147698-79-1Relevant academic research and scientific papers
Anti-influenza activity of diazaadamantanes combined with monoterpene moieties
Suslov, Evgeniy,Zarubaev, Vladimir V.,Slita, Alexander V.,Ponomarev, Konstantin,Korchagina, Dina,Ayine-Tora, Daniel M.,Reynisson, Jóhannes,Volcho, Konstantin,Salakhutdinov, Nariman
, p. 4531 - 4535 (2017)
The antiviral activity of several diaza-adamantanes containing monoterpenoid moieties against a rimantadine-resistant strain of the influenza A/Puerto Rico/8/34 (H1N1) virus was studied. Hetero-adamantanes containing monoterpene moieties at the aminal position of the heterocycle were found to exhibit lower activity compared to compounds with a diaza-adamantane fragment and a monoterpene moiety linked via an amino group at the 6-position of the hetero-adamantane ring. The highest selectivity index (a ratio of the 50% cytotoxic concentration to the 50% inhibitory concentration) out of 30 was observed for compound 8d, which contains a citronellal monoterpenoid moiety. Diaza-adamantane 8d was superior to its adamantane-containing analog 5 both in its anti-influenza activity and selectivity. Furthermore, 8d has more balanced physicochemical properties than 5, making the former a more promising drug candidate. Modelling these compounds against an influenza virus M2 ion channel predicted plausible binding modes to both the wild-type and the mutant (S31N).
SYNTHESIS AND CONVERSIONS OF POLYHEDRAL COMPOUNDS 17. CONVERSION OF 1,3-DIAZA- AND 1,3,5-TRIAZAADAMANTANES TO NITROGEN-CONTAINING PENTACYCLIC COMPOUNDS
Minasyan, G. G.,Agadzhanyan, Ts. E.,Adamyan, G. G.
, p. 94 - 98 (1994)
It has been shown that derivatives of 1,3-diaza- and 1,3,5-triazaadamantanes, and also derivatives of 3,7-diazabicyclononane, interact with 3,7-bis(bromoacetyl)-3,7-diaza- and 3,7-bis(bromoacetyl)-1,3,7-triazabicyclononanes in the presence of bases to form previously unknown types of heteropolyhedral structures - nitrogen-containing pentacyclic compounds.
Bispidine Platform as a Tool for Studying Amide Configuration Stability
Churakov, Andrei V.,Dalinger, Alexander I.,Gudovannyy, Alexey O.,Kalinin, Mikhail A.,Krut’Ko, Dmitry P.,Lyssenko, Konstantin A.,Medved’Ko, Alexey V.,Ponomarev, Konstantin Y.,Suslov, Eugeny V.,Vatsadze, Sergey Z.
, (2022/01/31)
In this work, the solution conformations of seventeen 3,7-diacyl bispidines were studied by means of NMR spectroscopy including VT NMR experiments. The acyl groups included alkyl, alkenyl, aryl, hetaryl, and ferrocene moieties. The presence of syn/anti-isomers and their ratios were estimated, and some reasons explaining experimental facts were formulated. In particular, all aliphatic and heterocyclic units in the acylic R(CO) fragments led to an increased content of the syn-form in DMSO-d6 solutions. In contrast, only the anti-form was detected in DMSO-d6 and CDCl3 in the case when R = Ph, ferrocenyl, (R)-myrtenyl. In the case of a chiral compound derived from the natural terpene myrtene, a new dynamic process was found in addition to the expected inversion around the amide N-C(O) bond. Here, rotation around the CO-C=C bond in the acylic R fragment was detected, and its energy was estimated. For this compound, ΔG for amide N-C(O) inversion was found to be equal to 15.0 ± 0.2 kcal/mol, and for the rotation around the N(CO)–C2′ bond, it was equal to 15.6 ± 0.3 kcal/mol. NMR analysis of the chiral bispidine-based bis-amide was conducted for the first time. Two X-ray structures are reported. For the first time, the unique syn-form was found in the crystal of an acyclic bispidine-based bis-amide. Quantum chemical calculations revealed the unexpected mechanism for amide bond inversion. It was found that the reaction does not proceed as direct N-C(O) bond inversion in the double-chair (CC) conformation but rather requires the conformational transformation into the chair–boat (CB) form first. The amide bond inversion in the latter requires less energy than in the CC form.
Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones
Dalinger, Alexander I.,Kalinin, Mikhail A.,Kuranov, Sergey O.,Munkuev, Aldar A.,Okhina, Alina A.,Ottenbacher, Roman V.,Patrusheva, Oxana S.,Ponomarev, Konstantin Y.,Rogachev, Artem D.,Salakhutdinov, Nariman F.,Suslov, Evgeniy V.,Vatsadze, Sergey Z.,Volcho, Konstantin P.
, (2021/12/20)
A number of new chiral bispidines containing monoterpenoid fragments have been ob-tained. The bispidines were studied as ligands for Ni-catalyzed addition of diethylzinc to chalcones. The conditions for chromatographic analysis by HPLC-UV were developed,
Conjugates of Bispidine and Monoterpenoids as Ligands of Metal Complex Catalysts for the Henry Reaction
Dalinger, A. I.,Komarova, N. I.,Korchagina, D. V.,Medvedko, A. V.,Mozhaitsev, E. S.,Patrusheva, O. S.,Ponomarev, K. Y.,Rogachev, A. D.,Salakhutdinov, N. F.,Suslov, E. V.,Vatsadze, S. Z.,Volcho, K. P.
, p. 1969 - 1981 (2021/01/13)
Abstract: A number of chiral chelating conjugates combining a bispidine central backbone and one or two pinene side fragments were synthesized. It was shown for the first time that the synthesized compounds are capable to act as catalysts in the Henry rea
Synthesis and analgesic activity of amines combining diazaadamantane and monoterpene fragments
Ponomarev, Konstantin,Morozova, Ekaterina,Pavlova, Alla,Suslov, Evgeniy,Korchagina, Dina,Nefedov, Andrej,Tolstikova, Tat'yana,Volcho, Konstantin,Salakhutdinov, Nariman
, p. 773 - 779 (2018/01/16)
Background: It was found earlier that compounds combining diazaadamantane and monoterpene moieties possessed promising analgesic activity along with low acute toxicity and the lack of ulcerogenic activity. Objective: In this paper, new structural analogues of the most active compounds were synthesized and evaluated for their analgesic activity. Methods: Their structures were confirmed by various analytical methods, such as 1H and13C NMR, HRMS. All of them were evaluated for analgesic activity at a dose of 20 mg/kg or less using acetic acid-induced writhing test and hot plate test. Results: Some compounds showed analgesic activity in acetic acid-induced writhing test. One of the synthesized compounds demonstrated high analgesic activity in both tests with 46% effect in acetic acid-induced writhing test and 89% effect in hot plate test. Both structural fragments of this compound did not possess any analgesic effect at a dose of 20 mg/kg. Conclusion: Structure-activity relationships indicated that the most active compound combines fragments of (–)-myrtenal and 6-amino-5,7-dimethyl-1,3-diazaadamantane. Both parts of the molecule are important for demonstrating analgesic activity.
SYNTHESIS AND TRANSFORMATIONS OF POLYHEDRAL COMPOUNDS. 14. OPENING OF HEXAHYDROPYRIMIDINE RING OF 2-SUBSTITUTED 1,3-DIAZAADAMANTANES BY ELECTROPHILIC REAGENTS
Agadzhanyan, Ts. E.,Arutyunyan, A. D.,Arutyunyan, G. L.
, p. 772 - 775 (2007/10/02)
It was found that a cleavage of the N-C bonds of C-mono- and C,C-disubstituted methylenediamino groups of 1,3-diazaadamantanes takes place by the action of electrophilic reagents.
