A series of nitrate ester analogues of the acetaminophen derivative SCP-1 were prepared by triflic acid catalyzed O-acylation of SCP-1 with chloroalkanoyl chlorides followed by nitration with silver nitrate. The chloroesters and corresponding nitrate esters were obtained in high yields. Preliminary hepatotoxicity studies revealed nitrate esters 5b (MD-38) and 5c (MD-39) to be well tolerated by human hepatocytes and had little effect on the three cytochrome P450 enzymes tested (CYP3A4, CYP2E1 and CYP2D6). In addition, the nitrate ester 5c (MD-39) exhibited antipyretic activity similar to acetaminophen.

中文翻译：

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对乙酰氨基酚衍生物SCP-1的硝酸酯类似物的合成，肝毒性评估和解热活性

对乙酰氨基酚衍生物SCP-1的一系列硝酸酯类似物的制备是通过三氟乙酸用氯代烷酰氯对SCP-1进行O-酰化，然后用硝酸银硝化来制备的。高产率地获得了氯酯和相应的硝酸酯。初步的肝毒性研究显示，人肝细胞对硝酸酯5b（MD-38）和5c（MD-39）具有很好的耐受性，并且对所测试的三种细胞色素P450酶（CYP3A4，CYP2E1和CYP2D6）的影响很小。另外，硝酸酯5c（MD-39）表现出与对乙酰氨基酚相似的解热活性。