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Article ; Online: Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores

Jevtić Ivana I. / Penjišević Jelena Z. / Ivanović Milovan D. / Kostić-Rajačić Slađana V.

Journal of the Serbian Chemical Society, Vol 84, Iss 7, Pp 639-

2019 Volume 647

Abstract: A scalable, cost-efficient and simple synthetic pathway towards potential bivalent opioid/dopamine receptor ligands was developed and optimized. Three novel compounds that contain both opioid and dopamine pharmacophores linked by the four methylene group ...

Abstract	A scalable, cost-efficient and simple synthetic pathway towards potential bivalent opioid/dopamine receptor ligands was developed and optimized. Three novel compounds that contain both opioid and dopamine pharmacophores linked by the four methylene group chain were synthesized in 33, 35 and 39 % overall yield after a four-step synthetic route starting from three commercially available N-aryl piperazines. The anilino piperidine precursor was easily prepared in three steps, as previously published, starting from 4- piperidone. The synthesis presented in this paper could be of interest for heterocyclic and general organic chemistry. The newly designed compounds possessing two pharmacophores, opioid and D2/D3, are potentially useful pharmacological probes. Of particular interest would be the simultaneous binding to both opioid and D2/D3 receptors, and the resulting pharmacological responses may be useful for the further understanding of tolerance and dependence phenomena in opioid clinical use and/or abuse. [Project of the Serbian Ministry of Education, Science and Technological Development, Grant no. 172032]
Keywords	piperidine ; piperazine ; heterocycles ; N-alkylation ; analgesics ; dopaminergic ; Chemistry ; QD1-999
Subject code	540
Language	English
Publishing date	2019-01-01T00:00:00Z
Publisher	Serbian Chemical Society
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article: Synthesis and pharmacological evaluation of novel cis and trans 3-substituted anilidopiperidines.

Jevtić, Ivana I / Savić Vujović, Katarina / Srebro, Dragana / Vučković, Sonja / Ivanović, Milovan D / Kostić-Rajačić, Slađana V

Pharmacological reports : PR

2020 Volume 72, Issue 4, Page(s) 1069–1075

Abstract: Background: 4-Anilidopiperidine class of synthetic opioid analgesics, with it's representative fentanyl, are by far the most potent and clinically significant for the treatment of the severe chronic and surgical pain. However, side effects of μ-opioids ... ...

Abstract	Background: 4-Anilidopiperidine class of synthetic opioid analgesics, with it's representative fentanyl, are by far the most potent and clinically significant for the treatment of the severe chronic and surgical pain. However, side effects of μ-opioids are often quite serious. In order to improve the pharmacological profile of this class of opioid analgesics, a novel fentanyl analogs were designed, synthesized and evaluated in vivo for their antinociceptive activity. Methods: The title compounds were prepared using known synthetic transformations, including N-bromoacetamide mediated Hofmann rearrangement, highly selective carbamate cleavage with trimethylsilyl iodide and dehydration of carboxamide group to nitrile in the presence of SOCl Results: The scalable synthetic route towards novel fentanyl analogs bearing nitrogen groups in position C Conclusion: Of ten compounds tested for their antinociceptive activity, compound cis-4 is characterized by high potency, rapid beginning and short duration of action and due to this might be incorporated in different pharmaceutical forms.
MeSH term(s)	Analgesics, Opioid/chemical synthesis ; Analgesics, Opioid/pharmacology ; Animals ; Dose-Response Relationship, Drug ; Fentanyl/chemical synthesis ; Fentanyl/pharmacology ; Mice ; Pain/drug therapy ; Pain/pathology ; Pain Measurement/drug effects ; Pain Measurement/methods ; Piperidines/chemical synthesis ; Piperidines/pharmacology
Chemical Substances	Analgesics, Opioid ; Piperidines ; Fentanyl (UF599785JZ)
Language	English
Publishing date	2020-07-01
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2186248-5
ISSN	1734-1140
ISSN	1734-1140
DOI	10.1007/s43440-020-00121-2
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: μ-opioid/D2 dopamine receptor pharmacophore containing ligands

Jevtić Ivana I. / Penjišević Jelena Z. / Savić-Vujović Katarina R. / Srebro Dragana P. / Vučković Sonja M. / Ivanović Milovan D. / Kostić-Rajačić Slađana V.

