Literature DB >> 21522688

3-(2,4-Dichloro-phen-oxy)-1-(4-meth-oxy-phen-yl)-4-(3-nitro-phen-yl)azetidin-2-one.

Mehmet Akkurt, Sevim Türktekin, Aliasghar Jarrahpour, Seid Ali Torabi Badrabady, Orhan Büyükgüngör.   

Abstract

In the title compound, C(22)H(16)Cl(2)N(2)O(5), the nearly planar four-membered β-lactam ring [maximum deviations of 0.011 (2) for the N atom] makes dihedral angles of 68.34 (13), 83.04 (13) and 3.37 (13)° with the dichloro-, nitro- and meth-oxy-phenyl rings, respectively. The crystal structure is stabilized by C-H⋯O hydrogen-bond inter-actions. In addition, a π-π stacking inter-action [centroid-centroid distance = 3.6622 (12) Å] is observed between the β-lactam and nitro-phenyl rings.

Entities:  

Year:  2010        PMID： 21522688      PMCID： PMC3050394          DOI： 10.1107/S1600536810052645

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background on β-lactams, see: Alcaide & Almendros (2001 ▶); Alcaide et al. (2007 ▶); Banik et al. (2004 ▶); Jarrahpour & Ebrahimi (2010 ▶); Jarrahpour & Zarei (2009 ▶); Jarrahpour et al. (2007 ▶); Turos et al. (2005 ▶); Vatmurge et al. (2008 ▶).

Experimental

Crystal data

C22H16Cl2N2O5 M = 459.27 Orthorhombic, a = 9.0406 (2) Å b = 17.8177 (5) Å c = 25.9964 (6) Å V = 4187.57 (18) Å3 Z = 8 Mo Kα radiation μ = 0.35 mm−1 T = 296 K 0.57 × 0.41 × 0.28 mm

