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Synthesis of new class of spirocarbocycle derivatives by multicomponent domino reaction and their evaluation for antimicrobial, anticancer activity and molecular docking studies
Published in Elsevier Masson SAS
2014
PMID: 24956555
Volume: 83
   
Pages: 190 - 207
Abstract
A series of 25 new spirocarbocycles were synthesized by a three component reaction that involves few cyclic nucleophiles, vinyl malononitriles and aldehydes with variable substitution patterns. All the synthesized compounds were evaluated for their antimicrobial activity and the compounds showed significant activity. Synthesized compounds 4c, 4i and 6i showed good anticancer activity against A549 cancer cell line. Molecular docking studies indicated that compound 4i had the greatest affinity for DNA gyrase receptor than others and compound 6i had the greatest affinity for anaplastic lymphoma kinase (ALK) receptor. These compounds can be better therapeutic agents for microbial and cancer cell lines. © 2014 Elsevier Masson SAS. All rights reserved.
About the journal
JournalData powered by TypesetEuropean Journal of Medicinal Chemistry
PublisherData powered by TypesetElsevier Masson SAS
ISSN02235234
Open AccessNo
Concepts (111)
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    3 AMINO 1 (4 CHLOROPHENYL) 1',3' DIOXO 1,1',3',6,7,8,9,9A OCTAHYDROSPIRO(BENZO[7]ANNULENE 2,2' INDENE) 4 CARBONITRILE
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    3 AMINO 1',3' DIOXO 1 4 TOLYL 1,1',3',6,7,8,9,9A OCTAHYDROSPIRO(BENZO[7]ANNULENE 2,2' INDENE) 4 CARBONITRILE
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    3 AMINO 2' OXO 1 4 TOLYL 1,6,7,8,9,9A HEXAHYDROSPIRO(BENZO[7]ANNULENE 2,3' INDOLINE) 4 CARBONITRILE
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    3' AMINO 1' (2 FLUOROPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (2 FLUOROPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (4 BROMOPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (4 BROMOPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2 NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (4 CHLOROPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4 ' CARBONITRILE
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    3' AMINO 1' (4 CHLOROPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3'2 NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (4 METHOXYPHENYL) 2 OXO 6' ,7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (4 METHOXYPHENYL) 2,6 DIOXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(CYCLOHEXANE 1,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (4AMETHOXYPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (FURAN 3 YL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (FURAN 3 YL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (NAPHTHALEN 1 YL) 1,3 DIOXO 1,3,6' ,7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (NAPHTHALEN 1 YL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2 NAPHTHALENE 4' CARBONITRILE
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    3' AMINO 1,3 DIOXO 1' (THIOPHEN 2 YL) 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1,3 DIOXO 1' 4 TOLYL 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 2 OXO 1' (PYRIDIN 2 YL) 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 2 OXO 1' (THIOPHEN 2 YL) 6',7',8',8A' ETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE 4' CARBONITRILE
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    3' AMINO 2 OXO 1' 4 TOLYL 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3.3 NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 2,6 DIOXO 1' 4 TOLYL 6',7',8',8A' TETRAHYDRO 1'H SPIROCYCLOHEXANE 1,2' NAPHTHALENE) 4' CARBONITRILE
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    6 AMINO 1',3' DIOXO 4 4 TOLYL 1',2,3,3A,3',4 HEXAHYDRO 2,5' SPIROBI[INDENE] 7 CARBONITRILE
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    6 AMINO 4 (2 FLUOROPHENYL) 1',3' DIOXO 1',2,3,3A,3',4 HEXAHYDRO 2,5' SPIROBI(INDENE) 7 CARBONITRILE
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    6 AMINO 4 (4 METHOXYPHENYL) 1',3' DIOXO 1',2,3,3A,3',4 HEXAHYDRO 2,5' SPIROBI(INDENE) 7 CARBONITRILE
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    Antiinfective agent
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    Antineoplastic agent
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    Spiro compound
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    Streptomycin
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    Unclassified drug
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    3 AMINO 1',3' DIOXO 1 PARA TOLYL 1,1',3',6,7,8,9,9A OCTAHY DROSPIRO(BENZO[7]ANNULENE 2,2' INDENE) 4 CARBONITRILE
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    3 AMINO 1,3 DIOXO 1' PARA TOLYL 1,3,6 ,7 ,8 ,8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE] 4' CARBONITRILE
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    3 AMINO 2 OXO 1 PARA TOLYL 1,6,7,8,9,9A HEXAHYDROSPIRO(BENZO [7]ANNULENE 2,3' INDOLINE) 4 CARBONITRILE
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    3' AMINO 1' (2 FLUOROPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4 CARBONITRILE
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    3' AMINO 1' (2 FLUOROPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLENE 3,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (4 BROMOPHENYL) 1,3 DIOXO 1,3,6',7' ,8',8A' HEXAHYDRO 1' SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARNONITRILE
