Article
Chemistry, Organic
Baptiste Picard, Takahide Fukuyama, Ilhyong Ryu
Summary: An improved carbonylation method for amide bond formation between aryl iodides and aromatic amines is presented, which does not require a phosphine ligand unlike conventional Pd catalysis. The catalyst system consists of bis(dibenzylideneacetone)palladium (0.5 mol %) and DBU (10 mol %). This method allows the synthesis of various aromatic amides and can be scaled to gram order synthesis under low carbon monoxide pressure.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dmitrii Kalinin, Trond Ulven
Summary: A chemoselective Pd-mediated carbonylative Negishi-type catalytic protocol for the synthesis of (hetero)-aryl ketones is described. The protocol utilizes the PEPPSI-IPr precatalyst and CO gas at atmospheric pressure to facilitate the carbonylative coupling between various C-(sp3)-hybridized organozinc reagents and a wide range of aryl iodides, including substrates with aldehyde, aniline, phenol, or carboxylic acid groups, and heteroaryls.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Pan Pan, Shihan Liu, Yu Lan, Huiying Zeng, Chao-Jun Li
Summary: A visible-light-induced, transition-metal and photosensitizer-free cross-coupling of aryl iodides with hydrazones was developed. Hydrazones were used as alternatives to organometallic reagents, making this cross-coupling mild and green. Mechanistic investigations revealed the formation of an electron donor-acceptor complex, generating an aryl radical via single-electron transfer.
Article
Chemistry, Organic
Che-Ming Hsu, Shao-Chi Lee, Hao-En Tsai, Yong-Ting Tsao, Cheng-Lin Chan, Shinje Minoza, Zong-Nan Tsai, Li-Yun Li, Hsuan-Hung Liao
Summary: In this study, we successfully activated the C-S bond in sp(3)-hybridized thiols by introducing a per-/polyfluoroaryl moiety, enabling the efficient removal of sulfur groups and the generation of aliphatic radicals that can react with aryl halides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Guoqing Yang, Yanwei Wang, Youai Qiu
Summary: A nickela-electrocatalyzed cross-electrophile coupling of aryl aziridines and aryl bromides has been developed to access synthetic useful beta-arylethylamines under mild and sustainable electrochemical conditions. This protocol exhibits excellent chemo- and regioselectivity, broad substrate scope, and good functional group compatibility. Mechanistic studies have confirmed that the observed regioselectivity and reactivity are due to the electro-induced ring-opening of aziridines to generate a benzyl radical intermediate as the active species. Furthermore, this strategy enables the cross-coupling with CO2 to access beta-amino acids under mild conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Xuan-Di Song, Meng-Meng Guo, Shuang Xu, Chuanji Shen, Xiaocong Zhou, Xue-Qiang Chu, Mengtao Ma, Zhi-Liang Shen
Summary: A nickel-catalyzed direct reductive cross-coupling of disubstituted cycloalkyl iodides with aryl iodides was developed, allowing for efficient stereocontrolled synthesis of a variety of cross-coupled products with high diastereoselectivity and wide functional group tolerance. The one-pot reaction is simple to operate, providing a convenient method for the synthesis of complex molecules.
Article
Chemistry, Organic
Dattatraya H. Dethe, Nagabhushana C. Beeralingappa, Amar Uike
Summary: This reaction method utilizes an oxidative cross-coupling reaction between activated olefins and vinyl boronate derivatives to selectively construct (E,E)-1,3-dienes under mild conditions without the need for a base or ligand. The reaction achieves exclusive stereoselectivity for the E,E-isomer using a less expensive [RuCl2(p-cymene)](2) catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Avishek Das, Nitin T. Patil
Summary: Reported in this study is a ligand-enabled gold-catalyzed C(sp2)-O cross-coupling reaction between aryl iodides and aliphatic alcohols. The usefulness of the method is demonstrated by successfully synthesizing a variety of aryl alkyl ethers, including complex biomolecules and medicinally relevant motifs. The importance of gold catalysis is highlighted by overcoming the selectivity issues commonly observed when other transition metals are used as catalysts for C-O cross-coupling reactions.
