@article { ISI:000248238400001, title = {Application of hydrolytic kinetic resolution (HKR) in the synthesis of bioactive compounds}, journal = {Tetrahedron}, volume = {63}, number = {13}, year = {2007}, month = {MAR}, pages = {2745-2785}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, keywords = {Biological activity, bis-epoxides, Hydrolytic kinetic resolution, meso-epoxides, Natural products, synthesis, terminal epoxides}, issn = {0040-4020}, doi = {10.1016/j.tet.2006.12.015}, author = {Kumar, Pradeep and Naidu, Vasudeva and Gupta, Priti} } @article { ISI:000267168600002, title = {Hydrolytic kinetic resolution as an emerging tool in the synthesis of bioactive molecules}, journal = {Synlett}, number = {9}, year = {2009}, month = {JUN}, pages = {1367-1382}, publisher = {GEORG THIEME VERLAG KG}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

A variety of racemic epoxides mainly derived from terminal olefins, such as aliphatic epoxides, multifuncitonalized epoxides and amine-substituted epoxides, have been successfully resolved into the enantiomerically pure epoxides and diols using Jacobsen{\textquoteright}s hydrolytic kinetic resolution (HKR) method. The chiral epoxides thus prepared were further elaborated by synthetic manipulation to provide a variety Of Compounds of biological interest. A general synthetic strategy for the construction Of S synlanti-1,3-polyol systems using iterative HKR has been developed, which was subsequently utilized in the synthesis of natural products with a broad range of biological activity. The protocol for the 1,3-polyols was also further extended to the synthesis of 1,3-amino alcohols.

}, keywords = {Biological activity, Hydrolytic kinetic resolution, Natural products, synthesis, terminal epoxides}, issn = {0936-5214}, doi = {10.1055/s-0029-1217171}, author = {Kumar, Pradeep and Gupta, Priti} } @article { ISI:000364968800017, title = {First enantioselective synthesis of surinamensinol B and a non-natural polysphorin analogue by a two-stereocentered hydrolytic kinetic resolution}, journal = {European Journal of Organic Chemistry}, volume = {33}, number = {33}, year = {2015}, month = {NOV}, pages = {7344-7351}, publisher = {WILEY-V C H VERLAG GMBH}, address = {POSTFACH 101161, 69451 WEINHEIM, GERMANY}, abstract = {

An efficient and economical approach to the synthesis of antitumor and anti-inflammatory surinamensinol B (1) and antimalarial polysphorin analogue 2 has been achieved with high enantiomeric purity (96\% ee) by starting from commercially available 3,4,5-trimethoxybenzaldehyde. The key steps of the strategy include a Co-catalyzed two-stereocentered hydrolytic kinetic resolution (HKR) of racemic 2[( methoxymethoxy)(3,4,5-trimethoxyphenyl)methyl] oxirane (13) as the chiral inducing step followed by a Mitsunobu reaction. Chiral epoxide 14 and chiral diol 15 were utilized in the syntheses of both compounds.

}, keywords = {Biological activity, Enantioselectivity, Kinetic resolution, Natural products, Total synthesis}, issn = {1434-193X}, doi = {10.1002/ejoc.201501009}, author = {Lalwani, Komal G. and Sudalai, Arumugam} } @article { ISI:000356927800001, title = {Synthesis of novel N-cyclopentenyl-lactams using the aube reaction}, journal = {Beilstein Journal of Organic Chemistry}, volume = {11}, year = {2015}, month = {JUN}, pages = {1060-1067}, publisher = {BEILSTEIN-INSTITUT}, address = {TRAKEHNER STRASSE 7-9, FRANKFURT AM MAIN, 60487, GERMANY}, abstract = {

A novel and convenient method utilizing the Aube reaction to access a new class of compounds that are similar to carbocyclic nucleosides is reported. The azido alcohol derived from Vince lactam undergoes the Aube reaction with various cyclic ketones to give cyclopentenyl-substituted lactams. Upon dihydroxylation, this affords the N-cyclopentenyl-lactam compounds in racemic form. Given the numerous uses of nucleosides and related compounds, we were interested in the synthesis of carbocylic nucleoside mimics. The attempts and results are described herein.

}, keywords = {Aube reaction, Biological activity, carbocyclic nucleosides, cyclopentenylated lactams, cyclopentylated lactams}, issn = {1860-5397}, doi = {10.3762/bjoc.11.119}, author = {Shinde, Madhuri V. and Ople, Rohini S. and Sangtani, Ekta and Gonnade, Rajesh G. and Reddy, D. Srinivasa} } @article {46826, title = {Synthesis of novel of 2, 5-disubstituted 1, 3, 4-oxadiazole derivatives and their in vitro anti-inflammatory, anti-oxidant evaluation, and molecular docking study}, journal = {Bioorganic \& Medicinal Chemistry Letters}, volume = {30}, year = {2020}, month = {JUN}, pages = {127136}, type = {Article}, abstract = {

A series of novel 2, 5-disubstituted 1, 3, 4-Oxadiazole derivatives as a potential anti-inflammatory, and antioxidant agent were synthesized via cyclisation. Hydrazide molecule treated with substituted acids in the presence of phosphorus oxychloride (POCl3) as an efficient reagent as well as solvent by conventional method with shorter reaction time and excellent yield. The newly synthesized 1, 3, 4-oxadiazole derivatives exhibited excellent to good anti-inflammatory and anti-oxidant activities compaired to the standard drugs. Molecular docking study on the crucial anti-inflammatory target-cyclooxygenase-2 (COX-2) revealed the ability of the scaffold to correctly recognize the active site and achieve significant bonded and non-bonded interactions with key residues therein. This study could identify potential compounds which can be pertinent starting points for structure-based drug design to obtain newer anti-inflammatory agents.

