with excellent yields and enantiopurities, as well as moderate-to-excellent diastereoselectivities. Depending on the structures of the aziridines, a competitive hydrogenolysis process with HEs as the hydrogen source was also observed in some cases.
Article
Biochemistry & Molecular Biology
Aymard Didier Tamafo Fouegue, Hilaire Tendongmo, Eric Sakue Ngankam, Rahman Abdoul Ntieche
Summary: This study investigated the adsorption behavior of 2-aminopyridine and 3-aminopyridine on the external surface of B12N12 and Al12N12 fullerene-like nanocages through theoretical analysis. The results showed that all FLN@X-AP states were spontaneously formed and that the boron nitride FLN strongly adsorbed the APs through B-N covalent interactions. Furthermore, the adsorption of APs significantly changed the HOMO-LUMO band gap of B12N12, enhancing its conductivity.
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS
(2023)
Article
Chemistry, Multidisciplinary
V. V. Dotsenko, K. V. Khalatyan, A. A. Russkikh, E. A. Varzieva, D. A. Kramareva, V. K. Vasilin, N. A. Aksenov, I. V. Aksenova
Summary: In this study, 2-amino-4-aryl-6-hexyl-7-hydroxy-4H-chromene-3-carbonitriles were synthesized in good yields through the three-component condensation of aromatic aldehydes with malononitrile and 4-hexylresorcinol in toluene in the presence of a base. The structure of the compounds was studied using two-dimensional NMR spectroscopy methods. The bioavailability parameters were predicted in silico, and possible protein targets were predicted by protein-ligand docking.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Reham Eid Abdelwahab, Ahmed F. Darweesh, Mohamed A. Ragheb, Ismail A. Abdelhamid, Ahmed H. M. Elwahy
Summary: A simple and effective method has been established for the synthesis of a new series of compounds linked to phenoxy-N-arylacetamide. The desired products were successfully obtained through specific reaction conditions using suitable substrates. The structures of the newly synthesized compounds were confirmed by elemental and spectral analysis. In addition, limitations were found in synthesizing the target products using other methods.
POLYCYCLIC AROMATIC COMPOUNDS
(2023)
Article
Chemistry, Organic
A. Rammohan, A. P. Krinochkin, D. S. Kopchuk, Ya K. Shtaitz, I. S. Kovalev, M. I. Savchuk, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin
Summary: This study tested various conditions for the inverse electron-demand aza-Diels-Alder reaction in order to obtain 4,5-diaryl-3-hydroxy-2,2'-bipyridine-6-carbonitriles from the series of 5-aryl-3-(2-pyridyl)-1,2,4-triazine-5-carbonitriles and 2-amino-4-aryloxazoles. Heating in 1,2-dichlorobenzene or under solvent-free conditions were found to be the most effective.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Janan Metghalchi Langroudi, Masoumeh Mazloumi, Hossein Taherpour Nahzomi, Farhad Shirini, Hassan Tajik
Summary: A suitable dicationic molten salt has been characterized using various analysis methods. The accurate structure of the catalyst has been determined through energy calculation and NMR chemical shift comparison. Its application in the synthesis of specific compounds has also been investigated.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Applied
Zhangmengjie Chai, Longkun Chen, Zhuoyuan Liu, Yulin Sun, Donghan Liu, Mingshuai Zhang, Yongchao Wang, Fuchao Yu
Summary: This study describes an oxidative [3 + 2 + 1] cyclization reaction between enaminones and N-alkenyl-2-pyrrolidinone for the synthesis of 4-alkylated 1,4-dihydropyridines (1,4-DHPs). By using terminal olefin as the C4 source of the 1,4-DHP skeleton, this synthetic strategy allows for the formation of a series of 1,4-DHPs through a 1,1-difunctionalization/cyclization process. The formation of two C(sp(3))-C(sp(2)) bonds and a C(sp(2))-N bond simultaneously and the confirmation of the hydrogen source on the newly formed methyl group of the 1,4-DHP skeleton are discussed, along with a proposed mechanism.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Inorganic & Nuclear
Tong Ping, Wu Jiang-Meng, Xu Ping, Wang Xiao-Ying, Li Hai-Nan, Wang Cheng, Yang Si-Qi, Zhou Jia-Hui, Xu Rui-Bo
Summary: Two novel binuclear copper(II) complexes were synthesized and characterized, and their antibacterial, antioxidant, and electrochemical properties were investigated.
