Article
Multidisciplinary Sciences
Lara E. Zetzsche, Jessica A. Yazarians, Suman Chakrabarty, Meagan E. Hinze, Lauren A. M. Murray, April L. Lukowski, Leo A. Joyce, Alison R. H. Narayan
Summary: This study demonstrates the use of cytochrome P450 enzymes for biocatalytic cross-coupling reactions, enabling the formation of sterically hindered biaryl bonds through oxidative C-C bond formation. By engineering the substrate and atroposelectivity of the P450 enzyme, a highly efficient and selective process has been developed.
Article
Multidisciplinary Sciences
Kai Yang, Yanfei Mao, Zhihan Zhang, Jie Xu, Hao Wang, Yong He, Peiyuan Yu, Qiuling Song
Summary: The authors report a tetracoordinate boron-directed dynamic kinetic asymmetric transformation (DyKAT) method for the construction of C-B axial chirality using racemic, configurationally stable 3-bromo-2,1-azaborines. By rational design of a reversible tetracoordinate boron intermediate, a series of challenging C-B axially chiral compounds were prepared with generally good to excellent enantioselectivities. This method can also be extended to prepare atropisomers bearing adjacent C-B and C-C diaxes with excellent diastereo- and enantio-control.
NATURE COMMUNICATIONS
(2023)
Article
Engineering, Environmental
Udayakumar Veerabagu, Zhaobin Chen, Jiao Xiang, Zihua Chen, Mingen Liu, Hong Xia, Fushen Lu
Summary: A novel Pd@carbon composite derived from cigarette butts was successfully prepared and exhibited improved dispersion and stability of Pd nanoparticles for the Suzuki-Miyaura cross-coupling reaction. The work not only addresses environmental concerns but also offers insights into the valorization of high-performance carbon nanomaterials at low cost and in large quantities.
JOURNAL OF ENVIRONMENTAL CHEMICAL ENGINEERING
(2021)
Article
Chemistry, Organic
Masato Tsuda, Taiki Morita, Hiroyuki Nakamura
Summary: The Suzuki-Miyaura cross-coupling of 3,4-disubstituted 5-bromoisoxazoles at the C5 position using Pd-2(dba)(3) and P(t-Bu)(3)center dot HBF4 catalysts successfully yielded trisubstituted isoxazoles while suppressing the formation of ketone 4 as a byproduct under the influence of bulky phosphine ligand P(t-Bu)(3)center dot HBF4.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Jin Zhang, Pei Zhang, Lei Shao, Ruihong Wang, Yangmin Ma, Michal Szostak
Summary: A highly chemoselective, solvent-free mechanochemical strategy for the cross-coupling of amides by N-C bond activation has been reported. The method shows excellent selectivity, functional group tolerance, and can be applied for late-stage functionalization of complex molecules. This extends the repertoire of N-C bond interconversions to solid-state environmentally friendly mechanochemical methods.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Asma Hrizi, Manon Cailler, Moufida Romdhani-Younes, Yvan Carcenac, Jerome Thibonnet
Summary: This study describes a method for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction. The reactivity of indole derivatives with iodine at position 3 was studied using various cross-coupling reactions. Sonogashira, Suzuki-Miyaura, Stille, and Heck cross-couplings provided a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.
Article
Chemistry, Organic
Yoshitaka Matsushima, Kohei Ishii, Alisa Huffaker, Eric A. Schmelz
Summary: The first concise method for the synthesis of zealexin B1, a maize sesquiterpenoid phytoalexin, was developed via Suzuki-Miyaura coupling. The yields of the coupling reaction were significantly different depending on the combination of boronate and triflate coupling partners.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Physical
Paul O. Peterson, Matthew Joannou, Eric M. Simmons, Steven R. Wisniewski, Junho Kim, Paul J. Chirik
Summary: The synthesis and characterization of phenoxy(imine) iron(II) alkyl precatalysts for C(sp2)-C(sp3) Suzuki-Miyaura cross-coupling reaction is reported. This method utilizes mild alkoxide bases and nonpolar solvents to achieve high efficiency C(sp2)-C(sp3) bond formation with various aryl boronic esters and alkyl bromides. The study also highlights the compatibility of the precatalysts with base-sensitive functionality and the role of boronate intermediates in transmetalation.