Data collection

Stoe IPDS 2 diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.826, T max = 0.909 38140 measured reflections 4199 independent reflections 3153 reflections with I > 2σ(I) R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.129 S = 1.05 4199 reflections 282 parameters H-atom parameters constrained Δρmax = 0.23 e Å−3 Δρmin = −0.34 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052645/om2390sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052645/om2390Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H16Cl2N2O5F(000) = 1888
Mr = 459.27Dx = 1.457 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 34508 reflections
a = 9.0406 (2) Åθ = 1.4–26.8°
b = 17.8177 (5) ŵ = 0.35 mm−1
c = 25.9964 (6) ÅT = 296 K
V = 4187.57 (18) Å3Prism, colourless
Z = 80.57 × 0.41 × 0.28 mm
Stoe IPDS 2 diffractometer4199 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3153 reflections with I > 2σ(I)
plane graphiteRint = 0.075
Detector resolution: 6.67 pixels mm-1θmax = 26.2°, θmin = 1.6°
ω scansh = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −22→22
Tmin = 0.826, Tmax = 0.909l = −32→32
38140 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.129w = 1/[σ2(Fo2) + (0.070P)2 + 0.3877P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4199 reflectionsΔρmax = 0.23 e Å−3
282 parametersΔρmin = −0.34 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0019 (5)
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.
xyzUiso*/Ueq
Cl10.21262 (8)0.86082 (4)0.66036 (3)0.0868 (3)
Cl2−0.34474 (8)0.78256 (5)0.70616 (3)0.0919 (3)
O10.19780 (15)0.74409 (8)0.58582 (5)0.0565 (5)
O20.4456 (2)0.72877 (11)0.50535 (6)0.0855 (7)
O30.0887 (3)0.49540 (13)0.78799 (7)0.1238 (12)
O40.0058 (3)0.45763 (14)0.71618 (9)0.1210 (10)
O50.9134 (2)0.44061 (12)0.55088 (7)0.0914 (7)
N10.4083 (2)0.61733 (10)0.55214 (6)0.0564 (6)
N20.0844 (3)0.49729 (13)0.74126 (8)0.0856 (9)
C10.0686 (2)0.74787 (11)0.61302 (7)0.0504 (6)
C20.0615 (2)0.80367 (12)0.65049 (7)0.0557 (6)
C3−0.0640 (3)0.81334 (13)0.67948 (8)0.0631 (7)
C4−0.1839 (3)0.76777 (13)0.67092 (8)0.0625 (7)
C5−0.1788 (2)0.71157 (14)0.63466 (8)0.0633 (7)
C6−0.0516 (2)0.70191 (13)0.60600 (7)0.0582 (7)
C70.2181 (2)0.68260 (13)0.55226 (7)0.0568 (7)
C80.3747 (3)0.68511 (13)0.53065 (7)0.0609 (7)
C90.2637 (2)0.60649 (12)0.57725 (7)0.0535 (6)
C100.2670 (2)0.60270 (11)0.63547 (6)0.0501 (6)
C110.3591 (2)0.64886 (13)0.66385 (7)0.0596 (7)
C120.3587 (3)0.64666 (15)0.71726 (8)0.0728 (9)
C130.2688 (3)0.59739 (15)0.74266 (8)0.0732 (9)
C140.1795 (3)0.55169 (13)0.71435 (8)0.0629 (7)
C150.1755 (2)0.55356 (12)0.66085 (7)0.0565 (6)
C160.5354 (2)0.57158 (12)0.55186 (7)0.0540 (6)
C170.6591 (2)0.59165 (13)0.52329 (8)0.0614 (7)
C180.7819 (2)0.54645 (14)0.52407 (8)0.0658 (8)
C190.7845 (3)0.48143 (15)0.55296 (8)0.0657 (8)
C200.6621 (3)0.46155 (15)0.58117 (9)0.0750 (8)
C210.5384 (3)0.50650 (14)0.58026 (8)0.0685 (8)
C220.9267 (3)0.37785 (19)0.58396 (10)0.0931 (11)
H3−0.067800.850400.704600.0760*
H5−0.260000.680500.629500.0760*
H6−0.047300.663800.581600.0700*
H70.141000.677900.525900.0680*
H90.209300.564200.562300.0640*
H110.422200.681900.646900.0720*
H120.419900.678800.735800.0870*
H130.268500.595100.778400.0880*
H150.112100.522200.642700.0680*
H170.658600.635400.503800.0740*
H180.864600.559800.504900.0790*
H200.662900.417900.600800.0900*
H210.455500.492600.599200.0820*
H22A0.849100.342700.576600.1110*
H22B0.919100.394100.619100.1110*
H22C1.020900.354200.578600.1110*
U11U22U33U12U13U23
Cl10.0833 (5)0.0746 (4)0.1024 (5)−0.0248 (3)0.0095 (3)−0.0215 (3)
Cl20.0737 (4)0.1076 (6)0.0944 (5)0.0119 (4)0.0284 (3)−0.0017 (4)
O10.0547 (8)0.0589 (9)0.0560 (7)0.0000 (7)0.0057 (6)0.0002 (6)
O20.0927 (13)0.0846 (12)0.0791 (10)0.0041 (10)0.0313 (9)0.0292 (9)
O30.194 (3)0.1049 (16)0.0724 (11)−0.0032 (17)0.0507 (14)0.0294 (10)
O40.161 (2)0.0992 (16)0.1027 (15)−0.0574 (17)0.0489 (15)−0.0058 (13)
O50.0724 (11)0.1072 (15)0.0946 (12)0.0299 (11)0.0292 (9)0.0270 (11)
N10.0581 (10)0.0616 (11)0.0496 (8)0.0027 (9)0.0153 (7)0.0052 (7)
N20.119 (2)0.0620 (13)0.0757 (14)0.0005 (14)0.0386 (13)0.0087 (10)
C10.0516 (11)0.0512 (11)0.0485 (9)0.0041 (9)−0.0012 (8)0.0065 (8)
C20.0615 (12)0.0478 (11)0.0579 (10)−0.0003 (9)−0.0014 (9)0.0013 (8)
C30.0738 (15)0.0539 (12)0.0615 (11)0.0062 (11)0.0063 (10)−0.0056 (9)
C40.0605 (13)0.0668 (14)0.0603 (11)0.0068 (11)0.0071 (9)0.0041 (10)
C50.0553 (12)0.0725 (14)0.0621 (11)−0.0060 (11)0.0001 (9)0.0017 (10)
C60.0594 (12)0.0628 (13)0.0523 (10)−0.0027 (10)−0.0015 (9)−0.0060 (9)
C70.0609 (12)0.0654 (13)0.0442 (9)0.0040 (10)0.0027 (8)0.0022 (9)
C80.0684 (13)0.0693 (14)0.0451 (9)0.0016 (11)0.0107 (9)0.0056 (9)
C90.0538 (11)0.0610 (13)0.0457 (9)−0.0024 (10)0.0092 (8)−0.0028 (8)
C100.0512 (11)0.0529 (11)0.0461 (9)0.0053 (9)0.0111 (8)0.0042 (8)
C110.0569 (12)0.0695 (14)0.0524 (10)−0.0043 (10)0.0026 (9)0.0046 (9)
C120.0780 (16)0.0854 (17)0.0551 (11)−0.0040 (13)−0.0052 (11)−0.0028 (11)
C130.0942 (18)0.0748 (16)0.0507 (10)0.0088 (14)0.0085 (11)0.0055 (11)
C140.0803 (15)0.0532 (12)0.0553 (11)0.0092 (11)0.0237 (10)0.0102 (9)
C150.0627 (12)0.0493 (11)0.0576 (10)0.0027 (10)0.0134 (9)−0.0015 (9)
C160.0550 (11)0.0611 (12)0.0460 (9)0.0001 (10)0.0110 (8)−0.0033 (8)
C170.0656 (13)0.0640 (13)0.0547 (11)−0.0022 (11)0.0173 (9)0.0018 (9)
C180.0588 (13)0.0769 (16)0.0618 (11)−0.0014 (12)0.0203 (10)−0.0004 (11)
C190.0609 (13)0.0759 (16)0.0604 (11)0.0090 (11)0.0145 (10)−0.0013 (10)
C200.0758 (15)0.0774 (16)0.0719 (13)0.0126 (13)0.0243 (11)0.0179 (12)
C210.0666 (14)0.0698 (15)0.0691 (13)0.0067 (12)0.0269 (11)0.0123 (11)
C220.086 (2)0.110 (2)0.0834 (16)0.0294 (17)0.0107 (14)0.0117 (15)
Cl1—C21.723 (2)C12—C131.367 (4)
Cl2—C41.739 (3)C13—C141.363 (3)
O1—C11.367 (2)C14—C151.392 (3)
O1—C71.413 (3)C16—C171.389 (3)
O2—C81.204 (3)C16—C211.375 (3)
O3—N21.216 (3)C17—C181.372 (3)
O4—N21.196 (3)C18—C191.381 (3)
O5—C191.375 (3)C19—C201.374 (4)
O5—C221.416 (4)C20—C211.376 (4)
