Literature DB >> 21580773

4-{3-[Hydr-oxy(phen-yl)meth-yl]-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-4-yl}benzene-sulfonamide.

Mehmet Akkurt, Ismail Celik, Gökçe Cihan, Gültaze Capan, Orhan Büyükgüngör.   

Abstract

In the title compound, C(15)H(14)N(4)O(3)S(2), the hydr-oxy group is disordered over two positions with occupancies of 0.619 (5) and 0.381 (5). The benzene ring attached to the heterocycle makes a dihedral angle of 86.92 (9)° with respect to the best plane through the five-membered ring. The crystal packing is stabilized by inter-molecular O-H⋯O, N-H⋯S, N-H⋯N, C-H⋯O and C-H⋯N hydrogen bonds, and N-H⋯π and C-H⋯π inter-actions.

Entities:  

Year:  2010        PMID： 21580773      PMCID： PMC2983783          DOI： 10.1107/S1600536810011402

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


Related literature

For the pharmacological activity of functionalized 1,2,4-triazoles, see: De La Rosa et al. (2006 ▶); Mavrova et al. (2009 ▶); Shiradkar et al. (2007 ▶). For annular tautomerism in 1,2,4-triazoles in the solid state and in solution, see: Buzykin et al. (2008 ▶); Dolzhenko et al. (2010 ▶). Two tautomeric fothione (C=S)r.m.s. for 3(5)-thioxo-1,2,4-triazoles may exist in the solid state. For the evidence for the thione (C=S) form, see: Karayel et al. (2007 ▶).

Experimental

Crystal data

C15H14N4O3S2 M = 362.44 Orthorhombic, a = 8.2498 (5) Å b = 13.5167 (7) Å c = 14.2522 (7) Å V = 1589.26 (15) Å3 Z = 4 Mo Kα radiation μ = 0.36 mm−1 T = 296 K 0.62 × 0.48 × 0.36 mm