CHINESE JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Buri Apparao, Alice R. Robert, Muthyala Murali Krishna Kumar, Rama Krishna Madaka, Pamerla Muralidhar, Suresh Maddila, Sreekantha B. Jonnalagadda
Summary: This study describes a facile, eco-friendly, and efficient approach for the multicomponent synthesis of 2-amino-pyran analogues using rutheia-doped alumina as a heterogeneous catalyst. The key benefits of this protocol include operational simplicity, economy, green reaction conditions, and high product yields. Additionally, the catalyst material can be recycled and reused up to eight runs without any significant loss of catalytic activity.
RESEARCH ON CHEMICAL INTERMEDIATES
(2023)
Article
Chemistry, Inorganic & Nuclear
Prakash N. Swami, Neha Meena, Hemant Joshi, Krishnan Rangan, Anil Kumar
Summary: This report presents the synthesis and characterization of a [CNHCNN]-pincer-type palladium(II) complex with a N-heterocyclic carbene (NHC)-derived pincer CNN ligand. The complex displayed a distorted square planar geometry around the palladium center. It was found to be an efficient catalyst for the oxidative amidation of aldehydes with 2-aminopyridines, achieving high yields under mild reaction conditions.
Article
Chemistry, Organic
Yipeng Zhou, Hongwei Zhou, Jianfeng Xu
Summary: A highly selective [3+2] cycloaddition reaction was achieved using a chiral catalyst, resulting in the synthesis of enantioenriched bicyclic pyrazolidinones.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
I. N. Bardasov, A. Yu Alekseeva, O. Ershov, M. A. Mar'yasov
Summary: The antiproliferative activity of 2-amino-4H-chromene-3-carbonitrile derivatives on various tumor cell lines was studied, with 4-aryl-2-oxo-2H-benzo[h]chromene-3-carbonitriles showing the most promising activity. These findings provide valuable information for the development of potential anticancer drugs.
PHARMACEUTICAL CHEMISTRY JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Sukriye Cakmak, Sevgi Kansiz, Mohammad Azam, Cem Cuneyt Ersanli, Onder Idil, Aysel Veyisoglu, Hasan Yakan, Halil Kutuk, Arunabhiram Chutia
Summary: A novel heterocyclic amide derivative was synthesized and investigated for its significant antioxidant and antimicrobial properties through experimental and computational studies.
Article
Chemistry, Multidisciplinary
Victor V. Dotsenko, Alexander Bespalov, Arthur S. Vashurin, Nicolai A. Aksenov, Inna Aksenova, Elena A. Chigorina, Sergey G. Krivokolysko
Summary: In this study, trans-2-amino-4-aryl-5-benzoyl-4,5-dihydrothiophene-3-carbonitriles were prepared through two different reaction pathways, and the mechanism of the first reaction was investigated using high-level quantum chemical calculations. A new approach to constructing the thieno[2,3-d]pyrimidine core system was demonstrated by reacting the prepared dihydrothiophenes with HCHO and RNH2 under noncatalyzed Mannich conditions.
Article
Biochemistry & Molecular Biology
Beatriz Chamorro, David Garcia-Vieira, Daniel Diez-Iriepa, Estibaliz Garagarza, Mourad Chioua, Dimitra Hadjipavlou-Litina, Francisco Lopez-Munoz, Jose Marco-Contelles, Maria Jesus Oset-Gasque
Summary: The neuroprotective and antioxidant activities of 1,1'-biphenyl nitrones (BPNs) 1-5 were investigated and compared to alpha-phenyl-N-tert-butylnitrone and N-acetyl-L-cysteine. Results showed that BPNs 1-5, particularly homo-bis-nitrone BPHBN5, exhibited superior neuroprotective and antioxidant properties, making it a promising compound for potential therapeutic applications in oxidative stress and ischemia models.
Article
Chemistry, Medicinal
Jose M. Alonso, Alejandro Escobar-Peso, Alejandra Palomino-Antolin, Daniel Diez-Iriepa, Mourad Chioua, Emma Martinez-Alonso, Isabel Iriepa, Javier Egea, Alberto Alcazar, Jose Marco-Contelles
Summary: The article discusses the relationship between cerebrovascular diseases and dementia caused by Alzheimer's disease, highlighting the importance of developing new dual therapeutic agents. A new small quinolylnitrone, MC903, is proposed as a potential dual therapy for stroke and Alzheimer's disease.
