Design, Synthesis and Biological Evaluation of and -like Double Warhead Quinolinones Bearing Dihydroxy Naphthalene Moiety as Epidermal Growth Factor Receptor Inhibitors with Potential Apoptotic Antiproliferative Action.

Our investigation includes the synthesis of new naphthalene-bis-triazole-bis-quinolin-2(1H)-ones 4a−e and 7a−e via Cu-catalyzed [3 + 2] cycloadditions of 4-azidoquinolin-2(1H)-ones 3a−e with 1,5-/or 1,8-bis(prop-2-yn-1-yloxy)naphthalene (2) or (6). All structures of the obtained products have been confirmed with different spectroscopic analyses. Additionally, a mild and versatile method based on copper-catalyzed [3 + 2] cycloaddition (Meldal−Sharpless reaction) was developed to tether quinolinones to O-atoms of 1,5- or 1,8-dinaphthols.

Bioactive hydroperoxyl cembranoids from the Red Sea soft coral Sarcophyton glaucum.

A chemical investigation of an ethyl acetate extract of the Red Sea soft coral Sarcophyton glaucum has led to the isolation of two peroxide diterpenes, 11(S) hydroperoxylsarcoph-12(20)-ene (1), and 12(S)-hydroperoxylsarcoph-10-ene (2), as well as 8-epi-sarcophinone (3). In addition to these three new compounds, two known structures were identified including: ent-sarcophine (4) and sarcophine (5). Structures were elucidated by spectroscopic analysis, with the relative configuration of 1 and 2 confirmed by X-ray diffraction.

Cyclooxygenase (COX)-1 and -2 inhibitory labdane diterpenes from Crassocephalum mannii.

Two new labdane diterpenes, 8alpha,19-dihydroxylabd-13 E-en-15-oic acid (1) and 13,14,15,16-tetranorlabdane-8alpha,12,14-triol (2), as well as an acetylated derivative, 8alpha-O-beta-D-glucopyranosyllabd-13 E-ene-15,19-diol-8alpha-2',3',4',6'-hexaacetate (3a), were isolated from the aerial parts of Crassocephalum mannii. The structures of 1, 2, and 3a were elucidated by spectroscopic data analysis. Selective inhibitory activity for 1 and 2 and their acetate derivatives, 1a and 2a, against cyclooxygenases (COX-1 and COX-2) was detected.