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    3' AMINO 1' (4 BROMOPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLENE 3,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (4 CHLOROPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (4 CHLOROPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLENE 3,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (4 METHOXYPHENYL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (4 METHOXYPHENYL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (FURAN 3 YL) 1,3 DIOXO 1,3,6',7' ,8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (FURAN 3 YL) 2 OXO 6' ,7',8',8A' TETRAHYDRO 1'H SPIRO[INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (NAPHTHALEN 1 YL) 1,3 DIOXO 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1' (NAPHTHALEN 1 YL) 2 OXO 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLENE 3,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 1,3 DIOXO 1' (THIOPHEN 2 YL) 1,3,6',7',8',8A' HEXAHYDRO 1'H SPIRO(INDENE 2,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 2 OXO 1' (THIOPHEN 2 YL) 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLENE 3,2' NAPHTHALENE) 4' CARBONITRILE
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    3' AMINO 2 OXO 1' PARA TOLYL 6',7',8',8A' TETRAHYDRO 1'H SPIRO(INDOLINE 3,2' NAPHTHALENE) 4' CARBONITRILE
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    6 AMINO 1',3' DIOXO 4 PARA TOLYL 1',2,3,3A,3',4 HEXAHYDRO 2,5' SPIROBI(INDENE) 7 CARBONITRILE
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    6 AMINO 4 (2 FLUOROPHENYL) 1',3' DIOXO 1',2,3,3A,3',4 HEXAHYDRO 2,5' SPIROBI(INDENE) 7 CARBONITRILE
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    6 AMINO 4 (4 METHOXYPHENYL) 1',3' DIOXO 1',2,3,3A,3',4 HEXAHYDRO 2,5' SPIROBI(INDENE) 7 CARBONITRILE
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    Antibiotic agent
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    Antifungal agent
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    Indene derivative
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    Unindexed drug
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    ANAPLASTIC LYMPHOMA KINASE
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    Dna topoisomerase (atp hydrolysing)
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    Protein tyrosine kinase
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    Antimicrobial activity
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    Antineoplastic activity
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    Article
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    Cancer cell line
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    Carbon nuclear magnetic resonance
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    Controlled study
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    DISK DIFFUSION
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    Drug screening
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    Drug synthesis
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    ENTEROBACTER AEROGENES
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    Human
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    Human cell
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    Infrared spectroscopy
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    KLEBSIELLA PNEUMONIAE
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    LUNG ADENOCARCINOMA
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    Methicillin resistant staphylococcus aureus
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    Micrococcus luteus
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    Minimum inhibitory concentration
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    Molecular docking
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    Nonhuman
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    PROTEUS VULGARIS
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    Proton nuclear magnetic resonance
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    RECEPTOR AFFINITY
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    Salmonella typhimurium
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    SHIGELLA FLEXNERI
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    STAPHYLOCOCCUS EPIDERMIDIS
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    Substitution reaction
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    Antibacterial activity
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    Antifungal activity
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    IC50
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    In vitro study
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    Reaction analysis
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    SALMONELLA ENTERICA SUBSP. ENTERICA SEROVAR TYPHIMURIUM
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    Staphylococcus aureus
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    Stereochemistry
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    Bacteria
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    Chemistry
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    Drug effects
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    Metabolism
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    Protein conformation
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    Synthesis
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    Tumor cell line
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    Anti-infective agents
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    Antineoplastic agents
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    Cell line, tumor
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    Chemistry techniques, synthetic
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    Humans
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    RECEPTOR PROTEIN-TYROSINE KINASES
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