Reepmeyer John C, Woodruff Jeffrey T
U.S. Food and Drug Administration, Division of Pharmaceutical Analysis, St. Louis, MO 63101, USA.
J Pharm Biomed Anal. 2007 Aug 15;44(4):887-93. doi: 10.1016/j.jpba.2007.04.011. Epub 2007 Apr 18.
An herbal dietary supplement, marketed as a natural product for the enhancement of sexual function, was analyzed by HPLC with photodiode array and mass spectral detection and found to contain a compound related to the synthetic phosphodiesterase-5 (PDE-5) inhibitors. Based on UV spectra, mass spectra and direct infusion MS(n), the structure of the compound was tentatively identified as a sildenafil analogue in which the sulfonyl group had been replaced with an acetyl group. This new analogue is similar to acetildenafil, a previously reported sildenafil analogue, but differs in that it contains an N-methyl group where acetildenafil contains an N-ethyl group. The structure of the unknown was unequivocally established by chemical cleavage of the phenacylamine group of the molecule to generate N-methylpiperazine; other cleavage products matched those generated from acetildenafil. Since the new compound has one less CH(2) group than acetildenafil, it was named nor-acetildenafil.
一种作为增强性功能的天然产品销售的草药膳食补充剂，通过配备光电二极管阵列和质谱检测的高效液相色谱法进行分析，发现其中含有一种与合成磷酸二酯酶-5（PDE-5）抑制剂相关的化合物。基于紫外光谱、质谱和直接进样质谱（n），该化合物的结构初步鉴定为一种西地那非类似物，其中磺酰基被乙酰基取代。这种新的类似物与之前报道的西地那非类似物乙酰基西地那非相似，但不同之处在于它含有一个N-甲基基团，而乙酰基西地那非含有一个N-乙基基团。通过对分子中的苯甲酰胺基团进行化学裂解生成N-甲基哌嗪，明确确定了未知物的结构；其他裂解产物与乙酰基西地那非产生的产物相匹配。由于新化合物比乙酰基西地那非少一个CH(2)基团，因此将其命名为去甲乙酰基西地那非。
