Synthesis and Biological Activities of Prenylated Tyrosine Derivatives (I), the Metabolites of Pithomyces ellis.

Abstract

Synthesis and Biological Activities of Prenylated Tyrosine Derivatives (I), the Metabolites of Pithomyces ellis. -Both compounds (I) show significant brine shrimp lethality, but weak antioxidant and antibacterial activities. -(VENKATESWARLU, S.; PANCHAGNULA, G. K.; SUBBARAJU*, G. V.; Indian J.

Two New Prenylated Glycine Derivatives from the Marine‐Derived Fungus Fusarium sp. TW56‐10

“…Further analysis of HMBC of δ H 3.49 (s, 2H) with δ C 174.1 (C, C‐3), C‐5, and C‐6, and δ H 3.72 (s, 2H) with δ C 176.3 (C, C‐1) and C‐3 indicated the presence of propionylglycine unit which attached to the benzene ring at C‐5. Upon extensive analysis of these data, 1 was assigned as a prenylated glycine derivatives N ‐({4‐[(3‐methylbut‐2‐en‐1‐yl)oxy]phenyl}acetyl)glycine as shown in Figure 2 and named fusarine [27] …”

Finding the Ajoene Sweet‐Spot: Structure‐Activity Relations that Govern its Blood Stability and Cancer Cytotoxicity

“…Thereafter, 2 was committed to a low temperature base hydrolysis of the vinyl acetate to form the enethiolate, which was S-sulfenylated by thiosulfonate, 3 (with its phenolic hydroxyl group unprotected), to form vinyl disulfide, 4, in 72 % yield as a 5 : 2 Z : E mixture of stereoisomers as the first of the library members. The thiotosylate reagent, 3, could be prepared in three high-yielding steps (> 95 % yield for each) from commercially available methyl (4hydroxyphenyl)acetate via ester reduction (LiAlH 4 ), [20] Appel hydroxyl group iodination (imidazole, I 2 , and PPh 3 ) [21] and finally substitution with sodium p-toluenethiosulfonate salt. The pivotal vinyl disulfide, 4, was thoroughly characterised by 1 H and 13 C NMR spectroscopy, IR spectroscopy and HRMS, returning favourable data throughout, Scheme 1.…”