A new synthesis of 3-arylthioindoles as selective COX-2 inhibitors using PIFA

Campbell, Jeffrey A.; Broka, Chris A.; Gong, Leyi; Walker, K.; Wang, Jinhai

doi:10.1016/j.tetlet.2004.03.153

Cited by 75 publications

(31 citation statements)

References 15 publications

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“…Campbell et al (2004a) used rational drug design and introduced 3-arylmethyl-,3-aryloxy-and 3-arylthio-moieties into the 6-methylsulfonylindole core to obtain potent COX-2 inhibitors. 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).…”

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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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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“…6 Over the past years, substantial efforts have been made on developing significant and reliable methods toward 3-sulfenylindoles through C-S bond-forming reactions. A variety of sulfenylating reagents, such as sulfonium salts, 7 quinone mono-O,S-acetals, 8 sulfonyl hydrazides, 9 sulfinates, 10 disulfides, 11 sulfenyl halides, 12 N -thioimides, 13 thiols, 14 arylsulfonyl chlorides, 15 and sulfinic acids, 16 have been developed as reaction partners for coupling with indoles. However, some of those sulfenylating agents are foul-smelling and volatile, or complicated and expensive, or air- and water-sensitive.…”

Section: Introductionmentioning

confidence: 99%

I₂-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents

et al. 2017

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Readily available triethylammonium thiolates were proven to be new and eco-friendly sulfenylating agents for the efficient and practical construction of sulfenylated indoles and pyrroles (48 examples) with good to excellent yields under metal-free and microwave irradiation conditions. The combination of I2 and DMSO enabled direct C-S bond formation, allowing easy and low-cost access to new functionalized C,S-tethered bisindoles and pyrrole-indole pairs with a wide diversity of substituents. The mechanism involving S-S and S-I bond-forming/breaking events was proposed.

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“…The introduction of 3-arylmethyl, 3-aryloxy and 3-arylthio moieties into a 6-methylsulfonylindole framework using rational drug design by the authors led to potent, selective COX-2 inhibitors. 3-Arylthioindoles with indoles bearing a 6-MeSO 2 and either a 2-methyl or 2-carboxymethyl substituent and 2-cyano-6-MeSO 2 -3-arylmethylindoles were reported as selective COX-2 inhibitors by Campbell et al [8,9]. A series of novel N-substituted indole carboxylic, acetic and propionic acid esters have been prepared and studied as possible COX-2 enzyme inhibitors by Olgen et al [10].…”

Section: Introdutionmentioning

confidence: 99%

Quantitative structure–activity relationship analysis of 2,3-diaryl indoles as selective cyclooxygenase-2 inhibitors

Sivaprakasam

Manivannan

Chaturvedi

2005

Journal of Enzyme Inhibition and Medicinal Chemistry

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Quantitative structure-activity relationship (QSAR) studies have been performed on a combined series of 2-sulfonylphenyl-3-phenyl-indoles and 2-phenyl-3-sulfonylphenyl-indoles with a common 2,3 vicinal diaryl indole scaffold, recently reported as selective COX-2 inhibitors. This study is aimed to throw light on this, special class of diaryl heterocyclic family of selective COX-2 inhibitors. A preliminary Fujita-Ban analysis on 32 compounds provided valuable insights about the role of different substituents R1 and R2 around the 2,3 vicinal diaryl rings and R3, at position-5 of the central indole moiety in explaining their in vitro COX-2 inhibitory activity. The contribution of R1, R2, R3 towards COX-2 inhibitory activity resulted in statistically significant linear multiple regression equation with r = 0.942, r(2) = 0.888, s = 0.532 and F = 7.92, q(2) = 0.516 for 29 compounds. Fujita-Ban model shows a negative contribution of SO2NH2 and SO2CH3 at the R1 position; a negative contribution of 4-Cl, 2-Cl, 3-Cl, 3-CH3, 4-SO2CH3, 4-Br and a positive contribution of 4-OCH3, 4-CH3 substituents at the R2 position. At the R3 position a negative contribution of F, Br and a positive contribution of Cl, CH3 is encountered. In the light of our preliminary investigation that electron donating groups at the para position of R2 are conducive for COX-2 inhibitory activity from the Fujita-Ban model, we attempted to correlate the COX-2 inhibitory activity with quantum chemical descriptors of semi-empirical AM1 optimized geometries of the title compounds. Correlation analysis showed the molecular electronic descriptor, MOPAC total energy as crucial in governing COX-2 inhibitory activity of all the reported 41 compounds.

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A new synthesis of 3-arylthioindoles as selective COX-2 inhibitors using PIFA

Cited by 75 publications

References 15 publications

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

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

I₂-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents

Quantitative structure–activity relationship analysis of 2,3-diaryl indoles as selective cyclooxygenase-2 inhibitors

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A new synthesis of 3-arylthioindoles as selective COX-2 inhibitors using PIFA

Cited by 75 publications

References 15 publications

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

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

I2-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents

Quantitative structure–activity relationship analysis of 2,3-diaryl indoles as selective cyclooxygenase-2 inhibitors

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I₂-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents