A novel route to a chiral building block for the preparation of cyclopentenyl carbocyclic nucleosides. Synthesis and anticancer activity of enantiomeric neplanocins A

Lukasik Beata; Mikina Maciej; Mikolajczyk Marian; Pawlowska Roza; Zurawinski Remigiusz

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A novel route to a chiral building block for the preparation of cyclopentenyl carbocyclic nucleosides. Synthesis and anticancer activity of enantiomeric neplanocins A

机译：用于制备环戊烯基核苷的手性积木的新途径。对映体Neplanocins A的合成和抗癌活性

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The synthesis of both enantiomers of 3-[(tert-butyldimethylsilyl)oxy]methyl-4,5-O-isopropylidenecyclopent-2-en-1-ol was accomplished in six steps based on optically inactive dimethylmeso-tartrate. This key intermediate in the synthesis of cyclopentenyl carbocyclic nucleosides was subsequently applied in the preparation of enantiomeric neplanocins A. The toxic effect of these compounds was investigated for a series of suspension and adherent cancer cell lines and normal human fibroblasts. (-)-Neplanocin A ((-)-NPA) was more toxic against all tested cancer cell lines than its dextrorotary counterpart. The highest toxicity with IC(50)values of 7 and 10 mu M was observed for the MOLT-4 and A431 cells, respectively. Moreover, (-)-NPAalso induced apoptosis in A431 cell while this effect was not observed for (+)-NPA.

机译：在基于光学活性的二甲基甲基酒桶 - 酒石酸酯，在六个步骤中完成了3 - [（叔丁基二甲基甲硅烷基）氧基]甲基-4,5-O-异丙基二氯丁-2-烯-1-OL的合成。随后施加在对映体Neplanocins A的制备中，在合成环戊烯基碳环核苷酸中的键中间体。研究了这些化合物的毒性作用，用于一系列悬浮液和粘附的癌细胞系和正常的人成纤维细胞。（ - ） - Neplanocin A（ - （ - ） - NPA）对所有测试的癌细胞系更具毒性，而不是其斜角运动的对应物。对于MOLT-4和A431细胞，分别观察到具有7和10μm的IC（50）值的最高毒性。此外，（ - ） - NPAALSO在A431细胞中诱导细胞凋亡，同时未观察到这种效果（+） - NPA。

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《RSC Advances》 |2020年第53期|共10页
作者
Lukasik Beata; Mikina Maciej; Mikolajczyk Marian; Pawlowska Roza; Zurawinski Remigiusz;
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Polish Acad Sci Ctr Mol &

Macromol Studies Div Organ Chem Sienkiewicza 112 PL-90363 Lodz Poland;

Polish Acad Sci Ctr Mol &

Macromol Studies Div Organ Chem Sienkiewicza 112 PL-90363 Lodz Poland;

Polish Acad Sci Ctr Mol &

Macromol Studies Div Organ Chem Sienkiewicza 112 PL-90363 Lodz Poland;

Polish Acad Sci Ctr Mol &

Macromol Studies Div Bioorgan Chem Sienkiewicza 112 PL-90363 Lodz Poland;

Polish Acad Sci Ctr Mol &

Macromol Studies Div Organ Chem Sienkiewicza 112 PL-90363 Lodz Poland;

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1. A novel route to a chiral building block for the preparation of cyclopentenyl carbocyclic nucleosides. Synthesis and anticancer activity of enantiomeric neplanocins A [J] . Lukasik Beata, Mikina Maciej, Mikolajczyk Marian, RSC Advances . 2020,第53期

机译：用于制备环戊烯基核苷的手性积木的新途径。对映体Neplanocins A的合成和抗癌活性
2. Synthesis and QSAR study of the anticancer activity of some novel indane carbocyclic nucleosides. [J] . Yao SW, Lopes VH, Fernandez F, Bioorganic and medicinal chemistry . 2003,第23期

机译：某些新型茚满碳环核苷的抗癌活性的合成和QSAR研究。
3. An Improved Approach to Chiral Cyclopentenone Building Blocks.Total Synthesis of Pentenomycin I and Neplanocin A [J] . John K.Gallos, Christos I.Stathakis, Stefanos S.Kotoulas, The Journal of Organic Chemistry . 2005,第17期

机译：手性环戊烯酮结构单元的一种改进方法。戊戊霉素I和奈普兰霉素A的全合成
4. Synthesis of a new set of polyamidoamine dendrimers and dendritic building blocks with potential application as carrier molecules for anticancer therapeutics [C] . Sabine Fuchs, Timo Kapp, Peter Franke PMSE Symposia . 2003

机译：用潜在应用作为抗癌治疗剂的载体分子的潜在应用的新型聚酰胺胺树枝状大分子和树突式建筑块的合成
5. Synthesis of chiral carbocyclic pentofuranosylamine analogs - versatile precursors for novel carbocyclic nucleosides. [D] . Mehta, Nimish S. 2000

机译：手性碳环戊呋喃糖胺类似物的合成-新型碳环核苷的多功能前体。
6. Flexible synthetic routes to poison-frog alkaloids of the 58-disubstituted indolizidine-class I: synthesis of common lactam chiral building blocks and application to the synthesis of (-)-203A (-)-205A and (-)-219F [O] . Naoki Toyooka, Dejun Zhou, Hideo Nemoto, 2007

机译：灵活的合成路线以生产I58-二取代的吲哚利嗪类毒蛙生物碱：常见内酰胺手性结构单元的合成及其在（-）-203A（-）-205A和（-）- 219F
7. A novel route to a chiral building block for the preparation of cyclopentenyl carbocyclic nucleosides. Synthesis and anticancer activity of enantiomeric neplanocins A [O] . Beata Łukasik, Maciej Mikina, Marian Mikołajczyk, 2020

机译：用于制备环戊烯基核苷的手性积木的新途径。对映体Neplanocins A的合成和抗癌活性

A novel route to a chiral building block for the preparation of cyclopentenyl carbocyclic nucleosides. Synthesis and anticancer activity of enantiomeric neplanocins A

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