Synthesis and antimicrobial activity of squalamine analogue

Quaternary Alkylammonium Conjugates of Steroids: Synthesis, Molecular Structure, and Biological Studies

“…Both compounds were much more active than the compounds (24) and (26). All synthesized conjugates (16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26) (Figure 2) [33]. The multistep reactions gave final products with very good yields.…”

“…On this basis, Kim et al described the synthesis of a squalamine analogue from bisnoralcohol (2) (Scheme 1) [16]. The structure of the product was confirmed by 1 H-NMR, 13 C-NMR, DEPT, COSY, HETCOR, and FT-IR, as well as low-and high-resolution mass spectra.…”

“…For example, 3α-spermidine-23,24-bisnor-5α-cholane (16) was found to be more active than other spermidine analogues (16)(17)(18)(19). However 3β-spermine-23,24-bisnor-5β-cholane (23) exhibits the highest biological activity among all the compounds (16)(17)(18)(19)(20)(21)(22)(23). The conjugate (17), which is similar to (24)(25)(26) with the exception of the functional group at position C(7), has comparable antimicrobial activity to (25).…”

“…The results showed that the stereochemistry of the C(3) and C(5) carbon atoms has a significant influence on the antimicrobial activity. For example, 3α-spermidine-23,24-bisnor-5α-cholane (16) was found to be more active than other spermidine analogues (16)(17)(18)(19). However 3β-spermine-23,24-bisnor-5β-cholane (23) exhibits the highest biological activity among all the compounds (16)(17)(18)(19)(20)(21)(22)(23).…”

“…The steroid-polyamine conjugate was isolated from the liver tissues of the dogfish shark (Squalus acanthias) [11][12][13][14]. This aminosterol is a novel broad-spectrum antibiotic and exhibits a biocidal activity against Gram-positive and Gram-negative bacteria, fungi, protozoa, and viruses [15][16][17][18][19][20][21][22][23]. The antimicrobial activity of the squalamine has inspired work to design and synthesize new derivatives of steroidal-polyamine conjugates [24][25][26][27][28][29][30][31][32].…”