Synthesis and Biological Activity of <i>N</i>‐Aroyl (Aryloxyacetyl)‐<i>N</i>′‐ferrocenyl Thiourea Derivatives

Zhang, Qiong; Zhao, Bo; Song, Yangyang; Hua, Chengwen; Gou, Xin; Chen, Bang; Zhao, Jihe

doi:10.1002/hc.21266

Cited by 22 publications

(7 citation statements)

References 25 publications

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“…In a recent report, the Zhang group identified ferrocenyl thioureas 53 as effective plant growth regulators. Most compounds displayed promising auxin and cytokinin activities and also for their application as plant hormones [164]. N-(4-acetylphenyl)-N'-(2-nitrobenzoyl)-thiourea was reported to be a considerable plant-growth regulator by Hu et al [64].…”

Section: Cholinesterase Inhibition Activitymentioning

confidence: 99%

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

et al. 2016

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1-(Acyl/aroyl)-3-(substituted)thioureas are privileged architectures that have received remarkable attention of researchers in view of their variable topological aspects, binding modes and broad spectrum promising pharmacological properties. Reactivity of acyl thiourea derivatives has presented various organic transformations into other demanding scaffolds and this is an attractive strategy for synthetic chemists to access heterocyclic cores. Multiple binding sites make them flexible ligands for complexation with transition metals thus occupying a distinct position in coordination chemistry. 1-(Acyl/aroyl)-3-(substituted)thioureas have also emerged as attractive candidates in various fields such as ion sensors, corrosion inhibitors, molecular electronics, in metal extraction and in pharmaceuticals. The medicinal chemistry of this organo-sulfur framework and the derived metal complexes has witnessed fantastic progress in the current era. In continuation of our efforts to compile data on the structural aspects and numerous applications of 1-(acyl/aroyl)-3-(substituted)thiourea analogs, continuous advances have prompted us to present an overview of the last 2 years literature on this exciting family of compounds through this review article.

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Section: Cholinesterase Inhibition Activitymentioning

confidence: 99%

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

et al. 2016

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“…10 An alternative route involving amination of ferrocenylacylazide Fc-C(O)N 3 with 10% NaOH failed to yield any significant amounts of 2 in our hands. 11 Hemiaminal 1 was reacted with 2 in a 2:1 molar ratio in benzene, at ambient temperature, under an inert atmosphere. 13 C NMR monitoring of the reaction after 10 min displayed new resonances at 77.4 (CH 2 ), 112.1(Fcipso), 67.9,63.4,57.4 (Fc), and 42.7 (NMe 2 ) ppm, respectively, assigned to the triamine FcN(CH 2 NMe 2 ) 2 (4).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Aminoferrocene [(η 5 -C 5 H 5 )Fe(η 5 -C 5 H 4 NH 2 )] (Fc-NH 2 , 2 ) was synthesized according to previous literature procedures . An alternative route involving amination of ferrocenylacylazide Fc-C(O)N 3 with 10% NaOH failed to yield any significant amounts of 2 in our hands . Hemiaminal 1 was reacted with 2 in a 2:1 molar ratio in benzene, at ambient temperature, under an inert atmosphere.…”

Section: Resultsmentioning

confidence: 99%

Aminomethylation of Aminoferrocene, [(η⁵-C₅H₅)Fe(η⁵-C₅H₄NH₂)], and (Anilino)chromiumtricarbonyl, [(η⁶-C₆H₅NH₂)Cr(CO)₃], by O-Triethylsilyl-hemiaminal, (Et₃SiOCH₂NMe₂): The Role of Disparate Organometallic Electronic Effects in Modifying Product Outcomes

2022

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The room-temperature reaction of O-triethylsilyl-hemiaminal, Et 3 SiOCH 2 NMe 2 , (1) with primary amines containing organometallic electron-donating ferrocenyl or electron-withdrawing arenechromiumtricarbonyl groups, Fc−NH 2 {Fc = [(η 5 -C 5 H 5 )Fe(η 5 -C 5 H 4 )] (2) and [(η 6 -C 6 H 5 NH 2 )Cr(CO) 3 ] (3), respectively}, led to separate and distinctive chemistry. The reaction between 1 and 2 initially produced the transient triamine FcN(CH 2 NMe 2 ) 2 (4), which transformed upon workup into 1,3,5-triferrocenyl-1,3,5-hexahydrotriazine (5). The reaction between 1 and 3 led to the isolation of the diamine [(C 6 H 5 NHCH 2 NMe 2 )Cr(CO) 3 ] (7) as the only product. The complexes 5 and 7 are stable materials and were readily characterized spectroscopically and structurally. The labile ferrocenyltriamine 4 was readily trapped by complexation with Mo(CO) 4 {presented as [(norbornadiene)Mo(CO) 4 ]} to form [FcN(CH 2 (NMe 2 ) 2 ]Mo(CO) 4 (6), coordinating the Mo atom in a bidentate manner via the terminal NMe 2 groups. The Me 2 NCH 2 group in 7 readily exchanged upon reaction with either Et 2 NH or Et 2 NCH 2 NEt 2 to yield the diamine [(η 6 -C 6 H 5 NHCH 2 NEt 2 )Cr(CO) 3 ] (8). The initial cyclic voltammetric analysis exhibited oxidation of each separate metal center in both 5 and 6.

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“…Firstly, they are low-toxic compounds, widely represented in the plant world (plants of the cruciferous family) [6,7]. Secondly, the chemistry of cycloalkane carbonylisocyanates is diverse and can be used in the synthesis of functionalized acylthioureas and acylthiosemicarbazides [8][9][10][11][12], as well as various heterocycles [13] which are characterized by growth-regulating, antibacterial, fungicidal and cytotoxicity activity. Thirdly, the modification of acyl isothiocyanates by fragments of substituted aminoarylcarboxylic (sulfo) acids is promising, as some of them (anthranilic, p-aminobenzoic acids) are important precursors of the synthesis of auxins and other natural compounds [14,15].…”

Section: актуальные вопросы фармацевтической и медицинской науки и практики 2021 т 14 № 1(35) с 4-11mentioning

confidence: 99%

Substituted (сycloalkylcarbonylthioureido)aryl-(benzyl-)carboxylic(sulfonic) acids: synthesis, antimicrobial and growth-regulating activity

Kholodniak¹,

Stavytskyi²,

Холодняк³

et al. 2021

АПФМНП

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Acylisothiocyanates are a promising class of organic compounds that are present in the plant world and can be used in the synthesis of disubstituted thioureas and various heterocycles. These derivatives are characterized by growth-regulating, antibacterial, fungicidal, cytotoxicity, and other activities. Modification of acylisothiocyanates by fragments of substituted aminoarylcarboxylic (sulfo) acids is promising, as some of them (anthranilic, p-aminobenzoic acids) are precursors for the auxins and other natural compounds synthesis. Their combined activity is also an important aspect. Namely the simultaneous manifestation of both fungicidal and restrictive activity. Based on this, the synthesis of new substituted (cycloalkylcarbonylthioureido)aryl-(benzyl-)carboxylic (sulfonic) acids is relevant as promising regulators of plant growth with antibacterial activity. The aim of this work is to search for effective compounds with growth-regulating and antimicrobial activity among substituted (cycloalkylcarbonylthioureido)aryl-(benzyl-)carboxylic (sulfonic) acids. Materials and methods. Methods of organic synthesis, physical and physical-chemical methods of analysis of organic compounds (IR, NMR 1H-spectroscopy, chromato-mass spectrometry, elemental analysis). Antimicrobial activity studies were performed on standard strains of bacteria and fungi (S. aureus ATCC 25923, E. coli ATCC 25922, P. aeruginosa ATCC 27853 and C. albicans ATCC 885-653). The effect of synthesized compounds on growth rates was evaluated on wheat (variety Grom). Results. An “in situ” method for the synthesis of substituted (cycloalkylcarbonylthioureido)aryl-(benzyl-)carboxylic (sulfonic) acids was proposed. It was shown that the latter could be easily synthesized by the sequential interaction of cyclopropanecarbonyl chloride, ammonium isothiocyanate, and aminoaryl-(benzyl-)carboxylic, sulfanilic acids or sulfamide. Data of 1H NMR spectra showed the peculiarities of the structure of the synthesized compounds, namely the presence of singlet signals of protons of urea, thioamide and carboxyl groups, multiple signals of methine and methylene protons of cyclopropane fragment. It was found that the synthesized compounds showed moderate antimicrobial activity against S. aureus and P. aeruginosa (MIC 50 μg/ml, MBC 100 μg/ml) and significant antifungal activity against C. albicans (MIC 25–50 μg/ml, MFC 25–50 μg/ml). A number of compounds were identified as effective regulators of wheat growth and exceed the natural analogue – heteroauxin (3-indolylacetic acid) in terms of auxin-like activity. Conclusions. A one-step method for the synthesis of substituted (cyclopropanecarbonylthioureido)aryl-(benzyl-)carboxylic (sulfonic) acids was developed. The physical-chemical properties of the synthesized compounds were studied using a set of methods (IR, 1H NMR spectroscopy, chromato-mass spectrometry, elemental analysis) and the features of the structure were discussed. The synthesized compounds reveal moderate antimicrobial, high antifungal activity, and growth-promoting activity.

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Synthesis and Biological Activity of N‐Aroyl (Aryloxyacetyl)‐N′‐ferrocenyl Thiourea Derivatives

Cited by 22 publications

References 25 publications

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

Aminomethylation of Aminoferrocene, [(η⁵-C₅H₅)Fe(η⁵-C₅H₄NH₂)], and (Anilino)chromiumtricarbonyl, [(η⁶-C₆H₅NH₂)Cr(CO)₃], by O-Triethylsilyl-hemiaminal, (Et₃SiOCH₂NMe₂): The Role of Disparate Organometallic Electronic Effects in Modifying Product Outcomes

Substituted (сycloalkylcarbonylthioureido)aryl-(benzyl-)carboxylic(sulfonic) acids: synthesis, antimicrobial and growth-regulating activity

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Synthesis and Biological Activity of N‐Aroyl (Aryloxyacetyl)‐N′‐ferrocenyl Thiourea Derivatives

Cited by 22 publications

References 25 publications

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

Aminomethylation of Aminoferrocene, [(η5-C5H5)Fe(η5-C5H4NH2)], and (Anilino)chromiumtricarbonyl, [(η6-C6H5NH2)Cr(CO)3], by O-Triethylsilyl-hemiaminal, (Et3SiOCH2NMe2): The Role of Disparate Organometallic Electronic Effects in Modifying Product Outcomes

Substituted (сycloalkylcarbonylthioureido)aryl-(benzyl-)carboxylic(sulfonic) acids: synthesis, antimicrobial and growth-regulating activity

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Aminomethylation of Aminoferrocene, [(η⁵-C₅H₅)Fe(η⁵-C₅H₄NH₂)], and (Anilino)chromiumtricarbonyl, [(η⁶-C₆H₅NH₂)Cr(CO)₃], by O-Triethylsilyl-hemiaminal, (Et₃SiOCH₂NMe₂): The Role of Disparate Organometallic Electronic Effects in Modifying Product Outcomes