Synthesis and Fluorescent Properties of Novel Isoquinoline Derivatives

Balewski, Łukasz; Sączewski, Franciszek; Gdaniec, Мaria; Kornicka, Anita; Cicha, Karolina; Jalińska, Aleksandra

doi:10.3390/molecules24224070

Cited by 20 publications

(20 citation statements)

References 37 publications

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“…The lowest ε max value was 666 M –1 cm –1 for SIQP III with the −OMe (ERG) substituent. The −C≡N (EWG) and −OCH 3 (ERG) at the para position of the phenyl ring produced a bathochromic shift 10 in the absorption band π → π* using values of SIQPs Δλ of 140 (I), 140 (II), and 139 nm (III). Higher Δλ values were found for SIQPs I and II (140) and the lowest for III (139 nm).…”

Section: Resultsmentioning

confidence: 99%

“…Saragi et al have reported basic physiochemical and electronic properties of spiroheterocyclics, and Mahns et al have reported their electronic properties, but no study has initiated their photocatalytic (PC) activities and vibrational splitting. Hongyan Xia et al have reported advanced spiropyrans and their applications with fluorescent materials as per fluorescence resonance energy transfer (FRET), but their PC activities have not been discussed yet (Table ). − Barkov et alreported regio- and stereoselective syntheses of spiroheterocyclics using the 1,3-dipolar cycloaddition reaction.…”

Section: Introductionmentioning

confidence: 99%

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Photocatalytic Reduction of Fluorescent Dyes in Sunlight by Newly Synthesized Spiroindenoquinoxaline Pyrrolizidines

Kumari

Singh

2020

ACS Omega

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Spiroindenoquinoxaline pyrrolizidines (SIQPs)—7-nitro-2′-phenyl-5′,6′,7′,7a′-tetrahydrospiro[indeno[1,2- b ]quinoxaline-11,3′-pyrrolizine]-1′,1′(2′ H )-dicarbonitrile (SIQP I), 2′-(4-cyanophenyl)-7-nitro-5′,6′,7′,7a′-tetrahydrospiro[indeno[1,2- b ]quinoxaline-11,3′-pyrrolizine]-1′,1′(2′ H )-dicarbonitrile (SIQP II), and 2′-(4-methoxyphenyl)-7-nitro-5′,6′,7′,7a′-tetrahydrospiro[indeno[1,2- b ]quinoxaline-11,3′-pyrrolizine]-1′,1′(2′ H )-dicarbonitrile (SIQP III)—have been synthesized through a one-pot cascade Knoevenagel condensation reaction in acetonitrile (ACN) with 91, 98, and 87% yields, respectively. Structures are characterized by 1 H NMR and 13 C NMR spectroscopy, nuclear Overhauser enhancement spectroscopy (NOESY), Fourier transform infrared (FT-IR) and UV–vis spectroscopy, thermogravimetric analysis (TGA), high-resolution mass spectroscopy (HRTEM), fluorescence and Raman spectroscopy, and energy-dispersive analysis by X-ray (EDX) spectroscopy. SIQPs in ACN photocatalyzed methylene blue (MB) but not phenolphthalein (HIn). SIQPs distinguished the quaternary atoms and dipoles of the fluorescent dye (MB) contrary to the quinonoid HIn structure. In sunlight, SIQPs without electricity input acted as a photonic sensor to detect fluorescent dyes in waste effluents of textile, paper, dyes, and other industries. Activation energy ( E a ), enthalpy (Δ H ), entropy (Δ S ), and Gibbs free energy (Δ G ) calculated from UV–vis absorption spectra show photocatalytic reduction (PCR) activities in the order SIQP II > III > I. The N-atom of pyrrolizidine and −NO 2 of nitro-indenoquinoxaline (NIQ) induced the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO) electrodynamics to enable the SIQPs to catalyze biochemical activities.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photocatalytic Reduction of Fluorescent Dyes in Sunlight by Newly Synthesized Spiroindenoquinoxaline Pyrrolizidines

Kumari

Singh

2020

ACS Omega

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“…Several isoquinolines were found to exhibit antitumor or antiproliferative activity. − In particular, the isoquinoline ring constitutes an important molecular part of the topical anesthetic drug quinisocaine (A), whereas the tetrahydroisoquinoline moiety is found in the structure of the antihypertensive drugs quinapril (B) and debrisoquine (C) (Figure ). Also, many tetrahydroisoquinolines are considered as antitumor, , anticonvulsant, antithrombotic, analgesic, anti-inflammatory, antifungal, and antibacterial agents . In particular, some tetrahydrothieno[2,3- c ]isoquinolines were synthesized and reported to possess considerable antibacterial and antifungal activities. , Pyrazoloisoquinolines are tricyclic compounds with important biological and medicinal properties and are used as B-Raf V600E inhibitors, mu opioid receptor (μ-OR) agonists, and p38 kinase inhibitors .…”