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, Physical
Avishek Das, Nitin T. Patil
Summary: A ligand-enabled gold-catalyzed C(sp2)-O cross-coupling reaction between aryl iodides and aliphatic alcohols is reported. The method is demonstrated to be useful for the synthesis of various aryl alkyl ethers, including complex biomolecules and medicinally relevant motifs. The importance of gold catalysis is highlighted in overcoming selectivity issues observed with other transition metal catalysts in C-O cross -coupling reactions.
Article
Chemistry, Organic
Xianqiang Kong, Yiyi Chen, Xiaohui Chen, Zheng-Xuan Lu, Wei Wang, Shao-Fei Ni, Zhong-Yan Cao
Summary: By combining electrocatalysis and nickel catalysis, a unified strategy has been applied to successfully achieve the decarboxylative cross-coupling of four types of alpha-oxocarboxylic acids and their derivatives with aryl trimethylammonium salts under mild conditions. Our strategy provides a practical way for preparing aryl ketones, amides, esters, or aldehydes.
Article
Chemistry, Organic
Regina M. Oechsner, Ivo H. Lindenmaier, Ivana Fleischer
Summary: We present a nickel catalyzed C-S cross-coupling reaction of aryl and alkenyl triflates with alkyl thiols. By using an air-stable nickel precatalyst, various thioethers could be synthesized under mild reaction conditions within a short reaction time. The reaction demonstrated a broad substrate scope, including pharmaceutically relevant compounds.
Article
Biochemistry & Molecular Biology
Aleksandra Blocka, Wojciech Chaladaj
Summary: We report a new method for the synthesis of highly substituted vinylidenecyclopentanes with good yields, complete selectivity, and excellent functional group tolerance. The mechanism involves the oxidative addition of bromoarene to Pd(0), followed by cyclization and reductive elimination. The high regio- and stereoselectivity can be attributed to the 5-exo-dig intramolecular addition of the enol form of the substrate to alkyne activated by the pi-acidic Pd(II) center.
Article
Chemistry, Organic
Jessica S. Graham, James H. Hunter, Michael J. Waring
Summary: DNA-encoded libraries are efficient for identifying ligands for protein targets, and incorporating arylamines is desirable. By applying micellar technology to DNA chemistry for the Buchwald-Hartwig reaction, a robust method for synthesizing DNA-conjugated aryl and heteroarylamines has been developed.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ladie Kimberly de la Cruz, Nicola Bauer, Alyssa Cachuela, Wing Sze Tam, Ravi Tripathi, Xiaoxiao Yang, Binghe Wang
Summary: A low-molecular-weight, solid CO surrogate that can release 2 equiv of CO with low-power LED activation is described. This surrogate can be widely used in various palladium-catalyzed carbonylative transformations and is compatible with protocols using blue-light activation for nonactivated alkyl halides. Additionally, the photolabile CO releasing scaffold can be incorporated into polymeric materials, resulting in the creation of new materials with CO-releasing capabilities.
Review
Biochemistry & Molecular Biology
Vishal Payyalot Koyiparambath, Krishnendu Prayaga Rajappan, T. M. Rangarajan, Abdullah G. Al-Sehemi, Mehboobali Pannipara, Vaishnav Bhaskar, Aathira Sujathan Nair, Sachithra Thazhathuveedu Sudevan, Sunil Kumar, Bijo Mathew
Summary: In recent years, Monoamine oxidase (MAO) has become a target for treating neurodegenerative diseases such as anxiety, depression, Alzheimer's, and Parkinson's diseases. Coumarins, known for their ease of synthesis, high therapeutic potential, and reversibility in inhibiting MAOs, are considered potent scaffold among several classes of inhibitors. This review focuses on the research in this field from 2014 to 2020, with a major emphasis on the structure-activity relationship of coumarin derivatives.
