Fused Systems Based on 2-Aminopyrimidines: Synthesis Combining Deprotolithiation-in situ Zincation with N-Arylation Reactions and Biological Properties

Madani Hedidi; Julien Maillard; William Erb; Frédéric Lassagne; Yury S.Halauko; Oleg A.Ivashkevich; Vadim E.Matulis; Thierry Roisnel; Vincent Dorcet; Monzer Hamzé; Ziad Fajloun; Blandine Baratte; Sandrine Ruchaud; Stéphane Bach; Ghenia Bentabed-Ababsa; Florence Mongin

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Fused Systems Based on 2-Aminopyrimidines: Synthesis Combining Deprotolithiation-in situ Zincation with N-Arylation Reactions and Biological Properties

机译：基于2-氨基嘧啶的融合系统：合成与N-芳基化反应和生物学性质的去质子化 - 原位锌合成

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Various aromatic ketones were first functionalized next to the carbonyl function by deprotolithiation in the presence of a zinc salt followed by iodolysis. The outcome of the reactions was analyzed, and in particular their regioselectivity in the light of the calculated pK_a values. Various halogenated ketones were next involved in coppercatalyzed twofold C-N bond formation to obtain fused systems based on 2-aminopyrimidines. Besides a potential antibacterial effect, 2- aminobenzothiopyrano[4,3,2-de]quinazoline was shown to inhibit PIM1 (IC_(50): 0.61 μM) and CDK2/cyclin A (IC_(50): 2.0 μM) kinases.

机译：通过在锌盐存在下通过碘溶解后的去污性首先在羰基官能下官能化各种芳香酮官能化。分析反应的结果，特别是在计算的PK_A值的光中尤其接收性。接下来参与各种卤代酮，参与铜催化的双重C-N键形成，得到基于2-氨基嘧啶的熔融系统。除了潜在的抗菌作用外，2-氨基苯甲酸胆碱[4,3,2-DE]喹唑啉被显示为抑制PIM1（IC_（50）：0.61μm）和CDK2 / cyclin A（IC_（50）：2.0μm）激酶。

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来源
《European journal of organic chemistry》 |2017年第39期|共13页
作者
Madani Hedidi; Julien Maillard; William Erb; Frédéric Lassagne; Yury S.Halauko; Oleg A.Ivashkevich; Vadim E.Matulis; Thierry Roisnel; Vincent Dorcet; Monzer Hamzé; Ziad Fajloun; Blandine Baratte; Sandrine Ruchaud; Stéphane Bach; Ghenia Bentabed-Ababsa; Florence Mongin;
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作者单位

Equipe Chimie Organique et Interfaces Institut des Sciences Chimiques de Rennes UMR 6226 CNRS - Université de Rennes 1 Batiment 10A Case 1003 Campus Scientifique de Beaulieu 35042 Rennes France;

Equipe Chimie Organique et Interfaces Institut des Sciences Chimiques de Rennes UMR 6226 CNRS - Université de Rennes 1 Batiment 10A Case 1003 Campus Scientifique de Beaulieu 35042 Rennes France;

Equipe Chimie Organique et Interfaces Institut des Sciences Chimiques de Rennes UMR 6226 CNRS - Université de Rennes 1 Batiment 10A Case 1003 Campus Scientifique de Beaulieu 35042 Rennes France;

Equipe Chimie Organique et Interfaces Institut des Sciences Chimiques de Rennes UMR 6226 CNRS - Université de Rennes 1 Batiment 10A Case 1003 Campus Scientifique de Beaulieu 35042 Rennes France;

UNESCO Chair of Belarusian State University 14 Leningradskaya Str. Minsk 220030 Belarus;

UNESCO Chair of Belarusian State University 14 Leningradskaya Str. Minsk 220030 Belarus;

Research Institute for Physico-Chemical Problems of Belarusian State University 14 Leningradskaya Str. Minsk 220030 Belarus;

Centre de Diffractométrie X Institut des Sciences Chimiques de Rennes UMR 6226 CNRS - Université de Rennes 1 Batiment 10B Campus de Beaulieu 35042 Rennes France;

Centre de Diffractométrie X Institut des Sciences Chimiques de Rennes UMR 6226 CNRS - Université de Rennes 1 Batiment 10B Campus de Beaulieu 35042 Rennes France;

