Article
Chemistry, Multidisciplinary
Nicola Zanda, Leijie Zhou, Esther Alza, Arjan W. Kleij, Miquel A. Pericas
Summary: The article presents an efficient synthesis method using TBD catalyst to convert epoxy amines to 2-oxazolidone, combining the use of CO2 as a C-1 source and halide-free organocatalysis to continuously synthesize a series of heterocyclic products over a two-week period.
Article
Chemistry, Multidisciplinary
Till Drennhaus, Dirk Leifert, Jessika Lammert, Jan Philipp Drennhaus, Klaus Bergander, Constantin G. Daniliuc, Armido Studer
Summary: In this study, enantioenriched chiral indoles were synthesized through a mild and efficient radical cascade reaction using a chiral copper-bisoxazoline complex. The targeted 2-fluoroalkylated 3-(alpha-cyanobenzy-lated) indoles were accessed with excellent enantioselectivity and good yields. Mechanistic studies revealed a negative nonlinear effect which explained the stereochemical outcome. The enantioenriched 3-(alpha-cyanobenzylated) indoles demonstrated scalability and potential utility as hubs for chiral tryptamines, indole-3-acetic acid derivatives, and triarylmethanes, and a formal synthesis of a natural product analogue was disclosed.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Till Drennhaus, Dirk Leifert, Jessika Lammert, Jan Philipp Drennhaus, Klaus Bergander, Constantin G. Daniliuc, Armido Studer
Summary: Enantioenriched chiral indoles were synthesized through a mild and efficient radical cascade reaction. The targeted indoles were accessed by stereochemical control using a chiral copper-bisoxazoline complex. The method demonstrated excellent enantioselectivity and good yields, and the mechanism was elucidated through mechanistic studies.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Kosuke Kato, Kazutada Ikeuchi, Takahiro Suzuki, Keiji Tanino
Summary: A new method for constructing the bicyclo[3.2.1]octane skeleton was developed using intramolecular alkylation. The total synthesis of 2-isocyanoallopupukeanane was achieved via a 17-step transformation, showcasing the significance of this synthetic method in constructing complex organic molecules.
Review
Chemistry, Organic
Ashutosh Dey, Vikash Kumar, Rana Chatterjee, Ananya Behera, Rohit Kumar Maurya, Amarender Goud Burra, Shubham Kumar, Mahender Khatravath, Rambabu Dandella
Summary: This review provides an overview of synthetic approaches for the preparation of phenanthridine and its derivatives from 2-isocyanobiphenyls, highlighting various novel and conventional methods that enable the direct formation of phenanthridine derivatives.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Matthew C. Leech, Alessia Petti, Nour Tanbouza, Andrea Mastrodonato, Iain C. A. Goodall, Thierry Ollevier, Adrian P. Dobbs, Kevin Lam
Summary: A new electrochemical method has been developed to prepare isocyanides from readily available aminotetrazole derivatives, which can tolerate a wide range of functional groups. Additionally, it was demonstrated that isocyanides can also be obtained through chemical oxidation, providing access to these compounds for those without electrosynthesis equipment. The feasibility of scaling up production using flow electrochemistry, as well as the potential use of electrochemically generated isocyanides in further reactions, has been also demonstrated.
Article
Chemistry, Multidisciplinary
Yu Jiang, Ming Li, Shuxin Liu, Rui Li, Yubin Zheng, Wangze Song, Nan Zheng
Summary: Thiocarbamates were synthesized in green solvents via a thiol-dioxazolone modified Lossen rearrangement under transition-metal free, additive free, and mild conditions. Polythiocarbamates were further prepared with excellent self-healing and shape-memory properties, showing great potential in the development of functional materials.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Shihui Wang, Jian Xu, Qiuling Song
Summary: This protocol discloses a method to construct polysubstituted quinolin-3-amines using Mn(III) acetate as a mild one-electron oxidant promoting a radical process. It offers a practical approach with high reaction efficiency and good compatibility of functional groups, providing a straightforward access to functional quinoline derivatives.
Article
Chemistry, Organic
Ming Yang, Xue-Cen Xu, Yue Gong, Yu-Long Zhao
Summary: A rhodium-catalyzed coupling cyclization has been developed for the first time with isocyanides and 2-azidophenyloxyacrylates. This reaction allows for the divergent syntheses of two significant N-heterocycles in a single step from readily available starting materials.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Shuai Jiang, Wen-Bin Cao, Xiao-Ping Xu, Shun-Jun Ji
Summary: A Co-catalyzed cyclization reaction of isocyanides, azides, and amines was developed to access quinazoline derivatives, featuring high atom economy, mild reaction conditions, excellent yields, and a broad substrate scope. The cascade reaction involved the formation of three to four C-N bonds and one or two rings, producing versatile intermediates for further transformations. The cobalt catalyst used in the reaction was found to be isolatable and reusable.