CHEMICAL BIOLOGY & DRUG DESIGN
(2021)
Article
Biochemical Research Methods
Bijo Mathew, Chonny Herrera-Acevedo, Sanal Dev, T. M. Rangarajan, Mohamed Saheer Kuruniyan, Punnoth Poonkuzhi Naseef, Luciana Scotti, Marcus Tullius Scotti
Summary: This study investigated and analyzed chalcone derivatives with potential reversible MAO-B inhibitory activity through experimental and theoretical approaches, revealing the relevant factors and models for MAO-B inhibition.
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING
(2022)
Review
Chemistry, Medicinal
T. M. Rangarajan, Bijo Mathew
Summary: Pyrazolines are five-membered heterocyclic compounds with two nitrogen atoms, serving as a privileged scaffold for diverse bioactive compounds. Synthesized from chalcones and hydrazine derivatives, they can greatly enhance physicochemical and pharmacological properties, particularly for CNS-related issues such as neurodegenerative disorders.
CURRENT TOPICS IN MEDICINAL CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Nisha Abdul Rehuman, Abdullah G. Al-Sehemi, Della Grace Thomas Parambi, T. M. Rangarajan, Orazio Nicolotti, Hoon Kim, Bijo Mathew
Summary: This review focuses on recent advances in quinazoline derivatives as inhibitors of AChE and MAO, highlighting their molecular determinants and structure-activity relationships on AChE and MAO inhibitory potencies.
Article
Chemistry, Physical
Jong Min Oh, T. M. Rangarajan, Reeta Chaudhary, Nicola Gambacorta, Orazio Nicolotti, Sunil Kumar, Bijo Mathew, Hoon Kim
Summary: A panel of chalcone derivatives were evaluated for their inhibitory activities, and HC6 was found to be the most potent inhibitor of MAO-B. HC3 and ACE7 also showed high inhibitory activity. These findings suggest that HC3 and HC6 hold promise as potential candidates for neurological disorder treatments.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Review
Chemistry, Medicinal
Sachithra T. Sudevan, T. M. Rangarajan, Abdullah G. Al-Sehemi, Aathira S. Nair, Vishal P. Koyiparambath, Bijo Mathew
Summary: This review article focuses on the potential application of monoamine oxidase (MAO) inhibitors in the treatment of neurological disorders. It provides a comprehensive summary of the innovative conceptual prospects, chemistry, and bioactivity of MAO inhibitors. The benzyloxy moiety attached to various scaffolds has been identified as a pivotal component in the inhibition of MAO.
ARCHIV DER PHARMAZIE
(2022)
Review
Engineering, Chemical
Aathira Sujathan Nair, Ashutosh Kumar Singh, Astik Kumar, Sunil Kumar, Sunitha Sukumaran, Vishal Payyalot Koyiparambath, Leena K. Pappachen, T. M. Rangarajan, Hoon Kim, Bijo Mathew
Summary: As people around the world consider 2020 as the year dominated by COVID-19, the medical community acknowledges it as one of the most successful years for drug approvals by the FDA, along with 1996. Both years witnessed the approval of 53 new drug molecules. In 2020, 53 new chemical entities and 13 biological medicines were approved, with a significant number of them containing fluorine or fluorine-containing functional groups and exhibiting diverse pharmacological activities.
Article
Biochemistry & Molecular Biology
Bijo Mathew, Veerasamy Ravichandran, Seenivasan Raghuraman, T. M. Rangarajan, Mohamed A. Abdelgawad, Iqrar Ahmad, Harun M. Patel, Hoon Kim
Summary: This study utilized candidates generated from unsaturated ketone as potent, reversible, and specific MAO-B inhibitors, and identified several compounds with potential MAO-B inhibitory activity in the micro- to nanomolar range through the synthesis and evaluation of aldoxime-chalcone ethers and hydroxylchalcones. Molecular descriptors such as ETA Shape P and MDEO-12 were found to play significant roles in MAO-B inhibition, suggesting the possibility of creating potential chalcone-based MAO-B inhibitors with the current 2D QSAR models. Further analysis of lead molecules was conducted through detailed molecular dynamics study to confirm the stability of the ligand-enzyme complex.
