Article
Chemistry, Physical
Jae Ho Shim, Ji Yeon Lee, Hyeon Soo Kim, Deok-Chan Ha
Summary: The study developed a catalyst with N-selectivity for the nitroso aldol reaction, using a quantum calculation. The reaction mechanism was determined and optimized, resulting in a high yield of the product with high enantioselectivity. The catalyst provides a less expensive and more environmentally friendly alternative for the reaction.
Article
Chemistry, Multidisciplinary
Stuart C. D. Kennington, Saul F. Teloxa, Miguel Mellado-Hidalgo, Oriol Galeote, Sabrina Puddu, Marina Bellido, Pedro Romea, Felix Urpi, Gabriel Aullon, Merce Font-Bardia
Summary: A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes was reported. The reaction gives high yields of O-TIPS-protected anti-aldol adducts with remarkable stereocontrol and atom economy. The removal of the achiral scaffold provides enantiomerically pure intermediates with synthetic interest for producing anti-alpha-amino-beta-hydroxy and alpha,beta-dihydroxy carboxylic derivatives, with theoretical calculations explaining the observed high stereocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Daiki Ishii, Shin-ichi Hirashima, Hiroshi Akutsu, Kosuke Nakashima, Yasuyuki Matsushima, Takaaki Sakai, Tsuyoshi Miura
Summary: This study demonstrates the successful stereoselective conjugate addition using (Z)-benzoyl acrylonitriles and achieving excellent enantioselectivities.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ryoga Hikawa, Mio Shimogaki, Taichi Kano
Summary: Novel threonine-derived amino sulfonamide organocatalysts were developed and successfully applied to asymmetric aldol reactions. The reactions produced anti-aldol adducts with high diastereo- and enantioselectivity when catalyzed by threonine-derived tosylamide, and syn-aldol adducts were obtained when using threonine-derived triflamide catalyst in reactions between alpha-siloxyacetone and aromatic aldehydes. In both cases, a significant improvement in diastereoselectivity was observed compared to threonine-derived carboxylic acid catalyst.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Yujiro Hayashi, Masashi Tomikawa, Naoki Mori
Summary: The asymmetric cross-aldol reaction is a synthetically relevant reaction. The reactivity and stereoselectivity of different catalysts were compared for the reaction, and it was found that the proper selection of catalysts can lead to the synthesis of chiral building blocks with high diastereoselectivities and enantioselectivities.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Medicinal
Gabriela Huelgas, Ratnasamy Somanathan, Julio M. Hernandez Perez, Haydee Rojas Cabrera, Maximiliano de la Higuera Macias, Alejandra Dominguez-Huerta, Rocio Sabala, Cecilia Anaya de Parrodi
Summary: This study synthesized novel organic compounds, and successfully carried out highly enantioselective and diastereoselective reactions using organocatalysts under solvent-free conditions in the presence of water, achieving effective stereoselective induction.
Article
Chemistry, Applied
Satoshi Sakai, Akane Fujioka, Koji Imai, Kei Uchiyama, Yohei Shimizu, Kosuke Higashida, Masaya Sawamura
Summary: The silver-catalyzed asymmetric aldol reaction of isocyanoacetic acid derivatives with aldehydes has been developed using a chiral prolinol-phosphine ligand as a hydrogen-bond-donating P,N,O ligand. DFT calculations revealed a stepwise reaction mechanism, involving C-C bond formation and subsequent enantioselectivity-determining ring formation. The prolinol moiety of the ligand activates the aldehyde through a two-point hydrogen bond, facilitating the stereocontrolled cyclization. Additional nonclassical hydrogen bonds and London dispersion interactions may also contribute to stereocontrol.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Jason Fang, Laura E. Turner, Michelle C. Y. Chang
Summary: Fluorine is a critical element in designing bioactive compounds, but the synthesis of stereogenic tertiary fluorides is challenging and limited to a few approved drugs. In this study, the aldol reaction of fluorinated donors catalyzed by HpcH and engineered variants was found to generate enantiopure secondary and tertiary fluorides. This method not only represents the first synthesis of tertiary fluorides via biocatalysis but also increases the diversity of fluorinated building blocks and enables the synthesis of fluorinated drug analogs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Sedigheh Sadat Naeimi, Peyman Salehi, Morteza Bararjanian
Summary: The synthesis of prolinamide derivatives of (R)-tetrahydropapaverine and their application as organocatalysts in asymmetric Aldol reaction were reported. Catalyst 2 showed the best catalytic activity in the reaction between cyclohexanone and 4-nitrobenzaldehyde, achieving up to 90% enantiomeric excess. Unlike the anti-stereoselectivity observed in the presence of L-proline alone, the hybridization with (R)-tetrahydropapaverine resulted in the formation of syn products as the major compounds.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Pragya Sharma, Sanjay Singh, Chinmoy Kumar Hazra
