Article
Chemistry, Multidisciplinary
Jingdong Wang, Yuxin Liu, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, Hai-feng Duan
Summary: A series of chiral thiourea compounds with multiple H-bond donors derived from hydroquinine have been reported. The aza-Henry reaction of isatin-derived ketimines and long-chain nitro-alkanes catalyzed by these chiral thioureas shows high enantioselectivity and excellent diastereoselectivity. This work represents the first report on long-chain nitroalkanes as substrates with excellent diastereoselectivity in metal-free catalytic systems.
Article
Chemistry, Applied
Gabriele Lupidi, Alessandro Palmieri, Marino Petrini
Summary: A novel riboflavin-promoted reaction of primary nitroalkanes coupled with a nitroaldol reaction was discovered, enabling the synthesis of functionalized nitro alcohols under mild reaction conditions. However, secondary nitroalkanes were consumed under the reaction conditions without yielding the expected nitroaldol products.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Thomas J. Struble, Ivor Smajlagic, Hayden Foy, Travis Dudding, Jeffrey N. Johnston
Summary: A pair of chiral bis(amidine) [BAM] proton complexes have been developed as catalysts for highly diastereo- and enantioselective direct aza-Henry reactions, leading to alpha-alkyl-substituted alpha,beta-diamino esters. Computational analysis supports distinct models for selectivity, with the more hindered binding cavity of the C-1-symmetric ligand favoring a pre-syn arrangement. Factors driving unusual high syn-diastereoselection include favorable dispersion forces from the anthracenyl substituent of the C-1-symmetric ligand.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jade A. Bing, Nathan D. Schley, Jeffrey N. Johnston
Summary: This research presents a comparative analysis of non-fluorinated and alpha-fluoro nitroalkanes in their additions to azomethines, revealing an unusual crossover and reversal in diastereoselection.
Review
Chemistry, Applied
Yong-Xing Song, Da-Ming Du
Summary: The aza-Michael addition cascade reaction is an important synthetic method for constructing functionalized C-N bonds, widely used in the synthesis of chiral drugs, intermediates, and natural products. This review highlights recent developments in asymmetric synthesis, including various types of aza-Michael addition triggered cascade reactions, reaction mechanisms, and derivatization experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Mateusz Dyguda, Artur Przydacz, Lukasz Albrecht
Summary: This manuscript describes the application of dearomative formal normal-electron-demand aza-Diels-Alder cycloaddition in the synthesis of tetrahydrofuropyridines. The method involves the aminocatalytic activation of 2-alkyl-3-furfurals and proceeds via the formation of dearomatized dienamine intermediate. The obtained cycloadducts can be further transformed into tetrahydrofuropyridines or functionalized cinnamates. The mechanism of the transformation was confirmed through DFT calculations.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Mateusz Dyguda, Artur Przydacz, Lukasz Albrecht
Summary: This manuscript describes the application of dearomative formal normal-electron-demand aza-Diels-Alder cycloaddition in the synthesis of tetrahydrofuropyridines. The developed approach utilizes aminocatalytic activation of 2-alkyl-3-furfurals that proceeds via formation of the dearomatized dienamine intermediate. The obtained cycloadducts can be further transformed into tetrahydrofuropyridines or functionalized cinnamates.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Wen-Kang Wang, Fei-Yun Bao, Si-Tian Wang, Sheng-Yin Zhao
Summary: A method for preparing 3-aminomethylated maleimides via Morita-Baylis-Hillman (MBH) reaction was developed. This study used maleimides and 1,3,5-triazinanes as substrates, and through the phosphine-catalyzed coupling, a series of 3-aminomethylated maleimide derivatives were obtained with a yield of 41-90%. Acylation, isomerization, and Michael addition reactions demonstrated the synthetic application of this method. Control experiments revealed that phosphorus ylide formation and elimination occur during the reaction pathway.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Maria Sanchez-Rosello, Marcos Escolano, Daniel Gavina, Carlos del Pozo
Summary: The asymmetric intramolecular aza-Michael reaction (IMAMR) is a convenient strategy for generating heterocycles with nitrogen-substituted stereocenters, finding widespread applications in the total synthesis of alkaloids and biologically relevant compounds. Recent developments in asymmetric versions of IMAMR mainly involve the use of organocatalysts, such as chiral imidazolidinones and diaryl prolinol derivatives. The use of N-sulfinyl imines with dual roles has also emerged as a versatile mode for performing the asymmetric IMAMR.
