An efficient, two-step synthetic strategy has been developed to access the quinolone, naphthyridone and benzonaphthyridone classes of chemotherapeutic agents from Baylis-Hillman adducts. The method involves tandem aza-Michael addition, SNAr cyclisation followed by oxidation of the resulting 4-hydroxy-1,2,3,4-tetrahydroquinoline or 4-hydroxy-1,2,3,4-tetrahydro-1,8-naphthyridine derivative using IBX, and works well with substrates having a wide variety of substitution pattern. © 2014 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.

Kannoth Manheri Muraleedharan

Department Of Chemistry

Napoleon John Victor

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Advanced Synthesis and Catalysis

The dual effect of FtsZ inhibition and oxidative stress by a group of 1,2-dihydroquinolines that culminate in bactericidal effect on mycobacterium strains is demonstrated. They inhibited the non-pathogenic Mycobacterium smegmatis mc2155 with MIC as low as 0.9 μg/mL and induced filamentation. Detailed studies revealed their ability to inhibit polymerization and GTPase activity of MtbFtsZ (Mycobacterial filamentous temperature sensitive Z) with an IC50value of ∼40 μM. In addition to such target specific effects, these compounds exerted a global cellular effect by causing redox-imbalance that was evident from overproduction of ROS in treated cells. Such multi-targeting effect with one chemical scaffold has considerable significance in this era of emerging drug resistance and could offer promise in the development of new therapeutic agents against tuberculosis. © 2016 Elsevier Masson SAS

European Journal of Medicinal Chemistry

FtsZ inhibition and redox modulation with one chemical scaffold: Potential use of dihydroquinolines against mycobacteria

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

Cambridge Crystallographic Data Centre (CCDC)

Advanced Synthesis & Catalysis

Copper-Catalyzed Domino SN2′/Coupling Reaction: A Versatile and Facile Synthesis of Cyclic Compounds from Baylis-Hillman Acetates

Tetrahedron

Efficient synthesis of novel benzo[b][1,8]naphthyridin-4(1H)-ones and pyrido[2,3-b]quinoxalin-4(1H)-ones from alkynones and primary amines

Chemical Communications

Transition metal-free one-pot synthesis of 2-substituted 3-carboxy-4-quinolone and chromone derivatives

Patents filed by public research institutions, 2000-02 and 2007-09

An expeditious and metal-free synthetic route towards quinolones, naphthyridones and benzonaphthyridones

Journal	Data powered by TypesetAdvanced Synthesis and Catalysis
Publisher	Data powered by TypesetWiley-VCH Verlag
ISSN	16154150
Open Access	No