《Novel [(N-alkyl-3-indolylmethylene)hydrazono]oxindoles arrest cell cycle and induce cell apoptosis by inhibiting CDK2 and Bcl-2: synthesis, biological evaluation and in silico studies》 was written by Al-Warhi, Tarfah; Abo-Ashour, Mahmoud F.; Almahli, Hadia; Alotaibi, Ohoud J.; Al-Sanea, Mohammad M.; Al-Ansary, Ghada H.; Ahmed, Hanaa Y.; Elaasser, Mahmoud M.; Eldehna, Wagdy M.; Abdel-Aziz, Hatem A.. Synthetic Route of C8H7N And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2020. The article conveys some information:
As a continuation for our previous work, a novel set of N-alkylindole-isatin conjugates is here designed and synthesized with the prime aim to develop more efficient isatin-based antitumor candidates. Utilizing the SAR outputs from the previous study, our design here is based on appending four alkyl groups with different length (Et and n-propyl), bulkiness (iso-propyl) and unsaturation (allyl) on N-1 of indole motif, with subsequent conjugation with different N-unsubstituted isatin moieties to furnish the target conjugates. As planned, the adopted strategy achieved a substantial improvement in the growth inhibitory profile for the target conjugates in comparison to the reported lead . The best results were obtained with N-propylindole -5-methylisatin hybrid which displayed broad spectrum anti-proliferative action with efficient sub-panel GI50 (MG-MID) range from 1.33 to 4.23 μM, and promising full-panel GI50 (MG-MID) equals 3.10 μM, at the NCI five-dose assay. Also, hybrid was able to provoke cell cycle disturbance and apoptosis in breast T-47D cells as evidenced by the DNA flow cytometry and Annexin V-FITC/PI assays. Furthermore, hybrid exhibited good inhibitory action against cell cycle regulator CDK2 protein kinase and the anti-apoptotic Bcl-2 protein (IC50= 0.85 ± 0.03 and 0.46 ± 0.02 μM, resp.). Interestingly, mol. docking for hybrid in CDK2 and Bcl-2 active sites unveiled that N-Pr group is involved in significant hydrophobic interactions. Taken together, the results suggested conjugate as a promising lead for further development and optimization as an efficient antitumor drug. The experimental process involved the reaction of 1H-Indole(cas: 120-72-9Synthetic Route of C8H7N)
1H-Indole(cas: 120-72-9) belongs to indole. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Synthetic Route of C8H7N
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Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles