Anticonvulsant activity, molecular modeling and synthesis of spirooxindole-4H-pyran derivatives using a novel reusable organocatalyst.
1-(2-Aminoethyl) piperazine
Anticonvulsant
Graphene oxide
Mice
Molecular docking
Pentylenetetrazole
Spirooxindole-4H-pyran
Journal
Molecular diversity
ISSN: 1573-501X
Titre abrégé: Mol Divers
Pays: Netherlands
ID NLM: 9516534
Informations de publication
Date de publication:
Dec 2022
Dec 2022
Historique:
received:
08
09
2021
accepted:
17
12
2021
pubmed:
27
1
2022
medline:
9
11
2022
entrez:
26
1
2022
Statut:
ppublish
Résumé
Fifteen derivatives of spirooxindole-4H-pyran (A
Identifiants
pubmed: 35079947
doi: 10.1007/s11030-021-10372-7
pii: 10.1007/s11030-021-10372-7
doi:
Substances chimiques
Anticonvulsants
0
Pyrans
0
Pentylenetetrazole
WM5Z385K7T
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
3129-3141Subventions
Organisme : Shiraz University of Medical Sciences
ID : 95-01 36-13130
Organisme : shiraz University of Medical Sciences
ID : 24020
Informations de copyright
© 2022. The Author(s), under exclusive licence to Springer Nature Switzerland AG.
Références
Marzouk AA, Bass AK, Ahmed MS, Abdelhamid AA, Elshaier YA, Salman AM et al (2020) Design, synthesis and anticonvulsant activity of new imidazolidindione and imidazole derivatives. Bioorg Chem. 101:104020
pubmed: 32599366
Kumar R, Singh T, Singh H, Jain S, Roy R (2014) Design, synthesis and anticonvulsant activity of some new 6, 8-halo-substituted-2h-[1, 2, 4] triazino [5, 6-b] indole-3 (5h)-one/-thione and 6, 8-halo-substituted 5-methyl-2h-[1, 2, 4] triazino [5, 6-b] indol-3 (5h)-one/-thione. EXCLI J 13:225
pubmed: 26417257
pmcid: 4464186
Tang DH, Malone DC, Warholak TL, Chong J, Armstrong EP, Slack MK et al (2015) Prevalence and incidence of epilepsy in an elderly and low-income population in the United States. J Clin Neurol 11(3):252–261
pubmed: 26022458
pmcid: 4507380
Banerjee B (2017) Recent developments on ultrasound-assisted one-pot multicomponent synthesis of biologically relevant heterocycles. Ultrason Sonochem 35:15–35
pubmed: 27771265
Cheng D, Ishihara Y, Tan B, Barbas CF III (2014) Organocatalytic asymmetric assembly reactions: synthesis of spirooxindoles via organocascade strategies. ACS Catal 4(3):743–762
Pavlovska TL, Redkin RG, Lipson VV, Atamanuk DV (2016) Molecular diversity of spirooxindoles. Synthesis and biological activity. Mol Divers 20(1):299–344
pubmed: 26419598
Akbari A, Azami-Sardooei Z, Hosseini-Nia A (2013) Synthesis and biological evaluation of 2-Amino-4H-pyran-3, 4, 5-tricarboxylate salt derivatives. J Korean Chem Soc 57(4):455–460
Zhang M, Fu Q-Y, Gao G, He H-Y, Zhang Y, Wu Y-S et al (2017) Catalyst-free, visible-light promoted one-pot synthesis of spirooxindole-pyran derivatives in aqueous ethyl lactate. ACS Sustain Chem Eng 5(7):6175–6182
Laskar S, Brahmachari G (2014) Access to biologically relevant diverse chromene heterocycles via multicomponent reactions (MCRs): recent advances. Org Biomol Chem 2:1–50
Mahdavi S, Habibi A, Dolati H, Habibi M (2014) Synthesis of 2-amino-4H-pyran derivatives via three component reaction in the presence of 4-Dimethylaminopyridine (DMAP) as catalyst