N1—C81.365 (3)C3—H30.9300
N1—C91.474 (3)C5—H50.9300
N1—C161.409 (3)C6—H60.9300
N2—C141.472 (3)C7—H70.9800
C1—C21.393 (3)C9—H90.9800
C1—C61.373 (3)C11—H110.9300
C2—C31.373 (3)C12—H120.9300
C3—C41.373 (4)C13—H130.9300
C4—C51.376 (3)C15—H150.9300
C5—C61.381 (3)C17—H170.9300
C7—C81.524 (3)C18—H180.9300
C7—C91.559 (3)C20—H200.9300
C9—C101.515 (2)C21—H210.9300
C10—C111.384 (3)C22—H22A0.9600
C10—C151.373 (3)C22—H22B0.9600
C11—C121.389 (3)C22—H22C0.9600
Cl1···O12.8458 (16)C15···Cl1vii3.580 (2)
Cl1···O4i3.400 (3)C16···C113.593 (3)
Cl1···C15i3.580 (2)C17···O23.148 (3)
Cl2···C12ii3.624 (3)C18···O5ix3.382 (3)
Cl2···O4iii3.452 (3)C21···C103.319 (3)
Cl2···C3iv3.615 (2)C3···H20i2.9100
Cl2···C12iv3.635 (3)C4···H12iv3.0500
Cl2···H12ii2.9200C6···H72.7500
Cl2···H22Bi3.0900C7···H113.0800
O1···Cl12.8458 (16)C7···H62.5400
O1···O23.077 (2)C8···H172.8000
O1···N13.081 (2)C8···H113.0500
O1···C113.020 (2)C9···H212.7300
O2···C7v3.287 (3)C9···H62.9900
O2···O13.077 (2)C10···H212.7600
O2···C173.148 (3)C18···H6xiii3.0000
O2···C1v3.298 (2)C18···H9xiv2.9900
O2···C6v3.147 (3)C20···H22A2.7100
O3···C3vi3.360 (3)C20···H22B2.8000
O3···C12iv3.407 (4)C22···H202.5300
O4···Cl1vii3.400 (3)C22···H7xiv3.0900
O4···Cl2viii3.452 (3)H3···O3xi2.6000
O5···C18ix3.382 (3)H3···O4xi2.8600
O1···H112.8000H6···C72.5400
O2···H7v2.5600H6···C92.9900
O2···H172.5500H6···C18ii3.0000
O3···H132.4200H6···H72.2500
O3···H3vi2.6000H7···C62.7500
O4···H152.4300H7···H62.2500
O4···H22Bii2.8700H7···O2x2.5600
O4···H3vi2.8600H7···C22xiv3.0900
O5···H18ix2.4800H9···H152.3900
N1···O13.081 (2)H9···C18xiv2.9900
N2···C13iv3.391 (4)H11···O12.8000
N1···H112.7200H11···N12.7200
C1···C103.201 (3)H11···C73.0800
C1···C113.429 (3)H11···C83.0500
C1···O2x3.298 (2)H12···Cl2xiii2.9200
C3···O3xi3.360 (3)H12···C4xii3.0500
C3···Cl2xii3.615 (2)H13···O32.4200
C6···C103.465 (3)H15···O42.4300
C6···C93.402 (3)H15···H92.3900
C6···O2x3.147 (3)H17···O22.5500
C7···O2x3.287 (3)H17···C82.8000
C8···C113.525 (3)H18···O5ix2.4800
C9···C63.402 (3)H20···C222.5300
C10···C213.319 (3)H20···H22A2.2400
C10···C63.465 (3)H20···H22B2.4000
C10···C13.201 (3)H20···C3vii2.9100
C11···O13.020 (2)H21···C92.7300
C11···C163.593 (3)H21···C102.7600
C11···C83.525 (3)H22A···C202.7100
C11···C13.429 (3)H22A···H202.2400
C12···O3xii3.407 (4)H22B···O4xiii2.8700
C12···Cl2xii3.635 (3)H22B···C202.8000
C12···Cl2xiii3.624 (3)H22B···H202.4000
C13···N2xii3.391 (4)H22B···Cl2vii3.0900
C1—O1—C7117.95 (15)C16—C17—C18119.5 (2)
C19—O5—C22117.8 (2)C17—C18—C19121.0 (2)
C8—N1—C995.73 (17)O5—C19—C18115.9 (2)
C8—N1—C16133.74 (19)O5—C19—C20124.6 (2)
C9—N1—C16130.53 (17)C18—C19—C20119.5 (2)
O3—N2—O4123.2 (3)C19—C20—C21119.7 (2)
O3—N2—C14118.3 (2)C16—C21—C20121.1 (2)
O4—N2—C14118.5 (2)C2—C3—H3120.00
O1—C1—C2115.86 (16)C4—C3—H3120.00
O1—C1—C6125.32 (17)C4—C5—H5120.00
C2—C1—C6118.82 (17)C6—C5—H5120.00
Cl1—C2—C1119.29 (14)C1—C6—H6120.00
Cl1—C2—C3119.96 (16)C5—C6—H6120.00
C1—C2—C3120.76 (19)O1—C7—H7114.00
C2—C3—C4119.3 (2)C8—C7—H7114.00
