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Conjugated pyrrole/aminoenone and pyrrole/aminoacrylonitrile ensembles: new motives in heterocyclic chemistry

,  , 
Olga Vital'evna Petrova 1
Olga Vital'evna Petrova
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2021.09.001
Published 2021-09-08
Focus article , Volume 31, Issue 5, 573-583
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Sobenina L. N. et al. Conjugated pyrrole/aminoenone and pyrrole/aminoacrylonitrile ensembles: new motives in heterocyclic chemistry // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 573-583.
GOST all authors (up to 50) Copy
Sobenina L. N., Sagitova E. F., Petrova O. V., Trofimov B. A. Conjugated pyrrole/aminoenone and pyrrole/aminoacrylonitrile ensembles: new motives in heterocyclic chemistry // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 573-583.
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TY - JOUR
DO - 10.1016/j.mencom.2021.09.001
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.001
TI - Conjugated pyrrole/aminoenone and pyrrole/aminoacrylonitrile ensembles: new motives in heterocyclic chemistry
T2 - Mendeleev Communications
AU - Sobenina, Lyubov Nikolaevna
AU - Sagitova, Elena Faritovna
AU - Petrova, Olga Vital'evna
AU - Trofimov, Boris Aleksandrovich
PY - 2021
DA - 2021/09/08
PB - Mendeleev Communications
SP - 573-583
IS - 5
VL - 31
ER -
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@article{2021_Sobenina,
author = {Lyubov Nikolaevna Sobenina and Elena Faritovna Sagitova and Olga Vital'evna Petrova and Boris Aleksandrovich Trofimov},
title = {Conjugated pyrrole/aminoenone and pyrrole/aminoacrylonitrile ensembles: new motives in heterocyclic chemistry},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.001},
number = {5},
pages = {573--583},
doi = {10.1016/j.mencom.2021.09.001}
}
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Sobenina, Lyubov Nikolaevna, et al. “Conjugated pyrrole/aminoenone and pyrrole/aminoacrylonitrile ensembles: new motives in heterocyclic chemistry.” Mendeleev Communications, vol. 31, no. 5, Sep. 2021, pp. 573-583. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.001.
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Keywords

acylethynylpyrrole
aminoacrylonitrile
aminoenone
bipyrrole
Cyclization
pyridine
Pyrrole
pyrrolizine
pyrrolo[1,2-a]pyrazine
pyrrolyl-isoxazole

Abstract

Methods for the preparation of two highly flexible synthetic building blocks, namely pyrrole/aminoenone and pyrrole/aminoacrylonitrile ensembles, on the basis of available starting materials such as 2-acylethynylpyrroles or pyrrole-2-carbodithioates, are summarized. The presence of several reactive centers in their molecules (pyrrole ring, enamine and carbonyl or nitrile moieties) ensures their multiple reactivity and application as versatile intermediates in the synthesis of heterocyclic ensembles such as pyrrolyl pyridines, bipyrroles, pyrrolyl-isoxazoles and condensed compounds, such as pyrrolo[3,2-a]pyrazines, pyrrolizines, which have high potential for use in medical chemistry and materials science.

References

2.
10.1016/j.mencom.2021.09.001_h0010
Zhang
Pot, Atom, and Step Economy (PASE) Synthesis, 2019
4.
Push-pull enamines in the synthesis of fused azaheterocycles
Dar'in D.V., Lobanov P.S.
Russian Chemical Reviews, 2015
5.
Methods of synthesis of conjugated ω-amino ketones
Smirnova Y.V., Krasnaya Z.A.
Russian Chemical Reviews, 2000
8.
(d) K. M. Al-Zaydi and L. M. Nhari, Orient. J. Chem., 2006, 22, 38808
9.
N-Propargylic β-enaminocarbonyls: powerful and versatile building blocks in organic synthesis
Arshadi S., Vessally E., Edjlali L., Ghorbani-Kalhor E., Hosseinzadeh-Khanmiri R.
RSC Advances, 2017
10.
Recent Progress in the Synthesis and Applications of Heterocycles Derived from Enaminonitriles
Bondock S., El-Gaber Tarhoni A., A. Fadda A.
Current Organic Chemistry, 2011
11.
Chemistry of Enaminonitriles of Pyrano[2,3-c]pyrazole and Related Compounds
Fadda A.A., El-Mekabaty A., Elattar K.M.
