Article
Chemistry, Physical
Giorgio Molteni, Alessandro Ponti
Summary: In this study, the accuracy of predicting the regioselectivity of uncatalyzed thermal azide 1,3-DCs using DFT calculations was investigated. Benchmark data was established and compared with results obtained using density functional approximations (DFAs). The study identified the key features for accurate regioselectivity and suggested potential improvements for future research.
Article
Biochemistry & Molecular Biology
Dmitriy D. Karcev, Mariia M. Efremova, Alexander P. Molchanov, Nikolai Rostovskii, Mariya A. Kryukova, Alexander S. Bunev, Dmitry A. Khochenkov
Summary: In this study, new highly functionalized 5-spiroisoxazolidines were synthesized through the 1,3-dipolar cycloaddition reaction, which showed good selectivity. The reversibility of these reactions allows for controlling the diastereoselectivity of cycloaddition. Additionally, the reduction reaction of the obtained adducts provides 1,3-aminoalcohols or spirolactones.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Guangjun Bao, Peng Wang, Guofeng Li, Changjun Yu, Yiping Li, Yuyang Liu, Zeyuan He, Tiantian Zhao, Jing Rao, Junqiu Xie, Liang Hong, Wangsheng Sun, Rui Wang
Summary: A new method for 1,3-dipolar cycloaddition reactions between different types of amino acids to generate various quaternary amino acids was disclosed in this study. This method can also be applied within peptide chains, providing a new approach for late-stage peptide modification and drug conjugation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Andrey Bubyrev, Ksenia Malkova, Grigory Kantin, Dmitry Dar'in, Mikhail Krasavin
Summary: A three-component synthesis of 1,5-disubstituted 1,2,3-triazoles can be achieved from alpha-acetyl-alpha-diazomethane sulfonamides, primary aliphatic amines, and aromatic aldehydes. The synthesis can proceed in two alternative variants based on the substitutions in the diazo reagent. Depending on the variant, the intermediates are either isolated and subjected to aromatization, or both transformations take place in a single step at room temperature.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kelvin J. Y. Wu, Amy E. Benedetto, Andrew G. Myers
Summary: The regioselectivity of a [3+2] dipolar cycloaddition reaction between a stabilized azomethine ylide and an electron-deficient dipolarophile is contrary to a previous report in this journal.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Javier E. Alfonso-Ramos, Ruben Van Lommel, David Hernandez-Castillo, Frank De Proft, Roy Gonzalez-Aleman, Erik V. Van der Eycken, Gerardo M. Ojeda-Carralero
Summary: 3-Dipolar cycloadditions are commonly used to form five-membered heterocycles, but the cycloadditions involving acyl-isocyanide ylides have not been well explored by the chemical community. In this study, we investigated the mechanistic features of the reaction between acyl-isocyanide ylides and dipolarophiles using density functional theory calculations. We explained the experimental results and predicted opposite regioselectivity for electron-poor and electron-rich dipolarophiles. This study provides insights for the design of new cycloaddition reactions based on the acyl-isocyanide ylides motif.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shandev Pookkandam Parambil, Santhini Pulikkal Veettil, Wim Dehaen
Summary: Cycloaddition reactions are rapid and powerful tools for constructing heterocycles and carbocycles. The [3+2] cycloadditions of nitroalkenes with various 1,3-dipoles are particularly interesting to organic chemists, leading to the synthesis of N-substituted and NH-1,2,3-triazoles and other five-membered N-heterocycles.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Inorganic & Nuclear
Daniel Vogler, Maurice Schenker, Kim Hao Ng, Elisabeth Kaifer, Hans-Jorg Himmel
Summary: Metal-free cycloaddition reactions can be used to synthesize new ditriazolyl-diborane molecules and can be applied as polydentate ligands for the synthesis of larger architectures. These ditriazolyl-diboranes can also be applied in coordination chemistry as ligands.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Thomas Abegg, Janine Cossy, Christophe Meyer
Summary: cis-1,2-Dialkenylcyclopropanes with a vinyl azide group were generated by Knoevenagel condensations and underwent cascade Cope and Winstein [3,3]-sigmatropic rearrangements under mild conditions. This reaction sequence allows for the synthesis of diversely substituted 1,4-cycloheptadienes with a secondary allylic azide containing up to three stereocenters.
Article
Chemistry, Organic
Asif Ali Qureshi, Arpula Sanjeeva Kumar, Sachin Chauhan, K. C. Kumara Swamy
Summary: This method provides a regio- and stereoselective thermal [3+2] cycloaddition protocol for the synthesis of 1,4,5-tri/1,5-disubstituted 1,2,3-triazoles using acetoxy allenoates as 1,2-dipoles. Different carbon positions of acetoxy allenoates lead to different triazole cores with good to high yields.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Sergey A. Cherkasov, Anastasiya D. Semikina, Polina M. Kaletina, Yulia F. Polienko, Denis A. Morozov, Alexander M. Maksimov, Igor A. Kirilyuk, Elena G. Bagryanskaya, Dmitriy A. Parkhomenko
Summary: The study investigated the kinetics of reactions between 11 different vinyl monomers and nitroxide- and alkoxyamine-containing aldonitrones, determining activation energies and pre-exponential factors. The influence of monomer structure on the rate of 1,3-dipolar cycloaddition was discussed, with different vinyl monomers showing varying rates of reaction.