Journal of the Serbian Chemical Society, Vol 85, Iss 6, Pp 711-

Synthesis and pharmacological evaluation

2020 Volume 720

Abstract: Herein, the synthesis and pharmacological evaluation of 13 novel compounds, designed as potential heterobivalent ligands for μ-opioid receptor (MOR) and dopamine D2 receptors (D2DAR), are reported. The compounds consisted of anilido piperidine and N-aryl ...

Abstract	Herein, the synthesis and pharmacological evaluation of 13 novel compounds, designed as potential heterobivalent ligands for μ-opioid receptor (MOR) and dopamine D2 receptors (D2DAR), are reported. The compounds consisted of anilido piperidine and N-aryl piperazine moieties, joined by a variable-length methylene linker. The two moieties represent MOR and D2DAR pharmacophores, respectively. The synthesis encompassed four steps, securing the final products in 28–42 % overall yields. The approach has a considerable synthetic potential, providing access to various related structures. Pharmacological tests involved in vitro competitive assay for D2DAR using [3H] spiperon, as a standard radioligand, and in vivo antinociceptive tests for MOR. The measured dopamine affinities were modest to low, while antinociceptive activity was completely absent. Therefore, the compounds of the general structure prepared in this research are unlikely to be useful as opioid–dopamine receptor heterobivalent ligands. [Project of the Serbian Ministry of Education, Science and Technological Development, Grant no. 172032]
Keywords	piperidine ; piperazine ; heterobivalent ; opioids ; analgesics ; dopami-nergic ; Chemistry ; QD1-999
Subject code	540
Language	English
Publishing date	2020-01-01T00:00:00Z
Publisher	Serbian Chemical Society
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Glutarimides

Popović-Đorđević Jelena B. / Vitnik Vesna D. / Vitnik Željko J. / Ivanović Milovan D.

Hemijska Industrija, Vol 69, Iss 5, Pp 523-

Biological activity, general synthetic methods and physicochemical properties

2015 Volume 536

Abstract: Glutarimides, 2,6-dioxopiperidines are compounds that rarely occur in natural sources, but so far isolated ones exert widespread pharmacological activities, which makes them valuable as potential pharmacotherapeutics. Glutarimides act as androgen ... ...

Abstract	Glutarimides, 2,6-dioxopiperidines are compounds that rarely occur in natural sources, but so far isolated ones exert widespread pharmacological activities, which makes them valuable as potential pharmacotherapeutics. Glutarimides act as androgen receptor antagonists, anti-inflammatory, anxiolytics, antibacterials, and tumor suppressing agents. Some synthetic glutarimide derivatives are already in use as immunosuppressive and sedative (e.g., thalidomide) or anxiolytics (buspirone) drugs. The wide applicability of this class of compounds, justify the interest of scientists to explore new pathways for its syntheses. General methods for synthesis of six-membered imide ring, are presented in this paper. These methods include: a) reaction of dicarboxylic acids with ammonia or primary amine, b) reactions of cyclization: amido-acids, diamides, dinitriles, nitrilo-acids, amido-nitriles, amido-esters, amidoacyl-chlorides or diacyl-chlorides, c) adition of carbon-monoxide on a,b-unsaturated amides, d) oxidation reactions, e) Michael adition of active methylen compounds on methacrylamide or conjugated amides. Some of the described methods are used for closing glutarimide ring in syntheses of farmacological active compounds sesbanimide and aldose reductase inhibitors (ARI). Analyses of the geometry, as well as, the spectroscopic analyses (NMR and FT-IR) of some glutarimides are presented because of their broad spectrum of pharmacological activity. To elucidate structures of glutarimides, geometrical parameters of newly synthesized tert-pentyl-1-benzyl-4-methyl-glutarimide-3-carboxylate (PBMG) are analyzed and compared with the experimental data from X-ray analysis for glutarimide. Moreover, molecular electrostatic potential (MEP) surface which is plotted over the optimized geometry to elucidate the reactivity of PBMG molecule is analyzed. The electronic properties of glutarimide derivatives are explained on the example of thalidomide. The Frontier Molecular Orbital (FMO) and their energies are presented, as well as the energy gap between them. [Projekat Ministarstva nauke Republike Srbije, br. 172032 i br. 172035]
Keywords	glutarimides ; biological activity ; syntheses of glutarimide derivatives ; spectral analysis ; electronic properties ; Chemistry ; QD1-999 ; Science ; Q
Subject code	540
Language	English
Publishing date	2015-01-01T00:00:00Z
Publisher	Association of Chemical Engineers, Belgrade
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: α-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives.