Article
Chemistry, Multidisciplinary
Naoki Yasukawa, Ami Yamanoue, Tsunayoshi Takehara, Takeyuki Suzuki, Shuichi Nakamura
Summary: The first enantioselective aza-Henry reaction of non-activated cyclic iminoesters, derived from cyclic amino acids, has been developed using a unique cinchona alkaloid sulfonamide/zinc(ii) catalyst. Good yields and enantioselectivities were observed, and the stereochemistry was explained by proposed transition state based on experiments and DFT calculations.
CHEMICAL COMMUNICATIONS
(2022)
Review
Chemistry, Applied
Maxim G. Vinogradov, Olga V. Turova, Sergei G. Zlotin
Summary: This review retrospectively considers the pivotal achievements and recent advances in catalytic asymmetric aza-DAR reported up to 2020, showcasing their potency for enantioselective synthesis of useful chiral piperidine, quinoline, pyridazine, oxazine, and oxadiazine derivatives. The data are systematized based on key electron transfer modes and attainable heterocyclic products, with significant attention to activation strategies and plausible reaction pathways over stereoselective cyclization processes. The review contains 310 references and 122 synthetic schemes.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Subaramaniam Thangamalar, Kannupal Srinivasan
Summary: The ring-opening reaction of nitro-substituted donor-acceptor cyclopropanes with pyrazoles in DMSO was investigated. Unexpectedly, the cyclopropanes underwent Kornblum-type ring-opening oxidation with DMSO to form aroylmethylidene malonates as intermediates in the reactions. The intermediates further underwent aza-Michael addition with pyrazoles in tandem manner to give the corresponding aza-Michael adducts. The highlights of the methodology include the occurrence of ring-opening/oxidation under neutral conditions with DMSO and formation of aza-Michael adducts with pyrazoles under catalyst-free conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Fabian Scharinger, Matthias Weil, Michael Schnuerch, Katharina Bica-Schroeder
Summary: We introduce a simple method for the synthesis of chiral diazabicycloalkanes in a single reaction step. This method is applicable to a wide range of enals and has high functional group tolerance.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Applied
Yulia Volkova, Sergey Baranin, Igor Zavarzin
Summary: This review provides a general overview of the utility of A(3) coupling in the synthesis of heterocycles, highlighting the variety of compounds that can be directly accessed from single reactions. The diverse methodologies for the synthesis of N,O,S-heterocycles based on A(3) coupling are presented, emphasizing the influence of reaction conditions and the use of additional reagents on the outcome of the transformations.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Multidisciplinary
S. V. Ryabukhin, D. V. Bondarenko, S. A. Trofymchuk, D. A. Lega, D. M. Volochnyuk
Summary: Modern organic chemistry plays a vital role in supporting pharmaceutical, agricultural, food, and material science products. Medicinal chemistry relies on advancements in organic chemistry to fine-tune molecular structures and create effective drugs. The rapid development of synthetic methods involving fluorine has brought attention to the unique properties of fluorinated compounds in medicine. The impact of medicinal chemistry on organic synthesis has also led to the discovery of new fluorinated topologies.
Article
Environmental Sciences
ZabnAllah M. Alaizeri, Hisham A. Alhadlaq, Saad Aldawood, Mohd Javed Akhtar, Maqusood Ahamed
Summary: This study examined the effect of silver doping on the photocatalytic and anticancer activity of indium oxide nanoparticles. The results showed that silver doping enhances the crystallinity, photocatalytic activity, and anticancer efficacy of indium oxide nanoparticles.
ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH
(2023)
Article
Chemistry, Medicinal
Karine Mardon, Jayendra Z. Patel, Juha R. Savinainen, Damion H. R. Stimson, Caitlin R. M. Oyagawa, Natasha L. Grimsey, Mary-anne Migotto, Grace F. M. Njiru, Brett R. Hamilton, Gary Cowin, Jari Yli-Kauhaluoma, Wim Vanduffel, Idriss Blakey, Rajiv Bhalla, Christopher Cawthorne, Sofie Celen, Guy Bormans, Kristofer J. Thurecht, Muneer Ahamed
Summary: Multimodal imaging, through PET and MALDI imaging, is used to discover and validate a new probe targeting the ABHD6 enzyme. The PET ligand [18F]JZP-MA-11 is reported to have specific uptake in ABHD6-rich tissues and major brain regions, with brain uptake confirmed in a nonhuman primate study. In vivo pharmacological response upon ABHD6 inhibition is observed using MALDI imaging. These synergistic imaging efforts hold promise for improving our understanding of ABHD6-mediated endocannabinoid metabolism in peripheral and central nervous system disorders.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Rashid Lateef, Marhaba, Payal Mandal, Kausar M. Ansari, Mohd Javed Akhtar, Maqusood Ahamed
Summary: CuO-rGO nanocomposites have attracted great attention due to their exceptional physicochemical properties. However, their effects on human and environmental health are not well understood. This study investigated the cytotoxicity and apoptosis response of CuO-rGO in normal rat kidney cells. The results showed that CuO-rGO induced cytotoxicity, generation of reactive oxygen species, and apoptosis. Further research is needed to elucidate the potential mechanisms of CuO-rGO toxicity at the molecular level.
