Synthesis and biological evaluation of new 5-methyl-N-(3-oxo-1-thia-4-azaspiro[4.5]-dec-4-yl)-3-phenyl-1H-indole-2-carboxamide derivatives

Güzel, Özlen; Terzioglu, Nalan; Çapan, Gültaze; Salman, Aydın

doi:10.3998/ark.5550190.0007.c12

Cited by 21 publications

(9 citation statements)

References 16 publications

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“…The carbon resonances of pyridine and spirothiazolidinone structures were assigned by chemical shifts and by comparison with previously reported 13 C NMR data for compounds having similar backbone structures. [14,[17][18][19]22] (expressed as the minimal cytotoxic concentration [MCC]) using microscopic scoring (Table 1).…”

Section: Chemistrymentioning

confidence: 99%

“…Effective inhibition of bacterial growth was noted for a few analogs bearing a 6-phenyl substituted imidazo [2,1-b]thiazole residue (Figure 2a) [15,16] and 3-phenyl substituted indole residue (Figure 2b). [17][18][19] Imidazo [2,1-b]thiazolesubstituted spirothiazolidinones have been reported to inhibit the growth of 50% of M. tuberculosis H37Rv at concentrations ranging from 0.76 to 4.5 μg/ml. Among the previously reported indolederived spirothiazolidinones, compounds bearing phenyl substituent at the 8-position of the spiro ring and a chlorine atom at the 5-position of the indole ring were found to be the most potent analogs.…”

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confidence: 99%

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Synthesis of new N‐(3‐oxo‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)pyridine‐3‐carboxamide derivatives and evaluation of their anti‐influenza virus and antitubercular activities

Cihan-Üstündağ

Acar

Naesens

et al. 2022

Archiv der Pharmazie

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We here report the synthesis, structural characterization, and evaluation of the antiviral and antitubercular activities of a novel series of hybrid spirothiazolidinone derivatives (2a–f and 3a–f) containing the nicotinohydrazide moiety, which is an isomer form of the approved antitubercular drug isoniazid. When evaluated for activity against influenza A/H1N1, A/H3N2, and B viruses, three of the new compounds proved to possess specific antiviral activity against the influenza A/H3N2 virus. The most active analog 3a, bearing a 2,8‐dimethyl group at the spiro ring, displayed an antiviral EC50 value of 5.2 µM. Compound 3a produced no cytotoxicity at 100 µM, the highest concentration tested, giving a selectivity index of at least 19. Structure–activity relationship analysis indicated that the absence of the methyl substituent at the 2‐position and the presence of a bulky substituent at the 8‐position of the spirothiazolidinone system caused a significant decrease in antiviral activity. The in vitro antitubercular activity of compounds 2a–f and 3a–f was determined for six different drug‐sensitive/drug‐resistant laboratory strains and clinical isolates of Mycobacterium tuberculosis. Compounds 2c, 2d, 3b, 3c, and 3d showed weak antitubercular activity against different strains, with MIC values of 125–250 μM.

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Section: Chemistrymentioning

confidence: 99%

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confidence: 99%

Synthesis of new N‐(3‐oxo‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)pyridine‐3‐carboxamide derivatives and evaluation of their anti‐influenza virus and antitubercular activities

Cihan-Üstündağ

Acar

Naesens

et al. 2022

Archiv der Pharmazie

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“…It is known that thiosemicarbazone and its derivatives exhibit biological activity. Thiosemicarbazones are chemical compounds have anti -tuberculosis properties [1,2] and are part of a group of tuberculostatic drugs. The thiosemicarbazone derivatives possess a various of antimicrobial (Staphylococcus epidermidis, Bacillus cereus, Moraxella cattarhalis, Staph, Saprophyticus, thiosemicarbazones and their complexes with metals have been cited here.…”

Section: Introductionmentioning

confidence: 99%

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2018

RJLBPCS

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This work presents results of studies of thiosemicarbazone 5-NO2-salicylic aldehyde immobilization on the ionic cross-linked polymers: AV-17(Cl) (containing strongly basic groups), Amberlite IRC-50 (containing carboxylic groups) and composite AV-17(Cr) (containing chromium compounds). It is demonstrated that the rate of sorption of thiosemicarbazone on AV-17(Cl) and AV-17(Cr) is described with the pseudo-second kinetic model and is limited by the intra-particle diffusion.The sorption isotherm on these sorbents is approximated by the BET sorption model. Polymers loaded with thiosemicarbazone retain metal cations from the solution of CuSO4, Co(NO3)2, ZnSO4, NiSO4, FeSO4 and Fe(NO3)3 as a result of their coordination with the electrons donor atoms of the substrate. Thus the immobilized complexes of thiosemicarbazone on polymers were obtained. The reverse processes -the sorption of thiosemicarbazone on the Amberlite IRC-50 polymer which has been complexed with metal cations were also investigated.

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“…However, homologs of 2-alkyl/aryl-substituted 4-thiazolidinones, namely spirothiazolidinones, are one of the most studied heterocyclic systems that show a wide range of biological activities such as antibacterial, [29,30] anticancer, [31,32] antifungal, [33] and antiviral activities. [34] In light of recent studies about the antitumor, antiproliferative, or anticancer effects of compounds bearing adamantane ring, [35][36][37][38][39][40] our aim is to synthesize several novel spirothiazolidinone compounds F I G U R E 1 Some drug molecules containing the adamantane ring bearing adamantane ring (Scheme 1).…”

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Synthesis, in vitro cytotoxic and apoptotic effects, and molecular docking study of novel adamantane derivatives

Turk‐Erbul

Karaman

Duran

et al. 2021

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4-(Adamantane-1-carboxamido)-3-oxo-1-thia-4-azaspiro [4.4]nonan-2-yl]acetic acid (4a) and [4-(adamantane-1-carboxamido)-8-nonsubstituted/substituted-3-oxo-1-thia-4-azaspiro[4.5]decane-2-yl]acetic acid (4b-g) derivatives were synthesized; their structures were verified by elemental analysis, infrared spectroscopy, 1 H nuclear magnetic resonance (NMR), 13 C NMR, and mass spectroscopy data; and their in vitro cytotoxicity activities were investigated against human hepatocellular carcinoma, human prostate adenocarcinoma, and human lung carcinoma cell lines (HepG2, PC-3, and A549, respectively), and a mouse fibroblast cell line (NIH/3T3). All compounds, except compound 4e, were found as cytotoxic, especially on A549 cells as compared with the other cells (selectivity index = 2.01-11.6). As a further step, the effects of compounds 4a-c on apoptosis induction were tested and the expression of selected apoptosis genes was analyzed. Among the selected compounds, compound 4a induced apoptosis remarkably.Moreover, computational calculations of the binding of compounds 4a-c to the BIR3 domain of the human inhibitor of apoptosis protein revealed ligand-protein interactions at the atomistic level and emphasized the importance of a hydrophobic moiety on the ligands for better binding.

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Synthesis and biological evaluation of new 5-methyl-N-(3-oxo-1-thia-4-azaspiro[4.5]-dec-4-yl)-3-phenyl-1H-indole-2-carboxamide derivatives

Cited by 21 publications

References 16 publications

Synthesis of new N‐(3‐oxo‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)pyridine‐3‐carboxamide derivatives and evaluation of their anti‐influenza virus and antitubercular activities

Synthesis of new N‐(3‐oxo‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)pyridine‐3‐carboxamide derivatives and evaluation of their anti‐influenza virus and antitubercular activities

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Synthesis, in vitro cytotoxic and apoptotic effects, and molecular docking study of novel adamantane derivatives

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