Synthetic Communications, 2013
13.
Simple Conversion of Enamines to 2H-Azirines and Their Rearrangements under Thermal Conditions
Li X., Du Y., Liang Z., Li X., Pan Y., Zhao K.
Organic Letters, 2009
15.
Synthesis of Polycarbonyl Pyrroles via K2S2O8-Mediated Oxidative Cyclization of Enamines
Gao P., Wang J., Bai Z., Shen L., Yan Y., Yang D., Fan M., Guan Z.
Organic Letters, 2016
17.
One-Pot Oxidation and Rearrangement of Propargylamines and in Situ Pyrazole Synthesis
Chen J., Properzi R., Uccello D.P., Young J.A., Dushin R.G., Starr J.T.
Organic Letters, 2014
24.
(a) H. M. F. Madkour, A. A. E. Afify, A. A. Abdalha, G. A. Elsayed and M. S. Salem, Phosphorus, Sulfur Silicon Relat. Elem., 2009, 184, 719; (b) M. A. Khalil, S. M. Sayed and M. A. Raslan, Am. J. Org. Chem., 2012, 2, 171; (c) A. A. Fadda and K. M. Elattar, J. Heterocycl. Chem., 2014, 51, 1697; (d) R. El-Sayed and I. Althagafi, J. Oleo Sci., 2016, 65, 177; (e) A. K. Elziaty, G. Bassioni, A. M. A. Hassan, H. A. Derbala and M. S. Abdel-Aziz, J. Chem., 2016, Article ID 5286462; (f) M. M. El-Shahawi and A. K. El-Ziaty, J. Chem., 2017, Article ID 5610707.
27.
10.1016/j.mencom.2021.09.001_h0115
Kerru
Molecules, 1909
30.
N-Heterocyclic carbene-catalyzed annulation of cyclic β-enamino esters with enals: access to functionalized indolo[2,3-a]quinolizidines
Hu S., Wang B., Zhang Y., Tang W., Fang M., Lu T., Du D.
Organic and Biomolecular Chemistry, 2015
33.
10.1016/j.mencom.2021.09.001_h0145
Chakrabarti
Junjappa, Synlett, 2005
34.
Beliaev N.A., Beryozkina T.V., Lubec G., Bakulev V.A.
Mendeleev Communications, 2019
35.
Belyaeva K.V., Nikitina L.P., Mal’kina A.G., Afonin A.V., Trofimov B.A.
Mendeleev Communications, 2020
36.
Ethynylation of pyrroles with 1-acyl-2-bromoacetylenes on alumina: a formal ‘inverse Sonogashira coupling’
Trofimov B.A., Stepanova Z.V., Sobenina L.N., Mikhaleva A.I., Ushakov I.A.
Tetrahedron Letters, 2004
37.
(b) B. A. Trofimov and L. N. Sobenina, in Targets in Heterocyclic Systems, eds. O. A. Attanasi and D. Spinelli, Italian Society of Chemistry, Rome, 2009, vol. 13, pp. 92-119
38.
Tomilin D.N., Soshnikov D.Y., Trofimov A.B., Gotsko M.D., Sobenina L.N., Ushakov I.A., Afonin A.V., Koldobsky A.B., Vitkovskaya N.M., Trofimov B.A.
Mendeleev Communications, 2016
39.
(d) E. F. Sagitova, D. N. Tomilin, O. V. Petrova, A. B. Budaev, L. N. Sobenina, B. A. Trofimov, G. Q. Yang and R. Hu, Mendeleev Commun., 2019, 29, 658
41.
Synthesis ofC-vinylpyrroles
Sobenina L.N., Demenev A.P., Mikhaleva A.I., Trofimov B.A.
Russian Chemical Reviews, 2002
42.
C-Vinylpyrroles as Pyrrole Building Blocks
Trofimov B.A., Sobenina L.N., Demenev A.P., Mikhaleva A.I.
Chemical Reviews, 2004
43.
Highly Functionalized Pyrrolylpyridines from 2-(Acylethynyl)-pyrroles
Trofimov B.A., Tomilin D.N., Sobenina L.N., Ushakov I.A.
Synthesis, 2020
44.
10.1016/j.mencom.2021.09.001_b0135
Sobenina
Synthesis, 2010
47.
