1.Design and synthesis of 2-phenyl-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-ones as potential anticancer agents starting from cytotoxic spiromamakone A.
Fuse S1, Inaba K, Takagi M, Tanaka M, Hirokawa T, Johmoto K, Uekusa H, Shin-Ya K, Takahashi T, Doi T. Eur J Med Chem. 2013 Aug;66:180-4. doi: 10.1016/j.ejmech.2013.05.030. Epub 2013 Jun 3.
The spirocycle is a key structure found in many bioactive compounds. From the cytotoxic and spirocyclic natural product, spiromamakone A (1) and its analogues, a more synthetically accessible spiroacetal template 4 was designed based on structural similarity analysis. A total of 50 compounds were rapidly synthesized in only one or two synthetic steps from the starting compound, and their cytotoxicity was evaluated. As a result, (±)-(2R*,5R*)-2-(4-iodophenyl)-7-chloro-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-one (7d-II) was discovered and found to be fifteen-fold more cytotoxic than 1. The easily accessible spiroacetal 7d-II appeared to act in a manner similar to the highly oxidized natural product, spiromamakone A (1).
2.Novel chloroquinoline derivatives incorporating biologically active benzenesulfonamide moiety: synthesis, cytotoxic activity and molecular docking.
Ghorab MM1, Alsaid MS2, Al-Dosari MS2, Nissan YM3, Al-Mishari AA4. Chem Cent J. 2016 Apr 5;10:18. doi: 10.1186/s13065-016-0164-1. eCollection 2016.
BACKGROUND: Quinoline derivatives have diverse biological activities including anticancer activity. On the other hand, many sulfonamide derivatives exhibited good cytotoxic activity. Hybrids of both moieties may present novel anticancer agents.
3.A practical post-modification synthesis of oligodeoxynucleotides containing 4,7-diaminoimidazo[5',4':4,5]pyrido[2,3-d]pyrimidine nucleoside.
Tarashima N1, Higuchi Y, Komatsu Y, Minakawa N. Bioorg Med Chem. 2012 Dec 15;20(24):7095-100. doi: 10.1016/j.bmc.2012.10.035. Epub 2012 Oct 29.
We describe herein the practical post-modification synthesis of oligodeoxynucleotides (ODNs) containing 4,7-diaminoimidazo[5',4':4,5]pyrido[2,3-d]pyrimidine nucleoside (ImN(N)). Since the ImN(N) nucleoside unit possessing tribenzoyl groups on its exocyclic amino groups as the protecting group was quite unstable under acidic conditions, cleavage of its glycosidic linkage in ODN has been suggested throughout the conditions of solid-phase synthesis. As an alternative approach, we investigated a post-modification synthesis of the desired ODNs containing the ImN(N) unit. Starting with protected 4-amino-7-chloro-1-(2-deoxy-β-D-ribofuranosyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine derivative 1, conversion into the corresponding phosphoramidite unit was examined. The p-bromobenzoyl group (p-BrBz) was the best protecting group of 4-amino group of 1 to give the phosphoramidite unit 9 for the post-modification synthesis. After carrying out the ODN synthesis linked to the controlled pore glass (CPG) support, the support was treated with ammonium hydroxide at 55 °C to remove the protecting groups, detach the ODN form the CPG support, and convert the 7-chloro group into a desired amino group.
Sweidan K1, Haddad SF, Aldamen MA, Al-Sheikhb A. Acta Crystallogr Sect E Struct Rep Online. 2013 Jul 3;69(Pt 8):o1191. doi: 10.1107/S1600536813016024. eCollection 2013.
The title compound, C25H26Cl2FN3O4S, contains two bio-active moieties (thio-barbituric acid and fluoro-quinolone). In the crystal, mol-ecules are linked via C-H⋯O and C-H⋯F hydrogen bonds, forming two-dimensional slab-like networks lying parallel to the bc plane. The benzene ring substituted by F and Cl atoms and the 4-chloro-butyl group seem to be partly disordered, however attempts to model the disorder were unsuccessful.