Synthesis, Structure Analysis, and Antitumor Activity of (<i>R</i>)‐2,4‐Dioxo‐5‐fluoro‐1‐[1‐(methoxycarbonyl) Ethylaminocarbonylmethyl]‐1,2,3,4‐tetrahydropyrimidine

Yuan, Ji-Xin; Cai, Xiaoqing; Chen, Di‐Mei; Hu, Mao‐Lin

doi:10.1002/cjoc.200790080

Cited by 11 publications

(13 citation statements)

References 17 publications

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“…In the crystal structure of the title compound, no significant differences appear in the bond distances and bond angles comparing to the similiar compounds [5]. The C7-N2 and C8-N1 bond distance [1.388(9) Å and 1.38(1) Å]are shorter than C-Nsingle bond of 1.443(4) Å [6]. The C2-C7 and C8-C9 bond lengths [1.48(1) Å and 1.50(1) Å]are both shorter than atypical C-C bond length [1.530(3) Å], but longer than atypical C=C double bond [1.331(2) Å] [7].…”

Section: Discussionmentioning

confidence: 84%

“…The C2-C7 and C8-C9 bond lengths [1.48(1) Å and 1.50(1) Å]are both shorter than atypical C-C bond length [1.530(3) Å], but longer than atypical C=C double bond [1.331(2) Å] [7]. The C7-O2 and C8-O1 bond lengths [1.207(9) Å and 1.205(9) Å]are longer than that of standard C=O double bond length 1.170 Å [6]. The partial double bond character of the structure is presumed as ar esult of the electron delocalization.…”

Section: Discussionmentioning

confidence: 98%

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Crystal structure of N,N-ditosyldibenzo-1,5-diazocane-2,6-dione, C28H22N2O6S2

Cai¹,

Liu²,

Yan³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

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C 28 H 22 N 2 O 6 S 2 ,monoclinic, C12/c1(no. 15), a =22.591(1) Å, b =13.3972(8) Å, c =19.874(1) Å, b =94.018(1)°, V =6000.3 Å 3 , Z =8,Rgt(F) =0.068, wRref(F 2 ) =0.178, T =298 K. N,N-ditosyldibenzo-1,5-diazocane-2,6-dione was prepared by reacting of p-toluenesulfonylchloride (0.01 mol) and as odium carbonate (0.03 mol) solution (40 mL) with 2-aminobenzoic acid (0.01 mol). The pH of the mixture was adjusted to 3after reacting 20 hours at room temperature, and then awhite solid of the title compound was obtained after filtration and column chromatography separation. The purified product was dissolved in 95 %etha-nol and single crystals were separated after 8days. Source of material Experimental detailsAll Hatoms were positioned geometrically and allowed to ride on their parent atoms at distances of d(Csp.96 or 0.97 Å with U iso = 1.5.U eq(parent atom). DiscussionThe sulfonamide family includes abroad-spectrum of synthetic bacteriostatic antibiotics used against most Gram-positive and many Gram-negative microorganisms and protozoa [1]. These compounds are commonly used in human and veterinary medicine for therapeutic and prophylactic purposes to fight common bacterial diseases [2]. Furthermore, in animal husbandry these substances are commonly used for the prevention and treatment of dairy cattle for several infectious diseases, prophylactic, or as feed additives to promote growth in farm animals [3,4]. In the crystal structure of the title compound, no significant differences appear in the bond distances and bond angles comparing to the similiar compounds [5]. The C7-N2 and C8-N1 bond distance [1.388(9) Å and 1.38 (1) . The partial double bond character of the structure is presumed as ar esult of the electron delocalization. The para-substituted phenyl ring shows approximately the expected C 2v symmetry so that for the two matching endocyclic bond angles this holds true even at the 2ο level. Therefore, it may be concluded that the angles at C16 (116.9(8)°), C23 (118.3(8)°)a nd C19 (121.5(8)°), C26 (120.8(7)°)a re significantly diminished and enlarged, respectively. According to the conclusions of Domenicano et al. [8], it follows that the Satom introduces asmall electron-withdrawing effect, whereas the methyl substituent introduces electron-releasing properties. The seven atoms of C1 to C7 and N1 are coplanar (r.m.s. deviation = 0.0241(3) Å,plane p1). Another seven atoms of C8 to C14 and N2 are coplanar with the r.m.s. deviation of 0.0210(3) Å (plane p2). The sulphur atom S1 and the phenyl group C15 to C21 are coplanar (r.m.s. deviation =0 .0317(6) Å,p lane p3). The other sulphur atom S2 and the phenyl group C22 to C28 are coplanar with the r.m.s. deviation of 0.0580(8) Å (plane p4). The dihedral angles formed by the plane p1 and p2, plane p3 and p4 are 76.5(2)°and 64.07°,respectively.

