Article
Chemistry, Organic
Chengwei Liu, Michal Szostak
Summary: Decarbonylative Sonogashira cross-coupling of carboxylic acids by palladium catalysis involves in situ activation of carboxylic acids to form aryl-Pd intermediate, followed by coupling with alkynes to generate new C(sp(2))-C(sp) bonds efficiently. This methodology can be applied to the derivatization of pharmaceuticals and mechanistic studies suggest the decarbonylation precedes transmetalation in this process.
Editorial Material
Chemistry, Physical
Valentine P. Ananikov
Summary: Methods for direct one-step replacement of a hydrogen atom in a C-H bond by an organic functional group can create enormous possibilities for synthetic applications. The discovery of the reaction of organopalladium complexes with olefins has opened a new era in catalysis and organic chemistry.
Article
Chemistry, Organic
Chenpeng Gao, Christopher A. Wilhelmsen, James P. Morken
Summary: Palladium-catalyzed conjunctive cross-coupling can be achieved using chiral phosphine-oxazoline based ligand structures. This reaction specifically works on Grignard-based boron ate complexes and does not require halide-scavenging additives used in other catalyst systems.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chenpeng Gao, Christopher A. Wilhelmsen, James P. Morken
Summary: Palladium-catalyzed conjunctive cross-coupling can be achieved using chiral phosphine-oxazoline ligand structures. Notably, the reaction can be performed on Grignard-based boron ate complexes without the need for halide scavenging additives required by other catalyst systems.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Dellamol Sebastian, Patrick H. Willoughby, Mahesh K. Lakshman
Summary: Cross-dehydrogenative coupling reactions were used to alkylate 4(3H)-quinazolinones with ethers and amides, with catalytic n-Bu4NI and t-BuOOH as oxidants. The reactions with amides were the first examples under these conditions. Mechanistic insights were obtained through inter- and intramolecular competitive experiments with protio and deuterio reactants, as well as radical inhibition experiments. Understanding of the relative reactivities of ethers was also achieved through pairwise competitions with 4(3H)-quinazolinone.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Reda G. Yousef, Helmy M. Sakr, Ibrahim H. Eissa, Ahmed. B. M. Mehany, Ahmed M. Metwaly, Mostafa A. Elhendawy, Mohamed M. Radwan, Mahmoud A. ElSohly, Hamada S. Abulkhair, Khaled. El-Adl
Summary: Eleven new quinoxaline derivatives were synthesized and tested against three human cancer cell lines, with compounds 11g, 11e, and 11c showing the most potent anti-proliferative activities. Compound 11g exhibited the highest potency compared to doxorubicin and sorafenib, and showed good inhibitory activity against VEGFR-2.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Kaan Karaoglu, Zehra Ozcifci, Melike Caliskan, Hakki Turker Akcay, Talat Baran
Summary: In this study, a ZnO-Pd nanocatalyst was prepared on activated carbon sourced from polymer debris for use in Heck-type coupling reactions. The hybrid material was characterized using techniques such as TEM, XRD, and BET surface area analysis. The designed hybrid catalyst exhibited a reaction yield of more than 90% in cross-coupling reactions and demonstrated remarkable stability up to 5 cycles in recycling tests.
INORGANIC CHEMISTRY COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Naoki Oku, Masahiro Murakami, Tomoya Miura
Summary: This article introduces a Suzuki-Miyaura cross-coupling reaction of alpha-chloroacetates or alpha-chloroacetamides with arylboronic acids under visible-light irradiation, providing a mild method for the synthesis of alpha-arylacetates and alpha-arylacetamides. Additionally, the authors successfully synthesized a key intermediate of the plant hormone auxin, indole-3-acetic acid derivative, from 1-Boc-indole in two steps by combining an iridium-catalyzed C-H borylation and a palladium-catalyzed cross-coupling reaction.
Article
Chemistry, Organic
Ravuri Srinath, Arindam Manna, Subhankar Shee, Vijay Babu Pathi, Saswati Ghosh, Krishnendu Khamaru, Nakul Chandra Maiti, Biswadip Banerji
Summary: A one-pot protocol for synthesizing tetracyclic triazole-piperazine-quinazolinone-fused N-heterocyclic scaffolds is reported, utilizing tandem click and cross-dehydrogentive coupling reactions with high atom economy. The method is highly functional group tolerable and has a broad substrate scope, with some derivatives showing strong white solid-state fluorescence.
Article
Chemistry, Physical
Chiara Palladino, Tommaso Fantoni, Lucia Ferrazzano, Beatrice Muzzi, Antonio Ricci, Alessandra Tolomelli, Walter Cabri
Summary: The copper-free Heck-Cassar-Sonogashira (HCS) reaction is a powerful method for C-C bond formation in organic synthesis and has several industrial applications. This study investigated the mechanism of the copper-free HCS reaction by conducting stoichiometric and catalytic reactions and analyzing the role of the base. The results showed that the base can accelerate the reduction of the precatalyst and decrease the energy barrier for the alkyne carbopalladation step.
