Synthesis and Evaluation of Curcumin-Related Compounds Containing Inden-2-one for Their Effects on Human Cancer Cells

Zhou, Daiying; Ding, Ning; Zhao, Suqing; Li, Dongli; Doren, Jeremiah Van; Qian, Yu; Wei, Xingchuan; Zheng, Xi

doi:10.1248/bpb.b14-00477

Cited by 13 publications

(15 citation statements)

References 23 publications

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“…[18][19][20] 2-Indanone-based dienones 2 have been used as building blocks for the synthesis of biologically active compounds. [18][19][20] 2-Indanone-based dienones 2 have been used as building blocks for the synthesis of biologically active compounds.…”

Section: Introductionmentioning

confidence: 99%

Molecular Structure, Intramolecular Hydrogen Bonding, Solvent‐Induced Isomerization, and Tautomerism in Azolylmethylidene Derivatives of 2‐Indanone

et al. 2017

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Bis adducts of 2‐indanone with 1H‐pyrrole‐2‐carbaldehyde, 1H‐imidazole‐2‐carbaldehyde, 1H‐imidazole‐5‐carbaldehyde, and 1H‐indazole‐3‐carbaldehyde 3–6 have been synthesized and the intertwined processes of tautomeric NH proton transfer, intra‐ and intermolecular H‐bond rupture and formation, and Z/Z, Z/E, and E/E‐isomerization have been studied by NMR and FTIR spectroscopy and by conducting DFT calculations. Pyrrole derivative 3 both in chloroform and in dimethyl sulfoxide (DMSO) exists exclusively in the form of the Z,Z‐isomer stabilized by two intramolecular N–H···O hydrogen bonds. For derivatives 4–6, the isomeric composition depends on the solvent so that in polar media such as DMSO and pyridine the Z,E‐ and E,E‐isomers predominate. The driving force for isomerization of 4–6 is stabilization of the Z,E‐ and E,E‐isomers in basic polar solvents due to formation of intermolecular NH···B and intramolecular C–H···N hydrogen bonds. The suggested mechanism of isomerization includes proton transfer from nitrogen to oxygen in the Z‐moiety followed by rotation about the C–C bond in the formed enol and isomerization of the latter to the E‐moiety of the ketone tautomer.

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Section: Introductionmentioning

confidence: 99%

Molecular Structure, Intramolecular Hydrogen Bonding, Solvent‐Induced Isomerization, and Tautomerism in Azolylmethylidene Derivatives of 2‐Indanone

et al. 2017

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“…General procedure for the synthesis of pyrazoline derivatives (7)(8)(9)(10)(11)(12) A solution of 2-(4-substituted benzylidene)-2,3-dihydro-1Hinden-1-one (1-6, 1.00 mmol) and 4-hydrazinobenzensulfonamide hydrochloride (1.10 mmol) in ethanol (50 mL) was heated in (100 C, 200 Watt, 3-7 barr) for 10-120 min [20 min, 3 barr (7), 60 min, 7 barr (8, 11); 30 min, 7 barr (9); 10 min, 7 barr (10); 120 min, 3 barr (12)]. The reactions were monitored by TLC.…”

Section: Methodsmentioning

confidence: 99%

“…The effects of novel benzenesulfonamides (7-12) derivatives were examined using the hydratase activity and recorded in triplicate analysis at each concentration used 54 . For this purpose, different concentrations of novel benzenesulfonamides (7)(8)(9)(10)(11)(12) derivatives were determined in preliminary assays. CA isoenzyme activities were measured in the presence of different quantity of them.…”

Section: Carbonic Anhydrase Enzyme Assaymentioning

confidence: 99%

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Synthesis and bioactivity studies on new 4-(3-(4-Substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides

Gül

Tuğrak

Sakagami

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

118

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A series of new 4-(3-(4-substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides (7-12) was synthesized starting from 2-(4-substitutedbenzylidene)-2,3-dihydro-1H-inden-1-one (1-6) and 4-hydrazinobenzenesulfonamide. The substituted benzaldehydes from which the key intermediate was prepared by introducing 2- or 4-substituents such as fluorine, hydroxy, methoxy, or the 3,4,5-trimethoxy moieties. The compounds were tested for their cytotoxicity, tumor-specificity and potential as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. The 3,4,5-trimethoxy and the 4-hydroxy derivatives showed interesting cytotoxic activities, which may be crucial for further anti-tumor activity studies, whereas some of these sulfonamides strongly inhibited both human (h) cytosolic isoforms hCA I and II.

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“…However, gemcitabine treatment is associated with several side effects and drug resistance [5]. Thus novel strategies involving less toxic agents for treatment of pancreatic cancer have been developed [7][8][9][10]. Integrative oncology is a new focus in cancer research that involves association of natural compounds, as nontoxic tools, with traditional chemotherapy [11].…”

Section: Introductionmentioning

confidence: 99%

Inhibitory effect of (−)-epigallocatechin-3-gallate and bleomycin on human pancreatic cancer MIA Paca-2 cell growth

Bimonte¹,

Leongito²,

Barbieri³

et al. 2017

European Journal of Cancer

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Synthesis and Evaluation of Curcumin-Related Compounds Containing Inden-2-one for Their Effects on Human Cancer Cells

Cited by 13 publications

References 23 publications

Molecular Structure, Intramolecular Hydrogen Bonding, Solvent‐Induced Isomerization, and Tautomerism in Azolylmethylidene Derivatives of 2‐Indanone

Molecular Structure, Intramolecular Hydrogen Bonding, Solvent‐Induced Isomerization, and Tautomerism in Azolylmethylidene Derivatives of 2‐Indanone

Synthesis and bioactivity studies on new 4-(3-(4-Substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides

Inhibitory effect of (−)-epigallocatechin-3-gallate and bleomycin on human pancreatic cancer MIA Paca-2 cell growth

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