# US 12,178,806 B1 · Method for contacting cancer cells with antitumor agent and apoptotic inducer > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,178,806 B1 - Document ID: US12178806B1 - Status: Granted - Kind: B1 - Application number: 18/799,676 - Filed: 2024-08-09 - Granted: 2024-12-31 - Earliest claimed: 2024-05-10 - Assignees: Imam Mohammad Ibn Saud Islamic University - Applicants: Imam Mohammad Ibn Saud Islamic University - Inventors: Tarek Ahmed Yousef; Saad Shaaban; Ahmed A. Al-Karmalawy; Marwa Sharaky - Web page: https://patentgrep.com/patent/US12178806B1 ## CPC - A61K 31/427: not condensed and containing further heterocyclic rings - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) ## Abstract A method for cytotoxically treating cancer cells includes contacting the cancer cells with a composition comprising a compound of Formula I. The compound of Formula I is contacted with the cancer cells in an amount effective to reduce the number of cancer cells by at least 50%. A method for preparing the compound of Formula I. ## Claims ### Claim 1 A method of cytotoxically treating cancer cells, comprising: contacting the cancer cells with a composition comprising a compound of Formula I: wherein the compound of Formula I is contacted with the cancer cells in an amount effective to reduce the number of cancer cells by at least 50%, wherein the contacting includes administering the composition orally, systemically or parenterally in combination with a carrier or excipient. ### Claim 2 (depends on 1) The method of claim 1, wherein the contacting includes inhibiting cell growth of the cancer cells through apoptosis. ### Claim 3 (depends on 2) The method of claim 2, wherein the apoptosis occurs through at least one of a p53 pathway, a BAX pathway, a caspases pathway, a BCL-2 pathway, an MMP2 pathway, and an MMP9 pathway. ### Claim 4 (depends on 1) The method of claim 1, further comprising: making the compound of Formula I by: dissolving 3-(2-(1,3-dioxoisoindolin-2-yl)ethyl)thiazolidine-2,4-dione and 2-hydroxy-5-nitrobenzaldehyde in a polar protic solvent to form a reaction mixture; adding an acid and a heterocyclic amine to the reaction mixture; and refluxing the reaction for 6 to 10 hours to form the compound of Formula I. ### Claim 5 (depends on 4) The method of claim 4, wherein a molar ratio of 3-(2-(1,3-dioxoisoindolin-2-yl)ethyl)thiazolidine-2,4-dione to 2-hydroxy-5-nitrobenzaldehyde is from 1:0.8 to 1:1.5. ### Claim 6 (depends on 4) The method of claim 4, wherein the compound of Formula I is formed in a yield of 83 to 87% based on an initial amount of the 3-(2-(1,3-dioxoisoindolin-2-yl)ethyl)thiazolidine-2,4-dione. ### Claim 7 (depends on 1) The method of claim 1, wherein the contacting includes contacting the compound of Formula I with human non-small cell lung cancer cells, A549, at a concentration of 100 μg/mL to provide a growth inhibition percentage of 76 to 80%. ### Claim 8 (depends on 1) The method of claim 1, wherein the contacting includes contacting the compound of Formula I with colorectal carcinoma cell line, HCT116, at a concentration of 100 μg/mL to provide a growth inhibition percentage of 84 to 88%. ### Claim 9 (depends on 1) The method of claim 1, wherein the contacting includes contacting the compound of Formula I with prostate cancer cells, PC3, at a concentration of 100 μg/mL to provide a growth inhibition percentage of 82 to 86%. ### Claim 10 (depends on 1) The method of claim 1, wherein the contacting includes contacting the compound of Formula I with pharynx squamous carcinoma cells, FaDu, at a concentration of 100 μg/mL to provide a growth inhibition percentage of 87 to 92%. ### Claim 11 (depends on 1) The method of claim 1, wherein the contacting includes contacting the compound of Formula I with triple-negative breast cancer cells, MDA-MB-468, at a concentration of 100 μg/mL to provide a growth inhibition percentage of 89 to 94 %. ### Claim 12 (depends on 1) The method of claim 1, wherein the contacting includes contacting the compound of Formula I with cervical cancer cells, HeLa, at a concentration of 100 μg/mL to provide a growth inhibition percentage of 69 to 73%. ### Claim 13 (depends on 1) The method of claim 1, wherein the contacting includes contacting the compound of Formula I with human non-small cell lung cancer cells, A549, to provide a half-maximal inhibitory concentration (IC50) value of 5.5 to 6.5 μg/mL. ### Claim 14 (depends on 1) The method of claim 1, wherein the contacting includes contacting the compound of Formula I with pharynx squamous carcinoma cells, FaDu, to provide a half-maximal inhibitory concentration (IC50) value of 4.5 to 5.5 μg/mL. ### Claim 15 (depends on 1) The method of claim 1, wherein the contacting includes contacting the compound of Formula I with triple-negative breast cancer cells, MDA-MB-468, to provide a half-maximal inhibitory concentration (IC50) value of 5 to 6 μg/mL. ### Claim 16 (depends on 1) The method of claim 1, wherein the contacting includes contacting the compound of Formula I with cervical cancer cells, HeLa, to provide a half-maximal inhibitory concentration (IC50) value of 4.5 to 5.5 μg/mL. ### Claim 17 (depends on 1) The method of claim 1, wherein the contacting includes contacting the compound of Formula I with human oral epithelial normal cells, OEC, at a concentration of 100 μg/mL to provide a growth inhibition percentage of 47 to 51%. ### Claim 18 (depends on 1) The method of claim 1, wherein the composition further comprises one or more pharmaceutically acceptable carriers. ### Claim 19 (depends on 18) The method of claim 18, wherein the composition is in the form of a pill, a liquid, a shot, a cream, and a patch. ### Claim 20 (depends on 1) The method of claim 1, wherein the compound of Formula I has a melting point of 252 to 259° C.