2‐Arylthienyl‐Substituted 1,3‐Benzothiazoles as New Nonlinear Optical Chromophores.

Costa, Susana P. G.; Batista, Rosa Maria Ferreira; Cardoso, Paulo; Belsley, M.; Raposo, M. Manuela M.

doi:10.1002/chin.200650121

Cited by 4 publications

(6 citation statements)

References 8 publications

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“…Synthesis of compound BTP-OH . The synthetic route started by reacting 4-bromophenol (2) and 5-formylthiophen-2-ylboronic acid (1) to yield 5-(4-hydroxyphenyl)thiophene-2-carbaldehyde (3) was conducted according to the reported method (Costa et al ., 2006). Sodium bisulphite was added to a solution of the three in absolute ethanol and stirred for 30 min.…”

Section: Methodsmentioning

confidence: 99%

Therapeutic efficacy of a newly synthesized benzimidazole compound BTP-OH against murine schistosomiasis mansoni

et al. 2020

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Because of the increasingly emerging praziquantel resistance, there is a crucial need to develop new anti-schistosomal agents. This work was conducted to assess the therapeutic efficacy of a new benzimidazole compound (BTP-OH) in mice experimentally infected with Schistosoma mansoni. A total of 40 Swiss albino female mice were divided into an infected untreated group and three infected treated groups (using praziquantel and BTP-OH). The compound activity was evaluated through parasitological, histopathological and scanning electron microscopy studies. Praziquantel and BTP-OH at both doses significantly reduced male (75%, 42.67% and 61.08%, respectively), female (71.45%, 48.94% and 68.13%, respectively) and total worm burden (75.21%, 42.42% and 62.28%, respectively), as well as tissue egg load in the liver (71.22%, 42.12% and 66.04%, respectively). In oogram, praziquantel significantly increased the percentage of dead eggs (65.89%), while BTP-OH significantly reduced the percentage of immature eggs (30.43% and 19.64%). BTP-OH significantly diminished granuloma count (33.87% and 44.77%) and diameter (39.23% and 49.40%), and caused ultrastructural changes in the tegument of adult schistosomes. This study provides evidence for the schistosomicidal efficacy of BTP-OH. However, future studies are needed to elucidate the full mechanisms of action and effects of BTP-OH on other human schistosomes.

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Section: Methodsmentioning

confidence: 99%

Therapeutic efficacy of a newly synthesized benzimidazole compound BTP-OH against murine schistosomiasis mansoni

et al. 2020

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“…Reaction progress was monitored by thin layer chromatography (0.25 mm thick precoated silica plates: Merck Fertigplatten Kieselgel 60 F254), while purification was effected by silica gel column chromatography (Merck Kieselgel 60; 230-400 mesh). NMR spectra were obtained on a Varian Unity Plus Spectrometer at an operating frequency of 300 MHz for 1 H and 75.4 MHz for 13 C or a Bruker Avance III 400 at an operating frequency of 400 MHz for 1 H and 100. 6 MHz for 13 C using the solvent peak as internal reference.…”

Section: Synthesis Generalmentioning

confidence: 99%

“…1 H NMR (acetone-d 6 ) δ = 6.09 (s, 1H, CH), 6.23 (d, 1H, J = 3.3 Hz, H3'), 6.79 (d, 1H, J = 3.3 Hz, H4'), 6.98 (dt, 2H, J = 7.6 and 1.4 Hz, 2 x H5), 7.11 (dt, 2H, J = 7.6 and 1.4 Hz, 2 x H6), 7.17 (d, 2H, J = 2.1 Hz, 2 x H2), 7.24 (m, 1H, H4''), 7.38-7.42 (m, 2H, H3'' and H5''), 7.44 (dt, 2H, J = 7.5 and 1.4 Hz, 2 x H7), 7.59 (d, 2H, J = 7.5 Hz, 2 x H4), 7.68 (d, 2H, J = 8.3 Hz, H2'' and H6''), 10.11 (s,2H,2 x NH). 13 (5'-(4''-methoxyphenyl)…”

Section: -((1h-indolmentioning

confidence: 99%

“…Hz, 2 x H2), 7.42 (d, 2H, J = 8.4 Hz, 2 x H7), 7.54-7.63 (m, 6H, H2'', H3'', H5'', H6'' and 2 x H4), 10.10 (s, 2H, 2 x NH). 13…”

Section: -((5'-(4''-bromophenyl)furan-2'-yl)(1h-indol-3-yl)methyl)-1mentioning

confidence: 99%

“…These compounds were obtained in moderate to good yields (40-65%) by condensation of indole with several formyl precursors 1 with substituents of different electronic nature in dry methanol in the presence of potassium hydrogensulfate [11] (Scheme 1). Formyl-arylfuran precursors 1a and 1c-d were commercially available and 5-(4'-methoxyphenyl)furan-2-carbaldehyde 1b [12] was synthesized by us through Suzuki cross-coupling reaction [13].…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