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Section: Discussionmentioning

confidence: 84%

Section: Discussionmentioning

confidence: 98%

Crystal structure of N,N-ditosyldibenzo-1,5-diazocane-2,6-dione, C28H22N2O6S2

Cai¹,

Liu²,

Yan³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

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“…and appropriate diaminoalkanes 2a-e (2 eq.) in absolute ethanol are refluxed for [16][17][18][19][20][21][22] 2c-e 4a-c …”

Section: Resultsmentioning

confidence: 99%

“…Recently, much attention has been paid to derivatives of pyrimidine, including their hydrogenation products. This class of compounds displays wide ranges of biological and pharmacological properties such as anti-inflammatory [14], analgesic [15], antitumor [16], antidepressant [17], antibacterial, antifungal, and antitubercular effects [18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives

Beyzaei

Aryan

Keshtegar

2014

Advances in Chemistry

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Synthesis of new imidazolidine and tetrahydropyrimidine derivatives 3a, b and 4a-c as cyclic 1,3-diamines under two reaction conditions (A and B) is described. Under reaction conditions-A, a suspension of (E)-2-cyano-2-(oxazolidin-2-ylidene)ethanethioamide 1 (1 eq.) and diaminoalkanes 2a-e (2 eq.) in absolute ethanol is heated under reflux for 16-22 h to afford 3a, b and 4a-c. Alternatively, under reaction conditions-B, a solution of thioamide 1 (1 eq.) in diaminoalkanes 2a-e (3 eq.) is stirred under solvent-free conditions at room temperature for 3 days to give desired products. Reaction conditions-A for having higher yields, shorter reaction times, and required less diamines is more effective than reaction conditions-B. Oxazolidine ring opening is observed by reacting compound 1 with all of the diamines 2a-e, but the thioamide group only reacts with nonbulky diamines 2a, b. The chemical structures of novel compounds were confirmed by 1 H NMR, 13 C NMR, elemental analysis, and FT-IR spectrometry.

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“…This class of compounds displays wide range of biological and pharmacological properties. Tetrahydropyrimidines are known to possess calcium antagonistic [3][4][5], anti-inflammatory [6][7][8], analgesic [9][10], antitumor [11][12], antidepressant [13], anti-bacterial and antifungal properties [14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Physicochemical properties of some tetrahydropyrimidine derivatives

Baluja¹,

Patel²

2018

ELSR

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Production of tetrahydropyrimidine and their derivatives is of great importance in organic chemistry. Presence of pyrimidine piece in different biological compounds that are used in several medications makes it a crucial component. In this study, some new tetrahydropyrimidine compounds are synthesized and their physicochemical properties such as such as density, refractive index, partition coefficients have been studied in different solvents at 308.15K.

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Synthesis, Structure Analysis, and Antitumor Activity of (R)‐2,4‐Dioxo‐5‐fluoro‐1‐[1‐(methoxycarbonyl) Ethylaminocarbonylmethyl]‐1,2,3,4‐tetrahydropyrimidine

Abstract: A new dipeptide compound, (R)-2,4-dioxo-5-fluoro-1- [1-(methoxycarbonyl)

Cited by 11 publications

References 17 publications

Crystal structure of N,N-ditosyldibenzo-1,5-diazocane-2,6-dione, C28H22N2O6S2

Crystal structure of N,N-ditosyldibenzo-1,5-diazocane-2,6-dione, C28H22N2O6S2

Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives

Physicochemical properties of some tetrahydropyrimidine derivatives

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