Nucleosteroids: carbocyclic nucleoside analogs of androst-4-en-17β-ol

New Purinyl-Steroid and Other Constituents from the Marine Fungus Penicillium brefeldianum ABC190807: Larvicidal Activities against Aedes aegypti

“…e 1 H-NMR spectrum (Table 1) of 1 in deuterated chloroform showed two purine hydrogen signals at δ [13] and adenine [14], which suggests that 1 is a hybrid of the two molecules. Considering that the C(3) ketocarbonyl carbon signal of the steroid nucleus is replaced by a new methine signal (δ H 5.32 (br dd, J � 5.2, 4.8 Hz); δ C 48.9), we inferred that the hybrid molecule was connected between C(3) of the steroid nucleus and N(9′) of the adenine moiety [15,16], and this deduction was further confirmed by heteronuclear multiple bond correlation . e chemical shift of C(3) (δ C 48.9 ppm (d)) revealed that the adenine moiety is α-oriented (axial direction) [15].…”

Steroids: reactions and partial synthesis

“…Some nucleoside analogues of androst-4-en-3β-ol have also been prepared. 32 A carbon-13 NMR study of 4-azasteroids, including finasteride, has been reported. 33 The NMR spectra of a series of 19-norsteroids possessing C-9 substituents have been examined.…”

Nucleosteroids: Synthesis of purinyl-steroid derivatives under mitsunobu reaction conditions

“…We already investigated the synthesis of several steroidpurine coupling products [5,6] through an approach based on nucleophilic reactions, as was previously described by van Lier et al [7]. To broaden the range of steroids potentially useful as starting materials for coupling with nitrogenated bases, we studied the feasibility of the conditions of the Mitsunobu reaction applied to the particular case of cholesterol.…”