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Synthesis and evaluation of arylfuryl-bis(indolyl)methanes as selective chromogenic and fluorogenic ratiometric receptors for mercury ion in aqueous solution

et al. 2014

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A series of arylfuryl-bis(indolyl)methane derivatives 2 were prepared in good yields by electrophilic substitution of indole with furyl aldehydes through a simple and mild hydrogensulfate-catalyzed reaction and studied as chemosensors for transition metal cations by performing spectrophotometric and spectrofluorimetric titrations.Selective recognition of Hg 2+ was achieved in organic aqueous mixture (CH 3 CN/H 2 O, 7:3) for the various receptors, with an easily detectable colour change from colourless to purple and also through a fluorescence quenching, making these compounds suitable for dual chromo-and ratiometric fluorogenic sensing of Hg 2+ . The binding stoichiometry between the receptors and Hg 2+ was found to be 1:1. The binding process was also followed by 1 H NMR titrations which corroborated the previous findings.Chemosensors and chemodosimeters that can monitor heavy metal ions with high sensitivity and selectivity are especially important owing to the great concern with environment and health. Among transition and heavy metals, mercury, from a variety of natural and anthropogenic sources and widely distributed in water, soil and air, is considered to be one of the most toxic because both ionic and elemental mercury can be converted by bacteria in the environment to methyl mercury, which subsequently bioaccumulates through the food chain. Mercury causes serious neurotoxic, genotoxic, and immunotoxic effects and thus poses severe risk for human beings and other organisms. Therefore, selective and sensitive detection of Hg 2+ has been an important topic of investigation [1]. Presently, several methods such as atomic absorption/emission spectroscopy, inductively coupled plasma-mass spectrometry, voltammetry, etc. can be used in order to detect Hg 2+ . However, all these methods have drawbacks such as expensive instrumentation, only measure the total metal ion content and are not suitable for on-site assays [2]. Therefore, an easy and straightforward method that detects and quantifies Hg 2+ is advantageous for instantaneous monitoring of environmental, biological, and industrial samples which occur in aqueous solution.Consequently, much attention has been paid to developing low-cost and easily-prepared colorimetric and/or fluorimetric mercury sensors that work in the aqueous medium [1ab,d-f,h-m]. Hg 2+ is usually associated with a fluorescence quenching by different mechanisms, so a ratiometric approach for its detection (simultaneous monitoring of fluorescence intensity at two different wavelengths) would be preferable, since it minimizes interferences from other species present in the media [1b,i,l]. Although indoles are predominant in natural compounds and widely applied in the synthesis of pharmaceutical products, they were only recently recognized as useful building blocks for the assembly of synthetic anionic receptors [3]. Among the several indole-based systems, triaryl-and triheteroarylmethanes have found wide range applications in different areas of chemistry, due to their structure (presence of a...

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An effective colorimetric sensor for detecting Cu²⁺ based on benzothiazole moiety

Suh

Choe

Kim

2021

Coloration Technology

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An effective colorimetric chemosensor, 2,4‐dichloro‐6‐((E)‐(((Z)‐3‐methylbenzo[d]thiazol‐2(3H)‐ylidene)hydrazono)methyl)phenol (HMD), was synthesised for Cu2+ detection. HMD with benzothiazole moiety showed a large bathochromic shift (153 nm) and a definite colour change for Cu2+. HMD could detect Cu2+ down to 0.47 μmol/L in the solution phase and could clearly distinguish it from other metal ions, even in the test strip. The binding mode between HMD and Cu2+ was determined to be 1:1 using Job plot and electrospray ionisation mass spectrometry. The sensing mechanism of HMD for Cu2+ was illustrated as the combination of metal‐to‐ligand charge transfer and intramolecular charge transfer via theoretical calculation.

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2‐Arylthienyl‐Substituted 1,3‐Benzothiazoles as New Nonlinear Optical Chromophores.

Cited by 4 publications

References 8 publications

Therapeutic efficacy of a newly synthesized benzimidazole compound BTP-OH against murine schistosomiasis mansoni

Therapeutic efficacy of a newly synthesized benzimidazole compound BTP-OH against murine schistosomiasis mansoni

Synthesis and evaluation of arylfuryl-bis(indolyl)methanes as selective chromogenic and fluorogenic ratiometric receptors for mercury ion in aqueous solution

An effective colorimetric sensor for detecting Cu²⁺ based on benzothiazole moiety

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2‐Arylthienyl‐Substituted 1,3‐Benzothiazoles as New Nonlinear Optical Chromophores.

Cited by 4 publications

References 8 publications

Therapeutic efficacy of a newly synthesized benzimidazole compound BTP-OH against murine schistosomiasis mansoni

Therapeutic efficacy of a newly synthesized benzimidazole compound BTP-OH against murine schistosomiasis mansoni

Synthesis and evaluation of arylfuryl-bis(indolyl)methanes as selective chromogenic and fluorogenic ratiometric receptors for mercury ion in aqueous solution

An effective colorimetric sensor for detecting Cu2+ based on benzothiazole moiety

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Product

Resources

About

An effective colorimetric sensor for detecting Cu²⁺ based on benzothiazole moiety