Data collection

Stoe IPDS 2 diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.815, T max = 0.879 8693 measured reflections 3666 independent reflections 3050 reflections with I > 2σ(I) R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.028 wR(F 2) = 0.066 S = 1.01 3666 reflections 245 parameters 4 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.22 e Å−3 Δρmin = −0.22 e Å−3 Absolute structure: Flack (1983 ▶), 1538 Freidel pairs Flack parameter: 0.14 (5) 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/S1600536810011402/bt5224sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011402/bt5224Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H14N4O3S2F(000) = 752
Mr = 362.44Dx = 1.515 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 14591 reflections
a = 8.2498 (5) Åθ = 1.4–28.0°
b = 13.5167 (7) ŵ = 0.36 mm−1
c = 14.2522 (7) ÅT = 296 K
V = 1589.26 (15) Å3Prism, colourless
Z = 40.62 × 0.48 × 0.36 mm
Stoe IPDS 2 diffractometer3666 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3050 reflections with I > 2σ(I)
plane graphiteRint = 0.036
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 2.1°
ω scansh = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −14→16
Tmin = 0.815, Tmax = 0.879l = −16→17
8693 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)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066w = 1/[σ2(Fo2) + (0.0413P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3666 reflectionsΔρmax = 0.22 e Å−3
245 parametersΔρmin = −0.22 e Å−3
4 restraintsAbsolute structure: Flack (1983), 1538 Freidel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.14 (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 esds 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*/UeqOcc. (<1)
S10.17287 (5)0.71648 (3)0.41130 (3)0.0371 (1)
S20.79576 (4)0.40875 (3)0.33694 (3)0.0315 (1)
O1A0.2506 (3)0.4120 (2)0.6848 (2)0.0621 (9)0.620 (4)
O20.92661 (14)0.43807 (13)0.39572 (10)0.0510 (5)
O30.77632 (18)0.30741 (11)0.31372 (14)0.0592 (5)
N1−0.03407 (16)0.55833 (11)0.60444 (10)0.0327 (4)
N2−0.01523 (16)0.63968 (11)0.54897 (10)0.0317 (4)
N30.18483 (14)0.54616 (10)0.51694 (9)0.0270 (3)
N40.81784 (19)0.46661 (14)0.23974 (11)0.0406 (5)
C1−0.03337 (19)0.35747 (13)0.66854 (13)0.0334 (5)
C2−0.0487 (2)0.33998 (14)0.76345 (13)0.0382 (5)
C3−0.1902 (3)0.29833 (14)0.79838 (14)0.0463 (6)
C4−0.3154 (2)0.27399 (15)0.73879 (17)0.0496 (6)
C5−0.2995 (2)0.29076 (16)0.64419 (16)0.0504 (6)
C6−0.1595 (2)0.33125 (15)0.60919 (14)0.0426 (6)
C7A0.1213 (9)0.4010 (5)0.6305 (6)0.0333 (16)0.620 (4)
C80.08859 (17)0.50199 (12)0.58420 (12)0.0295 (4)
C90.11550 (16)0.63506 (12)0.49321 (12)0.0282 (4)
C100.33246 (16)0.50982 (11)0.47478 (11)0.0264 (4)
C110.47832 (19)0.53833 (15)0.51248 (13)0.0369 (5)
C120.62079 (19)0.50687 (15)0.47033 (14)0.0379 (5)
C130.61324 (17)0.44786 (13)0.39193 (12)0.0289 (4)
