Article
Chemistry, Organic
Grand Lucie, Powderly Marian, Popowycz Florence, Jacolot Maiwenn
Summary: The regio- and diastereoselective synthesis of chiral amines derived from 1,4-D-sorbitan has been achieved through the borrowing hydrogen reaction, using a cooperative catalysis between an achiral iridium catalyst and diphenylphosphoric acid. The differential reactivities of the four hydroxyl groups on the 1,4-D-sorbitan scaffold have also been emphasized.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Connor M. Simon, Samantha L. Dudra, Ryan T. McGuire, Michael J. Ferguson, Erin R. Johnson, Mark Stradiotto
Summary: This study reveals a new reductive elimination pathway for nickel-catalyzed C-N cross-coupling, involving a bifurcated pathway and a base-promoted pathway for C-N reductive elimination.
Article
Chemistry, Organic
Rowan I. L. Meador, Robert E. Anderson, John D. Chisholm
Summary: Tertiary benzylic alcohols can react with oxoammonium salts in a tandem elimination/allylic oxidation reaction to synthesize allylic ethers in one step, which can then be cleaved under reductive conditions to yield allylic alcohols.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Physical
Hanna Stachowiak-Dluzynska, Grzegorz Hreczycho
Summary: A cobalt-catalyzed addition of hydrosilanes to unsaturated carbon-oxygen bonds has been developed using easily accessible and inexpensive PNP-type pincer ligands. The reaction efficiently transforms a wide range of ketones into silyl ethers or secondary alcohols with high yields. The use of silanes as both substrates and activators eliminates the need for external additives.
Article
Chemistry, Applied
Yao Deng, Yunyan Meng, Qiongtong Yang, Zixiu Liu, Ruifeng Fan, Jingchao Chen, Baomin Fan
Summary: The enantioselective reductive coupling of oxabenzonorbornadiene with vinyl bromide was developed using earth-abundant nickel catalyst with copper as Lewis acid co-catalyst. The asymmetric reductive coupling is applicable with a wide range of azabenzonorbornadienes and vinyl bromides under nickel/copper co-catalytic system, affording the cis ring-opening vinylation products in good yields with high optical purities. This study enables straightforward stereoselective preparation of chiral 2-vinyl-tetrahydronaphthalens from vinyl halides.
ADVANCED SYNTHESIS & CATALYSIS
(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, 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, Organic
Travis Menard, Aragorn Laverny, Scott E. Denmark
Summary: This method describes the catalytic, enantioselective carbosulfenylation of alkenes to construct difficult-to-generate, enantioenriched, 3,4-disubstituted chromans with moderate to high yields and excellent enantioselectivities. The resulting thioether moiety is amenable to various functional group manipulations and transformations, providing access to sulfur-containing functional groups present in natural products and pharmaceuticals.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Tian-Yuan Zhao, Li-Jun Xiao, Qi-Lin Zhou
Summary: A nickel-catalyzed desymmetric reductive cyclization/coupling of 1,6-dienes has been developed, providing an efficient method for constructing a chiral tertiary alcohol and a quaternary stereocenter by a single operation. The method exhibits excellent diastereoselectivity and high enantioselectivity, has a broad substrate scope, and shows good tolerance of functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Daniele Fiorito, Simone Scaringi, Clement Mazet
Summary: This review covers the one-pot reactions centered around transition metal-catalyzed isomerization of alkenes, showcasing their advantages in atom, step, and redox economy, as well as the preparation of value-added products that are difficult to access through conventional methods.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Zhuang Ma, Bei Zhou, Xinmin Li, Ravishankar G. Kadam, Manoj B. Gawande, Martin Petr, Radek Zboril, Matthias Beller, Rajenahally Jagadeesh
Summary: This method utilizes a special catalyst made of cobalt nanoparticles to efficiently prepare a variety of amines from inexpensive and readily available alcohols and amines, including N-methylamines and selected drug molecules.
Review
Chemistry, Organic
Chandrasekhar Bandari, Kenneth M. Nicholas
Summary: The utilization of abundant, CO2-neutral, renewable feedstocks is driving the discovery and development of new reactions that refunctionalize oxygen-rich substrates such as alcohols and polyols through C-O bond activation. The development of transition-metal-promoted reactions of renewable alcohols and epoxides that result in carbon-carbon bond-formation has expanded the diversity of carbon skeletons accessible and the potential for applications in chemical synthesis. Catalytic reductive coupling and cross-coupling reactions of epoxides are also highlighted, providing mechanistic insights into C-O activation and C-C bond formation.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Matthew J. Evans, Mathew D. Anker, Claire L. Mcmullin, Martyn P. Coles
Summary: The reaction of 9-diazo-9H-fluorene with potassium aluminyl generates a highly colored species and shows reactivity at a metal ketimide ligand. Density functional theory calculations help to understand the bonding and reaction mechanism.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Wenxin Lu, Qinglei Chong, Fanke Meng
Summary: A catalytic method for the construction of homoallylic alcohols from trans-1,3-dienes and anhydrides is presented. This method involves the generation of enantiomerically enriched allyl-Cu species which react selectively with a wide range of anhydrides. The functionalization of homoallylic alcohol products provides useful building blocks that are difficult to obtain through other methods.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Wen Zhang, Lingxiang Lu, Wendy Zhang, Yi Wang, Skyler D. Ware, Jose Mondragon, Jonas Rein, Neil Strotman, Dan Lehnherr, Kimberly A. See, Song Lin
Summary: Recent research in medicinal chemistry has found a correlation between an increase in sp(3) carbons in drug candidates and their improved success rate in clinical trials. This study focuses on the development of robust and selective methods for constructing carbon(sp(3))-carbon(sp(3)) bonds. By using electrochemistry, the researchers achieve the selective activation of alkyl halides based on their electronic and steric properties, allowing for high selectivity in carbon(sp(3))-carbon(sp(3)) cross-electrophile coupling. This new protocol shows improved chemoselectivity and does not require a transition metal catalyst.
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)
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
Green & Sustainable Science & Technology
Arun Kumar, Kulvir Singh Saini, Hemant Dasila, Rakesh Kumar, Kavita Devi, Yashpal Singh Bisht, Manish Yadav, Shivani Kothiyal, Aaradhana Chilwal, Damini Maithani, Prashant Kaushik
Summary: The continuous rice-wheat cropping system in South Asia has caused irreversible environmental damage. Farm experiments were conducted to assess the impact of different cropping systems under conservation agriculture practices on the yield, productivity, and profitability of wheat. The results showed that the highest grain yield and other important indicators were achieved under scenarios that involved full or partial conservation agriculture practices with legume inclusion. These findings suggest that adopting conservation agriculture soybean-wheat-summer moong cropping systems can enhance yield attributes, productivity, profitability, and sustainability in the region.
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.