Article
Chemistry, Organic
Jian-Bin Lu, Shu-Yuan Liang, Wu-Tao Gui, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: A relay catalytic protocol utilizing pyrrolidine and palladium catalysis has been developed for the asymmetric synthesis of 1,3-diamine derivatives from 3-substituted 1,3-dienes, sulfuric diamide, and aldehydes. This one-pot, three-component reaction offers the advantages of high atom step economy and operational simplicity, providing an efficient and straightforward access to valuable 1,3-diamines containing quaternary and tertiary stereogenic centers with moderate to good enantioselectivity.
Article
Chemistry, Organic
Jing Wang, Qian Yu, Zheng Wang, Zheteng Zhang, Linghui Zeng, Chong Zhang, Huajian Zhu, Jiaan Shao, Jiankang Zhang
Summary: A metal-free method for synthesizing 1-N-substituted 1,2,3-triazole-4-carboxamide derivatives was developed using azides, HFO-1233zd(E), and amines in an aqueous reaction medium. The reaction involved the defluorinative functionalization of the C(sp(3))-F bond in the trifluoromethyl group into amides.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Padmini C. Panjikar, Soumik Saha, Amrita Chatterjee, Mainak Banerjee
Summary: A catalyst-free and sustainable microwave method has been developed for the quick access to a diverse range of bridged bicyclo aza-sulfones from various aldehydes in one-pot. This method enables a clean reaction profile, easy work-up and high yields.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Francisco V. Gaspar, Marcelo F. M. F. Azevedo, Leonardo S. A. Carneiro, Samuel B. Ribeiro, Pierre M. Esteves, Camilla D. Buarque
Summary: This study reports the synthesis of new 4-acyl-1,2,3-triazoles through metal-free and solvent-free cycloaddition reactions, achieving high yields. The reaction mechanism for the synthesis of 4-acyl-1,2,3-triazoles was proposed based on experimental and theoretical data.
Article
Biochemistry & Molecular Biology
Shibaji Ghosh, Kalyanashis Jana, Padmaja D. Wakchaure, Bishwajit Ganguly
Summary: Galantamine, an approved drug for the treatment of mild to moderate Alzheimer's disease, acts by inhibiting the degradation of acetylcholine (ACh) through the separation of the catalytic triad of hAChE in the enzyme gorge. This study provides insights into the inhibition mechanism of hAChE by galantamine and its impact on ACh degradation process.
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS
(2022)
Article
Biochemical Research Methods
Padmaja D. Wakchaure, Bishwajit Ganguly
Summary: Riboswitches are metabolite-sensing structures that can regulate gene expression, and the thiamine pyrophosphate (TPP) riboswitch is a new target for antibiotic development. Experimental findings show that different ligands can similarly repress gene expression while inducing conformational changes that affect binding affinity and efficacy.
JOURNAL OF MOLECULAR GRAPHICS & MODELLING
(2021)
Article
Biochemical Research Methods
Tulsi R. Patel, Bishwajit Ganguly
Summary: This study utilized adamantane as a FLP molecular scaffold to design new FLP (ambiphilic molecule) for metal-free catalytic reduction of CO2 to methoxy borane. Compared to unsaturated phenylene FLPs, the saturated adamantane scaffold FLP showed improved Lewis acid and base characters, as well as lowered energy barriers in the reduction process.
JOURNAL OF MOLECULAR GRAPHICS & MODELLING
(2022)
Article
Chemistry, Organic
Manas Jyoti Sarma, Sana Jindani, Bishwajit Ganguly, Srihari Pabbaraja, Goverdhan Mehta
Summary: An efficient protocol for the synthesis of orthogonally strap diynones through one pot transition-metal-free reaction has been developed. Insights into the regioselective tandem Michael-anti-Michael processes have been gleaned through DFT calculations.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Padmaja D. Wakchaure, Bishwajit Ganguly
Summary: This study reveals the importance of pi-stacking energy and the ring size in the ligand binding of the TPP riboswitch. Ligands with higher pi-stacking energy and larger rings have a weaker ability to displace the radiolabeled thiamine from the riboswitch. Larger dispersive interactions and hydrogen-bonding interactions contribute to stabilizing the binding and enhancing the affinity of the ligand with the riboswitch.