C140.46561 (18)0.41826 (14)0.35441 (12)0.0353 (5)
C150.32367 (18)0.45127 (13)0.39608 (13)0.0352 (5)
C7B0.1184 (15)0.4081 (11)0.6206 (12)0.055 (5)0.380 (4)
O1B0.2021 (5)0.3451 (3)0.5701 (3)0.0600 (16)0.380 (4)
H2A0.035600.356100.804000.0460*
H3−0.200400.286800.862400.0560*
H2−0.080800.689100.549700.0380*
H4A0.734 (3)0.4531 (19)0.2033 (17)0.0660*
H4B0.848 (3)0.5258 (14)0.251 (2)0.0660*
H4−0.410200.246400.762500.0600*
H6−0.149000.341200.544900.0510*
H7A0.155100.356900.579500.0400*0.620 (4)
H110.481500.578200.565600.0440*
H120.720600.525600.494900.0450*
H140.462000.377000.302200.0420*
H150.223500.434000.371000.0420*
H5−0.383900.274600.603700.0600*
H1A0.261600.362800.717900.0930*0.620 (4)
H1B0.237800.301300.604200.0890*0.380 (4)
H7B0.190400.421500.673800.0660*0.380 (4)
U11U22U33U12U13U23
S10.0329 (2)0.0357 (2)0.0426 (2)−0.0029 (2)0.0009 (2)0.0101 (2)
S20.0211 (2)0.0390 (2)0.0344 (2)0.0051 (2)0.0029 (1)0.0016 (2)
O1A0.0366 (11)0.0597 (16)0.090 (2)−0.0082 (10)−0.0184 (11)0.0367 (15)
O20.0231 (5)0.0929 (12)0.0369 (7)0.0062 (6)−0.0020 (5)0.0003 (7)
O30.0482 (7)0.0366 (7)0.0928 (12)0.0067 (6)0.0273 (8)−0.0050 (8)
N10.0296 (6)0.0344 (8)0.0341 (7)0.0042 (5)0.0055 (5)0.0036 (6)
N20.0286 (6)0.0291 (7)0.0375 (8)0.0053 (5)0.0045 (5)0.0016 (6)
N30.0223 (5)0.0278 (6)0.0310 (7)0.0012 (5)0.0042 (5)−0.0001 (5)
N40.0343 (7)0.0527 (9)0.0349 (8)0.0026 (7)0.0023 (6)0.0022 (7)
C10.0311 (7)0.0298 (8)0.0392 (9)0.0017 (6)0.0023 (7)0.0063 (8)
C20.0401 (9)0.0372 (9)0.0373 (9)0.0029 (7)−0.0039 (7)0.0033 (8)
C30.0568 (11)0.0421 (10)0.0400 (10)0.0060 (9)0.0142 (9)0.0081 (8)
C40.0392 (9)0.0459 (11)0.0637 (13)−0.0063 (8)0.0146 (9)0.0049 (10)
C50.0405 (9)0.0509 (11)0.0598 (13)−0.0063 (9)−0.0057 (9)−0.0014 (10)
C60.0446 (10)0.0467 (11)0.0366 (10)−0.0007 (8)−0.0020 (8)0.0039 (8)
C7A0.036 (3)0.019 (2)0.045 (3)0.0050 (18)0.006 (2)0.015 (2)
C80.0253 (6)0.0313 (8)0.0318 (8)0.0009 (5)0.0035 (6)0.0015 (7)
C90.0245 (6)0.0292 (8)0.0310 (8)−0.0009 (6)−0.0009 (6)−0.0025 (7)
C100.0212 (6)0.0271 (7)0.0308 (7)0.0014 (5)0.0036 (5)0.0016 (6)
C110.0278 (7)0.0468 (10)0.0362 (9)0.0000 (7)−0.0034 (6)−0.0125 (8)
C120.0221 (7)0.0498 (10)0.0417 (10)0.0002 (6)−0.0043 (6)−0.0110 (8)
C130.0221 (6)0.0331 (8)0.0315 (8)0.0020 (5)0.0029 (5)0.0017 (7)
C140.0266 (7)0.0436 (10)0.0358 (9)−0.0003 (7)0.0021 (6)−0.0123 (8)
C150.0215 (6)0.0425 (9)0.0417 (9)−0.0028 (6)0.0005 (6)−0.0104 (8)
C7B0.019 (5)0.084 (11)0.063 (8)0.008 (5)0.008 (4)0.007 (7)
O1B0.069 (3)0.044 (2)0.067 (3)0.0257 (19)0.044 (2)0.0191 (19)
S1—C91.6727 (17)C3—C41.377 (3)
S2—O21.4227 (14)C4—C51.374 (3)
S2—O31.4183 (16)C5—C61.372 (3)
S2—N41.6012 (17)C7A—C81.540 (7)
S2—C131.7779 (15)C7B—C81.393 (15)
O1A—C7A1.326 (8)C10—C111.373 (2)
O1B—C7B1.312 (16)C10—C151.375 (2)
O1A—H1A0.8200C11—C121.387 (2)
O1B—H1B0.8200C12—C131.374 (3)
N1—C81.299 (2)C13—C141.389 (2)
N1—N21.363 (2)C14—C151.387 (2)
