Studies of 2-azaazulenium derivatives – 3: The nature of electron transitions and spectral properties of styryl dyes containing terminal groups of different types

Bricks, Julia L.; Stanova, А.V.; Ryabitsky, A.B.; Yashchuk, Valeriy M.; Kachkovsky, O.D.

doi:10.1016/j.molstruc.2012.08.034

Cited by 5 publications

(3 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A C C E P T E D ACCEPTED MANUSCRIPT 26 It was established that the local levels are less sensitive to the lengthening of the polymethine chain than donor or delocalized levels [136,159]. So, the spectral band corresponding to the local transitions in the vinylene series of the pyrylocyanines 30, R = Ph was found by M.A.…”

Section: A N U S C R I P Tmentioning

confidence: 99%

Molecular design of near infrared polymethine dyes: A review

et al. 2015

Self Cite

View full text Add to dashboard Cite

Section: A N U S C R I P Tmentioning

confidence: 99%

Molecular design of near infrared polymethine dyes: A review

et al. 2015

Self Cite

View full text Add to dashboard Cite

“…The synthesis of the target compounds XY3-17 , XY19 and XY20 was shown in Scheme 1 , Scheme 2 and Scheme 3 , respectively. Pyrylium salts were used as cationic dyes [ 14 ] and the methods to prepare these types of compounds were reported [ 15 ]. The target compounds XY3-17 and XY19 can be obtained efficiently by a dehydration condensation reaction of methyl pyrylium salt XY1A or XY1B and a different substituted aldehyde A1-16 under the heating condition in acetic anhydride, with single trans-olefin selectivity ( Scheme 1 and Scheme 2 ).…”

Section: Resultsmentioning

confidence: 99%

“…Pyrylium salt ( XY1A ) and 4-(Dimethylamino)benzaldehyde ( A1 ) showed no significant activity (MIC > 179.7 μM), which revealed that both fragments of the motif were required for antifungal activity. Pyrylium salt is a kind of cationic dye [ 14 ], in which the terminal groups have a dramatic effect on their properties, such as the properties of electron transition and spectral properties. Based on these properties, a series of pyrylium salt compounds ( XY2-17 ) with different substituents were synthesized.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Antifungal Evaluation of Novel Pyrylium Salt In Vitro and In Vivo

Zhang¹,

Li²,

Cui

et al. 2022

Molecules

View full text Add to dashboard Cite

Nowadays, discovering new skeleton antifungal drugs is the direct way to address clinical fungal infections. Pyrylium salt SM21 was screened from a library containing 50,240 small molecules. Several studies about the antifungal activity and mechanism of SM21 have been reported, but the structure–activity relationship of pyrylium salts was not clear. To explore the chemical space of antifungal pyrylium salt SM21, a series of pyrylium salt derivatives were designed and synthesized. Their antifungal activity and structure-activity relationships (SAR) were investigated. Compared with SM21, most of the synthesized compounds exhibited equivalent or improved antifungal activities against Candida albicans in vitro. The synthesized compounds, such as XY10, XY13, XY14, XY16 and XY17 exhibited comparable antifungal activities against C. albicans with MIC values ranging from 0.47 to 1.0 μM. Fortunately, a compound numbered XY12 showed stronger antifungal activities and lower cytotoxicity was obtained. The MIC of compound XY12 against C. albicans was 0.24 μM, and the cytotoxicity decreased 20-fold as compared to SM21. In addition, XY12 was effective against fluconazole-resistant C. albicans and other pathogenic Candida species. More importantly, XY12 could significantly increase the survival rate of mice with a systemic C. albicans infection, which suggested the good antifungal activities of XY12 in vitro and in vivo. Our results indicated that structural modification of pyrylium salts could lead to the discovery of new antifungal drugs.

show abstract