Article
Chemistry, Multidisciplinary
Lamia A. Siddig, Rukayat Bojesomo, Mohammad A. Khasawneh, Abdelouahid Samadi, Alejandro Perez Paz, Haythem A. Saadeh, Na'il Saleh
Summary: A novel multifunctional fluorescent molecule, Bz-8HQ, has been designed and synthesized with high yield. It exhibits responsiveness to multiple stimuli, including pH, CB7, and CAD, due to two distinct binding sites. Bz-8HQ also displays photoinduced electron transfer (PET) and fluorescence resonance energy transfer (FRET), making it a valuable tool in future biological and medical imaging applications.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Mourad Chioua, Jose Marco-Contelles
Summary: The new statin derivative MC609 and nitronestatins MC649 and MC645 were synthesized in overall yields of 80%, 77%, and 24% respectively. Different synthetic pathways were employed, including dehydration, Michael addition, reduction, and coupling reactions.
Article
Chemistry, Medicinal
Paloma Narros-Fernandez, Mourad Chioua, Sonia A. Petcu, Daniel Diez-Iriepa, Laura Cerrada-Galvez, Celine Decouty-Perez, Alejandra Palomino-Antolin, Eva Ramos, Victor Farre-Alins, Ana Belen Lopez-Rodriguez, Alejandro Romero, Jose Marco-Contelles, Javier Egea
Summary: NLRP3 plays a role in various inflammatory diseases, making the development of NLRP3 inflammasome small inhibitors a current area of interest. New N-sulfonylureas were obtained by modifying a previously described NLRP3 inhibitor, MCC950, and these derivatives showed potent inhibitory effects on IL-1 beta release. Compound 4b exhibited the greatest effect, similar to MCC950, and also showed a reduction in caspase-1 activation and IL-1 beta processing. In silico predictions confirmed the safety profile of compound 4b, and in vitro and in vivo studies further supported its anti-inflammatory properties.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Rocio Fernandez-Serra, Emma Martinez-Alonso, Alberto Alcazar, Mourad Chioua, Jose Marco-Contelles, Ricardo Martinez-Murillo, Milagros Ramos, Gustavo V. Guinea, Daniel Gonzalez-Nieto
Summary: Brain stroke is a common pathology that causes disability in older adults. Previous neuroprotective treatments have not been effectively translated into clinical practice, highlighting the need for novel targets. This study demonstrates the neuroprotective properties of 2-APB and its ability to improve cerebral blood perfusion by targeting spreading depolarization events in ischemic stroke.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Mohammad A. Khasawneh, Ayesha AlKaabi, Abdelouahid Samadi, Priya Antony, Ranjit Vijayan, Lamya Ahmed Al-Keridis, Haythem A. Saadeh, Nael Abutaha
Summary: A series of novel urea and thiourea derivatives of 8-hydroxyquinoline were designed, synthesized, and evaluated for their anticancer activities. The structures of the new compounds were determined using spectroscopic techniques, and their cytotoxicity against breast cancer cell lines was assessed. Molecular docking studies revealed potential interactions between these compounds and proteins associated with breast cancer.
ARABIAN JOURNAL OF CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Emma Martinez-Alonso, Alejandro Escobar-Peso, Alicia Aliena-Valero, German Torregrosa, Mourad Chioua, Rocio Fernandez-Serra, Daniel Gonzalez-Nieto, Youness Ouahid, Juan B. Salom, Jaime Masjuan, Jose Marco-Contelles, Alberto Alcazar
Summary: The study found that quinolylnitrone QN23 has neuroprotective effects in the treatment of acute ischemic stroke, reducing neuronal death and apoptosis, decreasing infarct volume, and restoring motor function, making it a promising preclinical candidate for this condition.