N2—C91.341 (2)C2—H2A0.9300
N3—C81.381 (2)C3—H30.9300
N3—C91.373 (2)C4—H40.9300
N3—C101.4442 (18)C5—H50.9300
N2—H20.8600C6—H60.9300
N4—H4A0.88 (2)C7A—H7A0.9800
N4—H4B0.85 (2)C7B—H7B0.9800
C1—C21.379 (3)C11—H110.9300
C1—C7A1.506 (8)C12—H120.9300
C1—C61.387 (2)C14—H140.9300
C1—C7B1.582 (14)C15—H150.9300
C2—C31.388 (3)
S1···N2i3.2744 (15)C8···O2xii3.122 (2)
S1···O3ii3.460 (2)C9···O2xii3.384 (2)
S1···H2Aiii3.0100C10···O1A3.341 (3)
S1···H1Aiii3.0100C10···O1B2.821 (4)
S1···H2i2.4600C12···C6v3.583 (3)
S1···H4iv3.0700C13···C2iii3.444 (3)
S2···H6v3.1300C14···C6vi3.565 (3)
S2···H1Bvi3.0000C14···C5vi3.573 (3)
O1A···N33.051 (3)C14···C2iii3.582 (3)
O1A···C103.341 (3)C15···O1B3.036 (5)
O1A···O3vii2.973 (3)C15···C5vi3.473 (3)
O1B···O3vii2.714 (4)C15···O2xii3.2805 (19)
O1B···C153.036 (5)C1···H4Ax3.09 (3)
O1B···N32.825 (4)C2···H1A2.6600
O1B···C102.821 (4)C2···H4Bx3.07 (2)
O2···N3v3.1076 (19)C2···H14vii3.0800
O2···C15v3.2805 (19)C3···H14vii3.0400
O2···C8v3.122 (2)C3···H4Bx2.79 (2)
O2···C9v3.384 (2)C4···H4Bx2.725 (19)
O3···C7Avi3.194 (7)C5···H15vii3.0500
O3···C1vi3.400 (2)C5···H4Bx2.94 (2)
O3···C7Bvi3.326 (15)C8···H62.9800
O3···O1Bvi2.714 (4)C9···H3xiii2.9900
O3···S1viii3.460 (2)C10···H7A2.9400
O3···O1Avi2.973 (3)H1A···S1x3.0100
O1A···H2A2.5700H1A···C22.6600
O1B···H62.9200H1A···H2A2.2300
O2···H122.5100H1A···O3vii2.3500
O2···H15v2.4800H1B···O3vii1.9000
O2···H6v2.5700H1B···S2vii3.0000
O3···H7Avi2.8700H2···S1xi2.4600
O3···H142.7600H2A···O1A2.5700
O3···H1Bvi1.9000H2A···S1x3.0100
O3···H1Avi2.3500H2A···H1A2.2300
O3···H4ix2.9000H2A···H7B2.4200
N1···N32.2008 (18)H3···C9xiv2.9900
N1···C63.240 (2)H4···O3xv2.9000
N1···N4x3.052 (2)H4···S1xvi3.0700
N2···N32.1285 (19)H4A···C1iii3.09 (3)
N2···S1xi3.2744 (15)H4A···N1iii2.18 (2)
N3···O1B2.825 (4)H4B···C2iii3.07 (2)
N3···N22.1285 (19)H4B···C3iii2.79 (2)
N3···O1A3.051 (3)H4B···C5iii2.94 (2)
N3···O2xii3.1076 (19)H4B···C4iii2.725 (19)
N4···C2iii3.447 (3)H6···S2xii3.1300
N4···N1iii3.052 (2)H6···O2xii2.5700
N4···C3iii3.450 (3)H6···C82.9800
N1···H12xii2.5900H6···H7A2.5700
N1···H4Ax2.18 (2)H6···O1B2.9200
N2···H12xii2.7800H7A···C102.9400
C1···O3vii3.400 (2)H7A···H62.5700
C2···C13x3.444 (3)H7A···O3vii2.8700
C2···N4x3.447 (3)H7B···H2A2.4200
C2···C14x3.582 (3)H12···N2v2.7800
C3···N4x3.450 (3)H12···N1v2.5900
C5···C15vii3.473 (3)H12···O22.5100
C5···C14vii3.573 (3)H14···C2vi3.0800
C6···C12xii3.583 (3)H14···O32.7600
C6···C14vii3.565 (3)H14···C3vi3.0400
C6···N13.240 (2)H15···C5vi3.0500
C7A···O3vii3.194 (7)H15···O2xii2.4800
C7B···O3vii3.326 (15)
O2—S2—O3119.49 (10)N3—C8—C7A125.5 (3)
O2—S2—N4106.68 (9)S1—C9—N2127.62 (12)
O2—S2—C13107.47 (8)S1—C9—N3129.04 (11)
O3—S2—N4106.42 (11)N2—C9—N3103.28 (14)
O3—S2—C13107.11 (9)N3—C10—C11118.74 (14)
N4—S2—C13109.42 (8)C11—C10—C15121.81 (14)
C7A—O1A—H1A109.00N3—C10—C15119.39 (12)
C7B—O1B—H1B109.00C10—C11—C12119.16 (17)
