Nandrolone phenylpropionate

Химические свойства

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Использование

Anabolic steroid; androgen.

Всемирная организация здравоохранения(ВОЗ)

Nandrolone phenylpropionate, an anabolic steroid, was introduced in 1959. In 1982, low dosage preparations were prohibited in Bangladesh due to inadmissible promotion of products containing anabolic steroids for malnourished children. Higher dosage preparations of nandrolone phenylpropionate remain available in many countries, including Bangladesh, for several highly specific but limited indications that apply to patients with chronic debilitating and emaciating diseases, particularly associated with neoplasia and some types of aplastic anaemia.

Синтез

Nandrolone phenylpropionate is prepared by reacting anhydrous MeCN with a mixture of 3-phenylpropanoic acid, aryneprecursor, nandrolone CsF, K2CO3, and 18-crown-6 in 70 ?? in an oil bath.
Add anhydrous MeCN (0.5 mL) to a mixture of 3-phenylpropanoic acid (30.0 mg, 0.2 mmol, 1.0 equiv), aryneprecursor (119.2 mg, 0.4 mmol, 2.0 equiv), nandrolone (82.3 mg, 0.3 mmol, 1.5 equiv), CsF (182.3 mg, 1.2 mmol, 6.0 equiv), K2CO3 (82.9 mg, 0.6 mmol, 3.0 equiv), and 18-crown-6 (158.6 mg, 0.6 mmol, 3.0 equiv). Warm the mixture to 70 ?? in an oil bath and stir at this temperature for8 hours. Remove all the volatiles directly on rotary evaporator. Purify by flash column chromatography with pet ether:EtOAc = 20:1. 1H NMR (400 MHz, CDCl3) |? 7.31-7.26(m,2H), 7.23-7.17(m,3H), 5.83 (s, lH), 4.65-4.58(m, lH), 2.95(t, J= 8.0 Hz,2H), 2.64(t, J= 8.0 Hz,2H), 2.51-2.36(m, 2H), 2.31-2.04(m, 5H), 1.86-1.79(m, 2H), 1.72-1.61 (m, 2H), 1.57-1.00(m, 8H),0.90-0.81(m, 1H), 0.79 (s, 3H)ppm.
Fig The synthetic method 1 of Nandrolone phenylpropionate