Hybrid molecules of carvacrol and benzoyl urea/thiourea with potential applications in agriculture and medicine

Pete, Umesh D.; Zade, Chetan M.; Bhosale, Jitendra D.; Tupe, Santosh G.; Chaudhary, Preeti; Dikundwar, Amol G.; Bendre, Ratnamala S.

doi:10.1016/j.bmcl.2012.07.017

Cited by 27 publications

(10 citation statements)

References 21 publications

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“…Some thiourea derivatives containing pyridine moieties have been synthesized and screened for antitumor, these compounds also showed stronger anti-inflammatory activity than ibuprofen [5]. On the other hand, thiourea derivatives have been used as agrochemicals such as fungicides, insecticides and herbicides [6][7][8]. The benzoyl thiourea ligands involving thiocarbonyl moieties could lead to complexation as mono or bidentate ligands with a series of hard and soft metal cations [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and antioxidant evaluation of N-(4-formylpiperazine-1-carbonothioyl)benzamide

Abosadiya¹

2020

Eur J Chem

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New benzoylthiourea derivative, N-(4-formylpiperazine-1-carbonothioyl)benzamide was prepared by the reaction of benzoylisothiocyanate with 1-piperazinecarboxaldehyde in acetone as solvent. The compound was characterized by FT-IR and multinuclear 1H and 13C NMR spectroscopy techniques. The benzoylthiourea molecule was obtained in crystalline form by recrystallization in DMSO. Single crystal X-ray diffraction study indicates that compound crystallized in triclinic crystal system and crystal data for C13H15N3O2S, space group P-1 (no. 2), a = 7.3016(9) Å, b = 7.7380(9) Å, c = 12.9815(16) Å, α = 103.581(4)°, β = 102.153(4)°, γ = 102.409(4)°, V = 669.46(14) Å3, Z = 2, T = 296(2) K, μ(MoKα) = 0.243 mm-1, Dcalc = 1.376 g/cm3, 31184 reflections measured (6.72° ≤ 2Θ ≤ 53.46°), 2822 unique (Rint = 0.0582) which were used in all calculations. The final R1 was 0.0501 (>2σ(I)) and wR2 was 0.1493 (all data). Intramolecular N-H···O hydrogen bond is stabilized the trans geometry of the thiono and the carbonyl groups. The heterocyclic piperazine ring makes a dihedral angle of 48.50(15)° with the benzene ring. Antioxidant test by DPPH method showed that compound exhibits good antioxidant activity of about 75%.

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Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and antioxidant evaluation of N-(4-formylpiperazine-1-carbonothioyl)benzamide

Abosadiya¹

2020

Eur J Chem

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“…Terpene hybrids reported in bibliography include hybrids between terpene-benzoylphenyl urea (BPU) [ 27 ], hybrid terpene-amino acid [ 28 , 29 ], hybrid terpene-quinone [ 17 , 30 ], hybrid terpene-anti-inflammatory agents [ 31 ], hybrid terpene-NSAID [ 32 ], among others. However, to date there is little information on the possible biological effect that hybrid molecules formed by the fusion of two different terpenes may have.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry

et al. 2018

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Naturally occurring terpenes were combined by click reactions to generate sixteen hybrid molecules. The diterpene imbricatolic acid (IA) containing an azide group was used as starting compound for the synthesis of all the derivatives. The alkyne group in the terpenes cyperenoic acid, dehydroabietinol, carnosic acid γ-lactone, ferruginol, oleanolic acid and aleuritolic acid was obtained by esterification using appropriate alcohols or acids. The hybrid compounds were prepared by combining the IA azide function with the different terpene-alkynes under click chemistry conditions. The cytotoxic activity of the terpene hybrids 1–16 was assessed against Vero cells and tumour cell lines (HEP-2, C6 and Raw 264.7). Compounds 1, 2, 3 and 7 showed cytotoxic activity against the tested cell lines. The antiviral activity of the compounds was evaluated against HSV-1 KOS, Field and B2006 strain. For the pairs of hybrid compounds formed between IA-diterpene (compounds 3–8, except for compound 7), a moderate activity was observed against the three HSV-1 strains with an interesting selectivity index (SI ≥10, SI = CC50/CE50) for some compounds.

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“…Primary acylureas and N‐phenyl acylureas are two common structural motifs in agrochemicals, and medicinal chemistry . These structural motifs serve as pesticides and insecticides exhibiting significant properties such as anti‐inflammatory, antihypnotic, antitumor,, analgesic, antihelmintic and antifungal (Figure ).…”

Section: Introductionmentioning

confidence: 99%

[Amberlyst-15 - (4Na₂ SO₄ -2H₂ O₂ -NaCl) Adduct]: Direct Access to Synthesize Acylureas via Oxidative Amidation of Aldehyde

et al. 2017

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A simple, efficient and straightforward approach for the synthesis of N‐acylureas has been demonstrated. Herein, novel method for the first time enables oxidative amidation of aldehydes and urea in presence of enclathrated H2O2 adduct and Amberlyst‐15 as catalyst is reported. Various aromatic, hetero‐aromatic and aliphatic aldehydes undergo oxidative amidation with urea and its analogues in moderate to excellent yields. The significant feature of this work includes metal free conditions, an efficient and neutral anhydrous source of H2O2 as oxidant, commercially available catalyst and recyclability of catalyst over several runs without considerable loss in activity.

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Hybrid molecules of carvacrol and benzoyl urea/thiourea with potential applications in agriculture and medicine

Cited by 27 publications

References 21 publications

Synthesis, crystal structure and antioxidant evaluation of N-(4-formylpiperazine-1-carbonothioyl)benzamide

Synthesis, crystal structure and antioxidant evaluation of N-(4-formylpiperazine-1-carbonothioyl)benzamide

Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry

[Amberlyst-15 - (4Na₂ SO₄ -2H₂ O₂ -NaCl) Adduct]: Direct Access to Synthesize Acylureas via Oxidative Amidation of Aldehyde

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Hybrid molecules of carvacrol and benzoyl urea/thiourea with potential applications in agriculture and medicine

Cited by 27 publications

References 21 publications

Synthesis, crystal structure and antioxidant evaluation of N-(4-formylpiperazine-1-carbonothioyl)benzamide

Synthesis, crystal structure and antioxidant evaluation of N-(4-formylpiperazine-1-carbonothioyl)benzamide

Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry

[Amberlyst-15 - (4Na2 SO4 -2H2 O2 -NaCl) Adduct]: Direct Access to Synthesize Acylureas via Oxidative Amidation of Aldehyde

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[Amberlyst-15 - (4Na₂ SO₄ -2H₂ O₂ -NaCl) Adduct]: Direct Access to Synthesize Acylureas via Oxidative Amidation of Aldehyde