Synthesis and in vitro activity of 6-amino-2,9-diarylpurines for Mycobacterium tuberculosis

Correia, Carla; Carvalho, M. Alice; Proença, M. Fernanda

doi:10.1016/j.tet.2009.06.065

Cited by 22 publications

(19 citation statements)

References 39 publications

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“…Morpholine proton signals would typically exist as two triplets or two broadened singlets. 43 The possibility of steric contact between the NCH 2 proton of the morpholine ring and the neighboring substituents was also confirmed by X-ray structural analysis data for an analog of compounds 4. 39 The structure of spiranes 4 also allowed to propose the existence of equilibrium between the enol 4' and ketone 4'' forms in solution phase (Scheme 5).…”

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confidence: 75%

Directed synthesis of new spiro-fused photochromes of diarylethene series

Belikov

Ievlev

Belikova

et al. 2015

Chem Heterocycl Comp

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518Diarylethenes (DAE, dihetarylethenes) are subject to intense study due to the possibility of using these compounds as photosensitive components in various applications, in particular, information processing, 1-4 optical switches for organic electronics, 5-7 and biosensors. 8 The potential for practical applications of DAE in the indicated areas motivate synthetic studies of photochromes with precisely designed photophysical parameters, such as thermal stability of the photoinduced form, 9-15 quantum yield of the forward and reverse photoreaction, 16-20 and the phototransformation cyclicity. 21-24 An important direction of study, with the goal of improving the practical characteristics of DAE, is the development of synthetic methods for obtaining DAE with intramolecular noncovalent interactions and steric hindrance. 25-31 One of the methods for creating a non-covalent interaction in DAE is the introduction of spiro-fused structures at the ethene linker. We should note that only isolated examples of spirofused DAE are known. 31-33 However, based on the current data, it is expected that the presence of spiro-fused moiety at the ethene linker could be used to confer certain useful properties to DAE. For example, some of the best forward quantum reaction yields have been demonstrated for spirofused DAE specifically due to the non-covalent interaction, caused by the presence of spirofusion. 31 By introducing or removing spirofusion it may be possible to tune the ability of DAE to undergo photochromic transformations. 32 The introduction of spirofusion may also be used for the preparation of DAE with several photoswitchable fragments. 33 The presented data show the importance of developing new approaches to the synthesis of diarylethenes featuring a rare combination of structural moieties, in particular spiro-fused systems. With this in mind, we set out to expand the range of available methods for the synthesis of DAE with spirofusion at the ethene linker.Recently we demonstrated a new approach to the synthesis of photochromic DAE, based on the transformations of intermediates obtained by reactions of tetracyanoethylene (TCNE) with 1,2-diarylethanones, namely, 3,4-diaryl-4-oxobutane-1,1,2,2-tetracarbonitriles. 34 At the same time, it is known that 4-oxoalkane-1,1,2,2-tetracarbonitriles based on some aliphatic and alkylaromatic ketones react with amines forming spiro compounds, containing an The reaction of tetracyanoethylated 1,2-diarylethanones with morpholine was used for directed synthesis of spiro-fused diarylethenes, 8-amino-1-imino(oxo)-6-morpholino-2-oxa-7-azaspiro[4.4]nona-3,6,8-triene-9-carbonitriles. The intermediates in this process were tetracyanoalkanone salts. The formation of spiranes was sensitive to the nature of aromatic substituents at the carbonyl group of 3,4-diaryl-4-oxobutane-1,1,2,2-tetracarbonitriles. The obtained spiro-fused diarylethenes exhibited photochromic properties.

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confidence: 75%

Directed synthesis of new spiro-fused photochromes of diarylethene series

Belikov

Ievlev

Belikova

et al. 2015

Chem Heterocycl Comp

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“…In these compounds (18), activity depends on the substituents present in C--2, C--6 and N--9 of the purine ring. 27 In 6,9--disubtituted purine derivatives, activity increases substantially when a C--l atom is presented in the 2--position. Purine derivatives with thienyl substituents exhibited better activity in non--replicating bacteria, although in these compounds a C--l atom in 2--position is not beneficial for activity.…”

Section: Nitrogen Heterocyclic Derivativesmentioning

confidence: 99%

“…34 The thiosemicarbazone--derived compounds have exhibited important anti--TB activity with an IC50 value of 2.59 µM/mL and it is compound (26). 35 Other moieties used in the design of anti--TB drugs are phenazine and benzothidiazine, particularly benzothidiazine 1,1--dioxide constituents are important anti--TB agents (27). These compounds indicate that the furan and thiophene group linked to benzothidiazine through a methylene bridge exhibited good anti--TB activity.…”

Section: Nitrogen Heterocyclic Derivativesmentioning

confidence: 99%

Antitubercular drugs: advances in nitrogen containing heterocyclic compounds and some other derivatives

Asif

2014

J PHARM CHEM

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Tuberculosis (TB) caused by Mycobacterium tuberculosis is an infectious disease. Control of TB is complicated by difficulties in the long--course chemotherapy treatment, the inability to eliminate latent microbes, and the increasing emergence of Multidrug Resistant (MDR) strains of M. tuberculosis. New anti--TB drugs are urgently needed, including developments of short--term treatments to minimize the emergence of drug resistance and new drugs to treat multidrug resistant tuberculosis and to eliminate the latent microbes. Many new structural anti--TB agents exhibited promising activities against susceptible and resistant strains of M. tuberculosis. The diarylquinoline with superior anti--tuberculotic activity and encouraging results of nitroimidazopyrans and oxazolidinones have generated considerable excitement.

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“…In these compounds (49, figure 15), activity depends on the substituents present in C2, C6 and N9 of the purine ring (Correia et al, 2009). In 6,9-disubtituted purine derivatives, activity increases substantially when a Cl atom is introduced in the 2-position.…”

Section: Nitrogen Heterocyclic Derivativesmentioning

confidence: 99%