Summary: The facile and efficient synthesis of a unique class of 4-aryl-hydrocoumarins with various applications in medicinal chemistry and natural products is reported. The authors have developed a Bronsted acid-catalyzed, multicomponent, one-pot approach for producing 4-aryl-coumarin derivatives. The practicality of this method is demonstrated through the synthesis of bioactive compounds, late-stage functionalization of natural products, and gram-scale synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Dattatraya N. Bhangare, Rohit G. Shinde, Pushpalata D. Pawar, Milind D. Nikalje, Mahendra N. Lokhande
Summary: This method utilizes Sc(OTf)(3) as a catalyst and (-)-menthol as a chiral auxiliary to achieve remarkable diastereoselectivity in the asymmetric aldol reaction. It offers mild reaction conditions, high yields, and excellent diastereoselectivity with a variety of substituted aromatic aldehydes. Sc(OTf)(3) demonstrates excellent diastereoselectivity at -45 degrees C under different reaction conditions.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Daeil Bae, Jin Won Lee, Do Hyun Ryu
Summary: New bifunctional secondary amine organocatalysts derived from L-proline were synthesized and applied in enantioselective Michael reactions in water, yielding high product yields and stereoselectivity. Investigations on the effect of phenyl group at (R)-C6 in the catalyst were conducted, and the successful formal synthesis of a novel histamine H3 receptor agonist, Sch 50971, demonstrated the synthetic utility of this reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Chonglong Li, Jihai Wang, Huiyun Ding
Summary: The novel helical poly(phenyl isocyanide) showed high optical activity in asymmetric aldol reaction and exhibited enhanced stereoselectivity compared to small molecule l-proline. The helical polymer catalysts can be easily recovered and reused for at least five cycles with maintained activity and stereoselectivity.
Article
Chemistry, Multidisciplinary
Saul F. Teloxa, Miguel Mellado-Hidalgo, Stuart C. D. Kennington, Pedro Romea, Felix Urpi, Gabriel Aullon, Merce Font-Bardia
Summary: A direct and asymmetric aldol reaction between N-azidoacetyl-1,3-thiazolidine-2-thione and aromatic aldehydes catalyzed by a chiral nickel(II)-Tol-BINAP complex has been developed. The reaction gives anti alpha-azido-beta-silyloxy adducts with excellent stereocontrol and high yields. The removal of thiazolidinethione allows for the synthesis of a wide array of enantiomerically pure derivatives, providing a new route to di- and tripeptide blocks containing a beta-aryl-beta-hydroxy-alpha-amino acid.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Gen-Fa Wen, Rui Zhang, Chu-Yu Zhang, Chao-Shan Da
Summary: This study compares and explores the catalytic efficiencies of structurally similar alpha- and beta-amino acids in an asymmetric aldol transformation. The results show that both types of amino acids achieve high catalytic efficiencies under different optimal conditions, and in some cases, the beta-amino acid even exhibits higher enantioselectivity than the alpha-amino acid.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Bilash Kuila, Rayees Naikoo, Dinesh Mahajan, Prabhpreet Singh, Gaurav Bhargava
Article
Cell Biology
Sima Kumari, Parmeshwar B. Katare, R. Elancheran, Hina L. Nizami, Bugga Paramesha, Sudheer Arava, Partha Pratim Sarma, Roshan Kumar, Dinesh Mahajan, Yashwant Kumar, Rajlakshmi Devi, Sanjay K. Banerjee
OXIDATIVE MEDICINE AND CELLULAR LONGEVITY
(2020)
Article
Pharmacology & Pharmacy
Sundeep Dugar, Francisco Villarreal, Frank H. Hollinger, Dinesh Mahajan, Israel Ramirez-Sanchez, Aldo Moreno-Ulloa, Guillermo Ceballos, George Schreiner
PHARMACOLOGICAL RESEARCH
(2020)
Article
Chemistry, Organic
Bilash Kuila, Priyanka Sharma, Dinesh Mahajan, Prabhpreet Singh, Gaurav Bhargava
SYNTHETIC COMMUNICATIONS
(2020)
Article
Chemistry, Medicinal
Chhuttan L. Meena, Padam Singh, Ravi P. Shaliwal, Varun Kumar, Arun Kumar, Anoop Kumar Tiwari, Shailendra Asthana, Ramandeep Singh, Dinesh Mahajan
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Medicine, Research & Experimental
Soumalya Sarkar, Deepika Kumari, Sonu Kumar Gupta, Vipin Sharma, Sumedha Mukhi, Parul Kamboj, Vedula Sasibhushan, Rajiva Kumar Rai, Sastry Lakshminarayana Jatavallabhula, Dinesh Mahajan, Yashwant Kumar, Ajay Kumar, Madhu Dikshit
Summary: The study indicates that both Saroglitazar and Hepano have protective effects against non-alcoholic fatty liver disease in a high-fat high-sugar diet model, showing significant impact on insulin resistance, obesity, dyslipidemia, and modulation of different lipid classes in circulation and liver tissue. Saroglitazar appears to be more efficacious than Hepano in combating diet-induced insulin resistance, obesity, and dyslipidemia.