Popović-Djordjević, Jelena B / Jevtić, Ivana I / Grozdanić, Nadja Dj / Šegan, Sandra B / Zlatović, Mario V / Ivanović, Milovan D / Stanojković, Tatjana P

Journal of enzyme inhibition and medicinal chemistry

2017 Volume 32, Issue 1, Page(s) 298–303

Abstract: The inhibitory activities of selected cyclic urea and carbamate derivatives (1-13) toward α-glucosidase (α-Gls) in in vitro assay were examined in this study. All examined compounds showed higher inhibitory activity ( ... ...

Abstract	The inhibitory activities of selected cyclic urea and carbamate derivatives (1-13) toward α-glucosidase (α-Gls) in in vitro assay were examined in this study. All examined compounds showed higher inhibitory activity (IC
MeSH term(s)	Carbamates/pharmacology ; Cell Line, Tumor ; Female ; Glycoside Hydrolase Inhibitors/pharmacology ; Humans ; Structure-Activity Relationship ; Urea/pharmacology
Chemical Substances	Carbamates ; Glycoside Hydrolase Inhibitors ; Urea (8W8T17847W)
Language	English
Publishing date	2017-12
Publishing country	England
Document type	Journal Article
ZDB-ID	2082578-X
ISSN	1475-6374 ; 1475-6366
ISSN (online)	1475-6374
ISSN	1475-6366
DOI	10.1080/14756366.2016.1250754
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Article: Docking studies suggest ligand-specific δ-opioid receptor conformations

Micovic, Vuk / Ivanovic, Milovan D / Dosen-Micovic, Ljiljana

Journal of molecular modeling. 2009 Mar., v. 15, no. 3

2009

Abstract: An automated docking procedure was used to study binding of a series of δ-selective ligands to three models of the δ-opioid receptor. These models are thought to represent the three ligand-specific receptor conformations. Docking results are in agreement ...

Abstract	An automated docking procedure was used to study binding of a series of δ-selective ligands to three models of the δ-opioid receptor. These models are thought to represent the three ligand-specific receptor conformations. Docking results are in agreement with point mutation studies and suggest that different ligands--agonists and antagonists--may bind to the same binding site under different receptor conformations. Docking to different receptor models (conformations) also suggests that by changing to a receptor-specific conformation, the receptor may open or close different binding sites to other ligands. [graphic removed]
Language	English
Dates of publication	2009-03
Size	p. 267-280.
Publisher	Springer-Verlag
Publishing place	Berlin/Heidelberg
Document type	Article
ISSN	0949-183X
DOI	10.1007/s00894-008-0396-7
Database	NAL-Catalogue (AGRICOLA)

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Article: Synthesis of Orthogonally Protected (±)-3-Amino-4-anilidopiperidines and (±)-3-N-Carbomethoxyfentanyl

Jevtić, Ivana I. / Došen-Mićović, Ljiljana I. / Ivanović, Evica R. / Todorović, Nina M. / Ivanović, Milovan D.

Synthesis

2017 Volume 49, Issue 14, Page(s) 3126–3136

Abstract: The synthesis of orthogonally protected cis - and trans -3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann ... ...

Abstract	The synthesis of orthogonally protected cis - and trans -3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann rearrangement, and carbamate cleavage, involved separated (±)- cis and (±)- trans intermediates. Complete retention of configuration was observed at position 3 of the piperidine ring. Specifically protected positions 1 and 3 at the piperidine scaffold allow for selective deprotection and introduction of diverse substituents at the respective nitrogen sites. The orthogonally protected anilidopiperidines open avenues to potentially pharmacologically active compounds, including opioids and various bivalent ligands for G protein-coupled receptors. In addition, a prototype of a novel class of fentanyl derivatives, possessing a 3-amino group, was synthesized by using the same approach.
Keywords	heterocycles ; rearrangement ; acylation ; protecting groups ; diastereoselectivity
Language	English
Publishing date	2017-04-03
Publisher	© Georg Thieme Verlag
Publishing place	Stuttgart ; New York
Document type	Article
ZDB-ID	2033062-5
ISSN	1437-210X ; 0039-7881
ISSN (online)	1437-210X
ISSN	0039-7881
DOI	10.1055/s-0036-1588985
Database	Thieme publisher's database

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Article ; Online: Structural requirements for ligands of the δ-opioid receptor

Mićović Vuk I. / Ivanović Milovan D. / Došen-Mićović Ljiljana

Journal of the Serbian Chemical Society, Vol 74, Iss 11, Pp 1207-

2009 Volume 1217

Abstract: The δ-opioid receptor is sensitive to ligand geometry. In order to assist the synthesis of new δ-selective opioid ligands, the structure elements of δ-selective opioid ligands necessary for their effective binding were investigated. The automated docking ...

