ABSTRACT
In a previous study, the X-ray structure of the title compound, C9H12N2O7P2·H2O, was reported [Takeuchi et al., (1998 â¶). Chem. Pharm. Bull. 46, 1703-1709], but neither atomic coordinates nor details of the geometry were published. The structure has been redetermined with high precision as its detailed knowledge is essential to elucidate the presumed polymorphism of minodronic acid monohydrate at room temperature. The mol-ecule crystallizes in a zwitterionic form with cationic imidazolium[1,2a]pyridine and anionic phospho-nate groups. The dihedral angle formed by the planes of the pyridine and imidazole rings is 3.55â (9)°. A short intra-molecular C-Hâ¯O contact is present. In the crystal, mol-ecules are linked by O-Hâ¯O, N-Hâ¯O and C-Hâ¯O hydrogen bonds and π-π inter-actions [centroid-to-centroid distance = 3.5822â (11)â Å], forming a three-dimensional structure.
ABSTRACT
An investigation of the polar glycosidic fraction from the leaves of myrtle afforded four galloylated nonprenylated phloroglucinol glucosides (3a-d) related to the endoperoxide hormone G3 (4) in terms of structure and biogenesis. Despite their close similarity, significant antibacterial activity was shown only by one of these compounds (3b, gallomyrtucommulone B), while the G3 hormone (4) was inactive.
Subject(s)
Glucosides/isolation & purification , Glucosides/pharmacology , Myrtus/chemistry , Phloroglucinol , Anti-Bacterial Agents , Glucosides/chemistry , Microbial Sensitivity Tests , Molecular Structure , Phloroglucinol/analogs & derivatives , Phloroglucinol/chemistry , Phloroglucinol/isolation & purification , Phloroglucinol/pharmacology , Plant Leaves/chemistry , Staphylococcus aureus/drug effectsABSTRACT
The acylative modification of IDN 5390 (3a), a 7,8-secotaxoid under preclinical development, was investigated. A modest decrease of potency was observed upon acylation of the primary and the enolic hydroxyls, suggesting that, just like in paclitaxel, the hydroxyl groups in the upper right-hand sector are not critical for cytotoxicity. The activity of these analogues, and especially of the chemically robust carbonates 3c and 3d, makes it unlikely that the activity of IDN 5390 is due to in vivo oxidation to a fledgling 7-aldehyde and re-aldolization to the corresponding taxane derivative.