Brahmachari G (2021) Green synthetic approaches for biologically relevant 2-amino-4H-pyrans and 2-amino-4H-pyran-annulated heterocycles in aqueous media. In: Green synthetic approaches for biologically relevant heterocycles. Elsevier, India, pp 471–504
Martínez-Grau A, Marco J (1997) Friedländer reaction on 2-amino-3-cyano-4H-pyrans: synthesis of derivatives of 4H-pyran [2, 3-b] quinoline, new tacrine analogues. Bioorg Med Chem Lett 7(24):3165–3170
Zhang W-H, Chen M-N, Hao Y, Jiang X, Zhou X-L, Zhang Z-H (2019) Choline chloride and lactic acid: a natural deep eutectic solvent for one-pot rapid construction of spiro [indoline-3, 4′-pyrazolo [3, 4-b] pyridines]. J Mol Liq 278:124–129
Vine KL, Locke JM, Ranson M, Pyne SG, Bremner JB (2007) An investigation into the cytotoxicity and mode of action of some novel N-alkyl-substituted isatins. J Med Chem 50(21):5109–5117
pubmed: 17887662
Logan J, Fox M, Morgan J, Makohon A, Pfau C (1975) Arenavirus inactivation on contact with N-substituted isatin beta-thiosemicarbazones and certain cations. J Gen Virol 28(3):271–283
pubmed: 809544
Pandeya SN, Raja AS, Stables JP (2002) Synthesis of isatin semicarbazones as novel anticonvulsants-role of hydrogen bonding. J Pharm Pharm Sci 5(3):266–271
pubmed: 12553895
Pandeya SN, Smitha S, Jyoti M, Sridhar SK (2005) Biological activities of isatin and its derivatives. Acta Pharm 55(1):27–46
pubmed: 15907222
Coaviche-Yoval A, Luna H, Tovar-Miranda R, Soriano-Ursúa MA, Trujillo-Ferrara JG (2019) Synthesis and biological evaluation of novel 2, 3-disubstituted benzofuran analogues of GABA as neurotropic agents. Med Chem 15(1):77–86
pubmed: 29792150
Divar M, Zomorodian K, Sabet R, Moeini M, Khabnadideh S (2019) An efficient method for synthesis of some novel spirooxindole-4H-pyran derivatives. Polycycl Aromat Compd 41:1–14
Mohammadi Ziarani G, Hosseini Mohtasham N, Lashgari N, Badiei A, Amanlou M, Bazl R (2012) Convenient one-pot synthesis of spirooxindole-4H-pyrans in the presence of SBA-Pr-NH2 and evaluation of their urease inhibitory activities. J Nanostruct 2(4):489–500
Wang L-M, Jiao N, Qiu J, Yu J-J, Liu J-Q, Guo F-L et al (2010) Sodium stearate-catalyzed multicomponent reactions for efficient synthesis of spirooxindoles in aqueous micellar media. Tetrahedron 66(1):339–343
Zhu S-L, Ji S-J, Zhang Y (2007) A simple and clean procedure for three-component synthesis of spirooxindoles in aqueous medium. Tetrahedron 63(38):9365–9372
Shanthi G, Subbulakshmi G, Perumal PT (2007) A new InCl3-catalyzed, facile and efficient method for the synthesis of spirooxindoles under conventional and solvent-free microwave conditions. Tetrahedron 63(9):2057–2063
Zhang M, Liu Y-H, Shang Z-R, Hu H-C, Zhang Z-H (2017) Supported molybdenum on graphene oxide/Fe3O4: an efficient, magnetically separable catalyst for one-pot construction of spiro-oxindole dihydropyridines in deep eutectic solvent under microwave irradiation. Catal Commun 88:39–44
Bahrami K, Khodaei MM, Fattahpour P (2011) SBA-15-Pr–SO 3 H as nanoreactor catalyzed oxidation of sulfides into sulfoxides. Catal Sci Technol 1(3):389–393
Meshram HM, Kumar DA, Prasad BRV, Goud PR (2010) Efficient and convenient polyethylene glycol (PEG)-mediated synthesis of spiro-oxindoles. Helv Chim Acta 93:648
