Synthesis, structure characterization and preliminary biological evaluation of novel 5-alkyl-2-ferrocenyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives

Xie, Yongsheng; Pan, Xiaohong; Zhao, Bao‐Xiang; Liu, Jinting; Shin, Dong‐Soo; Zhang, Jinhua; Zheng, Liang‐Wen; Zhao, Jing; Jiang, Miao

doi:10.1016/j.jorganchem.2008.01.043

Cited by 62 publications

(20 citation statements)

References 32 publications

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“…The five bacterium used here include Escherichia coli, Staphyloccus aurueus, Vibrio alginolyticus, Aeromonas hydrophila, and Bacillus subtilis. We tested the antimicrobial activity using the viable cells plate count method as described in the literature [7,8].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and bioactivity of novel benzisothiazolone derivatives as potential microbiocides

Xu¹,

Lin²,

Hou³

2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).Novel microbiocides 2-(hydroxymethyl)benzo [d]isothiazol-3(2H)-one (7) and (3-oxobenzo[d]isothiazol-2(3H)-yl)methyl benzencarboxylates (11a-c) were synthesized in good yields, and their structures were characterized by means of 1 H NMR, MS, and elemental analysis. The new compounds were tested preliminarily in laboratory assays against the aquicolous bacteria including Escherichia coli, Staphyloccus aurueus, Vibrio alginolyticus, Aeromonas hydrophila, and Bacillus subtilis. The results show all the synthesized compounds have good antimicrobial activity. The antimicrobial activity of all the tested compounds against all test bacteria is >96.6% at the concentration of 10 À2 mg mL À1. These compounds can be further developed for effective microbiocides in the future.

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Section: Resultsmentioning

confidence: 99%

Synthesis and bioactivity of novel benzisothiazolone derivatives as potential microbiocides

Xu¹,

Lin²,

Hou³

2009

Journal of Heterocyclic Chem

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“…Synthesis of 6-aryl-2-ferrocenyl-5-substituted-pyrazolo [1,5-a]pyrazin-4(5H)-one (6) The synthetic strategies adopted to obtain the target compounds are shown in Scheme 1. The key intermediates, ethyl 1-(2-aryl-2-oxoethyl)-3-ferrocenyl-1H-pyrazole-5-carboxylate 4, in the present study were synthesized from a-bromo-arylethanone 2 and ethyl 3-ferrocenyl-1H-pyrazole-5-carboxylate 1 as previously reported [27,30]. Ethyl 1-(2-aryl-2-oxoethyl)-3-ferrocenyl-1H-pyrazole-5-carboxylate 4 reacted with nonaromatic primary amine 5 in toluene in a sealed tube at 160-185 C to afford pyrazolo-pyrazinones derivatives 6 (Scheme 1).…”

Section: Chemistrymentioning

confidence: 97%

“…The dihedral angle between the substituted Cp ring (C1-C5) and the pyrazole ring (N1/N2/C11/C12/C13) of 12.0(2) in 6f and 13.1 (2) in 6g are in the range of that of the ferrocenyl-substituted pyrazole (8.20 w 45.36 ) [27,31,32]. The C1-C11 distance 1.459(4) Å of 6g is slightly shorter than that of 6f (1.467(4) Å).…”

Section: Single-crystal Structurementioning

confidence: 98%

“…In our previous paper, we reported that 5-alkyl-2-ferrocenyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives could inhibit A549 cell growth obviously in the concentrations of 5-40 mM after 48 h of the treatment and the cytotoxic potency was highly dependent on the substitution types and patterns on the pyrazinone ring, for example, replacing the alkyl at the N-position of pyrazinone ring with an arylalkyl group resulted in more effects on the growth of A549 cells [27,29]. In the present study, we observed that the nature and the position of substituent on the molecule influence effectively biological functions.…”

