Article
Chemistry, Organic
Potharaju Raju, Velu Saravanan, Vinayagam Pavunkumar, Arasambattu K. Mohanakrishnan
Summary: The one-pot synthesis of 3,4-benzo[c]-beta-carbolines and related compounds was successfully achieved through intramolecular Heck coupling reaction, with the ability to control product formation by employing specific protecting groups on different parts of the molecule.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Tzu-Lun Liu, Meng-Li Jhou, Cheng-En Hsieh, Chia-Jung Lin, Hsiu-Hui Su, Chih-Ming Chou
Summary: This study presents a protocol for the preparation of functionalized N-allyl-N-aryl sulfonamides via palladium-catalyzed intramolecular decarboxylative N-allylation reaction, showing good regioselectivity. Additionally, transformation of N-allyl-N-aryl sulfonamide into 4-aryl-1,2,3,4-tetrahydroquinoline and nitrogen-containing beta-hydroxysulfide bioactives has been demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xiaodong Gu, Kexin Liu, Limin Yang, Chengyi Xie, Mingliang Li, Jun (Joelle) Wang
Summary: This study reports a nickel-catalyzed asymmetric alpha-heteroarylation of ketones with fluorinated heteroarenes, providing products with all-carbon quaternary stereocenters in good yields and high enantiomeric excess values. The reaction conditions were also shown to be compatible with late-stage diversification of drug molecule donepezil.
Article
Multidisciplinary Sciences
Dong Liu, Zhao-Ran Liu, Zhen-Hua Wang, Cong Ma, Simon Herbert, Hartmut Schirok, Tian-Sheng Mei
Summary: In this study, the authors investigated the electrochemical asymmetric catalysis by utilizing both the anode and cathode as working electrodes. The asymmetric cross-coupling between alpha-chloroesters and aryl bromides was successfully achieved, demonstrating the synergistic involvement of cathodic reduction and anodic oxidation in the paired electrolysis. This electrolytic method provides a promising alternative for asymmetric catalysis in organic synthesis.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Chen Su, Wen-Hua Xu, Rui-Li Guo, Xing-Long Zhang, Xue-Qing Zhu, Ya-Ru Gao, Yong-Qiang Wang
Summary: This study developed a novel method for the synthesis of aporphine analogues, utilizing an intramolecular dehydrogenative coupling of two inert aryl C-H bonds. The method not only exhibits high compatibility with various functional groups, but has also been further applied for the synthesis of natural products aporphine and zenkerine.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Florian Papp, Daniel Sowa Prendes, Sourav Manna, Ann-Katrin Seitz, Sofiya Kostiukovska, Julian Loeffler, Viktoria H. Gessner, Lukas J. Goossen
Summary: Palladium complexes with ylide-functionalized phosphine ligands catalyze the arylation of N-protected hydantoins with aryl chlorides, enabling the synthesis of a wide variety of hydantoins, including derivatives of the anticonvulsant drugs phenytoin and mephenytoin. Selective monoarylations, sequential diarylations, and arylation-alkylation sequences have been achieved, along with stepwise deprotection strategies.
Article
Chemistry, Organic
Min Zhang, Zhangyi Fu, Anping Luo, Xingwen Pu, Menglei Wang, Ying Huang, Yudong Yang, Jingsong You
Summary: The study presents a concise route for site-selective arylation of polycyclic aromatic hydrocarbons with easily available aryl sources, contributing to the bottom-up preparation of pi-extended PAHs. Additionally, a C8-H annulation protocol has been developed to rapidly assemble benzanthrones by simply switching the solvent to 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP).
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Mingpan Yan, Longzhi Zhu, Xingxing Zhang, Shuang-Feng Yin, Nobuaki Kambe, Renhua Qiu
Summary: An efficient methodology for the synthesis of large sterically hindered triarylamines in a single step was developed, with good to excellent yields using inexpensive nickel catalyst. Various bromides and substituted 8-aminoquinolines can be tolerated in the reaction, and preliminary fluorescence results indicate potential in material chemistry for these sterically hindered and conjugated triarylamines.
Article
Chemistry, Multidisciplinary
Daniel Sowa Prendes, Florian Papp, Nagesh Sankaran, Nardana Sivendran, Frederike Beyer, Christian Merten, Lukas J. Goossen
Summary: Arylglycines, which are important pharmacophores in several top-selling drugs, can now be synthesized from abundant aryl chlorides using a Pd-catalyzed Schollkopf-type amino acid synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Matteo Corrieri, Lucia De Crescentini, Fabio Mantellini, Giacomo Mari, Stefania Santeusanio, Gianfranco Favi
Summary: A practical and environmentally friendly approach for the synthesis of pyrrolo[2,3-b]indoles has been developed using an intramolecular C-H bond amination reaction. This chemoselective transformation, which operates at 50 degrees C in water without the need for base or oxidant, relies on a Cu/Fe co-catalyst system. The easy product isolation and recyclability of the catalyst make it a promising method for the synthesis of fused N-heterocycles in pharmaceutical and medicinal chemistry.
Article
Chemistry, Organic
Mikhail Feofanov, Vladimir Akhmetov, Ryo Takayama, Konstantin Amsharov
Summary: A facile synthesis of N-arylated carbazoles via ladderization of fluorinated oligophenylenes is described, involving two subsequent nucleophilic substitutions triggered by an electronic transfer from dimsyl anions. The reaction allows effective one-pot formation of at least six C-N bonds with pronounced selectivity to the C-F bond placement.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Charlotte S. Richards-Taylor, Michael C. Willis
Summary: A synthetic route to benzosultams was reported, using palladium-catalysed aminsulfonylation of alkenyl iodides as the initial step, followed by an intramolecular transformation to form benzosultams. The method allows for good variation of starting alkenyl iodides and was shown to be more efficient than a related SNAr route.
Article
Chemistry, Organic
Lu Lei, Pei-Sen Zou, Zhi-Xin Wang, Cui Liang, Cheng Hou, Dong-Liang Mo
Summary: A regioselective Heck reaction catalyzed by a P-containing palladacycle was described, which affords 2-aryl-2,5-dihydrofurans and 2-aryl-2,3-dihydrofurans in good yields from 2,3-dihydrofuran with diaryliodonium salts and aryl iodides, respectively. Mechanistic studies and DFT calculations revealed the chemoselectivity and regioselectivity-determining step of this reaction.
Article
Chemistry, Organic
Xian Wei, Kun Wang, Weiwei Fang
Summary: In this study, an efficient catalytic system based on IPr-ligated chiral oxazoline palladacycles was developed for the alpha-arylation of aryl ketones with inactive aryl chlorides. The system tolerated a wide range of substrates at low catalyst loadings and resulted in good to excellent yields of the desired products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Applied
Bingxiang Xue, Jie Shen, Sourav Manna, Angelino Doppiu, Lukas J. Goossen
Summary: A new catalyst has been discovered that can selectively introduce a primary amino group into aromatic compounds, and it can efficiently promote the amination reaction to synthesize primary anilines within 30 minutes.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Cell Biology
Gregory D. Cuny, Alexei Degterev
Summary: RIPKs are a family of kinases that have been a mystery in terms of their functions and regulation. They play important roles in host defense functions, exhibiting both typical and atypical features. Despite belonging to distinct areas, there are emerging overarching themes that may unify the functions of this kinase family.
SEMINARS IN CELL & DEVELOPMENTAL BIOLOGY
(2021)
Review
Chemistry, Multidisciplinary
Mandeep Kaur Hunjan, Surabhi Panday, Anjali Gupta, Jayeeta Bhaumik, Parthasarathi Das, Joydev K. Laha
Summary: This review article summarizes the research on the functionalization of pyrroles, covering various catalytic and non-catalytic methods as well as modern catalysis aspects. The classical functionalization using Lewis acids, metal-catalyzed C-H functionalization, radical-based pyrrole functionalization under metal-free oxidative conditions, and pyrrole functionalization under photocatalyzed and electrochemical conditions are discussed in detail. The article highlights the scopes and limitations of different methods and emphasizes the recent investigations on aromatic nucleophillic substitution on pyrroles.
Article
Biochemistry & Molecular Biology
Seema Kirar, Dasharath Chaudhari, Neeraj S. Thakur, Sanyog Jain, Jayeeta Bhaumik, Joydev K. Laha, Uttam C. Banerjee
Summary: A novel A4 type porphyrin photosensitizer was successfully synthesized and encapsulated into gelatin nanoparticles for the development of hydrophilic phototherapeutic nanoagents. The synthesized nanoprobes exhibited good fluorescence performance, indicating potential application in bioimaging. The results of the study demonstrated that these nanoprobes can serve as effective phototherapeutic agents against cancer cells and microbes.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Joydev K. Laha, Mandeep Kaur Hunjan
Summary: The study reports a method for synthesizing dipyrromethanes at 90°C in the presence of K(2)S(2)O(8) with high yields. The method avoids the use of excess pyrrole, using instead a stoichiometric amount, and demonstrates potential for scale-up production of dipyrromethanes.
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
(2021)
Article
Chemistry, Organic
Joydev K. Laha, Mandeep Kaur Hunjan
Summary: This study demonstrates two different modes of decarboxylation observed with alpha-iminocarboxylic acids, leading to the synthesis of divergent heterocycles and pharmaceuticals. DMSO plays a crucial role in the reaction, while under copper-catalyzed conditions, a competitive decarboxylation leads to the formation of different products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Pharmacology & Pharmacy
Colin N. Haile, Miah D. Baker, Sergio A. Sanchez, Carlos A. Lopez Arteaga, Anantha L. Duddupudi, Gregory D. Cuny, Elizabeth B. Norton, Thomas R. Kosten, Therese A. Kosten
Summary: The study demonstrates that a Fentanyl vaccine, administered with the adjuvant dmLT, produces significant levels of anti-Fentanyl antibodies in rats and effectively neutralizes Fentanyl-induced antinociception. The vaccine also reduces Fentanyl levels in the brain and blocks Fentanyl-induced disruption of scheduled behavior. Furthermore, the vaccination prevents physiological changes and overall activity reduction caused by Fentanyl administration in male rats. These findings support the development of the vaccine for addressing Opioid Use Disorder in humans.
Article
Chemistry, Organic
Raghavender Boda, Gregory D. Cuny
Summary: In this study, the synthesis of Pallimamine and its non-natural diastereomer epi-pallimamine was successfully achieved, providing a novel approach for the synthesis of quaternary carbon-containing pentacyclic tetrahydroberberines.
Article
Chemistry, Medicinal
Seungheon Lee, Melissa S. Love, Ramkumar Modukuri, Arnab K. Chatterjee, Lauren Huerta, Ann P. Lawson, Case W. McNamara, Jan R. Mead, Lizbeth Hedstrom, Gregory D. Cuny
Summary: In this study, a structure-activity relationship analysis of BMS906024 revealed that the stereochemistry of the C-3 benzodiazepine and the succinyl beta-substituent play a crucial role in inhibiting Cryptosporidium parvum growth. However, removal of the succinyl alpha-substituent and switching the primary amide with secondary amides was still tolerated. It was also found that inhibition of C. parvum growth was correlated with Notch signaling inhibition, suggesting that further SAR analysis is necessary to differentiate these two activities.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Joydev K. Laha, Ummehani Tinwala, Mandeep Kaur Hunjan
Summary: The research aimed to develop persulfate mediated oxidative transformations that can be conducted at nearly room temperature using water as a solvent, eliminating the drawbacks of using organic solvents and higher temperatures in conventional metal persulfate reactions. This was achieved by utilizing choline persulfate for the reaction, demonstrating the Minisci reaction at 40 degrees C in water as the only solvent, and activating persulfate in an unconventional manner.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Joydev K. Laha, Neha Singh, Mandeep Kaur Hunjan
Summary: A tandem synthesis of unsymmetrical ureas from aryl- or pyridyl carboxamides and aminopyridines via Hofmann rearrangement has been reported, avoiding the direct use of isocyanates or the toxic phosgene for in situ generation of isocyanates. The study successfully trapped and characterized the pyridylisocyanates formed in the process.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Joydev K. Laha, Mandeep Kaur Hunjan
Summary: By utilizing the inexpensive oxidant K2S2O8 in water at room temperature, a sustainable and broad method for mild functionalization and synthesis of heterocycles has been demonstrated, avoiding the use of higher temperature, UV light, transition metals or bases typically required in traditional methods for persulfate activation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Nanoscience & Nanotechnology
Lijun Xie, Renfu Li, Biyun Zheng, Zuoxu Xie, Xuefen Fang, Tao Dai, Xinli Wang, Li Li, Liye Wang, Gregory D. Cuny, Jason Eriksen, Datao Tu, Zhuo Chen, Xiaozhong Wang, Xueyuan Chen, Ming Hu
Summary: Fluorescent probes for COX-2 imaging have been developed using a single-step process from rofecoxib, showing potential for strong fluorescence imaging of COX-2 in human cancer tissue. The most potent analogue, 2a1, exhibited promising COX-2 targeting activity and attractive fluorescent properties, highlighting its potential as a near infrared fluorescent probe for human cancer imaging in clinical settings.
ACS APPLIED BIO MATERIALS
(2021)
Article
Chemistry, Organic
Joydev K. Laha, Surabhi Panday, Monika Tomar, Ketul V. Patel
Summary: This study investigated the annulation reactions of ortho-substituted anilines and arylglyoxylates in the presence of K2S2O8 under metal-free neutral conditions, providing insights into the synthesis and mechanisms of nitrogen heterocycles. The study proposed multiple mechanistic pathways for the formation of heterocycles, highlighting the importance and versatility of using K2S2O8 as a reagent for decarboxylation and transition-metal-free conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Joydev K. Laha, Upma Gulati, Saima, Anjali Gupta, Harish Kumar Indurthi
Summary: An improved gram-scale synthesis of sildenafil has been developed using arylacetic acid, a cheap oxidant, and water, reducing costs by half and showing broad application in the synthesis of related derivatives.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Joydev K. Laha, Mandeep Kaur Hunjan
Summary: This study demonstrates two different reaction modes of using alpha-iminocarboxylic acids in the synthesis of heterocycles, successfully synthesizing a variety of N-heterocycles under reaction conditions in DMSO and opening up new pathways for the synthesis of pharmaceuticals.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