Article
Chemistry, Multidisciplinary
Tianze Zhang, Min Yu, Hanmin Huang
Summary: This study presents an efficient Fe-catalyzed intramolecular isonitrile-olefin coupling reaction for the synthesis of 3-substituted indoles. The protocol features low catalyst loading, mild reaction conditions, and excellent functional group tolerance.
Article
Chemistry, Multidisciplinary
Loredana Maiuolo, Fabrizio Olivito, Fortuna Ponte, Vincenzo Algieri, Matteo Antonio Tallarida, Antonio Tursi, Giuseppe Chidichimo, Emilia Sicilia, Antonio De Nino
Summary: The study developed an innovative, eco-sustainable, and cost-effective method for producing high-quality rigid polyurethane foam. By using a single initial addition of a cheap catalyst, the method proved effective for both the pre-polymer formation and polyurethane chain elongation, while also allowing the salt to be regenerated for a new catalytic cycle during the formation of the final polyurethane.
REACTION CHEMISTRY & ENGINEERING
(2021)
Article
Polymer Science
Sebastian Halupczok, Maria Pfister, Annemarie Ringhand, Corinna Fetsch, Alevtina Cubukova, Antje Appelt-Menzel, Robert Luxenhofer
Summary: The partial reduction of poly(2-ethyl-2-oxazoline) was investigated, and a series of polymers were synthesized using different reduction methods. The reduction degree can be controlled by reaction time or stoichiometry, impacting the materials properties significantly.
Article
Chemistry, Organic
Naziya Parveen, Solai Pandidurai, Govindasamy Sekar
Summary: Stereoselective, one-pot synthesis of 3-arylidene-2oxindoles has been achieved using binaphthyl stabilized palladium nanoparticles (Pd-BNP) as reusable catalyst. The synthesis involves Heck-like carbocyclization/ nucleophilic addition of N-(2-iodophenyl)-N-methyl-3-phenylpropiolamide, phenylacetylene, and secondary amine. The Pd-BNP nanocatalyst can be recovered and recycled for multiple catalytic cycles with negligible reduction in particle size, reactivity, and reaction yield.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jinhuan Dong, Junlin Hu, Xiaoli Liu, Shaoguang Sun, Lan Bao, Mengying Jia, Xianxiu Xu
Summary: An ionic cascade insertion/cyclization reaction has been developed for the synthesis of 2-halobenzothiazole/benzoselenazole derivatives, involving the introduction of a halogen atom during the formation of the five-membered ring.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Hyunbeom Lee, Hoang V. Le, Rui Wu, Emma Doud, Ruslan Sanishvili, John F. Kellie, Philip D. Compton, Boobalan Pachaiyappan, Dali Liu, Neil L. Kelleher, Richard B. Silverman
ACS CHEMICAL BIOLOGY
(2015)
Article
Chemistry, Multidisciplinary
Hoang V. Le, Dustin D. Hawker, Rui Wu, Emma Doud, Julia Widom, Ruslan Sanishvili, Dali Liu, Neil L. Kelleher, Richard B. Silverman
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Multidisciplinary Sciences
Rui Wu, Ruslan Sanishvili, Boris R. Belitsky, Jose I. Juncosa, Hoang V. Le, Helaina J. S. Lehrer, Michael Farley, Richard B. Silverman, Gregory A. Petsko, Dagmar Ringe, Dali Liu
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2017)
Review
Chemistry, Medicinal
Nicholas S. Akins, Tanner C. Nielson, Hoang V. Le
CURRENT TOPICS IN MEDICINAL CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Jose I. Juncosa, Kenji Takaya, Hoang V. Le, Matthew J. Moschitto, Pathum M. Weerawarna, Romila Mascarenhas, Dali Liu, Stephen L. Dewey, Richard B. Silverman
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Biochemistry & Molecular Biology
Jihong Xu, Fang Chen, Shuyan Wang, Nicholas S. Akins, Md Imran Hossain, Yi Zhou, Jinxi Huang, Jiafu Ji, Jin Xi, Wenzhen Lin, John Grothusen, Hoang Le, Renyu Liu
NEUROCHEMISTRY INTERNATIONAL
(2020)
Article
Biochemistry & Molecular Biology
Hassan Madkhali, Amer Tarawneh, Zulfiqar Ali, Hoang Le, Stephen J. Cutler, Ikhlas A. Khan, Zia Shariat-Madar
Summary: This study evaluated the pharmacological effects of black tea water extract on human kinin-forming enzymes, finding that black tea can reduce BK production by inhibiting kallikrein and activated FXII, thus exerting its anti-inflammatory effects.
