Synthesis and anti-cancer activity of 1,4-disubstituted imidazo[4,5-c]quinolines

Thigulla, Yadagiri; Akula, Mahesh; Trivedi, Prakruti; Ghosh, Balaram; Jha, Mukund; Bhattacharya, Anupam

doi:10.1039/c5ob01650a

Cited by 31 publications

(9 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2 Therefore, the desired compounds were screened for their anticancer activity using MTT assay. 24 In order to validate the assay, standard anticancer drug camptothecin was used as positive control. According to the result, six most active compounds (3a, 3b, 3c, 3d, 3j, 3k) were filtered by measuring their IC50 values against lung carcinoma cell A549 cells (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

Convenient Synthesis and Biological Evaluation of Bis(indolyl)methane Alkaloid and Bis(aryl)alkanes Derivatives with Anti-cancer Properties

Liang¹,

Xiao²,

Lin³

2020

Preprint

View full text Add to dashboard Cite

An efficient and metal free methodology for the synthesis of bis(indolyl)methanes (BIMs) and bis(aryl)alkanes derivatives in the presence of B(C6F5)3 by the condensation of primary amines with pyruvates with good to high yields have been successfully developed. Some BIMs derivatives displayed good in vitro antitumor activity, screened by MTT assay. Compound 3b show the best anti-cancer activity against lung carcinoma cell A549 cells with IC50 of 4.52 µM.

show abstract

Section: Resultsmentioning

confidence: 99%

Convenient Synthesis and Biological Evaluation of Bis(indolyl)methane Alkaloid and Bis(aryl)alkanes Derivatives with Anti-cancer Properties

Liang¹,

Xiao²,

Lin³

2020

Preprint

View full text Add to dashboard Cite

show abstract

“…All synthesized compounds were also evaluated for anti-cancer activity and few compounds were found active, in which the highest activity was exhibited by 4-(2-bromophenyl)-1-phenyl-1H-imidazo [4,5-c]quinoline having IC50: 103.3 μM. [34] The mechanism for yerbium triflate catalysed cyclization is shown in Scheme 47. The electrophilic attack of imidazole ring followed by oxidative aromatization is envisioned as key step in the formation of final product.…”

Section: Synthesis Of Fused Heterocyclesmentioning

confidence: 99%

TosMIC: A Powerful Synthon for Cyclization and Sulfonylation

Kumar

2020

ChemistrySelect

View full text Add to dashboard Cite

p‐tosylmethyl isocyanide (TosMIC) which is also known as van Leusen's reagent hold the three functionalized groups including the isocyanide and sulfonyl group and an alpha carbon which is acidic by nature. Tosyl set of this fortunate reagent acts as a good leaving group and assist the alpha carbon to contribute in a range of cyclization strategies. Exceptionally, TosMIC was also proved as a good sulfonylating and sulfomethylating reagent. TosMIC has proved as a powerful and versatile synthon and betrothed in the synthesis of broad range of heterocycles having pharmacological interest. This review is focused on synthetic utility of TosMIC in diverse range of heterocycles like five membered heterocycles, fused heterocycles, linked or tethered heterocycles, spiro compounds etc. It is also utilized for regio, chemo and stereoselective synthesis and production of sulfones and sulfinates. It serves as an important building block in various synthetic methodologies like multi component reaction, cyclization, domino, cascade and cycloaddition and metal catalysed reactions. Various new catalyst and novel methodologies were explored due to enormous use of this wonderful reagent.

show abstract

“…Recently, Bhattacharya and co-workers reported an efficient protocol for the synthesis of 1,4-diaryl-substituted imidazo [4,5-c]quinolines through a modified Pictet-Spengler reaction of 2-(1-aryl-1H-imidazol-5-yl)aniline with aromatic aldehydes using 20 mol% of Yb(OTf) 3 as a catalyst (Scheme 129). 162 The reaction involves the formation of the imine followed by electrophilic attack on the imidazole ring at the C4-position. Finally, aerial oxidation results in the formation of desired product.…”

Section: Imidazo[45-c]quinolinementioning

confidence: 99%

Ytterbium Triflate Catalyzed Synthesis of Heterocycles

Sakhuja¹,

Pericherla²,

Bajaj³

et al. 2016

Synthesis

View full text Add to dashboard Cite

Ytterbium(III) triflate is an efficient and water-tolerant Lewis acid that has been used as a catalyst for a wide range of organic transformations. Various three-, four-, five-, and six-membered, as well as fused, heterocycles have been synthesized using ytterbium triflate as catalyst in both organic and aqueous solvents. The reaction conditions are relatively mild and the catalyst can be readily recovered from the reaction mixtures to be reused. 1 Introduction 2 Three-Membered Heterocycles 3 Four-Membered Heterocycles 4 Five-Membered Heterocycles 5 Six-Membered Heterocycles 6 Benzo-Fused Heterocycles 7 Non-benzenoid Fused Heterocycles 8 Spiroheterocycles 9 Bridged Heterocycles 10 Conclusion

show abstract

Synthesis and anti-cancer activity of 1,4-disubstituted imidazo[4,5-c]quinolines

Cited by 31 publications

References 29 publications

Convenient Synthesis and Biological Evaluation of Bis(indolyl)methane Alkaloid and Bis(aryl)alkanes Derivatives with Anti-cancer Properties

Convenient Synthesis and Biological Evaluation of Bis(indolyl)methane Alkaloid and Bis(aryl)alkanes Derivatives with Anti-cancer Properties

TosMIC: A Powerful Synthon for Cyclization and Sulfonylation

Ytterbium Triflate Catalyzed Synthesis of Heterocycles

Contact Info

Product

Resources

About