Article
Chemistry, Organic
Anna L. Samsonenko, Anastasia S. Kostyuchenko, Tatyana Yu. Zheleznova, Vladislav Yu. Shuvalov, Igor S. Vlasov, Alexander S. Fisyuk
Summary: This article discusses the development of practical methods for synthesizing 4-azido-5-arylthiophene-2-carboxylates and 4-amino-5-arylthiophene-2-carboxylates using the Fiesselmann reaction. The decomposition of 4-azido-5-arylthiophene-2-carboxylates through photochemical and thermal processes, including microwave-assisted decomposition, was studied to synthesize fused 4H-thieno[3,2-b]pyrrole derivatives. These proposed methods allow for the synthesis of functionalized heteroacenes, which are important building blocks for organic semiconductors.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Bastian L. Springer, Kristina Holzschneider, Fabian Mohr, Stefan F. Kirsch
Summary: A new synthetic route for phenanthro[9,10-d]imidazoles is reported. The target compounds were synthesized through the aminolysis of readily accessible 10,10-diazidophenanthren-9(10H)-one with nucleophilic amines, followed by a self-condensation. X-ray single crystallography was used to determine the molecular structures, and the optical properties of the material were described.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Enrique Gil de Montes, Matteo A. Tallarida, Ana T. Carmona, Claudio D. Navo, Inmaculada Robina, Pilar Elias-Rodriguez, Gonzalo Jimenez-Oses, Antonio J. Moreno-Vargas
Summary: This study highlights the regioselective rearrangement of aminyl radicals, leading to the formation of novel bicyclic diazabicyclic compounds. The research explores the impact of different bridgehead atoms and substituents on the rearrangement reaction, while providing a detailed mechanistic proposal supported by computational studies.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zheng-Yang Gu, Ji-Bao Xia
Summary: A efficient [3 + 1 + 1] cyclization of vinyl oxiranes has been developed for the synthesis of oxazolidinones via tandem palladium catalysis. This reaction provides an atom- and step-efficient strategy to produce oxazolidinones from readily available azides and carbon monoxide under mild additive- and base-free conditions. Mechanistic studies demonstrated that the reaction occurred through an in situ generated isocyanate intermediate.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Organic
Jay Prakash Soni, Manasa Kadagathur, Nagula Shankaraiah
Summary: Organic azides, synthesized for the first time in 1864, have since garnered significant attention from chemists worldwide due to their unique electronic structure and chemical reactivity, leading to all-embracing research in the chemistry of azides. The recent focus (2015-2021) has been on utilizing azido-reductive cyclization approach with retention of a single nitrogen atom in the synthesis of organic molecules, particularly natural products and aza-heterocyclic frameworks.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yi Gong, Cai Wang, Feng Zhou, Kui Liao, Xi-Yu Wang, Ying Sun, Yan-Xue Zhang, Zhi Tu, Xin Wang, Jian Zhou
Summary: This study presents the first highly selective kinetic resolution of racemic alpha-chiral azides through Cu-catalyzed azide-alkyne cycloaddition (CuAAC). Newly developed pyridine-bisoxazoline (PYBOX) ligands bearing a C4 sulfonyl group enabled effective kinetic resolution and asymmetric CuAAC of racemic azides derived from privileged scaffolds such as indanone, cyclopentenone, and oxindole, leading to alpha-tertiary 1,2,3-triazoles with high to excellent ee values. DFT calculations and control experiments revealed that the C4 sulfonyl group decreased the Lewis basicity of the ligand and increased the electrophilicity of the copper center for better recognition of azides, while also functioning as a shielding group to enhance the efficacy of the chiral pocket of the catalyst.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(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
Chemistry, Multidisciplinary
Jing Liu, Hong-Li Huang, Chen Wang, Yinghua Li, Huaqiang Li, Honggang Hu, Shipeng He, Hua Tang, Fei Gao
Summary: A visible-light-driven cascade radical cyclization process has been established for the synthesis of alpha-carbonyl alkyl-substituted benzimidazo[2,1-alpha]isoquinolin-6(5H)-ones. This protocol offers an efficient and practical method with outstanding yields, mild reaction conditions, and excellent functional group tolerance.
Article
Chemistry, Applied
Raffaella Mancuso, Patrizio Russo, Melania Lettieri, Domenico Santandrea, Corrado Cuocci, Bartolo Gabriele
Summary: Polycyclic heterocyclic derivatives can be synthesized in one step by a carbonylative double cyclization approach, with yields ranging from 45% to 86%, showing promising potential for various applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Mandapati Bhargava Reddy, Eoghan M. Mcgarrigle
Summary: An unprecedented carboxylative sulfonylation reaction of (homo)propargyl amines with CO2 and sodium arylsulfinates under visible light irradiation has been developed, exhibiting high efficiency. The ruthenium-catalyzed photochemical protocol offers a wide range of substrates, resulting in good yields of 2-oxazolidinones and 2-oxazinones bearing alkyl sulfones under ambient reaction conditions. In situ double bond isomerization occurs in tandem. The mechanism of these radical-initiated carboxylative cyclizations involving sulfinyl radicals is explained based on control and quenching experiments.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Physical
K. Rajendran, Roshni Madampadi, Sayan Shee, Rameshkumar Subramaniam, Tuhin S. Khan, Shelaka Gupta, M. Ali Haider, Dinesh Jagadeesan
Summary: By utilizing the oxygen-vacancy-mediated reactivity of CaO/CuO and hydrazine monohydrate in isopropyl alcohol, a variety of amino-derivatives of N-heterocycles have been selectively synthesized by reducing their nitro analogues. The CaO/CuO composite is found to be a reusable and solvent-resilient solid reducing agent that shows promising results as an alternative to conventional catalysts.
Article
Chemistry, Multidisciplinary
Johannes Winter, Tobias Prenzel, Tom Wirtanen, Dieter Schollmeyer, Siegfried R. R. Waldvogel
Summary: The use of electric current provides a sustainable and efficient method for the synthesis of quinoline N-oxides from readily available nitro compounds. The reaction employs mild and reagent-free conditions, and uses a simple undivided electrolysis cell with constant current set-up, leading to high conversion and atom economy. The synthesis of 30 differently substituted quinoline N-oxides was successfully achieved in up to 90% yield. Mechanistic insights were obtained through cyclic voltammetry studies, and the technical relevance of the reaction was demonstrated through a 50-fold scale-up.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Minghui Qi, Muhammad Suleman, Jianwei Xie, Ping Lu, Yanguang Wang
Summary: We report a simple and efficient method for the selective C-H bond insertion of copper carbenes generated in situ from 4-diazo-1,4-dihydroisoquinolin-3-ones into beta-C(sp(2))-H bonds of N-sulfonyl enamides. This reaction yields a series of 4-(1,4,5,6-tetrahydropyridin-3-yl)-1,4-dihydroisoquinolin-3(2H)-ones with good to excellent yields. The reaction benefits from its simple and mild reaction conditions, the use of a cheap catalyst, readily accessible starting materials, and a broad substrate scope.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Maximilian Scheruebl, Constantin G. Daniliuc, Armido Studer
Summary: The article introduces the application of arynes as radical acceptors, showing how the stable radical TEMPO can react with different ortho-substituted benzynes to generate aryl radicals for subsequent cyclizations, eventually being trapped by TEMPO. This method provides a novel approach for the convenient synthesis of various dihydrobenzofurans, oxindoles, and sultones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xianqing Wu, Baixue Luan, Wenyu Zhao, Feng He, Xin-Yan Wu, Jingping Qu, Yifeng Chen
Summary: This study presents a nickel-catalyzed reductive cross-coupling reaction for the desymmetric dicarbofunctionalization of 1,6-dienes. By leveraging an underdeveloped chiral ligand, the reaction selectively forms pyrrolidinones bearing two nonadjacent stereogenic centers, enabling rapid synthesis of complex chiral fused-heterocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Physical
Kritika Laxmikeshav, Ambati Himaja, Nagula Shankaraiah
Summary: This article reviews the research progress and synthetic strategies of benzimidazole molecules as tubulin polymerisation modulators in medicinal chemistry. By evaluating the structure-activity relationships, it provides valuable references for the study and development of cytotoxic agents.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Review
Medicine, Research & Experimental
Janice Jacson Mandumpala, Stephin Baby, Antriya Annie Tom, Chandraiah Godugu, Nagula Shankaraiah
Summary: Triple-negative breast cancer (TNBC) is a highly lethal subtype of breast cancer with limited treatment options due to its complexity, drug resistance, and lack of therapeutic targets. Recent studies have shown the importance of epigenetic regulation in TNBC development, with a focus on histone methyltransferases and histone demethylases as potential targets for new targeted therapies in TNBC treatment.
Article
Chemistry, Organic
Jay Prakash Soni, Manda Sathish, Fabiane M. Nachtigall, Leonardo S. Santos, Nagula Shankaraiah
Summary: The Pictet-Spengler reaction is an efficient synthetic tool for constructing tetrahydro-beta-carbolines and tetrahydroisoquinolines, with a brown seaweed-derived alginic acid reported as an effective reusable catalyst. The protocol shows good yields with various aliphatic and aromatic aldehydes, and demonstrates sustainable synthesis of different compounds including a natural spirooxindole. The catalyst was found to be reusable with no significant deterioration in reaction yields observed up to the 6th cycle.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Jay Prakash Soni, G. Nikitha Reddy, Ziaur Rahman, Anamika Sharma, Akella Spandana, Regur Phanindranath, Manoj P. Dandekar, Narayana Nagesh, Nagula Shankaraiah
Summary: In this study, a series of new beta-carboline tethered indole-3-glyoxylamide derivatives were synthesized, which showed significant pharmacological properties and prominent cytotoxicity. The compounds exhibited remarkable cytotoxicity against human cancer cell lines, especially melanoma, and showed selective toxicity towards cancer cells compared to normal cells. The compounds induced apoptosis and showed potential as DNA binders and inhibitors of Topoisomerase II. Molecular modeling studies confirmed their excellent DNA intercalation potential. In addition, in silico analysis predicted the promising drug-like properties of the synthesized derivatives.
BIOORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Kritika Laxmikeshav, Pooja Sharma, Manisurya Palepu, Pravesh Sharma, Ashutosh Mahale, Joel George, Regur Phanindranath, Manoj P. Dandekar, Onkar Prakash Kulkarni, Narayana Nagesh, Nagula Shankaraiah
Summary: A new series of carboxamide-bearing benzimidazole derivatives have been investigated for their cytotoxicity on selected human tumor cells. Compounds 10g and 10m showed selective cytotoxicity towards SK-Mel-28 skin cancer cells and were safe for human non-cancerous lung epithelial cells.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Multidisciplinary
Stephy Elza John, Anamika Sharma, Shivani Gulati, Darshana Bora, Nagula Shankaraiah
Summary: In modern medicinal chemistry, a molecular hybridization approach was used to design and synthesize a new class of cis-stilbene-based 1,2,4-triazole/1,3,4-oxadiazole conjugates. These conjugates exhibited promising cytotoxicity against selected human cancer cell lines, with cis-stilbene-based 1,2,4-triazole conjugate 5a being the most effective against the A549 cell line. Mechanistic analysis revealed that 5a induced apoptosis, DNA damage, nuclear morphological changes, and ROS generation, and exhibited G2/M phase arrest and tubulin polymerization inhibition. Additionally, 5a showed no toxicity towards normal cells and demonstrated significant anti-cancer activity.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Kritika Laxmikeshav, Mone Sayali, Geetanjali Devabattula, Durgesh G. G. Valapil, Ashutosh Mahale, Pravesh Sharma, Joel George, Regur Phanindranath, Chandraiah Godugu, Onkar P. P. Kulkarni, Narayana Nagesh, Nagula Shankaraiah
Summary: A simple click protocol was used to synthesize 1,2,3-triazole-linked benzimidazoles as potential anticancer agents, which showed significant cytotoxicity against SK-Mel-28 cancer cells and no cytotoxicity against normal BEAS-2B cells. Compound 12j inhibited cellular migration, colony formation, and induced apoptosis in SK-Mel-28 cells.
ARCHIV DER PHARMAZIE
(2023)
Article
Chemistry, Physical
Darshana Bora, Anamika Sharma, Stephy Elza John, Nagula Shankaraiah
Summary: A series of new combretastatin-oxindole derivatives were synthesized using (E)-bis(phenyl) acrylohydrazides and substituted isatins. The cytotoxic activity of these derivatives was evaluated against various cancer cell lines, and compound 9o showed potent anti-cancer activity against lung cancer cells. It induced changes in nuclear morphology and apoptosis, inhibited tubulin polymerization, and had a binding interaction with the 3E22 protein.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Biochemistry & Molecular Biology
Akash P. Sakla, Biswajit Panda, Ashutosh Mahale, Pravesh Sharma, Kritika Laxmikeshav, Mursalim Ali Khan, Onkar Prakash Kulkarni, Chandraiah Godugu, Nagula Shankaraiah
Summary: In this study, regiospecific nucleophilic ring-opening of spiroaziridine oxindoles was performed to synthesize 3-substituted-thiooxindole derivatives as anticancer agents. Among the new compounds, 7d and 9c showed promising cytotoxic activity against HCT-116 cells with IC50 values of 6.73 ± 0.36 and 6.64 ± 0.95 μM, respectively. Further studies demonstrated significant alterations in nuclear and morphological characteristics, loss of mitochondrial membrane potential, and cell cycle arrest in G2-M phase for compound 9c. In addition, compound 9c exhibited tubulin polymerase inhibition with an IC50 value of 9.73 ± 0.18 μM, supported by docking interactions with tubulin.
BIOORGANIC & MEDICINAL CHEMISTRY
(2023)
Article
Polymer Science
Moises A. Rojas, John Amalraj, Leonardo S. Santos
Summary: In this study, a two-step methodology for synthesizing small silver nanoparticles embedded into hydrogels based on chitosan and hydroxypropyl methylcellulose biopolymers is reported. The eco-friendly and cost-effective process uses d-glucose as an external green reducing agent and purified water as a solvent. Characterization of the silver nanocomposite hydrogels was performed through various techniques, and their mechanical and antibacterial properties were evaluated. The theoretical analyses provided insights into the unique structural properties of the prepared nano-scaled materials.
Article
Chemistry, Organic
Sravani Sana, Srinivas Reddy Dannarm, Ramya Tokala, Sowmya Dastari, Manda Sathish, Rahul Kumar, Rajesh Sonti, Nagula Shankaraiah
Summary: A sustainable synthetic protocol for the construction of color-tunable fluorescent molecules has been achieved via ruthenium-catalyzed multiple C-H activation/annulation. The strategy provides easy access to a library of fused heterocyclic frameworks with significant yields. A systematic investigation of photophysical properties has also been conducted for the discovery of new fluorophores.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Sravani Sana, Sowmya Dastari, Dannarm Srinivas Reddy, Ramya Tokala, Manda Sathish, Rajesh Sonti, Nagula Shankaraiah
Summary: A sustainable protocol using a photoredox-mediated dual catalytic copper/ruthenium system has been developed for the construction of unsymmetrical diarylamines. This approach allows for the easy access to medicinally relevant amines by sequentially arylating ammonia with various (hetero)aryl bromides. The resulting mono-arylated amines can undergo a copper-mediated cross-coupling with aryl boronic acids, enabling the synthesis of the tyrosine kinase inhibitor Imatinib in an eco-friendly manner.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yellaiah Tangella, Jay Prakash Soni, Nagula Shankaraiah, Diana Abril, Manda Sathish
Summary: A versatile and efficient one-pot protocol has been developed for the synthesis of amides from easily accessible carboxylic acids and amines by employing trimethylsilyl azide as a promoter at room temperature. This reaction proceeds via an in situ generated acyl azide intermediates followed by the nucleophilic substitution of amines. Notably, most of the desired amides were obtained by simple filtration in excellent yields. The significant advantages like metal-free mild reaction conditions, higher yields, easily removable volatile byproducts, operational simplicity, and broad substrate scope make the transformation a useful contribution for the synthesis of biologically important amides.
Article
Biochemistry & Molecular Biology
Jay Prakash Soni, Shrilekha Chilvery, Anamika Sharma, G. Nikitha Reddy, Chandraiah Godugu, Nagula Shankaraiah
Summary: A series of 2-((3-(indol-3-yl)-pyrazol-5-yl)imino)thiazolidin-4-ones were designed and synthesized as potential and effective chemotherapeutic agents. Compound 6c exhibited the highest cytotoxicity against melanoma cancer cells and showed selectivity towards cancer cells. It induced early-stage apoptosis, arrested cell-cycle in the G2/M phase, and inhibited tubulin polymerization. Molecular modeling studies confirmed its stable binding to tubulin and interactions with active pocket residues.
RSC MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Darshana Bora, Khan Mehtab Samir, Anamika Sharma, Shrilekha Chilvery, Sapana Bansod, Stephy Elza John, Mursalim Ali Khan, Chandraiah Godugu, Nagula Shankaraiah
Summary: In this study, a new series of cis-stilbene-1,2,3-triazole congeners were synthesized and evaluated for their potential anticancer and tubulin polymerization inhibition activity. The most active compound, 9j, showed selective cytotoxicity against colorectal cancer cells and induced apoptotic cell death. It also inhibited tubulin polymerization and exhibited G2/M phase cell cycle arrest.
RSC MEDICINAL CHEMISTRY
(2023)