Synthesis and anticancer activity of cinnoline sulphonamides and 4‐heteroyclic derivatives: Cross‐coupling approach

• Published in: Journal of heterocyclic chemistry 2024-06, Vol.61 (6), p.958-970
• Main Authors: Yerrabelly, Jayaprakash Rao, Bommagani, Mohan Babu, Yerrabelly, Hemasri, Mullaguri, Sai Charitha, Kancha, Rama Krishna
• Format: Article
• Language: English
• Subjects: Anticancer properties; Chemical reactions; Couplings; Cross coupling; Leukemia; Sulfonamides
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.4816

A series of novel cinnoline sulphonamide derivatives and 4‐substuted cinnoline derivatives (13a‐h, 16a‐h and 17–31 total 33 analogues) were designed based on scaffold hopping techniques and evaluated for their antileukemic activity on wild type K562 as well as imatinib resistant cell lines (K562‐IR1 and K562‐IR2). Out of 33 analogues, five compounds (19, 22, 23, 28, and 31) exhibited potent antileukemic activity. An easy and efficient approach to synthesize numerous cinnoline derivatives by the various cross‐coupling reactions of 4‐chlorocinnoline has been developed and also demonstrated that metal‐free cross couplings give high product yield compared with metal catalyzed cross couplings. Design and synthesis of novel anticancer activity of cinnoline sulphonamides conjugates (13a‐h and 16a‐h), 16 derivatives are prepared with good yields (70%–90%) and 4‐heteroyclic derivatives (17–31): cross‐coupling approach. Most of the compounds were potent, in which compounds 19, 22, 23, 28 and 31 were well exhibited potent antileukemic activity. Compounds 22 and 23 are the antileukemic activity.