Crystal structure of 1-(benzyloxy)urea, C8H10N2O2

Mai, Xi; Xia, Hongying; Lu, Xiao-San; Liao, Yijing

doi:10.1524/ncrs.2009.0238

Cited by 4 publications

(9 citation statements)

References 5 publications

(8 reference statements)

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“…In the title crystal structure, the bond length of the carbonyl bond (C=O) is 1.225 Å which is in the normal range of 1.19 -1.23 Å, similar to that observed in our previous papers [2][3][4]. There are three significant atomic planes in the structure, two benzene rings and the urea plane (O1, N1, N2, C1).…”

Section: Discussionsupporting

confidence: 86%

Crystal structure of 1-(4-chlorobenzyloxy)-3-phenylurea, C14H13ClN2O2

Liao¹,

Mai²,

Sun³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Discussionsupporting

confidence: 86%

Crystal structure of 1-(4-chlorobenzyloxy)-3-phenylurea, C14H13ClN2O2

Liao¹,

Mai²,

Sun³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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“…There are three significant atomic planes in the structure: (a) benzene ring; (b) the urea plane; (c) O1, O2, C1 and C2 composed plane. The dihedral angle between the ester plane and the benzyl group is obviously smaller (only 3.3(2)°)compared to other hydroxyurea derivatives [4,5]. This may be related to the steric problems between the ester plane and the urea plane, which lead to the urea plane approaches to the benzene ring.…”

Section: Discussionmentioning

confidence: 95%

Crystal structure of ethyl 2-(3-(2-fluorobenzyloxy)ureido)acetate, C12H15FN2O4

Wei¹,

Mai²,

Xia³

et al. 2010

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialSynthesis of the title compound was accomplished by reaction of glycine ethyl ester hydrochloride (9 mmol) with N-(2-fluorobenzyloxy)-4-nitrophenylester (9 mmol) in dry methylene chloride (60 ml) in the presence of anhydrous triethylamine (18 mmol). The reaction mixture was stirred for 12 hand washed with 1MN aOH, 1MH Cl and water [1]. The organic fraction was dried with MgSO 4 ,filtered, and distilled at the reduced pressure at 25°Ctogive the desired compound as ayellow solid. The substance was recrystallized from purified ethyl ether, filtered, washed with ethyl ether to obtain acolorless solid and dried. Colorless column-shaped single crystals of the title compound suitable for X-ray diffraction analysis were obtained by slow evaporation of the mixed solvent ethanol/water (9:1, v/v)atroom temperature for six days (m.p. 51 -52°C). Experimental details DiscussionThe bond lengths of the carbonyl bonds (C=O) in the title crystal structure are in the normal range of 1.19 -1.23 Å,while the values in the similar hydroxyurea derivatives exceed 1.25 Å [2,3]. There are three significant atomic planes in the structure: (a) benzene ring; (b) the urea plane; (c) O1, O2, C1 and C2 composed plane. The dihedral angle between the ester plane and the benzyl group is obviously smaller (only 3.3(2)°)compared to other hydroxyurea derivatives [4,5]. This may be related to the steric problems between the ester plane and the urea plane, which lead to the urea plane approaches to the benzene ring. The urea plane forms adihedral angle of 81.8(2)°with the ester plane. The complex displays the intermolecular hydrogen bonds along [001] between the N2 and O3 with d(N2-O3) =2.805 Å.

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“…A reported synthesis of 1-(N-benzyloxycarbamoyl)benzotriazole (2) included the reaction of 1-(N-carbamoylchloride)benzotriazole with benzyloxyamine hydrochloride (15). In our research, 1,1'-carbonylbisbenzotriazole (1) was used in reactions with the corresponding oxyamine hydrochlorides (benzyloxyhydroxylamine hydrochloride, methoxyamine hydrochloride and ethoxyamine hydrochloride) and triethylamine in dioxane suspension.…”

Section: Chemistrymentioning

confidence: 99%

“…The white solid product was washed with HCl (pH 3) and water, recrystallized from ethyl acetate and hexane and dried over P 2 O 5 in vacuo. (5), N-hydroxybiuret (12), 4-(hydroxyaminocarbonyl)aminobenzoic acid (13), N-hydroxyurea (14), N,N',N''-trihydroxyisocyanuric acid (16) and N,N',N''-trihydroxibiuret (15) A mixture of 1-(N-benzyloxycarbamoyl)benzotriazole (2), N-benzyloxybiuret (6), 4-(benzyloxycabamoyl)aminobenzoic acid (7), N-benzyloxyurea (8), N,N',N''-tribenzyloxyisocyanuric acid (10) or N,N',N''-tribenzyloxybiuret (11) and 0.05 g palladium on carbon (Pd/C, 10%) in methanol (100 mL) was kept under hydrogen (r. t., normal pressure) for 1-10 hours. Pd/C was filtered off and methanol was evaporated.…”

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confidence: 99%

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Synthesis, antibacterial and cytotoxic activity evaluation of hydroxyurea derivatives

Kos¹,

Jadrijević-Mladar²,

Butula³

et al. 2013

Acta Pharmaceutica

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Hydroxyurea and its derivatives exhibit versatile biological activities. Hydroxyurea is currently used in the treatment of various neoplastic and non-neoplastic diseases such as cancer, sickle cell anemia and HIV (1). Derivatives of hydroxyurea were found to inhibit matrix zinc metaloproteinases (MMP), urease, carboanhydrase, carboxypeptidase, cyclooxygenase and 5-lipooxygenase. Early experiments on antibacterial properties and effects on tumor cell lines of hydroxyurea and low molecular mass derivatives were investigated in the 1960s (2-3). Recently, hydroxyurea was recognized as a leading compound in nitric oxide donor synthesis (4).

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Crystal structure of 1-(benzyloxy)urea, C₈H₁₀N₂O₂

Cited by 4 publications

References 5 publications

Crystal structure of 1-(4-chlorobenzyloxy)-3-phenylurea, C14H13ClN2O2

Crystal structure of 1-(4-chlorobenzyloxy)-3-phenylurea, C14H13ClN2O2

Crystal structure of ethyl 2-(3-(2-fluorobenzyloxy)ureido)acetate, C12H15FN2O4

Synthesis, antibacterial and cytotoxic activity evaluation of hydroxyurea derivatives

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