Camphorsulfonic acid catalysed facile tandem double Friedlander annulation protocol for the synthesis of phenoxy linked bisquinoline derivatives and discovery of antitubercular agents

Paul, Nidhin; Murugavel, Muthuchamy; Muthusubramanian, Shanmugam; Sriram, Dharmarajan

doi:10.1016/j.bmcl.2011.12.119

Cited by 20 publications

(7 citation statements)

References 80 publications

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“…Among all the compounds, the 5a and 5b were found to be the most active. The in vitro cytotoxicity (IC 50 ) of 5a and 5b on mouse embryonic fibroblast cell line (NIH 3T3) was reported as 333 and 887 mM, respectively, indicating that 37a and 37b are not cytotoxic 12 . Antimycobacterial activity of 2-aryloxyquinolines (6) and their pyrano[3,2-c]chromene (7) derivatives were assessed by Mungra et al Among the synthesized compounds, 6a and 7a showed more than 90% growth inhibition at the concentration of 260 and 250 mg/mL, respectively 13 .…”

Section: 3-disubstituted Quinolinesmentioning

confidence: 99%

“…In 4-adamantan-1-yl-quinoline-2-carboxylic acid alkylidenehydrazides (13), the substitution with small aryl/heteroaryl rings exhibited better activity than other bulkier substituents. The comparative molecular field analysis (CoMFA) indicated that the branched chain and cycloalkyl substituents are favored on the hydrazine nitrogen (12) and phenyl/quinoline substituents are favored on hydrazone nitrogen (13). Also, small electronegative substituents are conducive for the activity.…”

Section: 3-disubstituted Quinolinesmentioning

confidence: 99%

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Quinoline and quinolones: promising scaffolds for future antimycobacterial agents

Singh

Kaur

Mangla

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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Tuberculosis (TB) is still a major health concern worldwide. The increasing incidences of multi-drug-resistant tuberculosis (MDR-TB) necessitate the development of new anti-TB drugs acting via novel mode of action. The search of newer drugs for TB led to the identification of several quinoline-based antimycobacterial agents against both the drug-sensitive and MDR-TB. These agents have been designed by substituting quinoline scaffold with diverse chemical functionalities as well as by modifying quinoline/quinolone-based antibacterial drugs. Several of quinoline/quinolone derivatives displayed excellent antimycobacterial activity and were found free of cytotoxicity. This review highlights the critical aspects of design and structure-activity relationship of quinoline-and quinolone-based antimycobacterial agents.

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Section: 3-disubstituted Quinolinesmentioning

confidence: 99%

Section: 3-disubstituted Quinolinesmentioning

confidence: 99%

Quinoline and quinolones: promising scaffolds for future antimycobacterial agents

Singh

Kaur

Mangla

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…The same group was reported (Paul et al, 2012), and phenoxy linked bisquinolines were synthesized from the Friedländer annulation of 2‐(4‐acetylphenoxy)‐1‐aryl‐1‐ethanones ( 29 ) with 2‐aminobenzo‐phenone ( 24 ) using inexpensive, water soluble (±)‐camphor‐10‐sulfonic acid (CSA) as catalyst (Scheme 8). The synthesized mono ( 31 ) and bisquinolines ( 30 ) were showed good in vitro antimycobacterial activity against MTB, MICs ranging from 1.1 to 55.6 µM.…”

Section: Applications Of Friedländer Quinoline Synthesis In Medicinal...mentioning

confidence: 97%

Friedlӓnder's synthesis of quinolines as a pivotal step in the development of bioactive heterocyclic derivatives in the current era of medicinal chemistry

et al. 2022

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In the current scenario of medicinal chemistry, quinoline plays a pivotal role in the design of new heterocyclic compounds with several pharmacological properties, so the search for new synthetic methodologies and their application in drug discovery has been widely studied. So far, many procedures have been performed for the preparation of quinoline scaffolds, among which Friedländer quinoline synthesis plays an important role in obtaining these heterocycles. The Friedländer reaction involves condensation between 2‐aminobenzaldehydes and keto‐compounds. The quinoline nucleus, once obtained through the Friedländer synthesis, has been extensively modified so that these derivatives can exhibit a large number of biological activities such as anticancer, antimalarial, antimicrobial, antifungal, antituberculosis, and antileishmanial properties. In this work, the focus is on the applicability of the Friedländer reaction in the synthesis of various types of bioactive heterocyclic quinoline compounds, which to date has not been reported in the context of medicinal chemistry. The main part of this review selectively focuses on research from 2010 to date and will present highlights of the Friedländer quinoline synthesis procedures and findings to address biological and pharmacological activities.

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“…CSA has been demonstrated to be an efficient, nontoxic, ecofriendly, economical, and water soluble catalyst for several reactions such as synthesis of -amino carbonyl compounds [27], Friedel-Crafts reactions [28,29], Meyer-Schuster reactions [30], Friedlander annulations [31], synthesis ofhydroxy and -amino phosphonates [32], synthesis of 1,3,4oxadiazoles [33], synthesis of pseudoglycosides [34], synthesis of coumarins [35], synthesis of spirocyclic compounds [36], and rearrangement of 1,2-dialkynylallyl alcohols [37], and it is widely used in the optical resolution of amines [38].…”

Section: Introductionmentioning

confidence: 99%

(+)-CSA Catalyzed Multicomponent Synthesis of 1-[(1,3-Thiazol-2-ylamino)methyl]-2-naphthols and Their Ring-Closure Reaction under Ultrasonic Irradiation

Pelit

Turgut

2016

Journal of Chemistry

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New 1-[(1,3-thiazol-2-ylamino)methyl]-2-naphthols were obtained by condensation of 2-aminothiazole, aromatic aldehydes, and 2-naphthol in the presence of (+)-camphor-10-sulfonic acid ((+)-CSA) as an effective catalyst under ultrasound-promoted solvent-free conditions. The 1-[(1,3-thiazol-2-ylamino)methyl]-2-naphthol derivatives were converted in ring-closure reaction with formaldehyde to the corresponding naphthoxazine derivatives.

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Camphorsulfonic acid catalysed facile tandem double Friedlander annulation protocol for the synthesis of phenoxy linked bisquinoline derivatives and discovery of antitubercular agents

Cited by 20 publications

References 80 publications

Quinoline and quinolones: promising scaffolds for future antimycobacterial agents

Quinoline and quinolones: promising scaffolds for future antimycobacterial agents

Friedlӓnder's synthesis of quinolines as a pivotal step in the development of bioactive heterocyclic derivatives in the current era of medicinal chemistry

(+)-CSA Catalyzed Multicomponent Synthesis of 1-[(1,3-Thiazol-2-ylamino)methyl]-2-naphthols and Their Ring-Closure Reaction under Ultrasonic Irradiation

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