Article
Chemistry, Physical
Ye Zheng, Jaime A. Martinez-Acosta, Mohammed Khimji, Luiz C. A. Barbosa, Guy J. Clarkson, Martin Wills
Summary: Aromatic ketones with ortho-substituents showed high enantioselectivity under asymmetric transfer hydrogenation conditions, while N-methylimidazole-containing ketones exhibited unexpected enantioselectivity switches upon variation of the opposing aromatic group. Pyrrole-containing ketones were found to be resistant to reduction in this study.
Review
Chemistry, Inorganic & Nuclear
Han Peng, Vincent Ritleng, Christophe Michon
Summary: This article reviews the development of supported Noyori-Ikariya catalysts based on ruthenium, rhodium, and iridium for asymmetric transfer hydrogenation and related tandem reactions over the past 7 years. It highlights and discusses the synthesis, reactivity, and recycling of these catalysts.
COORDINATION CHEMISTRY REVIEWS
(2023)
Article
Chemistry, Multidisciplinary
Yifan Zhao, Jialei Hu, Ruyi Chen, Fengping Xiong, Hujun Xie, Hanfeng Ding
Summary: A new method has been developed for the efficient assembly of diversely functionalized polyquinane frameworks, leading to asymmetric total syntheses of various tetraquinane natural products in a concise and divergent manner.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Peng Lu, Hongliang Wang, Yihui Mao, Xin Hong, Zhan Lu
Summary: Investigation on asymmetric hydrogenation of olefins is vital for the synthesis of pharmaceutical molecules and chemical industry. A cobalt-catalyzed enantioconvergent hydrogenation method has been developed for common minimally functionalized E/Z-olefin mixtures.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Physical
Andrew M. R. Hall, Daniel B. G. Berry, Jaime N. Crossley, Anna Codina, Ian Clegg, John P. Lowe, Antoine Buchard, Ulrich Hintermair
Summary: This study reveals the existence of two diastereomeric hydride complexes under reaction conditions and their interconversion during transfer hydrogenation catalysis. Further computational analysis shows the differences in catalytic efficiency and stereoselectivity between different configurations.
Review
Chemistry, Multidisciplinary
Andrej Emanuel Cotman
Summary: Noyori-Ikariya-type ruthenium(II)-catalysts have been used for 25 years in asymmetric transfer hydrogenation for the synthesis of chiral secondary alcohols. Recent progress has been made in understanding the asymmetric reduction of complex ketones, controlling up to four stereocenters in a single transformation. Intriguing multi-chiral molecular architectures can be prepared via ATH for drug discovery.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Yujie Wang, Shihan Liu, Haobo Yang, Hengxu Li, Yu Lan, Qiang Liu
Summary: Research shows that a higher efficiency can be achieved by substituting an N-M' group (M' = alkali metals) for the N-H moiety using a large excess of metal alkoxides (M'OR), but the metal-hydride amidate intermediate has not yet been isolated. Furthermore, it is found that M/NM' bifunctional catalysis is superior to classic M/NH bifunctional catalysis in hydrogenation reactions.
Article
Chemistry, Physical
Masa Sterle, Matej Hus, Matic Lozinsek, Anamarija Zega, Andrej Emanuel Cotman
Summary: Stereopure CF3-substituted syn-1,2-diols were synthesized through the reductive dynamic kinetic resolution of corresponding alkyl ketones, yielding products with >95% ee and >87:13 syn/anti ratio. This method provides a rapid access to stereopure bioactive molecules. Moreover, DFT calculations were conducted on three types of Noyori-Ikariya ruthenium catalysts to demonstrate their general ability to control stereoselectivity through hydrogen bond acceptor SO2 region and CH/pi interactions.