Article
Nanoscience & Nanotechnology
Soniya Agarwal, Shyamolima Bairagi, Masshuda Madni Khatun, Kalyanjyoti Deori
Summary: A surfactant free solid solution of NiZn with a hierarchical architecture was synthesized using a one-pot colloidal approach. The formation of hierarchical crystal growth and atomic level alloying of metals was confirmed through field emission scanning electron microscopy and transmission electron microscopy-energy-dispersive X-ray data. This well-alloyed, magnetically separable, non-noble metal-based solid solution has shown potential to replace palladium-based catalysts in Suzuki-Miyaura cross-coupling reactions. The nanostructured catalyst, formed by the assembly of triangular spiked and sheet-like structures, is stable and outperforms most reported transition metal-based catalysts.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Organic
Wen-Xin Li, Bo-Wen Yang, Xuan Ying, Zhuo-Wen Zhang, Xue-Qiang Chu, Xiaocong Zhou, Mengtao Ma, Zhi-Liang Shen
Summary: The direct cross-coupling of diaryl sulfoxides with aryl bromides via C-S bond cleavage was achieved using nickel(II) as the catalyst, 1,2-bis(diphenylphosphino)ethane (dppe) as the ligand, and magnesium turnings as the reducing metal in THF. This reaction showed a wide range of substrates and could be used for gram-scale synthesis. The one-pot reaction is operationally simple and economically efficient.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Antonio J. LaPorte, Yao Shi, Jason E. Hein, Martin D. Burke
Summary: Stereospecific Csp(3) Suzuki-Miyaura cross-coupling simplifies the synthesis of stereochemically complex small molecules, but current methods are not compatible with complex building blocks commonly found in natural products and other complex targets. This study presents a method for embedding the alpha-methyl-beta-hydroxyl motif within stereochemically defined secondary alkyl boronic ester building blocks, allowing for stereospecific cross-coupling. The use of beta-aryloxysilyl groups addresses the decrease in reactivity and side reactions associated with beta-oxygen-containing Csp(3) boronic esters. Mechanistic studies reveal the activation of a dihydroxysiloxaborolate as a transmetalation partner in a stereospecific process that retains configuration.
Article
Chemistry, Multidisciplinary
P. S. Pharande, G. S. Rashinkar, D. M. Pore
Summary: A novel cellulose-supported Schiff base Pd(II) complex was successfully designed and synthesized, showing high catalytic activity and reusability in the Suzuki Miyaura cross-coupling of phenyl boronic acid and aryl halides. The method exhibited high TONs and TOFs, low catalyst loading, and the synthesis of novel biphenyl derivatives.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
Article
Chemistry, Organic
Feiyan Yang, Chuan Wang
Summary: In this study, we employ polycyclic aryl-activated alkyl ammonium triflates as the electrophilic aryl-activated alkylating agent in the nickel-catalyzed hydroxyl- or sulfonamide-directed cross-electrophile coupling reaction with phenyl benzoates, resulting in the synthesis of diverse aryl ketones under mild conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jacob R. Ludwig, Eric M. Simmons, Steven R. Wisniewski, Paul J. Chirik
Summary: A cobalt-catalyzed method for the C(sp(2))-C(sp(3)) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides was developed, with cobalt-ligand combinations being assessed through high-throughput experimentation. The use of cobalt(II) sources with trans-N,N'-dimethylcyclohexane-1,2-diamine (DMCyDA, L-1) resulted in optimal yield and selectivity. The transformation allowed for diverse steric and electronic properties on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile, with radical trap experiments supporting the formation of electrophile-derived radicals during catalysis.
Article
Chemistry, Physical
Abdulelah Taher Ali Mohammed, Lijian Wang, Ronghua Jin, Guohua Liu, Chunxia Tan
Summary: The high stability heterogeneous catalyst HS@PdPPh2@MSN was constructed by immobilizing bis((diphenylphosphino)ethyltriethoxysilane)palladium acetate onto the inner wall of a mesoporous organicsilicane hollow shell, showing a well-defined single-site active species within the silicate network. It enabled an efficient Suzuki-Miyaura cross-coupling reaction with up to 95% yield in mild conditions, and could be reused at least five times with good activity, making it a cost-effective and easily synthesized candidate for fine chemical engineering.