}, keywords = {1, 3, 4-Oxadiazole, Anti-inflammatory, Anti-Oxidant, Biological activity, computational chemistry}, issn = {0960-894X}, doi = {10.1016/j.bmcl.2020.127136}, author = {Kashid, Bharat B. and Salunkhe, Pravin H. and Dongare, Balasaheb B. and More, Kishor R. and Khedkar, Vijay M. and Ghanwat, Anil A.} } @article {47499, title = {Diversity in chemical structures and biological properties of plant alkaloids}, journal = {Molecules}, volume = {26}, year = {2021}, month = {JUN}, pages = {3374}, type = {Review}, abstract = {Phytochemicals belonging to the group of alkaloids are signature specialized metabolites endowed with countless biological activities. Plants are armored with these naturally produced nitrogenous compounds to combat numerous challenging environmental stress conditions. Traditional and modern healthcare systems have harnessed the potential of these organic compounds for the treatment of many ailments. Various chemical entities (functional groups) attached to the central moiety are responsible for their diverse range of biological properties. The development of the characterization of these plant metabolites and the enzymes involved in their biosynthesis is of an utmost priority to deliver enhanced advantages in terms of biological properties and productivity. Further, the incorporation of whole/partial metabolic pathways in the heterologous system and/or the overexpression of biosynthetic steps in homologous systems have both become alternative and lucrative methods over chemical synthesis in recent times. Moreover, in-depth research on alkaloid biosynthetic pathways has revealed numerous chemical modifications that occur during alkaloidal conversions. These chemical reactions involve glycosylation, acylation, reduction, oxidation, and methylation steps, and they are usually responsible for conferring the biological activities possessed by alkaloids. In this review, we aim to discuss the alkaloidal group of plant specialized metabolites and their brief classification covering major categories. We also emphasize the diversity in the basic structures of plant alkaloids arising through enzymatically catalyzed structural modifications in certain plant species, as well as their emerging diverse biological activities. The role of alkaloids in plant defense and their mechanisms of action are also briefly discussed. Moreover, the commercial utilization of plant alkaloids in the marketplace displaying various applications has been enumerated.}, keywords = {alkaloid, Biological activity, classification, defense, Enzyme, modification}, doi = {10.3390/molecules26113374}, author = {Bhambhani, Sweta and Kondhare, Kirtikumar R. and Giri, Ashok P.} } @article {49558, title = {Synthesis, biological screening, and molecular docking of hybrid pyrazole scaffolds for antitubercular and antimicrobial activity}, journal = {ChemistrySelect}, volume = {10}, year = {2025}, month = {JAN}, pages = {e202404830}, type = {Article}, abstract = {

This study reports the synthesis, characterization, and docking analysis of 21 novel compounds, including asymmetric dihydropyridines (4a-4o) and chalcones (6a-6f), derived from coupling 1,3-(substituted)-diphenyl-1H-pyrazole-4-carbaldehyde with active methylene compounds and 3-acetyl-4-hydroxycoumarin, respectively. Structural confirmation was achieved through 1H and 13C NMR, IR, and mass spectrometry. Biological screening against mycobacterium tuberculosis H37Ra identified compounds 4b, 4d, 4f, 4g , 4i, 4k, 6e, and 6f as significant antitubercular agents. Antibacterial evaluation at 30 mu g/mL showed selective inhibition of gram-positive bacteria, with compound 6e active against Staphylococcus aureus and Bacillus subtilis, and 6f showing activity specifically against S. aureus. Docking studies indicated effective InhA binding (Delta G = -3.52 to -7.27 kcal/mol) and inhibition constants ranging from 2640 to 4.71 mu M. Key binding interactions with residues TYR156 and ILE192 were observed, enhancing affinity, particularly for compound 6e. The SAR analysis emphasized the enhanced antitubercular potency of 2-chloroacetyl and 2,4-dichlorobenzoyl substitutions in the dihydropyridine series, while in the chalcone series, specific substitutions, such as the 3-nitro substitution in 6e, enhance antitubercular and antimicrobial potency due to stronger hydrogen bonding and increased polar surface area, while the 4-fluoro substitution in 6f confers selective activity against S. aureus.

}, keywords = {1, 4-dihydropyridine, 4-hydroxy coumarin, Biological activity, In silco studies, Pyrazole}, issn = {2365-6549}, doi = {10.1002/slct.202404830}, author = {Bavishi, Abhay and Vala, Hardev and Radadiya, Ashish and Swami, Sagar and Thakrar, Shailesh and Sarkar, Dhiman and Shah, Anamik} }