Synthesis and Biological Activity Evaluation of 3,4,7,8-Tetrahydro-3,3-Dimethyl-11-Aryl-2H-Pyridazino[1,2-a]Indazole-1,6,9(11H)-Triones by Using an Acidic Ionic Liquid 1-Methylimidazolium Trinitromethanide {[HMIM]C(NO2)3} as a Green Catalyst

被引：1

作者：

Majedi, Soma ^{[1
]}

Karamian, Roya ^{[2
]}

Farida, Seyed Flamed Moazzami ^{[2
]}

Asadbegy, Mostafa ^{[2
]}

Alizadeh, Hojjat ^{[3
]}

机构：

[1] Bu Ali Sina Univ, Fac Chem, Hamadan 6517838395, Iran

[2] Bu Ali Sina Univ, Fac Sci, Dept Biol, Hamadan, Iran

[3] Rooyana Vet Lab, Saqqez, Kurdistan, Iran

来源：

POLYCYCLIC AROMATIC COMPOUNDS | 2021年 / 41卷 / 05期

关键词：

1-Methylimidazolium trinitromethanide{[HMIM]C(NO2)(3)}; antibacterial properties; anticancer activity; antioxidant activity; ionic liquid catalyst; pyridazino[1; 2-a]indazoles; ONE-POT SYNTHESIS; SOLVENT-FREE; ANTIMICROBIAL ACTIVITY; EFFICIENT CATALYST; HETEROCYCLIC-COMPOUNDS; ANTIOXIDANT ACTIVITY; ANTICANCER AGENTS; DERIVATIVES; CANCER; COPPER(II);

D O I：

10.1080/10406638.2019.1653942

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3,4,7,8-tetrahydro-3,3-dimethyl-11-aryl-2H-pyridazino[1,2-a]indazole-1,6,9(11H)-triones 5a-j were synthesized by a one-pot cyclocondensation of four components such as succinic anhydride, hydrazine hydrate, benzaldehyde derivatives and dimedone at room temperature through a multi-component reaction and solvent-free condition by using 1-methyl imidazolium trinitromethanide {[HMIM]C(NO2)(3)} as a very effective ionic liquid catalyst. All synthesized compounds which are soluble in DMSO were subjected to antibacterial activity assay against Escherichia coli, Salmonella enteritidis, Staphylococcus aureus, and Bacillus cereus. Results showed that the compounds had antibacterial activity against some bacteria tested. In addition, the antioxidant activity of the compounds was evaluated by DPPH free radical scavenging assay. Our results indicated that most of the compounds had excellent dose-dependent antiradical properties. Based on obtained data, the compounds possessed moderate to excellent bactericidal effect on both Gram-positive and Gram-negative bacteria. Moreover, the compounds 5b and 5g exhibited the most anti-proliferative potencies against MCF-7 (breast carcinoma), A549 (non-small lung carcinoma) and AGS (gastric carcinoma) cell lines.

引用

页码：1107 / 1122

页数：16

共 10 条

[1] Solvent-free, four-component synthesis of 3,4,7,8-tetrahydro-3,3-dimethyl-11-aryl-2H-pyridazino[1,2-a]indazole-1,6,9(11H)-triones; using 1-butyl-3-methylimidazolium hydroxide ([bmim]OH) as a green and reusable catalyst
Pouramiri, Behjat
Kermani, Esmat Tavakolinejad
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2016, 13 (06) : 1011 - 1017
[2] Solvent-free, four-component synthesis of 3,4,7,8-tetrahydro-3,3-dimethyl-11-aryl-2H-pyridazino[1,2-a]indazole-1,6,9(11H)-triones; using 1-butyl-3-methylimidazolium hydroxide ([bmim]OH) as a green and reusable catalyst
Behjat Pouramiri
Esmat Tavakolinejad Kermani
Journal of the Iranian Chemical Society, 2016, 13 : 1011 - 1017
[3] One-pot, four-component synthesis of new 3,4,7,8-tetrahydro-3,3-dimethyl-11-aryl-2H-pyridazino[1,2-a]indazole-1,6,9(11H)-triones and 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-triones using an acidic ionic liquid N,N-diethyl-N-sulfoethanammonium chloride ([Et3N-SO3H]Cl) as a highly efficient and recyclable catalyst
Pouramiri, Behjat
Kermani, Esmat Tavakolinejad
TETRAHEDRON LETTERS, 2016, 57 (09) : 1006 - 1010
[4] One-pot synthesis and antibacterial activities of novel 1H-pyridazino[1,2-a]indazole-1,6,9(2H,11H)-triones
Sayyafi, Maryam
Soorki, Ali Abolhasani
Bazgir, Ayoob
CHEMICAL & PHARMACEUTICAL BULLETIN, 2008, 56 (09) : 1289 - 1291
[5] Ionic Liquid Catalyzed One-Pot Synthesis of 2H-Pyridazino[1,2-a]indazole-1,6,9(11H)-triones Via Three-Component Reaction under Solvent-Free Conditions
Ding, Maohua
Guo, Hongyun
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (06) : 2061 - 2065
[6] The Mannich reaction in the synthesis of N,S-containing heterocycles 11. Synthesis of 3,3′-(1,4-phenylene)-bis(8-aryl-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-9-carbonitriles)
Dotsenko, V. V.
Krivokolysko, S. G.
Litvinov, V. P.
RUSSIAN CHEMICAL BULLETIN, 2012, 61 (01) : 131 - 135
[7] The Mannich reaction in the synthesis of N,S-containing heterocycles 11. Synthesis of 3,3′-(1,4-phenylene)-bis(8-aryl-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-9-carbonitriles)
V. V. Dotsenko
S. G. Krivokolysko
V. P. Litvinov
Russian Chemical Bulletin, 2012, 61 : 131 - 135
[8] Synthesis of Novel Bioactive Candidates 4-Aryl-1H-indeno[1,2-d]pyrimidine-2,5-diones Using {[HMIM]C(NO2)3} as a Dual Rule Ionic Liquid Catalyst: An Experimental and Theoretical Evaluation of Their Corresponding Antioxidant Activities
Majedi, Soma
Karamian, Roya
Farida, Seyed Hamed Moazzami
POLYCYCLIC AROMATIC COMPOUNDS, 2020, 40 (04) : 1151 - 1163
[9] Mild basic ionic liquids as catalyst for the multi-component synthesis of 7-amino-1,3-dioxo-1,2,3,5-tetrahydropyrazolo[1,2-a][1,2,4]triazole and 6,6-dimethyl-2-phenyl-9-aryl-6,7-dihydro-[1,2,4]triazolo[1,2-a]indaznole-1,3,8(2H,5H,9H)-trione derivatives
Shaterian, Hamid Reza
Azizi, Kobra
JOURNAL OF MOLECULAR LIQUIDS, 2013, 183 : 8 - 13
[10] Synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-triones using 1,4-disulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium dihydrogen sulfate {DABCO(HSO3)2(HSO4)2} as a new ionic liquid catalyst
Shirini, Farhad
Safarpoor, Mohaddeseh
Langarudi, Nikoo
Goli-Jolodar, Omid
DYES AND PIGMENTS, 2015, 123 : 186 - 195

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