Synthesis and biological evaluation of N-substituted indole esters as inhibitors of cyclo-oxygenase-2 (COX-2)

Ölgen, Süreyya; Nebioğlu, Doğu

doi:10.1016/s0014-827x(02)01233-8

Cited by 19 publications

(16 citation statements)

References 21 publications

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“…The replacement of N-1 substituent of indomethacin with cyclopropyl methyl, cyclopropyl ethyl, o-tolyl groups etc. does not improve the COX-2 efficacy profile of these compounds [87]. Using indole as the central template, a series of 2-sulfonylphenyl-3-phenyl- [88] and 2-phenyl-3-sulfonylphenyl-indoles [89] have been synthesized and investigated for COX-2 inhibitory activities and led to the discovery of compounds 95, 96 and 97 (Chart 32) as highly potent COX-2 inhibitors.…”

Section: Bicyclic Heterocycles As the Central Core Of Cox-2 Inhibitorsmentioning

confidence: 99%

Current Status of COX-2 Inhibitors

Singh¹,

Mittal

2008

MRMC

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The two isoforms of enzyme cyclooxygenase viz. COX-1 and COX-2 play key roles in the metabolism of arachidonic acid. The enzyme COX-2, when over expressed, leads to more production of prostaglandins causing inflammation and it also participates in the propagation of cancer. Therefore, COX-2 becomes the cellular target of a number of chemical entities for the treatment of inflammatory diseases as well as for the chemotherapy of cancer. In the present review, an up to date status of the compounds investigated for COX-2 inhibition has been given so that a collective view of the existing COX-2 inhibitors could be helpful for the design of safer anti-inflammatory drugs. In order to cover the maximum reported COX-2 inhibitors, a unique classification on the basis of the central core of the molecule (carrying mostly the phenyl moieties) has been followed, an outline of which has been given below: [structure: see text]. Each category of compounds has been discussed with suitable examples giving the IC(50) (for COX-2) values and the selectivity towards COX-2 over COX-1 of most potent compounds.

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Section: Bicyclic Heterocycles As the Central Core Of Cox-2 Inhibitorsmentioning

confidence: 99%

Current Status of COX-2 Inhibitors

Singh¹,

Mittal

2008

MRMC

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“…They also reported two series of 3-arylthioindoles as selective COX-2 inhibitors in which indole had 6-methylsulfonyl with either 2-methyl or 2-carboxymethyl substituents in one series and a 2-cyano-6-methylsulfonyl substituent in another series (Campbell et al, 2004b;Campbell et al, 2004c). Another novel series of N-substituted-indole carboxylic, acetic, and propionic acid esters was reported (Olgen and Nebioglu, 2002). Receptor docking studies of N-substituted-indole-2-carboxylic acid esters was also studied (Olgen et al, 2001).…”

Section: Introductionmentioning

confidence: 98%

QSAR analysis of 2-sulfonylphenyl-3-phenyl-indole derivatives as novel anti-inflammatory compounds

Dhondge

Chaturvedi

2008

Med Chem Res

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The systematic variation of substituents around the indole ring has led to the exploration of a large number of potent anti-inflammatory agents with minimum adverse effects. Hence, a new series of diaryl heterocycles, i.e., substituted 2-sulfonylphenyl-3-phenyl-indole derivatives, was selected and subjected to quantitative structure-activity relationship (QSAR) analysis. Different statistically significant models were obtained with an electronic descriptor highest occupied molecular orbital (HOMO) and a steric descriptor shape coefficient.

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“…Therefore, indole structure represents a highly relevant heterocyclic system. Many pharmacodynamic compounds containing indole nucleus have been reported to possess a wide variety of biological properties, namely, anti-inflammatory [1, 2], anticonvulsant [3], cardiovascular [4], antibacterial [5], COX-2 inhibitor [6, 7], and antiviral activities [8]. More specifically, several reports describe that indole-2-carbohydrazides and related compounds are endowed with antihistaminic [9], antidepressant [10], and MAO inhibitory activities [11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Antimicrobial, DNA Cleavage, and Antioxidant Studies of Some Metal Complexes Derived from Schiff Base Containing Indole and Quinoline Moieties

Karekal

Biradar

Mruthyunjayaswamy

2013

Bioinorganic Chemistry and Applications

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A new Schiff base of 5-chloro-3-phenyl-1H-indole-2-carboxyhydrazide and 3-formyl-2-hydroxy-1H-quinoline (HL), and its Cu(II), Co(II), Ni(II), Zn(II), Cd(II), and Hg(II) complexes have been synthesized and characterized in the light of microanalytical, IR, H1 NMR, UV-Vis, FAB-mass, ESR, XRD, and TGA spectral studies. The magnetic susceptibility measurements and low conductivity data provide evidence for monomeric and neutral nature of the complexes. On the basis of spectral studies and analytical data, it is evident that the Schiff base acts as tridentate ligand. The Cu(II), Co(II), and Ni(II) complexes were octahedral, whereas Zn(II), Cd(II), and Hg(II) complexes were tetrahedral in nature. The redox behavior of the Cu(II) complex was investigated by electrochemical method using cyclic voltammetry. In order to evaluate the effect of metal ions upon chelation, both the ligand and its metal complexes were screened for their antibacterial and antifungal activities by minimum inhibitory concentration (MIC) method. The DNA cleavage experiment performed using agarose gel electrophoresis method showed the cleavage of DNA by all the metal complexes. The free radical scavenging activity of newly synthesized compounds has been determined at a different concentration range by means of their interaction with the stable free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH).

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Synthesis and biological evaluation of N-substituted indole esters as inhibitors of cyclo-oxygenase-2 (COX-2)

Cited by 19 publications

References 21 publications

Current Status of COX-2 Inhibitors

Current Status of COX-2 Inhibitors

QSAR analysis of 2-sulfonylphenyl-3-phenyl-indole derivatives as novel anti-inflammatory compounds

Synthesis, Characterization, Antimicrobial, DNA Cleavage, and Antioxidant Studies of Some Metal Complexes Derived from Schiff Base Containing Indole and Quinoline Moieties

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