Article
Chemistry, Medicinal
Shan Jiang, Christos Iliopoulos-Tsoutsouvas, Fei Tong, Christina A. Brust, Catherine M. Keenan, Jimit Girish Raghav, Tian Hua, Simiao Wu, Jo-Hao Ho, Yiran Wu, Travis W. Grim, Nikolai Zvonok, Ganesh A. Thakur, Zhi-Jie Liu, Keith A. Sharkey, Laura M. Bohn, Spyros P. Nikas, Alexandros Makriyannis
Summary: Novel cannabinergic probes have been developed to stabilize cannabinoid receptors through tight binding interactions, exhibiting high binding affinity and potent agonist activity. A key ligand, 27a, displays exceptional megagonist properties, acting centrally and peripherally, distinguishing it from previously reported megagonists.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Michael S. Malamas, Spiro Pavlopoulos, Shakiru O. Alapafuja, Shrouq Farah, Alexander Zvonok, Khadijah A. Mohammad, Jay West, Nicholas Thomas Perry, Dimitrios N. Pelekoudas, Girija Rajarshi, Christina Shields, Honrao Chandrashekhar, Jodi Wood, Alexandros Makriyannis
Summary: N-Acylethanolamines, particularly the palmitoylethanolamide hydrolyzed by NAAA, have been studied for their role in inflammation, pain, and drug addiction. Through synthesis and structure-activity relationship studies, potent inhibitors for hNAAA have been developed with high selectivity against other enzymes. These inhibitors have been identified as pharmacological tools for investigating the role of NAAA in various physiological processes.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Correction
Pharmacology & Pharmacy
Chandrashekhar Honrao, Xiaoyu Ma, Shashank Kulkarni, Vinit Joshi, Michael Malamas, Alexander Zvonok, JodiAnne Wood, Roger A. Kautz, David Strand, Jason J. Guo, Alexandros Makriyannis
FRONTIERS IN PHARMACOLOGY
(2021)
Article
Chemistry, Medicinal
Michael S. Malamas, Manjunath Lamani, Shrouq Farah, Khadijah A. Mohammad, Christina Yume Miyabe, Girija Rajarshi, Simiao Wu, Nikolai Zvonok, Honrao Chandrashekhar, JodiAnne Wood, Alexandros Makriyannis
Summary: Fine-tuning 2-arachidonoylglycerol (2-AG) metabolism in the brain through inhibition of a/b-hydrolase domain containing 6 (ABHD6) shows promise in the treatment of epilepsy, neuropathic pain, and inflammation. ABHD6 inhibitors may also have implications in Type-2 diabetes, metabolic syndrome, and other diseases in the periphery.
Article
Chemistry, Medicinal
Tao Hu, Guoxun Zheng, Dongxiang Xue, Simeng Zhao, Fei Li, Fang Zhou, Fei Zhao, Linshan Xie, Cuiping Tian, Tian Hua, Suwen Zhao, Yueming Xu, Guisheng Zhong, Zhi-Jie Liu, Alexandros Makriyannis, Raymond C. Stevens, Houchao Tao
Summary: The study investigates the rational remodeling of atypical scaffolds for introducing azobenzene in the development of photoswitchable ligands for the cannabinoid receptor 2 (CB2). By optimizing spacer length and attachment position, AzoLig 9 exhibits excellent thermal bistability, decent photopharmacological switchability between configurations, and high subtype selectivity. This structure-guided approach provides new impetus for expanding chemical spaces for customization in diverse photopharmacological studies and beyond.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Clinical Neurology
Mauro Congiu, Laura Micheli, Michele Santoni, Claudia Sagheddu, Anna Lisa Muntoni, Alexandros Makriyannis, Michael S. Malamas, Carla Ghelardini, Lorenzo Di Cesare Mannelli, Marco Pistis
Summary: The study showed that NAAA inhibition with the novel brain permeable NAAA inhibitor AM11095 can enhance the analgesic effects of morphine, delay the development of tolerance to morphine, and reduce neuroinflammation in the spinal cord.
Article
Biochemistry & Molecular Biology
Shrouq I. Farah, Samantha Hilston, Ngan Tran, Nikolai Zvonok, Alexandros Makriyannis
Summary: The interaction profiles of 2-AG, 1-AG, and 3-AG with endocannabinoid enzymes and CB1 receptor show differences in affinity and potency. The stereochemistry is crucial for the MGL enzyme, with 3-AG being the best substrate and 1-AG demonstrating the worst substrate profile. Both 1-AG and 3-AG are efficiently hydrolyzed by hABHD6 without preference.
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS
(2022)
Article
Neurosciences
Jenny L. Wilkerson, Lauren B. Alberti, Ganesh A. Thakur, Alexandros Makriyannis, Erin D. Milligan
Summary: CB2R agonists can impact the expression of TRPV1 in the spinal cord and DRG, critical for combating allodynia.
