Apricoxib, A COX-2 inhibitor.
APRICOXIB
A COX-2 inhibitor.
C19H20N2O3S
Mol wt: 356.439
CAS: 197904-84-0
CS-701; TG01, R-109339, Benzenesulfonamide, 4-[2-(4-ethoxyphenyl)-4-methyl-1H-pyrrol-1-yl]-;
4-[2-(4-ethoxyphenyl)-4-methyl-1H-pyrrol-1-yl]benzenesulfonamide .
Published online Aug 19, 2011. doi: 10.1016/j.bmcl.2011.08.050
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An efficient synthesis of apricoxib (CS-706), a selective cyclooxygenase inhibitor, was developed using copper catalysed homoallylic ketone formation from methyl 4-ethoxybenzoate followed by ozonolysis to an aldehyde, and condensation with sulphanilamide. This method provided multi-gram access of aprocoxib in good yield. Apricoxib exhibited potency equal to celecoxib at inhibition of prostaglandin E2 synthesis in two inflammatory breast cancer cell lines.
c26. Synthesis of Apricoxib (1):
Homoallylic ketone (8) (5.0 g, 21.53 mmol) in 180 mL of CH2Cl2/MeOH (1:5) was treated with ozone bubbles at −78°C until a blue coloration persisted. The ---------------------------------DELETED...................................... The crude brown material was purified by silica gel flash chromatography using a gradient of EtOAc in hexane to give apricoxib as white solid (5.5 g, 15.43 mmol, 71%).
m.p. 161–163°C (lit. 135–139°C14).
1H NMR (CDCl3, 300.0 MHz) δ 1.32 (t, J = 6.9 Hz, 3H), 2.1 (s, 3H), 3.92 (q, J = 6.9 Hz, 2H), 4.95 (s, 2H), 6.14 (m, 1H), 6.63 (m, 1H), 6.69 (d, J = 6.6 Hz, 2H), 6.94 (d, J = 6.6 Hz, 2H), 7.13 (d, J = 6.6 Hz, 2H), 7.74 (d, J= 6.6 Hz, 2H).
13C NMR (CDCl3, 75.0 MHz) δ 11.7, 14.8, 63.4, 82.4, 113.2, 114.4, 121.0, 121.1, 124.9, 125.2, 127.4, 129.7, 133.6, 138.7, 144.2, 158.0
M+H Calcd: 357.1273; Found, 357.1252.
01
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1H, 13C, and COSY NMR spectra of compounds 1 and 8.
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