JOURNAL OF KING SAUD UNIVERSITY SCIENCE
(2023)
Article
Multidisciplinary Sciences
Maqusood Ahamed, Mohd Javed Akhtar, M. A. Majeed Khan, Hisham A. Alhadlaq
Summary: Due to their exceptional properties, copper oxide nanoparticles (CuO NPs) are widely used in various fields. However, they are toxic to living organisms and no effective method is available to mitigate their health hazards. This study investigates the cytoprotective mechanism of protocatechuic acid (PCA) against CuO NPs toxicity in liver cells. The results show that pre-treatment with PCA can effectively mitigate the cytotoxicity and oxidative stress induced by CuO NPs.
JOURNAL OF KING SAUD UNIVERSITY SCIENCE
(2023)
Article
Multidisciplinary Sciences
Mohd Javed Akhtar, Maqusood Ahamed, Hisham Alhadlaq
Summary: Pt-coated Au nanoparticles exhibited higher uptake and cytotoxicity in human breast cancer cells compared to non-cancerous cells. The nanoparticles induced oxidative stress and loss of mitochondrial membrane potential. These findings suggest the potential of Pt-Au nanoparticles as a promising option for cancer therapy.
JOURNAL OF KING SAUD UNIVERSITY SCIENCE
(2023)
Article
Engineering, Biomedical
Maqusood Ahamed, Rashid Lateef, M. A. Majeed Khan, Pavan Rajanahalli, Mohd Javed Akhtar
Summary: A green and cost-effective method was reported to synthesize ZrO2-doped ZnO/reduced graphene oxide nanocomposites (ZnO/ZrO2/rGO NCs) using ginger rhizome extract. The ZnO/ZrO2/rGO NCs exhibited significantly enhanced anticancer activity in human lung and breast cancer cells compared to ZnO nanoparticles (NPs). Furthermore, the NCs demonstrated good cytocompatibility in normal cells. This study highlights the importance of medicinal herb-mediated synthesis of ZnO-based nanocomposites for biomedical research.
JOURNAL OF FUNCTIONAL BIOMATERIALS
(2023)
Article
Biochemistry & Molecular Biology
Weijing Chu, Zachary H. Houston, Nicholas L. Fletcher, Pie Huda, Muneer Ahamed, Ting Xiang Lim, Bryan W. Day, Mark Pinkham, Kristofer J. Thurecht
Summary: This study developed a multifunctional polymer platform for treating treatment-resistant glioblastoma (GBM) by using targeted nanomedicine. The polymer was synthesized via reversible addition fragmentation chain transfer polymerization and included temozolomide (TMZ) as a polymerizable monomer, PEG units for biocompatibility, and hydrazide moieties for attaching a secondary drug. The polymer showed improved therapeutic efficacy in overcoming resistance to TMZ when attached with a DNA repair protein inhibitor. Targeted delivery to GBM tumors using a specific antibody further enhanced the therapeutic effect of the polymer. The study highlights the potential benefit of this formulation for delivering multi-drug combinations to resistant GBM tumor cells.
Article
Environmental Sciences
Mohd Javed Akhtar, Maqusood Ahamed, Hisham Alhadlaq
Summary: A review of recent literature suggests that bismuth oxide nanoparticles (Bi2O3 NPs) show appreciable response in cells with epithelial origin only at concentrations above 40-50 μg/mL. However, in human endothelial cells (HUVE cell line), the toxicological profile of Bi2O3 NPs showed much steeper cytotoxicity, with 50% cytotoxicity observed at a much lower concentration of 6.7 μg/mL. The study also found that Bi2O3 NPs induced reactive oxygen species (ROS), lipid peroxidation (LPO), and depletion of intracellular antioxidant glutathione (GSH) in HUVE cells.
