Finally, adding the substituted aniline to the intermediate, followed by cyclization, afforded the product 1a– 1j. This scheme supposes that the initial addition of 1,3-cyclohexanedione to the isatin yielded the intermediate, which then reacted with an extra molecule of 1,3-cyclohexanedione. We have not established an exact mechanism for the formation of spiro-1,3,8-trione derivatives, however, a sensible possibility is shown in Scheme 1. The corresponding spiro-1,3,8-trione 1a– 1j was obtained in smart yields in similar conditions, which are shown in Table 1. The 13C-NMR spectrum of compounds 1a– 1j exhibited peaks at δ 126.9 to 127.8, corresponding to the 2- position of C in the isatin ring. The 1H NMR spectrum of compounds 1a– 1j showed a singlet at δ 10.10 to 10.26, attributable to N–H protons present in the isatin ring. Compound 1h exhibited an absorption band for the Cl–C group at 799 cm −1 and compounds 1b, 1f and 1i displayed an absorption band for the NO 2–C group at 1504–1523 cm −1. The IR spectrum of the compounds ( 1a– 1j) showed an absorption band at 3258 to 3500 cm −1 due to N–H stretching, an absorption band at 2922 to 3234 cm −1 due to Ar–H stretching, an absorption band at 1664 to 1716 cm −1 due to C=O stretching, and another absorption band at 1276 to 1516 cm −1 due to C–N stretching. All synthesized compounds were characterized by IR, 1H and 13C-NMR analysis. The synthetic methodology was evaluated with isatins, substituted anilines, and 1,3-cyclohexanedione, and the procedure followed that of. Based on the above results, we prepared new 10-phenyl-3,4,6,7–tetra hydro-1 H-spiro -1,3,8-trione derivatives via Grindstone Chemistry and the new compounds were screened for anticancer activity. Apparently, this methodology is very effective for endothermic reactions. In Grindstone Chemistry, reactions are often performed by grinding the reactants for many minutes, without using any organic solvent. ![]() Some spiroindoles exhibit medicinally important activity, as shown in Figure 1. The formation of 10-phenyl-3,4,6,7-tetrahydro-1 H-spiro -1,3,8-trione as a by-product is a part of our program aimed at the preparation of heterocyclic compounds, particularly spirooxindoles. ![]() Grindstone Chemistry may involve a small alteration and has established that several reactions are often carried out in high yields by grinding two or more solids. The ‘Grindstone Chemistry’ technique has been used as an inexperienced and speedy methodology for the synthesis of organic compounds. The acridines exhibit antiprotozoal, antihelmintic antineoplastic and antiviral activities. ![]() Primarily, anticancer potency, as well as a number of other factors such as topoisomerase and telomerase inhibition, initiation of ROS mediated oxidative stress, cell cycle arrest, and interaction with P-glycoprotein, also come into play which makes the acridine/acridone moiety a privileged scaffold for anticancer chemotherapy. Moreover, the spiro oxindole system is also a nucleus scaffold of many non-natural pharmaceutical elements with a wide assortment of biological uses, such as inhibitors of the human NK-1 receptor, antimicrobials, antineoplastics, and antibiotics. The spiro oxindole may be an advantageous heterocyclic core present in a sizable number of novel inhibitors with microtubule assembly, whereas pteropodines act as positive modulators of muscarinic M2 and 5-HT2 receptors. ![]() Additionally, at present isatin and its derivatives may also be the most helpful beginning resources or ancestors within the synthesis of a good variety of spirocyclic indoles. The advantages of acridine as a helpful nucleus in medicinal chemistry has consequently led to new designs, and the growth of its bi- and tri-analogues for delivering superior effects in targeted therapy compared to mono-analogues.
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