From Acylethynylpyrroles to Pyrrolo[1,2-a]pyrazines in One Step
Sagitova E.F., Sobenina L.N., Trofimov B.A.
Russian Journal of Organic Chemistry, 2020
48.
10.1016/j.mencom.2021.09.001_b0155
Kaur
J. Pharm. Chem. Chem. Sci., 2017
49.
Nanostructured Fused Pyrrole Thin Films: Encoding Nano “Bits” with Temporary Remanence
Canjeevaram Balasubramanyam R.K., Kandjani A.E., Jones L.A., Periasamy S.R., Wong S., Narayan R., Bhargava S.K., Ippolito S.J., Basak P.
Advanced Electronic Materials, 2018
50.
New class of antitubercular compounds: synthesis and anti-tubercular activity of 4-substituted pyrrolo[2,3-c]quinolines
Akula M., Sridevi J.P., Yogeeswari P., Sriram D., Bhattacharya A.
Monatshefte fur Chemie, 2014
51.
Synthesis and antioxidant activity of new tetraarylpyrroles.
Lehuédé J., Fauconneau B., Barrier L., Ourakow M., Piriou A., Vierfond J.
European Journal of Medicinal Chemistry, 1999
52.
10.1016/j.mencom.2021.09.001_b0175
Raines
Patent US, 2016
53.
Pyrroles and other heterocycles as inhibitors of p38 kinase.
de Laszlo S.E., Visco D., Agarwal L., Chang L., Chin J., Croft G., Forsyth A., Fletcher D., Frantz B., Hacker C., Hanlon W., Harper C., Kostura M., Li B., Luell S., et. al.
Bioorganic and Medicinal Chemistry Letters, 1998
54.
10.1016/j.mencom.2021.09.001_b0185
Chang
Patent EP, 1996
55.
Pyrrolizines: Promising scaffolds for anticancer drugs
Belal A., El-Gendy B.E.
Bioorganic and Medicinal Chemistry, 2014
58.
Efficient synthesis of some new antiproliferative N-fused indoles and isoquinolines via 1,3-dipolar cycloaddition reaction in an ionic liquid
Sutariya T.R., Labana B.M., Parmar N.J., Kant R., Gupta V.K., Plata G.B., Padrón J.M.
New Journal of Chemistry, 2015
60.
Ethyl benzoate bearing pyrrolizine/indolizine moieties: Design, synthesis and biological evaluation of anti-inflammatory and cytotoxic activities
Attalah K.M., Abdalla A.N., Aslam A., Ahmed M., Abourehab M.A., ElSawy N.A., Gouda A.M.
Bioorganic Chemistry, 2020
61.
Antimalarial activity of novel pyrrolizidinyl derivatives of 4-aminoquinoline
Sparatore A., Basilico N., Casagrande M., Parapini S., Taramelli D., Brun R., Wittlin S., Sparatore F.
Bioorganic and Medicinal Chemistry Letters, 2008
62.
10.1016/j.mencom.2021.09.001_b0220
Barsoum
Boll. Chim. Farm., 2003
63.
New aromatase inhibitors. Synthesis and biological activity of aryl-substituted pyrrolizine and indolizine derivatives
Sonnet P., Dallemagne P., Guillon J., Enguehard C., Stiebing S., Tanguy J., Bureau R., Rault S., Auvray P., Moslemi S., Sourdaine P., Séralini G.
Bioorganic and Medicinal Chemistry, 2000
65.
Arylpyrrolizines as Inhibitors of Microsomal Prostaglandin E2 Synthase-1 (mPGES-1) or as Dual Inhibitors of mPGES-1 and 5-Lipoxygenase (5-LOX)
Liedtke A.J., Keck P.R., Lehmann F., Koeberle A., Werz O., Laufer S.A.
Journal of Medicinal Chemistry, 2009
67.
10.1016/j.mencom.2021.09.001_b0245
Garzan
Dis., 2017
69.
Deorphaning Pyrrolopyrazines as Potent Multi-Target Antimalarial Agents
Reker D., Seet M., Pillong M., Koch C.P., Schneider P., Witschel M.C., Rottmann M., Freymond C., Brun R., Schweizer B., Illarionov B., Bacher A., Fischer M., Diederich F., Schneider G., et. al.
Angewandte Chemie - International Edition, 2014
70.