Cl2—C4—C3119.04 (17)C9—C7—H7114.00
Cl2—C4—C5119.95 (19)N1—C9—H9112.00
C3—C4—C5121.0 (2)C7—C9—H9112.00
C4—C5—C6119.2 (2)C10—C9—H9112.00
C1—C6—C5120.9 (2)C10—C11—H11120.00
O1—C7—C8109.01 (16)C12—C11—H11120.00
O1—C7—C9116.85 (15)C11—C12—H12120.00
C8—C7—C986.19 (15)C13—C12—H12120.00
O2—C8—N1132.6 (2)C12—C13—H13121.00
O2—C8—C7135.7 (2)C14—C13—H13121.00
N1—C8—C791.71 (17)C10—C15—H15121.00
N1—C9—C786.33 (14)C14—C15—H15121.00
N1—C9—C10115.51 (15)C16—C17—H17120.00
C7—C9—C10117.40 (16)C18—C17—H17120.00
C9—C10—C11121.20 (17)C17—C18—H18120.00
C9—C10—C15119.76 (16)C19—C18—H18120.00
C11—C10—C15119.03 (16)C19—C20—H20120.00
C10—C11—C12121.0 (2)C21—C20—H20120.00
C11—C12—C13120.2 (2)C16—C21—H21120.00
C12—C13—C14118.4 (2)C20—C21—H21119.00
N2—C14—C13118.87 (19)O5—C22—H22A109.00
N2—C14—C15118.4 (2)O5—C22—H22B109.00
C13—C14—C15122.7 (2)O5—C22—H22C109.00
C10—C15—C14118.67 (19)H22A—C22—H22B110.00
N1—C16—C17120.69 (19)H22A—C22—H22C109.00
N1—C16—C21120.09 (18)H22B—C22—H22C109.00
C17—C16—C21119.2 (2)
C7—O1—C1—C2171.82 (16)C4—C5—C6—C1−0.5 (3)
C7—O1—C1—C6−8.5 (3)C8—C7—C9—C10115.53 (17)
C1—O1—C7—C9−78.4 (2)C9—C7—C8—O2−177.4 (3)
C1—O1—C7—C8−173.88 (16)O1—C7—C9—N1−110.79 (16)
C22—O5—C19—C18173.6 (2)O1—C7—C8—O2−60.3 (3)
C22—O5—C19—C20−6.6 (4)C9—C7—C8—N11.51 (15)
C16—N1—C8—O2−2.3 (4)O1—C7—C8—N1118.62 (16)
C8—N1—C16—C21176.3 (2)O1—C7—C9—C106.1 (2)
C8—N1—C16—C17−3.4 (3)C8—C7—C9—N1−1.40 (14)
C9—N1—C16—C17177.12 (19)C7—C9—C10—C11−60.5 (2)
C16—N1—C9—C1062.5 (3)C7—C9—C10—C15118.4 (2)
C8—N1—C9—C71.56 (15)N1—C9—C10—C1139.2 (3)
C9—N1—C8—C7−1.60 (15)N1—C9—C10—C15−141.92 (19)
C16—N1—C8—C7178.8 (2)C9—C10—C11—C12178.2 (2)
C9—N1—C8—O2177.4 (2)C11—C10—C15—C14−0.4 (3)
C9—N1—C16—C21−3.3 (3)C15—C10—C11—C12−0.8 (3)
C16—N1—C9—C7−178.78 (19)C9—C10—C15—C14−179.34 (19)
C8—N1—C9—C10−117.14 (19)C10—C11—C12—C131.4 (4)
O4—N2—C14—C15−1.1 (4)C11—C12—C13—C14−0.7 (4)
O3—N2—C14—C15179.6 (2)C12—C13—C14—C15−0.5 (4)
O4—N2—C14—C13179.6 (3)C12—C13—C14—N2178.8 (2)
O3—N2—C14—C130.3 (4)C13—C14—C15—C101.0 (4)
C6—C1—C2—C3−0.9 (3)N2—C14—C15—C10−178.2 (2)
C2—C1—C6—C51.4 (3)N1—C16—C21—C20−179.0 (2)
O1—C1—C6—C5−178.31 (19)C17—C16—C21—C200.6 (3)
C6—C1—C2—Cl1179.03 (15)N1—C16—C17—C18179.40 (19)
O1—C1—C2—C3178.88 (18)C21—C16—C17—C18−0.2 (3)
O1—C1—C2—Cl1−1.2 (2)C16—C17—C18—C19−0.2 (3)
C1—C2—C3—C4−0.6 (3)C17—C18—C19—C200.3 (3)
Cl1—C2—C3—C4179.51 (17)C17—C18—C19—O5−179.9 (2)
C2—C3—C4—C51.6 (3)O5—C19—C20—C21−179.7 (2)
C2—C3—C4—Cl2−177.69 (17)C18—C19—C20—C210.1 (4)
C3—C4—C5—C6−1.0 (3)C19—C20—C21—C16−0.6 (4)
Cl2—C4—C5—C6178.21 (17)
D—H···AD—HH···AD···AD—H···A
C3—H3···O3xi0.932.603.360 (3)140
C7—H7···O2x0.982.563.287 (3)131
C17—H17···O20.932.553.148 (3)123
C18—H18···O5ix0.932.483.382 (3)165
Ring-2Ring-3Ring-4
Ring-168.34 (13)83.04 (13)3.37 (13)
Ring-247.32 (11)70.49 (10)
Ring-383.00 (11)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C3—H3⋯O3i0.932.603.360 (3)140
C7—H7⋯O2ii0.982.563.287 (3)131
C17—H17⋯O20.932.553.148 (3)123
C18—H18⋯O5iii0.932.483.382 (3)165