Section: Effects Of the Compounds On The Viability And The Morphologymentioning

confidence: 99%

“…In our previous papers, we synthesized a series of novel pyrazole derivatives including ethyl 1-(2 0 -hydroxy-3 0 -aroxypropyl)-3-aryl-1H-pyrazole-5-carboxylate derivatives, ethyl 1-arylmethyl-3-aryl-1H-pyrazole-5-carboxylate derivatives, 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide derivatives, and 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives [21][22][23][24][25]. Furthermore, we were interested in the synthesis of pyrazole-fused heterocycles, such as 6-(aroxymethyl)-2-aryl-6,7-dihydropyrazolo [5,1-c] [1,4]oxazin-4-one derivatives, 5-alkyl-2-ferrocenyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one and 5-alkyl-2-aryl-6,7-dihydropyrazolo-[1,5-a]pyrazin-4(5H)-one [26][27][28][29]. The evaluation of biological activity showed that these compounds can inhibit A549 lung cancer cell growth.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, single-crystal characterization and preliminary biological evaluation of novel ferrocenyl pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives

Xie¹,

Zhao²,

Su³

et al. 2010

European Journal of Medicinal Chemistry

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Aggregation induced emission (AIE)‐active N‐arylated ferrocenyl pyrazole‐based push–pull chromophores: Structural, photophysical, theoretical and effect of substitution on second‐order non‐linear optical properties

David

Kamini

Thirumoorthy

et al. 2021

Applied Organom Chemis

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In this study, we report the synthesis and structural characterization of Narylated ferrocenyl pyrazole [Fc-Pz-(CF 3)-C 6 H 5-R] (R = CH 3 , 1; OCH 3 2), where Pz = pyrazole and Fc = ferrocenyl = Fe(η 5-C 5 H 5)(η 5-C 5 H 4) chromophores with D-π-A-π-D system. The solvatochromic behaviour of compounds 1 and 2 was investigated in various solvents from non-polar to polar. When solvent polarity increases, the charge transfer process produces the more polarized excited state, and consequently, positive solvatochromism was observed. The emission performance of the compounds is weak luminescence in CH 3 CN solution but becomes high emissive in a mixture of water/CH 3 CN fraction at (f w) 90%, demonstrating aggregation-induced emission (AIE) characteristics, and the mechanism of AIE has been attributed to restricted intramolecular rotation (RIR) process. The time-resolved fluorescence lifetime studies have been demonstrated in water/ CH 3 CN mixture at 90%, as it shows three relaxation pathways in their fluorescence decay. In addition, density functional theory calculations have been employed to optimize the geometry of the molecules, followed by computation of dipole moment (μ), first hyperpolarizability (β) using various functionals (B3LYP, long-range corrected CAM-B3LYP and LC-BLYP) and frontier molecular orbital levels for understanding the charge transfer, electrochemical and non-linear optical (NLO) properties. The second-order non-linear optical properties were studied by hyper-Rayleigh scattering (HRS) technique using an incident wavelength at 1064 nm. The chromophores exhibited the first hyperpolarizability (β HRS = 38.6 × 10 −30 e.s.u. for 1 and β HRS = 116.8 × 10 −30 e.s. u. for 2) and were found to be 6.8 times greater than that of the reference material, p-nitroaniline (pNA) (β HRS = 17.1 × 10 −30 e.s.u.). Also, compound 2 shows higher NLO effect because the presence of-OCH 3 group makes effective charge transfer process by mesomeric effect (+M).

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Synthesis, structure characterization and preliminary biological evaluation of novel 5-alkyl-2-ferrocenyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives

Cited by 62 publications

References 32 publications

Synthesis and bioactivity of novel benzisothiazolone derivatives as potential microbiocides

Synthesis and bioactivity of novel benzisothiazolone derivatives as potential microbiocides

Synthesis, single-crystal characterization and preliminary biological evaluation of novel ferrocenyl pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives

Aggregation induced emission (AIE)‐active N‐arylated ferrocenyl pyrazole‐based push–pull chromophores: Structural, photophysical, theoretical and effect of substitution on second‐order non‐linear optical properties

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