Synthesis and Conversions of Polyhedral Compounds. 32. Synthesis and Antibacterial Activity of Azaadamantane-Containing Azomethine Dihydrochlorides

Arutyunyan, G. L.; Arutyunyan, A. D.; Gevorkyan, K. A.; Gasparyan, S. P.; Paronikyan, R. V.; Stepanyan, G. M.; Minasyan, N. S.

doi:10.1007/s11094-018-1834-1

Cited by 6 publications

(3 citation statements)

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“…The antibacterial activity of azomethines ( 54–66 ) (Scheme 7) in the form of dihydrochlorides was studied [ 39 ] against gram-positive ( S. aureus 209p, S. aureus 1) and gram-negative ( Sh. dysent.…”

Section: Biological Activity Of Azaadamantanesmentioning

confidence: 99%

“…The antibacterial activity of the 7-amino-triazaadamantane derivatives ( 97 ) and ( 98 ) in the form of hydrochloric acid salts that contained the naphthyl and 5-nitrofuryl substituents, respectively, was studied by Arutyunyan et al ( Table 4 ) [ 39 ]. Nitrofuryl-containing compound ( 98 ) showed moderate bacteriostatic activity against gram-positive and gram-negative bacteria.…”

Section: Biological Activity Of Azaadamantanesmentioning

confidence: 99%

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Azaadamantanes, a New Promising Scaffold for Medical Chemistry

et al. 2021

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Azaadamantanes are nitrogen-containing analogs of adamantane, which contain one or more nitrogen atoms instead of carbon atoms. This substitution leads to several specific chemical and physical properties. The azaadamantane derivatives have less lipophilicity compared to their adamantane analogs, which affects both their interaction with biological targets and bioavailability. The significant increase in the number of publications during the last decade (2009–2020) concerning the study of reactivity and biological activity of azaadamantanes and their derivatives indicates a great theoretical and practical interest in these compounds. Compounds with pronounced biological activity have been already discovered among azaadamantane derivatives. The review is devoted to the biological activity of azaadamantanes and their derivatives. It presents the main methods for the synthesis of di- and triazaadamantanes and summarizes the accumulated data on studying the biological activity of these compounds. The prospects for the use of azaadamantanes in medical chemistry and pharmacology are discussed.

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Section: Biological Activity Of Azaadamantanesmentioning

confidence: 99%

Section: Biological Activity Of Azaadamantanesmentioning

confidence: 99%

Azaadamantanes, a New Promising Scaffold for Medical Chemistry

et al. 2021

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“…These provide a reliable method for the subsequent derivation of multifunctional 2-azaadamantane and its skeleton isomer 2-azaprotoadamantane, which might be used as basic scaffolds for high energy density cage-like compounds. Keywords azaadamantane; azaprotoadamantane; functionalization; ammonolysis; cyclization, nitramine; synthesis design 氮杂金刚烷是一类刚性的、具有多个衍生位点的笼型有机骨架, 是很多天然产物(例如 Daphodhamine B [1][2] 及 Terengganensine A [3] )、药物(可以用于止吐 [4] 、镇痛 [5][6] 、抗病毒 [7] 、抗菌 [8][9][10] 及抗肿瘤 [11][12] )、含能材料 [13][14] 、有机催化剂 [15][16][17][18][19][20][21][22] 及有机配体 [23][24][25] 等物质的核心单元, 一直是有机化学家的研究热点. 氮杂金刚烷衍生物的合成也取得了相当大的进展.…”

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confidence: 99%

Synthesis of 4,8,9,10-Tetrafunctionalized 2-Azaadamantanes and Their 2-Azaprotoadamantane Skeleton Isomers

Cai¹,

Li²,

Zhou³

et al. 2023

Chinese Journal of Organic Chemistry

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The multi-step synthesis of rigid and multifunctionalized azaadamantane skeletons from small molecules has always been a challenge in the field of adamantane chemistry. In this work, the bisepoxidized intermediate was obtained via ketalization, bromination, elimination, and Prilezhaev oxidation using bicyclo[3.3.1]nonane-2,6-dione as the raw material, which was then ammonolyzed and cyclized to generate 9,10-dihydroxy-2-azaadamantane-4,8-dione bis(ethylene ketal) with ammonia at 120 ℃. After that, 9,10-dinitroyloxy-2-nitro-2-azaadamantane-4,8-dione bis(ethylene ketal) was synthesized by N,O-nitration with the overall yield of 10% over six steps. Furthermore, when the bisepoxidized intermediate was ammonolyzed at 135 ℃, a skeleton isomer 4,10-dihydroxy-2-azaprotoadamantane-5,9-dione bis(ethylene ketal) was formed, which was then transformed to the corresponding O-nitrated and N,O-dinitrated derivatives through N-acetylation, deketalization and nitration, respectively. These provide a reliable method for the subsequent derivation of multifunctional 2-azaadamantane and its skeleton isomer 2-azaprotoadamantane, which might be used as basic scaffolds for high energy density cage-like compounds. Keywords azaadamantane; azaprotoadamantane; functionalization; ammonolysis; cyclization, nitramine; synthesis design 氮杂金刚烷是一类刚性的、具有多个衍生位点的笼型有机骨架, 是很多天然产物(例如 Daphodhamine B [1][2] 及 Terengganensine A [3] )、药物(可以用于止吐 [4] 、镇痛 [5][6] 、抗病毒 [7] 、抗菌 [8][9][10] 及抗肿瘤 [11][12] )、含能材料 [13][14] 、有机催化剂 [15][16][17][18][19][20][21][22] 及有机配体 [23][24][25] 等物质的核心单元, 一直是有机化学家的研究热点. 氮杂金刚烷衍生物的合成也取得了相当大的进展. 例如具有一个或多个取代基的氮杂金刚烷, 包括 4-取代 [26][27] 、2,4- [28] 、2,6- [4] 、3,5-二取代 [29] , 多取代 1-氮杂金刚烷 [30][31][32][33] 包括 2-和 4-单取代 [34][35] 、2,6-二取代 [39] , 多取代 2-氮杂金刚烷 [14,[37][38] ; 二氮杂金刚烷如 2,6-二取代 [39] 及多取代 2,6-二氮杂金刚烷 [37,40] 、4-取代及多取代 1,3-二氮杂金刚烷 [41][42][43][44] 的合成有机化学研究论文 2218 http://sioc-journal.cn/

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