Article
Chemistry, Medicinal
Nicholas S. Akins, Nisha Mishra, Hannah M. Harris, Narendar Dudhipala, Seong Jong Kim, Adam W. Keasling, Soumyajit Majumdar, Jordan K. Zjawiony, Jason J. Paris, Nicole M. Ashpole, Hoang Le
Summary: This study introduces a method to create compounds with dual agonism on opioid receptors. In vitro and in vivo studies show that these compounds have analgesic activity while avoiding harmful side effects.
Review
Endocrinology & Metabolism
Mohammed F. Salahuddin, Alaa N. Qrareya, Fakhri Mahdi, Emaya Moss, Nicholas S. Akins, Jing Li, Hoang V. Le, Jason J. Paris
Summary: Forty years into the HIV pandemic, neuroHIV still affects 50% of infected individuals, and there is evidence that HIV can cause hormonal dysfunction. Although combination antiretroviral therapy (cART) is successful, it cannot eliminate HIV from the central nervous system, leading to neurological disorders. In addition, people living with HIV commonly experience endocrine disorders, which may contribute to other health issues. Hormone therapy may have potential as an adjunctive treatment for HIV-associated neuroendocrine dysfunction.
JOURNAL OF NEUROENDOCRINOLOGY
(2022)
Article
Chemistry, Organic
Md Imran Hossain, Md Imdadul H. Khan, Seong Jong Kim, Hoang Le
Summary: Here, we report a method for synthesizing 3,4,5-trisubstituted isoxazoles in water under mild basic conditions at room temperature. This method provides an environmentally friendly access to these important structures found in bioactive natural products and pharmaceuticals.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Biochemistry & Molecular Biology
Ayoub Kdimy, Meryem El Yadini, Abdelkarim Guaadaoui, Ilhame Bourais, Souad El Hajjaji, Hoang Le
Summary: This review systematically summarizes the traditional uses, phytochemical composition, and diverse pharmacological activities of Capparis spinosa L., as well as the synthetic routes to derivatives of identified chemical components to enhance biological activities and pharmacokinetic profiles. The review also discusses the benefits of C. spinosa L. in adapting to climate change and its socio-economic value in rural economies.
CHEMISTRY & BIODIVERSITY
(2022)
Review
Chemistry, Medicinal
Md Imdadul H. Khan, Benjamin J. Sawyer, Nicholas S. Akins, Hoang V. Le
Summary: This review summarizes the history, design strategy, discovery, and development of KOR ligands. It also discusses the classification, mechanisms, and pharmacokinetic, pharmacodynamic, and behavioral studies of KOR agonists and antagonists.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Nicholas S. Akins, Mohammed F. Salahuddin, Pankaj Pandey, Seong Jong Kim, Fakhri Mahdi, Md Imdadul H. Khan, Emaya M. Moss, Charlie J. Worth, Madeline M. Keane, Amar G. Chittiboyina, Robert J. Doerksen, Jason J. Paris, Hoang V. Le
Summary: The KOR is involved in the regulation of reward and mood, and drug abuse increases its activation. Long-acting KOR antagonists have been shown to alleviate withdrawal symptoms, but their use in humans comes with safety concerns. This study found that a short-acting KOR antagonist showed efficacy in reducing withdrawal behavior in mice, and computational studies provided insights for the design of future antagonists.
ACS CHEMICAL NEUROSCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Md Imran Hossain, Ajit G. Thomas, Fakhri Mahdi, Amna T. Adam, Nicholas S. Akins, Morgan M. Woodard, Jason J. Paris, Barbara S. Slusher, Hoang V. Le
Summary: The study demonstrates that l-gamma-methyleneglutamine and its derivatives have significant inhibitory effects on breast cancer cell growth, particularly in triple-negative breast cancer cells. Importantly, these compounds show low toxicity to normal cells, making them promising novel therapeutics for various subtypes of breast cancer.
Article
Biochemistry & Molecular Biology
Romila Mascarenhas, Hoang V. Le, Kenneth D. Clevenger, Helaina J. Lehrer, Dagmar Ringe, Neil L. Kelleher, Richard B. Silverman, Dali Liu