Abstract	The δ-opioid receptor is sensitive to ligand geometry. In order to assist the synthesis of new δ-selective opioid ligands, the structure elements of δ-selective opioid ligands necessary for their effective binding were investigated. The automated docking procedure with a flexible ligand was used to simulate the binding of 17 δ-selective ligands to the δ-receptor. It was found that voluminous N-alkyl groups reduce the binding potency of naltrindole derivatives by preventing the ligands from adopting the preferred conformation in the receptor. This was confirmed by enantiospecific binding of chiral compounds where only one enantiomer adopts the naltrindole-like preferred conformation in the binding pocket. Voluminous groups replacing the hydroxyl group in the 3-hydroxybenzyl fragment of naltrindole analogs reduce the binding potency due to unfavorable steric interactions with the receptor. The two diastereoisomers of the potent δ-opioid ligand SNC80 confirmed the preferred binding conformation and the major receptor-ligand interactions.
Keywords	molecular modeling ; δ-opioid receptor ; ligand-receptor interactions ; docking simulation ; Chemistry ; QD1-999
Subject code	540
Language	English
Publishing date	2009-01-01T00:00:00Z
Publisher	Serbian Chemical Society
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Docking studies suggest ligand-specific delta-opioid receptor conformations.

Micovic, Vuk / Ivanovic, Milovan D / Dosen-Micovic, Ljiljana

Journal of molecular modeling

2008 Volume 15, Issue 3, Page(s) 267–280

Abstract: An automated docking procedure was used to study binding of a series of delta-selective ligands to three models of the delta-opioid receptor. These models are thought to represent the three ligand-specific receptor conformations. Docking results are in ... ...

Abstract	An automated docking procedure was used to study binding of a series of delta-selective ligands to three models of the delta-opioid receptor. These models are thought to represent the three ligand-specific receptor conformations. Docking results are in agreement with point mutation studies and suggest that different ligands--agonists and antagonists--may bind to the same binding site under different receptor conformations. Docking to different receptor models (conformations) also suggests that by changing to a receptor-specific conformation, the receptor may open or close different binding sites to other ligands.
MeSH term(s)	Binding Sites ; Ligands ; Models, Molecular ; Protein Conformation ; Receptors, Opioid, delta/antagonists & inhibitors ; Receptors, Opioid, delta/chemistry ; Receptors, Opioid, delta/metabolism ; Structure-Activity Relationship ; Thermodynamics
Chemical Substances	Ligands ; Receptors, Opioid, delta
Language	English
Publishing date	2008-12-04
Publishing country	Germany
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1284729-X
ISSN	0948-5023 ; 1610-2940
ISSN (online)	0948-5023
ISSN	1610-2940
DOI	10.1007/s00894-008-0396-7
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Article: Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide

Jevtić, Ivana I. / Došen-Mićović, Ljiljana / Ivanović, Evica R. / Ivanović, Milovan D.

Synthesis

2016 Volume 48, Issue 10, Page(s) 1550–1560

Abstract: An efficient, one-pot procedure for the Hofmann rearrangement of aromatic and aliphatic amides has been developed. Methyl and benzyl carbamates are produced with N -bromoacetamide in the presence of lithium hydroxide or lithium methoxide, in high yields. ...

Abstract	An efficient, one-pot procedure for the Hofmann rearrangement of aromatic and aliphatic amides has been developed. Methyl and benzyl carbamates are produced with N -bromoacetamide in the presence of lithium hydroxide or lithium methoxide, in high yields. β-Phenylamino amides gave five-membered cyclic ureas stereospecifically. Side products of aryl or benzyl bromination were minimized. This procedure offers an easy access to various protected amines or diamines, which represent important synthetic precursors.
Keywords	Hofmann rearrangement ; amides ; stereoselectivity ; cyclization ; heterocycles
Language	German
Publishing date	2016-03-11
Publisher	© Georg Thieme Verlag
Publishing place	Stuttgart ; New York
Document type	Article
ZDB-ID	2033062-5
ISSN	1437-210X ; 0039-7881
ISSN (online)	1437-210X
ISSN	0039-7881
DOI	10.1055/s-0035-1561405
Database	Thieme publisher's database

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