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首页> 外文期刊>RSC Advances >Access to steroidal pyridazines via modified thiohydrazides
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Access to steroidal pyridazines via modified thiohydrazides

机译：通过改性的硫代肼进入甾醇哒嗪

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摘要

An approach to steroids annulated with pyridazines via cascade imination/electrocyclization of chlorovinyl aldehydes with oxamic acid thiohydrazides is disclosed. A mechanistic rationalization was performed using real-time ~(1) H NMR spectroscopy and computational studies. A series of 18-nor-5α-androsta-2,13-diene[3,2- d ]pyridazines, androsta-2-ene[3,2- d ]pyridazines and Δ ~(1,3,5(10)) -estratrieno[16,17- d ]pyridazines were synthesized from native hormones. These compounds were screened for cytotoxicity against the human estrogen-responsive breast cancer cell line MCF-7 and the estrogen-independent breast cancer cell line MDA-MB-231. The structure–activity relationship analysis revealed that the annulation of the pyridazine moiety to the A-ring of the 17β-hydroxy-5α-androsta-2-ene core provides high antiproliferative activity. Compounds 7a and 10b exhibited higher antiproliferative potency than the drug cisplatin. 5α-Androsta-2-ene[3,2- d ]pyridazine 10c showed good selectivity against the MCF-7 breast cancer cells.
机译：公开了一种通过酸胆嗪与丙酰基醛与氧基酸硫代酰肼的氯酰醛的级联/电循环的类固醇的方法。使用实时〜（1）H NMR光谱和计算研究进行机械合理化。一系列18-NOR-5α-ANDROSTA-2,13-二烯[3,2-D]哒嗪，Androsta-2-eNE [3,2-D]哒嗪和δ〜（1,3,5（10） ）-estratrieno [16,17-d]哒嗪由天然激素合成。将这些化合物筛选对人雌激素响应乳腺癌细胞系MCF-7和雌激素无关的乳腺癌细胞系MDA-MB-231的细胞毒性。结构 - 活性关系分析显示，吡啶嗪部分与17β-羟基-5α-肾甲烷-2-烯核的A环的环节提供高抗增殖活性。化合物7a和10b表现出比药物顺铂更高的抗增殖效力。 5α-androsta-2-eNE [3,2-D]吡啶啶10c对MCF-7乳腺癌细胞显示出良好的选择性。

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