Article
Pharmacology & Pharmacy
Damijan Knez, Daniel Diez-Iriepa, Mourad Chioua, Andrea Gottinger, Milica Denic, Fabien Chantegreil, Florian Nachon, Xavier Brazzolotto, Anna Skrzypczak-Wiercioch, Anze Meden, Anja Pislar, Janko Kos, Simon Zakelj, Jure Stojan, Kinga Salat, Julia Serrano, Ana Patricia Fernandez, Aitana Sanchez-Garcia, Ricardo Martinez-Murillo, Claudia Binda, Francisco Lopez-Munoz, Stanislav Gobec, Jose Marco-Contelles
Summary: This study describes the development of quinolylnitrones (QNs) as multifunctional ligands inhibiting cholinesterases and monoamine oxidases for the therapy of neurodegenerative diseases.
ACTA PHARMACEUTICA SINICA B
(2023)
Article
Multidisciplinary Sciences
Beatriz Chamorro, Sara Izquierdo-Bermejo, Julia Serrano, Dimitra Hadjipavlou-Litina, Mourad Chioua, Francisco Lopez-Munoz, Jose Marco-Contelles, Ricardo Martinez-Murillo, Maria Jesus Oset-Gasque
Summary: Cerebral ischemia is a growing global problem and the leading cause of disability. Researchers have focused on finding neuroprotective drugs that target the molecular processes involved in cerebral ischemia. Six new quinolylnitrones (QNs) have been discovered, which show promising neuroprotective and antioxidant properties against ischemia-reperfusion in neuronal cultures. Among these QNs, QN6 demonstrates the highest antioxidant power and neuroprotective effect, making it a potential candidate for cerebral ischemia therapy.
SCIENTIFIC REPORTS
(2023)
Article
Polymer Science
H. M. Abd El-Salam, Ali M. El Shafey, Abdelouahid Samadi, Mahmoud K. Abdel-Latif
Summary: Current research focuses on the removal of iron and ammonia from groundwater using a poly acrylic-poly acrylamide hydrogel grafted with 3-chloroaniline. The effects of agitation time, dosage, and adsorbent temperature on the removal process sensitivity were investigated. The hydrogel showed efficient regeneration and selective removal of iron and ammonia.
Article
Chemistry, Medicinal
Tim Keuler, Carina Lemke, Paul W. Elsinghorst, Isabel Iriepa, Mourad Chioua, Maria Angeles Martinez-Grau, Christopher D. Beadle, Tatiana Vetman, Francisco Lopez-Munoz, Timo Wille, Ulrike Bartz, Winnie Deuther-Conrad, Jose Marco-Contelles, Michael Guetschow
Summary: The multifactorial nature of Alzheimer's disease requires the development of drugs that can target different relevant pathways. In this study, we synthesized a series of tailored chromanones and identified compound 19 as a representative compound with balanced pharmacological properties. Compound 19 showed inhibitory activities against human acetyl- and butyrylcholinesterase, monoamine oxidase-B, and high affinity to sigma 1 and sigma 2 receptors.
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2022)
Article
Chemistry, Medicinal
Tim Keuler, Carina Lemke, Paul W. Elsinghorst, Isabel Iriepa, Mourad Chioua, Maria Angeles Martinez-Grau, Christopher D. Beadle, Tatiana Vetman, Francisco Lopez-Munoz, Timo Wille, Ulrike Bartz, Winnie Deuther-Conrad, Jose Marco-Contelles, Michael Gutschow
Summary: The multifactorial nature of Alzheimer's disease necessitates the development of agents that can target multiple relevant pathways. In this study, we synthesized a series of tailored chromanones and evaluated their biological activities. One representative compound (compound 19) was identified, which exhibited balanced pharmacological properties and showed inhibitory activities against acetylcholinesterase, butyrylcholinesterase, monoamine oxidase-B, and high affinity to sigma 1 and sigma 2 receptors. Our findings provide a framework for the development of chromanone-based multineurotarget agents.
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2022)
Meeting Abstract
Biochemistry & Molecular Biology
D. Kolic, G. Sinko, L. Jean, M. Chioua, J. Dias, J. Marco-Contelles, Z. Kovarik
Article
Chemistry, Multidisciplinary
Lamia A. Siddig, Mohammad A. Khasawneh, Abdelouahid Samadi, Haythem Saadeh, Nael Abutaha, Mohammad Ahmed Wadaan
Summary: A new series of urea and thiourea derivatives containing benzimidazole group have been designed and synthesized as potential anticancer agents. Two compounds showed higher cytotoxicity in MCF-7 breast cancer cells compared to MDAMB-231 cells, and induced apoptosis via activation of Caspase-3/7 pathway.