Chen M-N, Di J-Q, Li J-M, Mo L-P, Zhang Z-H (2020) Eosin Y-catalyzed one-pot synthesis of spiro [4H-pyran-oxindole] under visible light irradiation. Tetrahedron 76(14):131059
Didaskalou C, Kupai J, Cseri L, Barabas J, Vass E, Holtzl T et al (2018) Membrane-grafted asymmetric organocatalyst for an integrated synthesis–separation platform. ACS Catal 8(8):7430–7438
Zhu Y, Murali S, Cai W, Li X, Suk JW, Potts JR et al (2010) Graphene and graphene oxide: synthesis, properties, and applications. Adv Mater 22(35):3906–3924
pubmed: 20706983
Singh RK, Kumar R, Singh DP (2016) Graphene oxide: strategies for synthesis, reduction and frontier applications. RSC Adv 6(69):64993–65011
Kwan YCG, Ng GM, Huan CHA (2015) Identification of functional groups and determination of carboxyl formation temperature in graphene oxide using the XPS O 1s spectrum. Thin Solid Films 590:40–48
Wang S, Li X, Liu Y, Zhang C, Tan X, Zeng G et al (2018) Nitrogen-containing amino compounds functionalized graphene oxide: synthesis, characterization and application for the removal of pollutants from wastewater: a review. J Hazard Mater 342:177–191
pubmed: 28829983
Leng L, Xu S, Liu R, Yu T, Zhuo X, Leng S et al (2020) Nitrogen containing functional groups of biochar: an overview. Bioresour Technol 298:122286
pubmed: 31690478
Mohammadi-Khanaposhtani M, Shabani M, Faizi M, Aghaei I, Jahani R, Sharafi Z et al (2016) Design, synthesis, pharmacological evaluation, and docking study of new acridone-based 1, 2, 4-oxadiazoles as potential anticonvulsant agents. Eur J Med Chem 112:91–98
pubmed: 26890115
Asadollahi A, Asadi M, Hosseini FS, Ekhtiari Z, Biglar M, Amanlou M (2019) Synthesis, molecular docking, and antiepileptic activity of novel phthalimide derivatives bearing amino acid conjugated anilines. Res Pharm Sci 14(6):534
pubmed: 32038733
pmcid: 6937752
Enna SJ (2007) The GABA receptors. The GABA receptors. Springer, pp 1–21
Watanabe M, Maemura K, Kanbara K, Tamayama T, Hayasaki H (2002) GABA and GABA receptors in the central nervous system and other organs. In: Jeon KW (ed) International review of cytology, vol 213. Academic Press, New York, pp 1–47
Li M-M, Duan C-S, Yu Y-Q, Xu D-Z (2018) A general and efficient one-pot synthesis of spiro [2-amino-4H-pyrans] via tandem multi-component reactions catalyzed by Dabco-based ionic liquids. Dyes Pigm 150:202–206
Molla A, Hussain S (2016) Base free synthesis of iron oxide supported on boron nitride for the construction of highly functionalized pyrans and spirooxindoles. RSC Adv 6(7):5491–5502
Lamie PF, El-Kalaawy AM, Latif NSA, Rashed LA, Philoppes JN (2021) Pyrazolo [3, 4-d] pyrimidine-based dual EGFR T790M/HER2 inhibitors: design, synthesis, structure–activity relationship and biological activity as potential antitumor and anticonvulsant agents. Eur J Med Chem 214:113222
pubmed: 33545637
Sirakanyan SN, Spinelli D, Geronikaki A, Kartsev V, Hakobyan EK, Petrou A et al (2021) Synthesis and neurotropic activity of new heterocyclic systems: Pyridofuro [3, 2-d] pyrrolo [1, 2-a] pyrimidines, Pyridofuro [3, 2-d] pyrido [1, 2-a] pyrimidines and Pyridofuro [3′, 2′: 4, 5] pyrimido [1, 2-a] azepines. Molecules 26(11):3320
pubmed: 34205930
pmcid: 8198642