Symmetry codes: (i) ; (ii) ; (iii) .

  7 in total

1.  Synthesis of anticancer beta-lactams: mechanism of action.

Authors:  Bimal K Banik; Frederick F Becker; Indrani Banik
Journal:  Bioorg Med Chem       Date:  2004-05-15       Impact factor: 3.641

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  N-Methylthio beta-lactam antibacterials: effects of the C3/C4 ring substituents on anti-MRSA activity.

Authors:  Edward Turos; Cristina Coates; Jeung-Yeop Shim; Yang Wang; J Michelle Leslie; Timothy E Long; G Suresh Kumar Reddy; Alex Ortiz; Marci Culbreath; Sonja Dickey; Daniel V Lim; Eduardo Alonso; Javier Gonzalez
Journal:  Bioorg Med Chem       Date:  2005-09-26       Impact factor: 3.641

4.  Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-Schiff bases of isatin and their derivatives.

Authors:  Aliasghar Jarrahpour; Dariush Khalili; Erik De Clercq; Chanaz Salmi; Jean Michel Brunel
Journal:  Molecules       Date:  2007-08-07       Impact factor: 4.411

Review 5.  Beta-lactams: versatile building blocks for the stereoselective synthesis of non-beta-lactam products.

Authors:  Benito Alcaide; Pedro Almendros; Cristina Aragoncillo
Journal:  Chem Rev       Date:  2007-07-25       Impact factor: 60.622

6.  Synthesis and antimicrobial activity of beta-lactam-bile acid conjugates linked via triazole.

Authors:  Namdev S Vatmurge; Braja G Hazra; Vandana S Pore; Fazal Shirazi; Pradnya S Chavan; Mukund V Deshpande
Journal:  Bioorg Med Chem Lett       Date:  2008-01-31       Impact factor: 2.823

7.  Synthesis of some new mono- and bis-polycyclic aromatic spiro and bis-nonspiro-beta-lactams.

Authors:  Aliasghar Jarrahpour; Edris Ebrahimi
Journal:  Molecules       Date:  2010-01-22       Impact factor: 4.411
  7 in total
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1.  3-(2,4-Di-chloro-phen-oxy)-1-(4-meth-oxy-benz-yl)-4-(4-nitro-phen-yl)azetidin-2-one.

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-07-02
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