Article
Chemistry, Multidisciplinary
Tommaso Fantoni, Sara Bernardoni, Alexia Mattellone, Giulia Martelli, Lucia Ferrazzano, Paolo Cantelmi, Dario Corbisiero, Alessandra Tolomelli, Walter Cabri, Federica Vacondio, Francesca Ferlenghi, Marco Mor, Antonio Ricci
Summary: The use of N-hydroxyethylpyrrolidone (HEP)/water/N,N,N',N'-tetramethyl guanidine (TMG) as solvent/base mixture and sulfonated phosphine ligands in the Heck-Cassar and Sonogashira protocols allows for high yields and fast conversion under mild conditions, with the catalyst being recyclable without leakage or metal contamination.
Article
Chemistry, Multidisciplinary
Yifan Wang, Yuanyuan Ping, Wangqing Kong
Summary: A cooperative Pd/Cu-catalyzed three-component cross-coupling reaction of alkynes, B 2 Pin 2 and alkenetethered aryl halides is reported. This reaction proceeds under mild conditions and shows broad substrate scope, providing a variety of heterocycles containing tetrasubstituted alkenylboronate moieties in synthetically useful yields with excellent chemoselectivity and regioselectivity. An enantioselective cascade cyclization/cross-coupling process has also been developed for the synthesis of enantiomerically enriched oxindole bearing a tetrasubstituted alkenylboronate moiety.
CHINESE CHEMICAL LETTERS
(2023)
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
Xin-Xing Wu, Hao Ye, Guomin Jiang, Lanping Hu
Summary: This study describes a palladium-catalyzed domino Heck cyclization/Hiyama coupling reaction where the sigma-alkylpalladium intermediate is trapped with arylsilanes. A wide range of aryl-tethered alkenes and arylsilanes are compatible with the reaction conditions, showing good yields and excellent functional group tolerance. This approach presents a more practical and sustainable alternative to the conventional domino Heck cyclization/Suzuki coupling reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Integrative & Complementary Medicine
Haleh Forouhandeh, Vahideh Tarhriz, Masoumeh Zadehkamand, Parina Asgharian
Summary: The cytotoxicity and mortality mechanisms of Artemisia marschalliana essential oil and extracts were investigated in this study. The results showed that the 60% dichloromethane extract exhibited the strongest cytotoxicity on breast cancer cells, while the 80% fraction showed the most cytotoxicity on liposarcoma cancer cells. Flow cytometry analysis confirmed the apoptosis mechanism in killing cancer cells. Additionally, the essential oil of Artemisia marschalliana showed considerable cytotoxic properties.
BMC COMPLEMENTARY MEDICINE AND THERAPIES
(2023)
Article
Chemistry, Medicinal
Saleha Banu, Rajitha Bollu, Rajashaker Bantu, Lingaiah Nagarapu, Sowjanya Polepalli, Nishant Jain, Radhika Vangala, Vijjulatha Manga
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2017)
Article
Chemistry, Medicinal
Suresh Kasaboina, Venkatesh Ramineni, Saleha Banu, Yadagiri Bandi, Lingaiah Nagarapu, Naresh Dumala, Paramjit Grover
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2018)
Article
Chemistry, Medicinal
Saleha Banu, Rajitha Bollu, Mohammad Naseema, P. Mary Gomedhika, Lingaiah Nagarapu, K. Sirisha, C. Ganesh Kumar, Shravan Kumar Gundasw
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2018)
Article
Biochemistry & Molecular Biology
Hanmanth Reddy Vulupala, Yasodakrishna Sajja, Pankaj K. Bagul, Raviteja Bandla, Lingaiah Nagarapu, Sanjay K. Benerjee
BIOORGANIC CHEMISTRY
(2018)
Article
Biochemistry & Molecular Biology
Saleha Banu, Rajitha Bollu, Lingaiah Nagarapu, Jagadeesh Babu Nanubolu, Perumal Yogeswari, Dharmarajan Sriram, Shravan Kumar Gunda, Divyasphoorthi Vardhan
CHEMICAL BIOLOGY & DRUG DESIGN
(2018)
Article
Chemistry, Organic
Suresh Kasaboina, Rajitha Bollu, P. Mary Gomedhika, Venkatesh Ramineni, Lingaiah Nagarapu, Naresh Dumala, Paramjit Grover, Jagadeesh Babu Nanubolu
TETRAHEDRON LETTERS
(2018)
Article
Chemistry, Physical
Suresh Kasaboina, Rajitha Bollu, Venkatesh Ramineni, P. Mary Gomedhika, Kavitha Korra, Sai Roopika Basaboina, Uma Devi Holagunda, Lingaiah Nagarapu, Naresh Dumala, Paramjit Grover, Raju Bathini, M. Vijjulatha
JOURNAL OF MOLECULAR STRUCTURE
(2019)
Article
Chemistry, Physical
Ramineni Venkatesh, Suresh Kasaboina, Nishant Jain, Sridhara Janardhan, Uma Devi Holagunda, Lingaiah Nagarapu
JOURNAL OF MOLECULAR STRUCTURE
(2019)
Article
Chemistry, Medicinal
Satheeshvarma Vanaparthi, Rajashaker Bantu, Nishant Jain, Sridhara Janardhan, Lingaiah Nagarapu
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Chemistry, Medicinal
Rajitha Bollu, Saleha Banu, Suresh Kasaboina, Rajashaker Bantu, Lingaiah Nagarapu, Sowjanya Polepalli, Nishant Jain
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2017)
Article
Chemistry, Medicinal
Rajitha Bollu, Saleha Banu, Rajashaker Bantu, A. Gopi Reddy, Lingaiah Nagarapu, K. Sirisha, C. Ganesh Kumar, Shravan Kumar Gunda, Kamal Shaik
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2017)
Article
Chemistry, Medicinal
Yasodakrishna Sajja, Sowmya Vanguru, Hanmanth Reddy Vulupala, Rajashaker Bantu, Perumal Yogeswari, Dharmarajan Sriram, Lingaiah Nagarapu
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2017)
Article
Biochemistry & Molecular Biology
Yasodakrishna Sajja, Sowmya Vanguru, Hanmanth Reddy Vulupala, Lingaiah Nagarapu, Yogeswari Perumal, Dharmarajan Sriram, Jagadeesh Babu Nanubolu
CHEMICAL BIOLOGY & DRUG DESIGN
(2017)
Article
Chemistry, Medicinal
Sowmya Vanguru, Lavanya Jilla, Yasodakrishna Sajja, Rajashaker Bantu, Lingaiah Nagarapu, Jagadeesh Babu Nanubolu, Bala Bhaskar, Nishant Jain, Sreekanth Sivan, Vijjulatha Manga
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2017)
Article
Chemistry, Medicinal
Ramineni Venkatesh, Suresh Kasaboina, Deepthi Bidayat, Nikhil U. Kumar, Nishant Jain, Saritha Jostna Tangeda, Rajashaker Bantu, Sridhara Janardhan, Lingaiah Nagarapu
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2017)
Article
Chemistry, Medicinal
Shibin Zhao, Julian Maceren, Mia Chung, Samantha Stone, Raphael Geiben, Melissa L. Boby, Bradley S. Sherborne, Derek S. Tan
Summary: Antibiotic resistance is a major threat to public health, with Gram-negative bacteria presenting unique challenges due to their low permeability and efflux pumps. Limited understanding of the chemical rules for overcoming these barriers hinders antibacterial drug discovery. Efforts to address this issue, such as screening compound libraries and using cheminformatic analysis, have led to the design of sulfamidoadenosines with diverse substituents, showing potential utility in accumulation in Escherichia coli.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Jichun Li, Qing Li, Shuai Xia, Jiahuang Tu, Longbo Zheng, Qian Wang, Shibo Jiang, Chao Wang
Summary: This study successfully developed a short peptide mimetic as a MERS-CoV fusion inhibitor by reproducing the key recognition features of the HR2 helix. The resulting 23-mer lipopeptide showed comparable inhibitory effect to the 36-mer HR2 peptide HR2P-M2. This has important implications for developing short peptide-based antiviral agents to treat MERS-CoV infection.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Krista Jaunsleine, Linda Supe, Jana Spura, Sten van Beek, Anna Sandstrom, Jessica Olsen, Carina Halleskog, Tore Bengtsson, Ilga Mutule, Benjamin Pelcman
Summary: Beta(2)-adrenergic receptor agonists can stimulate glucose uptake by skeletal muscle cells and are therefore potential treatments for type 2 diabetes. The chirality of compounds has a significant impact on the activity of these agonists. This study found that certain synthesized compounds showed higher glucose uptake activity. These findings provide important information for the design of novel beta(2)AR agonists for T2D treatment.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Xin Xu, Jia Chen, Guan Wang, Xiaojuan Zhang, Qiang Li, Xiaobo Zhou, Fengying Guo, Min Li
Summary: The study focuses on EZH2, a promising therapeutic target for various types of cancers. Researchers designed and synthesized a series of novel derivatives aiming to enhance the EZH2 inhibition activity. Among them, compound 28 displayed potent EZH2 inhibition activity and showed high anti-proliferative effects in lymphoma cell lines and xenograft mouse models. The study suggests that compound 28 has potential as a therapeutic candidate for EZH2-associated cancers.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Wei Zhang, Wei Liu, Ya-Dong Zhao, Li-Zi Xing, Ji Xu, Rui-Jun Li, Yun-Xiao Zhang
Summary: This study developed a series of aromatic amide derivatives based on Rhein and investigated their inhibitory activity against alpha-Syn aggregation. Two of these compounds showed promising potential in treating Parkinson's disease by stabilizing alpha-Syn's conformation and disassembling alpha-Syn oligomers and fibrils.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Mani Sharma, S. S. S. S. Sudha Ambadipudi, Neeraj Kumar Chouhan, V. Lakshma Nayak, Srihari Pabbaraja, Sai Balaji Andugulapati, Ramakrishna Sistla
Summary: Therapeutically active lipids in drug delivery systems can enhance the safety and efficacy of treatment. The liposome formulation created using synthesized biologically active lipids showed additive anti-cancer effects and reduced tumorigenic potential.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)