Article
Biotechnology & Applied Microbiology
Saheb Ali, Kattakgoundar Govindaraj Sudha, Natesan Thirumalaivasan, Maqusood Ahamed, Saravanan Pandiaraj, Vijayarangan Devi Rajeswari, Yamini Vinayagam, Muthu Thiruvengadam, Rajakumar Govindasamy
Summary: This study focused on the synthesis of magnesium oxide (MgO) nanoparticles (NPs) using Abrus precatorius L. bark extract through the green chemistry method. Characterization techniques such as XRD, FTIR, SEM, TEM, and UV-visible analysis were used to confirm the synthesis of MgO NPs. The synthesized MgO NPs exhibited small particle size and specific surface area. The study also assessed the efficacy of MgO NPs in dye degradation, antioxidant activity, and toxicity using zebrafish embryos and human melanoma cancer cells (A375).
BIOENGINEERING-BASEL
(2023)
Article
Biochemistry & Molecular Biology
Annukka Kallinen, Karine Mardon, Samuel Lane, Andrew P. Montgomery, Rajiv Bhalla, Damion H. R. Stimson, Muneer Ahamed, Gary J. Cowin, David Hibbs, Eryn L. Werry, Roger Fulton, Mark Connor, Michael Kassiou
Summary: This study synthesized fluorinated 5-azaindole compounds and evaluated their pharmacological characteristics and in vivo performance. The results showed that these compounds exhibited specific binding to CB2 receptors and demonstrated specific binding behavior in rats with neuroinflammation, suggesting the need for further evaluation of these compounds in other neuroinflammation models.
ACS CHEMICAL NEUROSCIENCE
(2023)
Article
Multidisciplinary Sciences
Mohd Javed Akhtar, Maqusood Ahamed, Hisham Alhadlaq
Summary: This study compares the effects of two types of cobalt-based nanoparticles on lung cells and finds that cobalt nanoparticles are more toxic to cells than cobalt-iron oxide nanoparticles, possibly due to the higher release of Co2+ ions by cobalt nanoparticles. Additionally, the study suggests that CalceinAM alone is insufficient to assess the toxicity of cobalt-based nanoparticles, and other methods should be used for further confirmation.
JOURNAL OF KING SAUD UNIVERSITY SCIENCE
(2024)
Article
Chemistry, Multidisciplinary
ZabnAllah M. Alaizeri, Hisham A. Alhadlaq, Saad Aldawood, Mohd Javed Akhtar, Maqusood Ahamed
Summary: Graphene derivatives and metal oxide-based nanocomposites (NCs) are investigated for various applications. This study demonstrates that the integration of rGO and Bi2O3 enhances photocatalytic and anticancer efficacy, and the prepared Bi2O3-WO3/rGO NCs exhibit improved activity.
Article
Materials Science, Multidisciplinary
Maqusood Ahamed, Mohd Javed Akhtar, M. A. Majeed Khan
Summary: In this study, we synthesized Acacia nilotica (L.) fruit extract-green produced ZrO2/RGO nanocomposites (NCs) and investigated their anticancer properties. The results showed that ZrO2/RGO NCs were more effective than pure ZrO2 NPs in inhibiting the growth of different human cancer cells (A549, HepG2, and MCF7), while also exhibiting greater cytocompatibility in normal cell lines (IMR90 and MCF10A). Mechanistic evidence suggested that the anticancer response of ZrO2/RGO NCs was attributed to the production of intracellular reactive oxygen species and the reduction of glutathione, leading to oxidative stress.
MATERIALS TODAY COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Sitah Alanazi, ZabnAllah M. Alaizeri, Rashid Lateef, Nawal Madkhali, Abdullah Alharbi, Maqusood Ahamed
Summary: This study investigates the anticancer potential of Zn-doped SnO2 nanoparticles (NPs) and demonstrates that Zn doping enhances the anticancer efficacy of SnO2 NPs. The physicochemical properties of the NPs are characterized using various techniques, revealing changes in the crystalline size and band gap energy after Zn doping. In vitro studies show that Zn-doped SnO2 NPs exhibit increased anticancer activity in breast cancer cells.
APPLIED SCIENCES-BASEL
(2023)
Article
Multidisciplinary Sciences
Rashid Lateef, Israr Ahmad, Abbas Ali Mahdi, Pavan Rajanahalli, Mohd Javed Akhtar, Maqusood Ahamed
Summary: Recent research has found that metal oxide nanoparticles may pose a threat to the health of pregnant individuals and developing fetuses. This study aimed to investigate the preventative effects of solanesol on the harmful effects caused by copper oxide (CuO) and nickel oxide (NiO) nanoparticles in human placental cells. The results showed that solanesol significantly alleviated the cytotoxicity and apoptosis induced by the nanoparticles. Further research is needed to explore the pharmacological potential of solanesol against nanoparticle-generated pregnancy problems.
JOURNAL OF KING SAUD UNIVERSITY SCIENCE
(2023)