Synthesis and DFT studies of an antitumor active spiro-oxindole

Abstract

An anti-oncological active spiro-oxindole 7 was synthesized regioselectively via [3+2]-cycloaddition reaction of azomethine ylide to exocyclic olefinic linkage of 4-piperidone 6, exhibiting properties against diverse tumor cell lines including leukemia, melanoma and cancers of the lung, colon, brain, ovary, breast, prostate, and kidney. Compound 7 crystallizes in the monoclinic system and P21/c space group with four molecules in the unit cell. The structure was also studied by AM1, PM3 and DFT techniques. DFT studies support the reaction's stereochemical selectivity and determine the molecular electrostatic potential and frontier molecular orbitals.

Synthesis and molecular modeling studies of cholinesterase inhibitor dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines]

“…The latter is formed via condensation of amino acid (sarcosine) with isatin(s). 34 The IR spectrum of compound 8a (example of the synthesized compounds) shows strong bands at n ¼ 1786, 1713 cm À1 assignable for the stretching vibration of carbonyl groups. 1 H-NMR spectrum of 8a reveals the diastereotopic methylene protons of pyrrolidinedionyl H 2 C-4 00 and pyrrolidinyl H 2 C-5 0 at d H ¼ 2.37, 2.71 and 3.49, 3.84, respectively.…”

“…[24][25][26][27] The biologically active spiro-indoles developed by our group also prompted the current study. [28][29][30]…”

Synthesis and 2D-QSAR Study of Active Benzofuran-Based Vasodilators

“…Convergence to a local minimum was achieved when the energy gradient was ≤0.01 kcal/mol. The Restricted Hartree–Fock (RHF) method was used in spin-pairing for the two semiempirical tools [ 39 , 40 , 41 , 42 , 43 , 44 ]. The resulting output files were exported to CODESSA PRO that includes MOPAC capability for final geometry optimization.…”

Synthesis and Biological Evaluation of Some Novel Claisen Products of 5‐Oxo‐1‐phenylpyrrolidine‐3‐carboxylic Acid as Antimicrobial and Antioxidant Agents

“…Pyrrolidine derivatives are also valuable chiral building blocks for the synthesis of more complex compounds and therefore can be useful as chiral auxiliaries and ligands for asymmetric synthesis . The moiety has also attracted much attention as a result of varied pharmacological properties displayed by its derivatives which include antagonists, cholinesterase inhibitory, antimicrobial, antitumor, anti‐inflammatory, anti‐HIV, antidiabetic, Mcl‐1 inhibitors and anticancer properties . Chalcones were first isolated from flavonoid biosynthesis in plants and since then many studies have been focused on structural modifications of the chalcone scaffold and the large variety of its biological activities .…”