Laboratoire Microbiologie Santé et Environnement (LMSE) EDST Faculté de Santé Publique Lebanese University Tripoli Lebanon;

Laboratory of Applied Biotechnology Azm Center for Research in Biotechnology and its Applications EDST &

Faculty of Science III Lebanese University Tripoli Lebanon;

Sorbonne Universités UPMC Univ Paris 06 CNRS USR3151 "Protein Phosphorylation and Human Disease" Unit Plateforme de criblage KISSf Station Biologique de Roscoff Place Georges Teissier 29688 Roscoff France;

Sorbonne Universités UPMC Univ Paris 06 CNRS USR3151 "Protein Phosphorylation and Human Disease" Unit Plateforme de criblage KISSf Station Biologique de Roscoff Place Georges Teissier 29688 Roscoff France;

Sorbonne Universités UPMC Univ Paris 06 CNRS USR3151 "Protein Phosphorylation and Human Disease" Unit Plateforme de criblage KISSf Station Biologique de Roscoff Place Georges Teissier 29688 Roscoff France;

Laboratoire de Synthèse Organique Appliquée Faculté des Sciences Exactes et Appliquées Université d'Oran 1 Ahmed Ben Bella BP 1524 El M'Naouer 31000 Oran Algeria;

Equipe Chimie Organique et Interfaces Institut des Sciences Chimiques de Rennes UMR 6226 CNRS - Université de Rennes 1 Batiment 10A Case 1003 Campus Scientifique de Beaulieu 35042 Rennes France;

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正文语种 eng
中图分类有机化学;
关键词
Synthetic methods; Ketones; Pyrimidines; Copper; C-N bond formation; Biological activity;

机译：合成方法;酮;嘧啶;铜;C-N键形成;生物活性;

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1. Fused Systems Based on 2-Aminopyrimidines: Synthesis Combining Deprotolithiation-in situ Zincation with N-Arylation Reactions and Biological Properties [J] . Madani Hedidi, Julien Maillard, William Erb, European journal of organic chemistry . 2017,第39期

机译：基于2-氨基嘧啶的融合系统：合成与N-芳基化反应和生物学性质的去质子化 - 原位锌合成
2. Peptide Nanofiber Templated Zinc Oxide Nanostructures as Non-precious Metal Catalyzed N-Arylation of Amines, One-Pot Synthesis of ImidazoHeterocycles and Fused Quinazolines [J] . Taherinia Zahra, Ghorbani-Choghamarani Arash, Hajjami Maryam Catalysis Letters . 2019,第1期

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3. Three-Component Reaction: Synthesis, Characterization, and Biological Study of Some Fused Bridgehead Nitrogen Heterocyclic Systems Containing 4-Methylthiophenyl Moiety [J] . K. Manjunathaa Boja Poojarya Prajwal L. Loboa N. Suchetha Kumarib amp, C. Anoopc Phosphorus, Sulfur, and Silicon and the Related Elements . 2011,第3期

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5. Inverse electron demand Diels-Alder (IEDDA)-driven domino reactions of chromone-fused electron deficient dienes: New methodology for the synthesis of xanthones and xanthone-based polycyclic heteroaromatic molecules. [D] . Dang, Anh-Thu T. 2009

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6. 2-Aminopyrimidine based 4-aminoquinoline anti-plasmodial agents. Synthesis biological activity structure–activity relationship and mode of action studies [O] . Kamaljit Singh, Hardeep Kaur, Kelly Chibale, -1

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7. Fused Systems Based on 2-Aminopyrimidines: Synthesis Combining Deprotolithiation-in situ Zincation with N -Arylation Reactions and Biological Properties [O] . Hedidi, Madani, Maillard, Julien, Erb, William, 2017

机译：基于2-氨基嘧啶的熔融系统：原位去锂化与N-芳基化反应及生物学性质相结合的合成
8. REACTIONS OF URANIUM CARBIDE IN A FUSED KCl-LiCl/ZINC SYSTEM [R] . William C. Robinson, Premo Chiotti 1964

机译：硬质合金KCl-LiCl /锌系中碳化镉的反应

Fused Systems Based on 2-Aminopyrimidines: Synthesis Combining Deprotolithiation-in situ Zincation with N-Arylation Reactions and Biological Properties

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