JOURNAL OF PHYSICAL CHEMISTRY B
(2022)
Article
Chemistry, Physical
Padmaja D. Wakchaure, Bishwajit Ganguly
Summary: The FMN riboswitch is a potential drug target for new antibiotics, and the neutral ligand 5FDQD has shown activity against Clostridium difficile infection. Computational simulations revealed that the fluorine atom on the phenyl ring in 5FDQD plays a crucial role in enhancing its binding affinity with the FMN riboswitch.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2022)
Article
Chemistry, Physical
Surjit Bhai, Bishwajit Ganguly
Summary: Hexagonal boron nitride (h-BN) sheets have high affinity towards DNA/RNA and can be used as a sensing platform. The absorption and emission properties of DNA nucleobases on h-BN and Al_hBN sheets were studied, showing different adsorption trends at the same level of theory. The van der Waals interactions significantly contribute to the adsorption of nucleobases on h-BN sheets, while electrostatic interactions were revealed between nucleobases and the Al_hBN sheet. The quenching phenomenon of nucleobase-tagged fluorophores was also investigated, showing potential for sequence-specific phenomenon detection.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2022)
Article
Chemistry, Organic
Kumares Sarkar, Tanmaya Pathak
Summary: Terminal vinyl sulfones derived from styrene epoxide and monomesylated glycerol were reacted with benzylazide in a metal-free condition to regioselectively obtain 1,4-disubstituted 1,2,3-triazoles via Eliminative Azide-Olefinic Cycloaddition (EAOC) reactions. The use of a N, N-dimethyl ethanolammonium formate-water mixture significantly reduced reaction time and increased yield. Furthermore, the reaction of azido sugars with terminal vinyl sulfone modified carbohydrates yielded 1,4-disubstituted 1,2,3-triazole linked bissacharides, providing a potential route for direct connection of carbon units to sugar bodies.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Anusuya Saha, Bishwajit Ganguly
Summary: In this work, the lower stability of dyes containing cyanoacrylic acid anchoring group on the semiconductor surface was reported. Calculations and experiments were performed to design and analyze a series of new dyes, and one of them showed good optical properties and stability, which is promising for application in dye-sensitized solar cells.
JOURNAL OF MOLECULAR MODELING
(2022)
Article
Chemistry, Organic
Aniket Gupta, Anusuya Saha, Ajijur Rahaman, Jogendra Kumar, Eringathodi Suresh, Bishwajit Ganguly, Sukalyan Bhadra
Summary: A monoprotected amino acid Bz-Gly-OH plays a assisting role in the allylic alkylation of various compounds during enamine-palladium catalysis. Density functional theory calculations suggest that Bz-Gly-OH assists in the formation of an enamine which attacks the pi-allylpalladium complex through an outer sphere mechanism. The preliminary result indicates an asymmetric allylic alkylation under a new mode of bifunctional catalysis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Ashrukana Das, Swagata Dasgupta, Tanmaya Pathak
Summary: This study demonstrates the design and screening of a new class of benzene-based triazolylated semicircular hybrid molecules as ribonuclease A inhibitors. The addition of a carboxylic acid group at the C1-position of the 1,3,5-trisubstituted benzene ring and the reduction of arm lengths of 3,5-substituents enhance the inhibitory properties significantly.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Pampa Mondal, Swagata Dasgupta, Tanmaya Pathak
Summary: Molecular docking studies showed that N-1,4-disubstituted-1,2,3-triazole tethered carboxymethylated thymidine and uridine can potentially bind to the P1, B1, and P2 subsites of ribonuclease A. The findings from this study, combined with previous experimental observations, were used to guide the design of a range of 1,4-disubstituted 1, 2, 3-triazole tethered carboxymethylated pyrimidine nucleosides.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Shuvankar Dey, Anshu Kumar, Pradip Kumar Mondal, Deepak Chopra, Rupam Roy, Sana Jindani, Bishwajit Ganguly, Chaithra Mayya, Dhiraj Bhatia, Vinod K. Jain
Summary: Globally, 3 billion people are consuming water with moderately high concentrations of fluoride and arsenic. The development of a simple point of care device or home device for the detection of fluoride/arsenic ensures safety before consuming water. An aluminium complex of rhodamine B functionalized oxacalix[4]arene (L) was designed as a recyclable probe for the detection of aqueous fluoride and arsenate with good consistency in performance. The device was tested with water samples, synthetic fluoride standards, dental care products, and achieved successful in-vitro sensing.
SCIENTIFIC REPORTS
(2022)
Article
Chemistry, Organic
Aniket Gupta, Anusuya Saha, Ajijur Rahaman, Jogendra Kumar, Eringathodi Suresh, Bishwajit Ganguly, Sukalyan Bhadra
Summary: A monoprotected amino acid Bz-Gly-OH is found to assist in the asymmetric allylic alkylation reaction by enaminepalladium catalysis, attacking the pi-allylpalladium complex through an outer sphere mechanism. This discovery potentially offers a new mode of bifunctional catalysis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Nanoscience & Nanotechnology
Sanjay Yadav, Nishu Choudhary, Surjit Bhai, Gopal Bhojani, Shruti Chatterjee, Bishwajit Ganguly, Alok R. Paital
Summary: The development of a recyclable fluorogenic napthalimide-based functionalized mesoporous silica material (SiO2@NBDBIA) for selective sensing and removal of oxoanions has shown low detection limits and high adsorption capacities for CrO42-, Cr2O72-, and MnO4- ions. The material demonstrates reversible hydrogen-bonded binding with oxoanions, enabling its recyclability, and has been successfully used as a fluorescence probe for detecting oxoanions in water samples and living organisms.
ACS APPLIED BIO MATERIALS
(2021)
