Total Synthesis of a TNBC-Selective Cytotoxic Bromo Nor-eremophilane, PC-A, and Its Preliminary Structure–Activity Relationships,Journal of Natural Products

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Total Synthesis of a TNBC-Selective Cytotoxic Bromo Nor-eremophilane, PC-A, and Its Preliminary Structure–Activity Relationships
Journal of Natural Products ( IF 3.3 ) Pub Date : 2024-03-04 , DOI: 10.1021/acs.jnatprod.3c01075
Sayaka Maeda ₁ , Wakana Nakayama ₁ , Yohei Saito ₁ , Momoko Sagano ₁ , Masuo Goto ₂ , Kyoko Nakagawa-Goto _{1,

2}

Affiliation

PC-A (1), a bromo nor-eremophilane, showed selective antiproliferative activity against a triple-negative breast cancer (TNBC) cell line. This unique activity prompted us to establish a total synthesis to facilitate a structure–activity relationship (SAR) study and selectivity optimization. An enantioselective first total synthesis of 1 was achieved starting from (R)-carvone through a side chain extension with a Mukaiyama aldol reaction and decalin construction. The synthesized decalin derivatives and debromo PC-A (2) were evaluated for antiproliferative activity against five human tumor cell lines, including TNBC, to assess preliminary SAR correlations.

中文翻译：

TNBC 选择性细胞毒性溴代去甲瑞莫兰 (PC-A) 的全合成及其初步构效关系

PC-A ( 1 ) 是一种溴代去甲灵，对三阴性乳腺癌 (TNBC) 细胞系表现出选择性抗增殖活性。这种独特的活性促使我们建立全合成，以促进构效关系（SAR）研究和选择性优化。以 ( R )-香芹酮为原料，通过 Mukaiyama 羟醛反应和十氢化萘结构进行侧链延伸，实现了1的对映选择性首次全合成。评估了合成的十氢萘衍生物和去溴 PC-A ( 2 ) 对五种人类肿瘤细胞系（包括 TNBC）的抗增殖活性，以评估初步的 SAR 相关性。

更新日期：2024-03-04

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