Synthesis of novel β-lactams bearing an anthraquinone moiety, and evaluation of their antimalarial activities

Jarrahpour, Aliasghar; Ebrahimi, Edris; Khalifeh, Reza; Sharghi, Hashem; Sahraei, Mohammad; Sinou, Véronique; Latour, Christine; Brunel, Jean Michel

doi:10.1016/j.tet.2012.04.011

Cited by 39 publications

(11 citation statements)

References 25 publications

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“…All bond lengths and bond angles are normal and comparable with those reported for related compounds (Butcher et al, 2011;Atioğlu et al, 2014;Jarrahpour et al, 2012). 147.47, 144.82, 134.88, 131.22, 131.17, 130.50, 128.10, 127.43, 127.30, 123.95, 121.54, 118.29, 115.04…”

Section: D-supporting

confidence: 87%

Crystal structure of 2-[4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1,3-dione dimethyl sulfoxide monosolvate

et al. 2015

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In the title solvated compound, C28H19N2O4·C2H6OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 Å). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy- and chlorophenyl rings and the ring plane of the 1H-benzo[de]isoquinoline-1,3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intramolecular C—H⋯O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and methoxybenzene rings. In the crystal, the components are linked by C—H⋯O hydrogen bonds, C—H⋯π interactions and aromatic π–π stacking interactions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) Å], resulting in a three-dimensional network, The dimethyl sulfoxide solvent molecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.

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Section: D-supporting

confidence: 87%

Crystal structure of 2-[4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1,3-dione dimethyl sulfoxide monosolvate

et al. 2015

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“…All bond lengths and bond angles are normal and comparable with those reported for related compounds (Çelik et al, 2015;Butcher et al, 2011;Atioğlu et al, 2014;Jarrahpour et al, 2012;Jarrahpoor & Khalili, 2007;Jarrahpour & Ebrahimi, 2010 centroids of the N2/C4/C5/C10/C11/C15, C5-C10, C17-C22 and C24-C29 rings, respectively; symmetry codes:…”

Section: D-supporting

confidence: 82%

Crystal structure of 2-[(3S,4S)-4-(anthracen-9-yl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]-2-aza-2H-phenalene-1,3-dione unknown solvate

Çeli̇k¹,

Akkurt²,

Jarrahpour³

et al. 2015

Acta Cryst E

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The central β-lactam ring of the title compound, C36H24N2O4, is almost planar (r.m.s. deviation = 0.003 Å) and makes dihedral angles of 17.17 (19), 89.76 (17) and 78.44 (17)° with the benzene ring, the anthracene ring (r.m.s. deviation = 0.003 Å) and the 1H-benzo[de]isoquinoline-1,3(2H)-dione moiety, which is nearly planar [maximum deviation = 0.098 (2) Å], respectively. The molecular structure is stabilized by an intramolecular C—H⋯N hydrogen bond. In the crystal, molecules are linked via C—H⋯π and π–π stacking interactions [centroid–centroid distances = 3.5270 (19) and 3.779 (2) Å], forming a three-dimensional structure. A region of disordered electron density, probably disordered solvent molecules, was treated with the SQUEEZE procedure in PLATON [Spek (2015 ▸). Acta Cryst. C71, 9–18], which indicated a solvent cavity of 322 Å3 containing approximately 91 electrons. Their formula mass and unit-cell characteristics were not taken into account during the refinement.

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“…In addition, it possess many other pharmacological activities such as human cytomegalovirus protease inhibitors (Borthwick et al, 1998), LHRH antagonists (Guillon et al, 2007), cholesterol absorption inhibitors (Burnett, 2004), anticancer agents (Banik et al, 2010;O'Boyle et al, 2010), antihyperglycemic (Goel et al, 2004, antimalarial (Jarrahpour et al, 2012), anti-HIV (Sperka et al, 2005), anti-inflammatory and analgesic activities (Saturnino et al, 2000).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of some new β-lactam-triazole hybrids

et al. 2015

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A series of novel b-lactams was synthesized from different imines and a special ketene derived from Nendo-5-norbornene-2,3-dicarboxyloylglycine 1 via the [2 ? 2] ketene imine cycloaddition. Then, b-lactams 3a-h were treated with 1-azido-4-nitrobenzene 4 to afford blactam-triazole hybrids 5a-h. Of the twenty-three b-lactams tested against chloroquine-resistant P. falciparum K14 strain, 3a and 3d showed IC 50 \ 20 lM, while 3j, 3m, 5a-5f exhibited IC 50 \ 50. These newly synthesized blactams were also tested against S. aureus, E. coli, P. aeruginosa, C. albicans and C. glabrata and showed no activity below 125 lg/mL.

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Synthesis of novel β-lactams bearing an anthraquinone moiety, and evaluation of their antimalarial activities

Cited by 39 publications

References 25 publications

Crystal structure of 2-[4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1,3-dione dimethyl sulfoxide monosolvate

Crystal structure of 2-[4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1,3-dione dimethyl sulfoxide monosolvate

Crystal structure of 2-[(3S,4S)-4-(anthracen-9-yl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]-2-aza-2H-phenalene-1,3-dione unknown solvate

Synthesis and biological evaluation of some new β-lactam-triazole hybrids

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