Abstract
Coumarin is an important six-membered aromatic heterocyclic pharmacophore, widely distributed in natural products and synthetic molecules. The versatile and unique features of coumarin nucleus, in combination with privileged sulfonamide moiety, have enhanced the broad spectrum of biological activities. The research and development of coumarin, sulfonamide-based pharmacology, and medicinal chemistry have become active topics, and attracted the attention of medicinal chemists, pharmacists, and synthetic chemists. Coumarin sulfonamide compounds and analogs as clinical drugs have been used to cure various diseases with high therapeutic potency, which have shown their enormous development value. The diversified and wide array of biological activities such as anticancer, antibacterial, anti-fungal, antioxidant and anti-viral, etc. were displayed by diversified coumarin sulfonamides. The present systematic and comprehensive review in the current developments of synthesis and the medicinal chemistry of coumarin sulfonamide-based scaffolds give a whole range of therapeutics, especially in the field of oncology and carbonic anhydrase inhibitors. In the present review, various synthetic approaches, strategies, and methodologies involving effect of catalysts, the change of substrates, and the employment of various synthetic reaction conditions to obtain high yields is cited.
Highlights
Ever since the first time that coumarin 1 was isolated from natural source tonka bean (Dipteryx odorata), commonly known as cumaru, in 1820 by Vogel [1,2]
The series of pyrazole moiety containing coumarin sulfonamides was tested for antiproliferation activities in vitro, against four cancer cell lines (HeLa, HepG2, F10, A549) and two non-cancer cell lines (293T, L02)
The results of this study demonstrated that the derivatives 86, 87, and 89 (Figure 15) are non-toxic angiogenesis inhibitors, and the compound 86 proved to be a promising anti-angiogenic agent
Summary
Ever since the first time that coumarin 1 was isolated from natural source tonka bean (Dipteryx odorata), commonly known as cumaru, in 1820 by Vogel [1,2]. Coumarin sulfonamide derivatives and analogs have therapeutic potential against different types of cancer cell lines and CAs (carbonic anhydrases). CAs are metalloenzymes which are present in all life forms, and are essential for equilibria between different simple but significant reaction species, such as carbon dioxide, proton, and bicarbonate [40–44]. The ι-CAs were discovered in marine phytoplankton, as well as in some bacteria [45–55]. CAs inhibition mechanism with coumarins was unraveled with kinetic and X-ray crystallographic techniques. The first natural product, coumarin, was bound to human isoform hCA-II, but the formation of the enzyme inhibitor complex is not a rapid process, it takes 6 h for incubation period, while other classes take just 15 min for the incubation period [61–66]. The coumarin sulfonamides’ anticancer and CAs inhibition activities are discussed below in more detail
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