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS
(2023)
Article
Multidisciplinary Sciences
Sachithra Thazhathuveedu Sudevan, Jong Min Oh, Mohamed A. Abdelgawad, Mohammed A. S. Abourehab, T. M. Rangarajan, Sunil Kumar, Iqrar Ahmad, Harun Patel, Hoon Kim, Bijo Mathew
Summary: This study evaluated the inhibitory effects of fifteen benzyloxy ortho/para-substituted chalcones on human monoamine oxidases. The results showed that these compounds exhibited strong inhibitory activity against hMAO-B, making them potential candidates for drug development.
SCIENTIFIC REPORTS
(2022)
Editorial Material
Chemistry, Organic
K. Anusha, Megha Mahesh, Shikha Shikha, T. M. Rangarajan, Sharda Pasricha
Article
Chemistry, Organic
Abhay Srivastava, Nishita Avasthi, Sachid Anand, Divya Yadav, T. M. Rangarajan, Sharda Pasricha
Article
Biochemistry & Molecular Biology
Ashutosh Kumar Singh, Seong-Min Kim, Jong Min Oh, Mohamed A. Abdelgawad, Mohammed M. Ghoneim, T. M. Rangarajan, Sunil Kumar, Sachithra Thazhathuveedu Sudevan, Daniela Trisciuzzi, Orazio Nicolotti, Hoon Kim, Bijo Mathew
Summary: Eight derivatives of benzyloxy-derived halogenated chalcones were synthesized and tested for their ability to inhibit monoamine oxidases (MAOs). BB4 and BB2 showed the most effective inhibition of MAO-B with IC50 values of 0.062 μM and 0.093 μM, respectively. These compounds exhibited higher selectivity for MAO-B and can be considered potential drug candidates for neurodegenerative diseases.
CHEMICAL BIOLOGY & DRUG DESIGN
(2023)
Article
Chemistry, Multidisciplinary
Karuppaiah Perumal, Jiseong Lee, Sesuraj Babiola Annes, Subburethinam Ramesh, T. M. Rangarajan, Bijo Mathew, Hoon Kim
Summary: A metal-free approach using tBuOK as a catalyst was developed to obtain novel pseudoindoxyl derivatives through hydroxylation and rearrangement reactions. The inhibitory activities of spiro pseudoindoxyl compounds and their N-benzylated derivatives against MAO enzymes were evaluated. Among the tested compounds, 11f showed the highest inhibitory activity against MAO-B, followed by 11h, 11j, 11d, and 11i. Compound 11f was found to be a potent, reversible, and competitive inhibitor of MAO-B activity.
Article
Education, Scientific Disciplines
Sharda Pasricha, T. M. Rangarajan
Summary: In this section, readers are encouraged to ask questions that may arise in a classroom setting. We provide strategies for addressing these questions and invite responses from readers. The classroom is also a platform for discussing broader issues and sharing personal experiences and perspectives on teaching and learning science.
RESONANCE-JOURNAL OF SCIENCE EDUCATION
(2023)
Review
Chemistry, Multidisciplinary
Amritha Manoharan, Jayalakshmi Jayan, T. M. Rangarajan, Kuntal Bose, Feba Benny, Reshma Susan Ipe, Sunil Kumar, Neelima Kukreti, Mohamed A. Abdelgawad, Mohammed M. Ghoneim, Hoon Kim, Bijo Mathew
Summary: Click chemistry is a fast and efficient method for combining desired chemical entities. It plays a crucial role in drug discovery and can be used in various areas such as peptide targeting and biomolecule quantification.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
