Photoinduced synthesis and antitumor activity of a phakellistatin 18 analog with an isoindolinone fragment

Abstract

Cyclic peptides has become a powerful modality in drug development. Naturally isolated cyclic peptides such phakellistatins have been found with broad-spectrum bioactivity. In this paper we have prepared an analog...

Synthesis of 2-Benzyl-3-(2-oxo-2-phenylethyl)isoindolin-1-one Derivatives in Water under Catalyst-Free Conditions

“…All major chemicals and solvents were obtained from commercial sources and used without further purification. 1 H NMR and 13 C NMR spectra were recorded on a Bruker Avance III-500 spectrometer (Swiss Bruker, Switzerland). Mass spectrometry was performed using an LTQ-XL linear ion trap mass spectrometer (Thermo Fisher Scientific, USA).…”

“…yield: 57.3 mg (88%). 1 H NMR (500 MHz, CDCl3) δ 7.91 (dt, J = 7.0, 2.9 Hz, 1H), 7.79 (dd, J = 8. 13 C NMR (126 MHz, CDCl3) δ 197.1, 168.6, 145.9, 137.1, 136.3, 133.7, 131.9, 131.8, 128.7, 128.7, 128.5, 128.1, 128.0, 127.5, 123.9, 122.9, 55.9, 44.7, 42.1.…”

“…yield: 72.1 mg (87%). 1 H NMR (500 MHz, CDCl3) δ 7.91 (dd, J = 6.1, 2.0 Hz, 1H), 7.84 (d, J = 8.2 Hz, 2H), 7.66 (d, J = 8.4 Hz, 2H), 7.55 -7.45 (m, 2H), 7.41 -7.36 (m, 1H), 7.17 (ddd, J = 29.1, 15.5, 7.2 Hz, 5H), 5.27 (t, J = 6.1 Hz, 1H), 4.94 (d, J = 15.5 Hz, 1H), 4.66 (d, J = 15.5 Hz, 1H), 3.48 (dd, J = 17.8, 5.7 Hz, 1H), 3.17 (dd, J = 17.8, 6.6 Hz, 1H). 13 C NMR (126 MHz, CDCl3) δ 196.2, 168.6, 145.5, 138.7, 137.1, 132.0, 131.7, 128.9, 128.7, 128.7, 128.4, 127.9, 127.6, 124.0, 122.7, 55.9, 44.9, 42.5.…”

“…Nitrogen-containing heterocycles, an important class of heterocyclic compounds, form the basic skeletons of many drugs, natural products, and functional materials. [1][2][3][4] Because of their unique pharmacological and biological activity, they are widely used in the synthesis of medicines and pesticides. [5][6][7][8] They exhibit diverse biological activities such as antibacterial, [9] antiparkinsonian, [10] antiinflammatory, [11] antipsychotic, [12] antihypertensive, [13] anticancer, [14] and selective NaV1.7 blocking activity [15] .…”

Recent Advances in Small Peptides of Marine Origin in Cancer Therapy

“…Phakellistatin 14 ( Table 2 and Figure 4 ) showed cancer cell growth inhibitory activity (GI 50 : 5 μg/mL) against P388 cells, and Phakellistatins 13 is reported to be cytotoxic at an effective dose of 10 ng/mL (GI 50 ) against BEL-7404 (human liver cancer cells) cells [ 91 , 92 ]. Due to its good antitumor activity in vitro and in vivo, many researchers have modified this structure in the hope of synthesizing potential Marine drugs with a better anti-cancer effect [ 93 ]. The Microsclerodermins are cyclic hexapeptides isolated from a deep-water sponge of the genus Microscleroderma in 1994.…”