Article
Pharmacology & Pharmacy
Barbara Romano, Ester Pagano, Fabio A. Iannotti, Fabiana Piscitelli, Vincenzo Brancaleone, Giuseppe Lucariello, Maria Francesca Nani, Ferdinando Fiorino, Rosa Sparaco, Giovanna Vanacore, Federica Di Tella, Donatella Cicia, Ruggero Lionetti, Alexandros Makriyannis, Michael Malamas, Marcello De Luca, Giovanni Aprea, Maria D'Armiento, Raffaele Capasso, Bernardo Sbarro, Tommaso Venneri, Vincenzo Di Marzo, Francesca Borrelli, Angelo A. Izzo
Summary: The research shows the functional importance of N-acyl ethanolamine acid amidase (NAAA) in colorectal cancer (CRC) progression, with its inhibition counteracting tumor growth and affecting the composition of tumor secretome. NAAA is proposed as a valid drug target for the treatment of CRC growth and development.
BRITISH JOURNAL OF PHARMACOLOGY
(2022)
Article
Chemistry, Medicinal
Ioannis P. Papanastasiou, Markos-Orestis Georgiadis, Christos Iliopoulos-Tsoutsouvas, Carol A. Paronis, Christina A. Brust, Ngan K. Tran, Lipin Ji, Xiaoyu Ma, JodiAnne T. Wood, Nikolai Zvonok, Fei Tong, Laura M. Bohn, Spyros P. Nikas, Alexandros Makriyannis
Summary: This study merged the features of nabilone and AM2389 and optimized the C3 side chain. Among the nabilone analogs, AM8936 exhibited balanced and potent agonist activity on the CB1 receptor, making it a potential candidate for further development.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Arman A. Sadybekov, Anastasiia Sadybekov, Yongfeng Liu, Christos Iliopoulos-Tsoutsouvas, Xi-Ping Huang, Julie Pickett, Blake Houser, Nilkanth Patel, Ngan K. Tran, Fei Tong, Nikolai Zvonok, Manish K. Jain, Olena Savych, Dmytro S. Radchenko, Spyros P. Nikas, Nicos A. Petasis, Yurii S. Moroz, Bryan L. Roth, Alexandros Makriyannis, Vsevolod Katritch
Summary: Structure-based virtual ligand screening using V-SYNTHES method is effective in rapidly identifying high-scoring compounds from a large chemical space, with experimental results demonstrating successful hit rates and potencies. This approach shows promise for lead discovery and is easily scalable for use with diverse docking algorithms.
Article
Anesthesiology
Xiaoyan Lin, Zhili Xu, Lawrence Carey, Julian Romero, Alexandros Makriyannis, Cecilia J. Hillard, Elizabeth Ruggiero, Marilyn Dockum, George Houk, Ken Mackie, Phillip J. Albrecht, Frank L. Rice, Andrea G. Hohmann
Summary: This study investigated the cell types expressing CB2 receptor and found that CB2 expressed in previously unrecognized populations of skin cells may serve as a potential target for suppressing chemotherapy-induced neuropathic pain.
Article
Multidisciplinary Sciences
Othman Benchama, Sergiy Tyukhtenko, Michael S. Malamas, Mark K. Williams, Alexandros Makriyannis, Hava Karsenty Avraham
Summary: This study found that the use of MAGL inhibitor AM9928 can effectively block the adhesion and migration of TNBC cells, reduce the secretion of pro-inflammatory factors by cells, and inhibit the activation of HBMECs and cytokine secretion caused by TNBC. Animal experiments showed that AM9928 can inhibit the growth of mammary tumors in the mammary fat pads and reduce the permeability changes of the blood brain barrier, thus reducing the metastasis of TNBC in the brain. These findings suggest that MAGL inhibitors have the potential to be a novel strategy for TNBC treatment.
SCIENTIFIC REPORTS
(2022)
Correction
Chemistry, Medicinal
Thanh C. Ho, Joseph J. Mullins, Marcus A. Tius, Spyros P. Nikas, Ngan K. Tran, Fei Tong, Nicolai Zvonok, Alexandros Makriyannis
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Cell Biology
Suthakar Ganapathy, Jian Liu, Tianqi Yu, Rui Xiong, Qiang Zhang, Alexandros Makriyannis, Changyan Chen
Summary: Hexavalent chromium (Cr(VI)) pollution is a serious environmental and health concern. This study reveals the role of protein kinase C (PKC) in Cr(VI)-induced carcinogenesis and drug resistance, and suggests that PKC can be a potential biomarker for early detection of health damages and a therapeutic target for developing new treatments for diseases caused by Cr(VI).
