Synthesis of 3,4-diaryl- and 4-acyl-3-arylpyrroles and study of their antimitotic activity

A Two-Step Approach to a Hexacyclic Lamellarin Core via 1,3-Dipolar Cycloaddition of Isoquinolinium Ylides to Nitrostilbenes

“…Active MnO 2 was synthesized according to a known method and used within a month. The preparation and characteristics of 6,7-dimethoxyisoquinoline, nitrostilbenes 2a , 2b , 2c , 2e , and 2f , and 2g were identical to those reported previously.…”

“…Yellowish solid; 480 mg, 56% yield; mp 158−159 °C; 1 H NMR (DMSO-d 6 , 500 MHz) δ 9.17 (d, 1H, J = 7.6 Hz), 7.30 (s, 1H), 7.22 (broad s, 2H), 7.16 (d, 1H, J = 7.6 Hz), 6.98 (d, 2H, J = 8.6 Hz), 6.92 (s, 1H), 6.65 (s, 1H), 6.60 (s, 1H), 4.04 (q, 2H, J = 7.0 Hz), 3.87 (s, 3H), 3.78 (s, 3H), 3.76 (s, 3H), 3.59 (s, 3H), 3.55 (s, 3H), 3.22 (s, 3H), 0.92 (t, 3H, J = 7.0 Hz); 13 C{ 1 H} NMR (DMSO-d 6 , 125 MHz) δ 161. 4, 158.6, 151.6, 149.2, 148.8, 141.9, 132.5, 131.6, 129.6, 127.8, 123.0, 122.7, 118.9, 118.2, 116.9, 115.9, 113.9, 112.5, 112.1, 108.2, 104.7, 98.2, 59.1, 56.5, 56.1, 55.9, 55.6, 55.2, 54.6, 13.7; MS (70 eV) for C 33 H 33 NO 8 m/z (%) 571 [M] + (40), 498 (6), 69 (32), 29 (100), 15 (31). Anal.…”

Toward “E‐Ring‐Free” Lamellarin Analogues: Synthesis and Preliminary Biological Evaluation

“…Other commercially available solvents and reagents were used without further purification. Pyridinium ylides 1 and 1 a , [25] nitrostilbenes 2 and 2 a – 2 c [24a,26] have been synthesized according to the described methods. Compounds 5 a – 5 c were prepared according to the published procedure [21] .…”

α‐Substituted Chalcones: A Key Review

“…A paper published by Samet and colleagues [136] described the synthesis of different pyrrole derivatives from α‐nitrochalcones (reaction 7, Figure 31). The antimitotic activity of the synthesized pyrroles was investigated on a sea urchin embryo model.…”