Article
Chemistry, Multidisciplinary
Camilla Russo, Matthew C. Leech, Jamie M. Walsh, Joe I. Higham, Lisa Giannessi, Emmanuelle Lambert, Cyrille Kiaku, Darren L. Poole, Joseph Mason, Charles A. I. Goodall, Perry Devo, Mariateresa Giustiniano, Marco Radi, Kevin Lam
Summary: Hydrogenation reactions are commonly used in various scientific fields for the synthesis of pharmaceuticals, natural products, and functional materials. However, the use of toxic and expensive catalysts in these reactions often leads to impractical, hazardous, and limited conditions. This article presents a new, general, practical, efficient, mild, and high-yielding hydrogen-free electrochemical method for reducing alkene, alkyne, nitro, and azido groups. Furthermore, this method has been successfully applied in deuterium labelling.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yanping Xia, Sen Wang, Rui Miao, Jianhua Liao, Lu Ouyang, Renshi Luo
Summary: Cationic iridium complexes were demonstrated to catalyze the transfer hydrogenation of oximes, providing access to N-alkoxy amines and hydroxylamines. The reaction rate was accelerated by trifluoroacetic acid. The practical application of this method was demonstrated by the synthesis of a fungicide in high yields, and the asymmetric synthesis of chiral N-alkoxy amines showed potential for further development.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Rurong Yu, Feiyue Hao, Xinyu Zhang, Zhongbing Fang, Zhengneng Jin, Guyue Liu, Guoliang Dai, Jiashou Wu
Summary: A method for selectively reducing 2-pyridyl ketones and related N-heteroaryl compounds using cobalt stearate as a catalyst and DMF as a hydride source has been developed. The chelation with cobalt activates the ketone substrate, making this method highly chemoselective. A possible reaction mechanism has been proposed based on control experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Patrick D. Parker, Xintong Hou, Vy M. Dong
Summary: Tandem catalysis allows for constructing complex structures quickly from simple building blocks to address diverse challenges. This article focuses on using tandem hydrogenation to prepare complex natural products and presents tandem catalysis involving transfer hydrogenation. Lastly, recent breakthroughs and opportunities for asymmetric hydrogenation are highlighted.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Yu Nie, Qianjia Yuan, Feng Gao, Masahiro Terada, Wanbin Zhang
Summary: An efficient iridium-catalyzed double asymmetric hydrogenation of 2,5-dialkylienecyclopentanones is reported, delivering chiral 2,5-disubstituted cyclopentanones in excellent yields and stereoselectivities. The results suggest that the two C=C bonds were hydrogenated in a stepwise manner and the second stereocenter was controlled by the chiral catalyst and the chirality of monohydrogenated product. The hydrogenated products can be prepared on a gram-scale and are easily derivatized.
Article
Chemistry, Organic
Yu Nie, Qianjia Yuan, Feng Gao, Masahiro Terada, Wanbin Zhang
Summary: Herein, we report an efficient iridium-catalyzed double asymmetric hydrogenation of 2,5-dialkylienecyclopentanones, delivering the chiral 2,5-disubstituted cyclopentanones in excellent yields and stereoselectivities. The results of the kinetic experiments and control experiments indicated that the two C=C bonds were hydrogenated in a stepwise manner and the second stereocenter was synergistically controlled by the chiral catalyst and the chirality of monohydrogenated product. The hydrogenated products can be prepared on a gram-scale and are easily derivatized.
Review
Chemistry, Inorganic & Nuclear
Pavel A. Dub
Summary: This minireview discusses the accelerative role of alkali metal alkoxides in two important catalytic processes: hydrogenation of ketones and esters with Noyori-type molecular catalysts. The author offers their perspective on the unique mechanistic aspects of these reactions, a subject that remains controversial and often misunderstood.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Gaddam Kiranmai, Priyanka N. N. Makhal, Ramya Tokala, Nagula Shankaraiah, Narayana Nagesh, Neelima D. D. Tangellamudi, Arbaz Sujat Shaikh, G. Parimala Devi, Dilep Kumar Sigalapalli, Venkata Rao Kaki, Bathini Nagendra Babu
Summary: A new series of mercaptoacetamide-linked pyrimidine-1,3,4-oxadiazole hybrids were designed and synthesized. The in vitro cytotoxic potential of these compounds was evaluated against various cancer cell lines, and compound 9p showed high potency and selectivity. The compound was found to inhibit the topoisomerase II enzyme and bind effectively with CT-DNA, leading to apoptosis. Molecular modeling studies confirmed the binding of compound 9p at the active site of the DNA-topoisomerase II complex. These findings suggest that mercaptoacetamide-linked pyrimidine-1,3,4-oxadiazole derivatives could be promising scaffold for the development of effective anticancer agents and topoisomerase II inhibitors.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(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
Luan A. Martinho, Thaissa P. F. Rosalba, Gustavo G. Sousa, Claudia C. Gatto, Jose Roberto S. Politi, Carlos Kleber Z. Andrade
Summary: A novel alpha-acyloxyamide derivative was synthesized using waste cellulose-derived solvent Cyrene in a Passerini-3CR with carboxylic acids and isocyanides. The reaction exhibited good yield and diastereoselectivity under mild conditions. Kinetic and thermodynamic effects were identified as possible factors contributing to the results based on DFT calculations and experimental findings.
MOLECULAR DIVERSITY
(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
Biochemistry & Molecular Biology
Thaissa Pasquali F. Rosalba, Guilherme D. R. Matos, Carlos Eduardo M. Salvador, Carlos Kleber Z. Andrade
Summary: Over the past decade, nanotechnology has played a significant role in the advancement of health sciences, particularly in the field of controlled drug delivery systems. Peptoids, obtained through the Ugi 4-component reaction, have shown promise as nanocarriers for drug delivery. This study presents a process control strategy for the development of lipid-peptoid-based customized drug delivery systems. More than 20 lipid-peptoid nanocomposites were successfully synthesized and analyzed for their potential as nanoparticle drug carriers, particularly in cancer treatment.
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)