BIOMEDICINE & PHARMACOTHERAPY
(2021)
Article
Ecology
Archana Pant, Tushar K. Maiti, Dinesh Mahajan, Bhabatosh Das
Summary: The efficacy of drugs varies among individuals, and the gut microbiota plays a crucial role in this variation. The commensal microbiota in the human gut possesses enzymes that can modify drugs, resulting in activation, inactivation, toxification, altered stability, poor bioavailability, and rapid excretion. Recent studies have revealed complex interactions between the gut microbiome and therapeutic drugs. Therapeutic drugs can influence the composition and functions of the gut microbiome, and these changes can affect drug metabolism and treatment outcomes.
Editorial Material
Microbiology
Bhabatosh Das, Dinesh Mahajan, Jasna Rakonjac
FRONTIERS IN MICROBIOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Rayees Ahmad Naikoo, Rupesh Kumar, Rashmi Sharma, Dinesh Mahajan, Gaurav Bhargava
Summary: The manuscript describes a highly regioselective 6-exo-dig iodo/bromo cyclization of functionalized N-propagyl-amino-pyrimidinones under ambient conditions, resulting in the synthesis of functionalized pteridines with excellent yields. The optimized procedures are mild, operationally simple, and effective with different substrates. The synthesis of functionalized pteridines is of great significance due to their potential pharmacological profile.
Article
Chemistry, Organic
Banni Preet Kaur, Vivek Sharma, Subash Chandra Sahoo, Swapandeep Singh Chimni
Summary: Enantiopure bis-heterocyclic molecules containing pyrazole and isoxazole were synthesized via a low-catalyst loading Michael addition reaction under mild conditions with high yields and enantiomeric excess. These derivatives can be further transformed into potentially bio-active molecules with significant applications. The synthesis of these bis-heterocyclic molecules can be efficiently carried out in one pot without any loss of enantiopurity, adding to their significance.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Arun Kumar, Pankaj Sharma, Nidhi Sharma, Yashwant Kumar, Dinesh Mahajan
Summary: A sustainable approach for N-formylation of aromatic and aliphatic amines using sodium borohydride and carbon dioxide gas is reported. The method is catalyst-free, does not require pressure or specialized reaction assembly. The in situ formation of formoxy borohydride species in formamide-based solvents is critical for the success of the N-formylation reactions.
Article
Chemistry, Multidisciplinary
John Napoleon, Sarbjit Singh, Sandeep Rana, Mourad Bendjennat, Vikas Kumar, Smitha Kizhake, Nicholas Y. Palermo, Michel M. Ouellette, Tom Huxford, Amarnath Natarajan
Summary: IKK beta is a key regulator in the NF-kappa B pathway and serves as a drug target for chronic inflammatory diseases and cancer. The non-toxic inhibitor 13-197 was discovered to reduce tumor growth through ATP non-competitive inhibition, targeting an allosteric pocket between the kinase and ubiquitin like domains.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Banni Preet Kaur, Jasneet Kaur, Swapandeep Singh Chimni
Summary: Arenesulfonyl indoles, with a good leaving group, serve as effective precursors for vinylogous imine intermediates generated in situ under basic conditions. These intermediates readily react with other nucleophilic reagents to yield C-3 substituted indole derivatives. The success of this substrate in organic synthesis is attributed to the stability of arylsulfonyl-containing substrates, mild reaction conditions, and the wide variety of nucleophiles involved.
Article
Chemistry, Medicinal
Naveen Kumar, Akshay Kumar, Subash Chandra Sahoo, Swapandeep Singh Chimni
Review
Chemistry, Organic
Jasneet Kaur, Banni Preet Kaur, Swapandeep Singh Chimni
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