Section: Introductionmentioning

confidence: 99%

“…9−12 In particular, the isoquinoline ring constitutes an important molecular part of the topical anesthetic drug quinisocaine (A), whereas the tetrahydroisoquinoline moiety is found in the structure of the antihypertensive drugs quinapril (B) and debrisoquine (C) (Figure 1). 13 Also, many tetrahydroisoquinolines are considered as antitumor, 14,15 anticonvulsant, antithrombotic, 16 analgesic, 17 anti-inflammatory, 18 antifungal, and antibacterial agents. 19 In particular, some tetrahydrothieno[2,3-c]isoquinolines were synthesized and reported to possess considerable antibacterial and antifungal activities.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Characterization of Novel Functionally Substituted Planar Pyrimidothienoisoquinolines and Nonplanar (3aR, 4S, 9aS)-pyrazolo[3,4-g]isoquinolines

et al. 2021

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6,7,-thiones 2a,b are prepared and dehydrated to give 7-acetyl-8-aryl-4-cyano-1,6-dimethyl-6hydroxy-7,8-dihydrodroisoquinolin-3(2H)-thiones 6a,b via a novel method by heating with acetyl chloride in acetic acid. The reaction of both compounds 2a,b and 6a,b with N-aryl-2chloroacetamides 7a−c under two different conditions gave the same corresponding products, 7acetyl-8-aryl-3-(N-aryl)carbamoylmethylsulfanyl-4-cyano-1,6-dimethyl-7,8-dihydroisoquinolines 8a−e, in high yields. On treatment of compounds 8a,b,e in methanol with a slightly excess molar amount of sodium methoxide, they underwent intramolecular Thorpe−Ziegler cyclization followed by spontaneous aromatization, providing the planar 7-acetyl-1-amino-6-aryl-2-(Naryl)carbamoyl-5,8-dimethyl-8,9-dihydrothieno[2,3-c] isoquinolines 9a,b,e in good yield. Cyclocondensation reactions of 6a,b with phenyl hydrazine, thiosemicarbazide, or hydrazine hydrate led to the formation of nonplanar (3aR, 4S, 9aS)-pyrazolo[3,4-g]isoquinolines 11a, 11b, and 13, respectively. The reaction of compound 13 with 2-chloromethylquinazolin-4(3H)-one in the presence of anhydrous sodium acetate gave the expected thienopyrazoloisoquinolone 14. Heating the latter compound ( 14) with triethyl orthoformate in glacial acetic acid afforded the fused heptacyclic compound 15. All of the synthesized compounds were characterized based on their full spectral analyses such as IR, 1 H nuclear magnetic resonance (NMR), and mass spectrometry (MS). Moreover, the crystal structure of compound 6a was elucidated by X-ray diffraction analysis.

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“…Several bioactive materials were identified using GC/Mass spectroscopy and the traced compounds were characterized by ChemSpider Database. Many of these compounds were found to have antibacterial, antifungal and anti-inflammatory effects according to that reported by several previous studies [56][57][58][59][60][61]. In addition, GC/Mass spectra revealed the presence of peaks in the range of 320 to 537 m/z.…”

Section: Plos Onementioning

confidence: 56%

Virulence profiles of some Pseudomonas aeruginosa clinical isolates and their association with the suppression of Candida growth in polymicrobial infections

et al. 2020

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Pseudomonas aeruginosa is an opportunistic pathogen that can cause a variety of diseases especially in the hospital environment. However, this pathogen also exhibits antimicrobial activity against Gram-positive bacteria and fungi. This study aimed to characterize different virulence factors, secreted metabolites and to study their role in the suppression of Candida growth. Fifteen P. aeruginosa isolates were tested for their anticandidal activity against 3 different Candida spp. by the cross-streak method. The effect on hyphae production was tested microscopically using light and scanning electron microscopy (SEM). Polymerase chain reaction was used in the detection of some virulence genes. Lipopolysaccharide profile was performed using SDS-polyacrylamide gel stained with silver. Fatty acids were analyzed by GC-MS as methyl ester derivatives. It was found that 5 P. aeruginosa isolates inhibited all tested Candida spp. (50–100% inhibition), one isolate inhibited C. glabrata only and 3 isolates showed no activity against the tested Candida spp. The P. aeruginosa isolates inhibiting all Candida spp. were positive for all virulence genes. GC-Ms analysis revealed that isolates with high anticandidal activity showed spectra for several compounds, each known for their antifungal activity in comparison to those with low or no anticandidal activity. Hence, clinical isolates of P. aeruginosa showed Candida species-specific interactions by different means, giving rise to the importance of studying microbial interaction in polymicrobial infections and their contribution to causing disease.

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Synthesis and Fluorescent Properties of Novel Isoquinoline Derivatives

Cited by 20 publications

References 37 publications

Photocatalytic Reduction of Fluorescent Dyes in Sunlight by Newly Synthesized Spiroindenoquinoxaline Pyrrolizidines

Photocatalytic Reduction of Fluorescent Dyes in Sunlight by Newly Synthesized Spiroindenoquinoxaline Pyrrolizidines

Synthesis and Characterization of Novel Functionally Substituted Planar Pyrimidothienoisoquinolines and Nonplanar (3aR, 4S, 9aS)-pyrazolo[3,4-g]isoquinolines

Virulence profiles of some Pseudomonas aeruginosa clinical isolates and their association with the suppression of Candida growth in polymicrobial infections

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