10.1016/j.mencom.2021.09.001_b0260
Kolli
Pharma Chem., 2018
72.
An update into the medicinal chemistry of translocator protein (TSPO) ligands
Barresi E., Robello M., Costa B., Da Pozzo E., Baglini E., Salerno S., Da Settimo F., Martini C., Taliani S.
European Journal of Medicinal Chemistry, 2021
73.
8-Hydroxy-3,4-dihydropyrrolo[1,2-a]pyrazine-1(2H)-one HIV-1 integrase inhibitors
Fisher T.E., Kim B., Staas D.D., Lyle T.A., Young S.D., Vacca J.P., Zrada M.M., Hazuda D.J., Felock P.J., Schleif W.A., Gabryelski L.J., Anari M.R., Kochansky C.J., Wai J.S.
Bioorganic and Medicinal Chemistry Letters, 2007
74.
Synthesis and Mechanism Studies of 1,3-Benzoazolyl Substituted Pyrrolo[2,3-b]pyrazine Derivatives as Nonintercalative Topoisomerase II Catalytic Inhibitors
Li P., Zeng P., Chen S., Yao P., Mai Y., Tan J., Ou T., Huang S., Li D., Gu L., Huang Z.
Journal of Medicinal Chemistry, 2015
75.
Pyrrolo[1,2-a]pyrazine and pyrazolo[1,5-a]pyrazine: Novel, potent, and selective series of Vasopressin1b receptor antagonists
Arban R., Bianchi F., Buson A., Cremonesi S., Fabio R.D., Gentile G., Micheli F., Pasquarello A., Pozzan A., Tarsi L., Terreni S., Tonelli F.
Bioorganic and Medicinal Chemistry Letters, 2010
76.
Pyrrolopyrazines as Selective Spleen Tyrosine Kinase Inhibitors
Padilla F., Bhagirath N., Chen S., Chiao E., Goldstein D.M., Hermann J.C., Hsu J., Kennedy-Smith J.J., Kuglstatter A., Liao C., Liu W., Lowrie L.E., Luk K.C., Lynch S.M., Menke J., et. al.
Journal of Medicinal Chemistry, 2013
77.
Discovery of GDC-0853: A Potent, Selective, and Noncovalent Bruton’s Tyrosine Kinase Inhibitor in Early Clinical Development
Crawford J.J., Johnson A.R., Misner D.L., Belmont L.D., Castanedo G., Choy R., Coraggio M., Dong L., Eigenbrot C., Erickson R., Ghilardi N., Hau J., Katewa A., Kohli P.B., Lee W., et. al.
Journal of Medicinal Chemistry, 2018
78.
Fragment-based discovery of potent ERK2 pyrrolopyrazine inhibitors
Burdick D.J., Wang S., Heise C., Pan B., Drummond J., Yin J., Goeser L., Magnuson S., Blaney J., Moffat J., Wang W., Chen H.
Bioorganic and Medicinal Chemistry Letters, 2015
79.
10.1016/j.mencom.2021.09.001_b0295
Zhao
Patent WO, 2019
81.
10.1016/j.mencom.2021.09.001_b0305
Micheli
Bioorg. Med. Chem. Lett., 1804
82.
10.1016/j.mencom.2021.09.001_b0310
Cheng
Patent WO, 2005
83.
10.1016/j.mencom.2021.09.001_b0315
Prunier
J. Med. Chem., 1808
84.
Acylethynylpyrroles as a platform for the one-pot access to 2-(pyrrol-2-yl)-3-acylpyridines via the dihydrogenative annelation with propargylamine
Sobenina L.N., Sagitova E.F., Markova M.V., Ushakov I.A., Ivanov A.V., Trofimov B.A.
Tetrahedron Letters, 2018
85.
Sagitova E.F., Sobenina L.N., Tomilin D.N., Markova M.V., Ushakov I.A., Trofimov B.A.
Mendeleev Communications, 2019
86.
Facile coupling of 2-(1-ethylthioethenyl)pyrroles with amines: A route to 2-(1-aminoethenyl)pyrroles and 1-amino-3-iminopyrrolizines
Trofimov B.A., Sobenina L.N., Mikhaleva A.I., Petrova O.V., Drichkov V.N., Ushakov I.A., Tarasova O.A., Toryashinova D.D., Rusakov Y.Y., Krivdin L.B.
Journal of Heterocyclic Chemistry, 2007
88.
Synthesis of functionalized 2,2′- and 2,3′-bipyrroles via 3-imino-3H-pyrrolizine-2-carbonitriles
Petrova O.V., Sagitova E.F., Sobenina L.N., Ushakov I.A., Borodina T.N., Smirnov V.I., Trofimov B.A.
Tetrahedron Letters, 2016
90.
Annelated pyrrolo-pyrimidines from amino-cyanopyrroles and BMMAs as leads for new DNA-interactive ring systems
Lauria A., Bruno M., Diana P., Barraja P., Montalbano A., Cirrincione G., Dattolo G., Almerico A.M.
Bioorganic and Medicinal Chemistry, 2005
91.
Adenosine Kinase Inhibitors. 6. Synthesis, Water Solubility, and Antinociceptive Activity of 5-Phenyl-7-(5-deoxy-β-d-ribofuranosyl)pyrrolo[2,3-d]pyrimidines Substituted at C4 with Glycinamides and Related Compounds
Bookser B.C., Ugarkar B.G., Matelich M.C., Lemus R.H., Allan M., Tsuchiya M., Nakane M., Nagahisa A., Wiesner J.B., Erion M.D.
Journal of Medicinal Chemistry, 2005
93.
Synthesis of 3- and 5-amino-5-(3)-(pyrrol-2-yl)isoxazoles
Sobenina L.N., Drichkov V.N., Mikhaleva A.I., Petrova O.V., Ushakov I.A., Trofimov B.A.
Tetrahedron, 2005
94.
Design of Novel Bioisosteres of β-Diketo Acid Inhibitors of HIV-1 Integrase
Sechi M., Sannia L., Carta F., Palomba M., Dallocchio R., Dessì A., Derudas M., Zawahir Z., Neamati N.
Antiviral Chemistry and Chemotherapy, 2005
96.
Synthesis and Antimicrobial Activity of a New Class of Sulfone Linked Bisheterocycles
Padmavathi V., Lakshmi T.R., Venkatesh B.C., Mahesh K.
International Journal of Organic Chemistry, 2011
97.
Identification of phenylisoxazolines as novel and viable antibacterial agents active against Gram-positive pathogens.
Barbachyn M.R., Cleek G.J., Dolak L.A., Garmon S.A., Morris J., Seest E.P., Thomas R.C., Toops D.S., Watt W., Wishka D.G., Ford C.W., Zurenko G.E., Hamel J.C., Schaadt R.D., Stapert D., et. al.
Journal of Medicinal Chemistry, 2002
98.
Synthesis, antimycobacterial screening and ligand-based molecular docking studies on novel pyrrole derivatives bearing pyrazoline, isoxazole and phenyl thiourea moieties
Joshi S.D., Dixit S.R., Kirankumar M.N., Aminabhavi T.M., Raju K.V., Narayan R., Lherbet C., Yang K.S.
European Journal of Medicinal Chemistry, 2016
99.
Ligand-Based Design of Allosteric Retinoic Acid Receptor-Related Orphan Receptor γt (RORγt) Inverse Agonists
Meijer F.A., Doveston R.G., de Vries R.M., Vos G.M., Vos A.A., Leysen S., Scheepstra M., Ottmann C., Milroy L., Brunsveld L.
Journal of Medicinal Chemistry, 2019
100.
Identification and profiling of 3,5-dimethyl-isoxazole-4-carboxylic acid [2-methyl-4-((2S,3′S)-2-methyl-[1,3′]bipyrrolidinyl-1′-yl)phenyl] amide as histamine H3 receptor antagonist for the treatment of depression
Gao Z., Hurst W.J., Czechtizky W., Hall D., Moindrot N., Nagorny R., Pichat P., Stefany D., Hendrix J.A., George P.G.
Bioorganic and Medicinal Chemistry Letters, 2013
102.
A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative
Yang Z., Zhang K., Gong F., Li S., Chen J., Ma J.S., Sobenina L.N., Mikhaleva A.I., Yang G., Trofimov B.A.
Beilstein Journal of Organic Chemistry, 2011
103.
A DFT Study of Pyrrole-Isoxazole Derivatives as Chemosensors for Fluoride Anion
Jin R., Sun W., Tang S.
International Journal of Molecular Sciences, 2012