N2—N1—C8104.79 (13)C11—C12—C13119.46 (15)
N1—N2—C9113.44 (14)S2—C13—C12119.51 (11)
C9—N3—C10123.12 (13)S2—C13—C14119.16 (13)
C8—N3—C9108.06 (12)C12—C13—C14121.33 (14)
C8—N3—C10128.82 (13)C13—C14—C15118.87 (16)
N1—N2—H2123.00C10—C15—C14119.35 (14)
C9—N2—H2123.00C3—C2—H2A120.00
H4A—N4—H4B122 (2)C1—C2—H2A120.00
S2—N4—H4A108.6 (16)C2—C3—H3120.00
S2—N4—H4B109.2 (19)C4—C3—H3120.00
C2—C1—C7B124.8 (6)C3—C4—H4120.00
C2—C1—C7A119.9 (3)C5—C4—H4120.00
C6—C1—C7A121.1 (4)C6—C5—H5120.00
C6—C1—C7B116.2 (6)C4—C5—H5120.00
C2—C1—C6119.05 (16)C5—C6—H6120.00
C1—C2—C3119.89 (17)C1—C6—H6120.00
C2—C3—C4120.42 (19)O1A—C7A—H7A106.00
C3—C4—C5119.63 (17)C8—C7A—H7A106.00
C4—C5—C6120.21 (18)C1—C7A—H7A106.00
C1—C6—C5120.78 (19)C8—C7B—H7B103.00
O1A—C7A—C8107.0 (5)C1—C7B—H7B103.00
O1A—C7A—C1121.0 (6)O1B—C7B—H7B103.00
C1—C7A—C8110.6 (5)C10—C11—H11120.00
O1B—C7B—C8118.7 (12)C12—C11—H11120.00
C1—C7B—C8114.5 (8)C11—C12—H12120.00
O1B—C7B—C1111.9 (10)C13—C12—H12120.00
N1—C8—N3110.41 (14)C15—C14—H14121.00
N1—C8—C7A124.1 (3)C13—C14—H14121.00
N3—C8—C7B123.4 (6)C10—C15—H15120.00
N1—C8—C7B126.1 (6)C14—C15—H15120.00
O2—S2—C13—C127.66 (18)C2—C1—C6—C51.6 (3)
O2—S2—C13—C14−172.54 (15)C7A—C1—C6—C5179.4 (3)
O3—S2—C13—C12137.22 (16)C2—C1—C7A—O1A8.1 (7)
O3—S2—C13—C14−42.98 (18)C2—C1—C7A—C8−118.0 (4)
N4—S2—C13—C12−107.81 (16)C6—C1—C7A—O1A−169.6 (4)
N4—S2—C13—C1471.99 (16)C6—C1—C7A—C864.3 (6)
C8—N1—N2—C90.93 (18)C1—C2—C3—C40.2 (3)
N2—N1—C8—N30.02 (18)C2—C3—C4—C50.3 (3)
N2—N1—C8—C7A179.2 (4)C3—C4—C5—C60.2 (3)
N1—N2—C9—S1175.96 (12)C4—C5—C6—C1−1.2 (3)
N1—N2—C9—N3−1.44 (18)O1A—C7A—C8—N1−109.8 (5)
C9—N3—C8—N1−0.90 (18)O1A—C7A—C8—N369.3 (6)
C9—N3—C8—C7A179.9 (4)C1—C7A—C8—N123.9 (7)
C10—N3—C8—N1179.74 (14)C1—C7A—C8—N3−157.0 (3)
C10—N3—C8—C7A0.6 (4)N3—C10—C11—C12−177.57 (16)
C8—N3—C9—S1−175.99 (13)C15—C10—C11—C12−0.3 (3)
C8—N3—C9—N21.37 (17)N3—C10—C15—C14178.55 (15)
C10—N3—C9—S13.4 (2)C11—C10—C15—C141.3 (3)
C10—N3—C9—N2−179.23 (13)C10—C11—C12—C13−0.1 (3)
C8—N3—C10—C11−94.4 (2)C11—C12—C13—S2179.21 (15)
C8—N3—C10—C1588.3 (2)C11—C12—C13—C14−0.6 (3)
C9—N3—C10—C1186.3 (2)S2—C13—C14—C15−178.22 (14)
C9—N3—C10—C15−90.99 (19)C12—C13—C14—C151.6 (3)
C6—C1—C2—C3−1.2 (3)C13—C14—C15—C10−1.9 (3)
C7A—C1—C2—C3−178.9 (3)
Cg2 and Cg3 are centroids of the C1–C6 and C10–C15 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O3vii0.822.352.973 (3)134
N2—H2···S1xi0.862.463.2744 (15)158
N4—H4A···N1iii0.88 (2)2.18 (2)3.052 (2)171 (2)
C2—H2A···O1A0.932.572.881 (3)100
C6—H6···O2xii0.932.573.442 (2)155
C12—H12···O20.932.512.892 (2)105
C12—H12···N1v0.932.593.499 (2)165
C15—H15···O2xii0.932.483.2805 (19)145
C2—H2A···Cg3x0.932.903.502 (2)124
N4—H4B···Cg2iii0.85 (2)2.67 (2)3.218 (2)123 (2)
C14—H14···Cg2vi0.932.833.463 (2)126
Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1A—H1A⋯O3i0.822.352.973 (3)134
N2—H2⋯S1ii0.862.463.2744 (15)158
N4—H4A⋯N1iii0.88 (2)2.18 (2)3.052 (2)171 (2)
C6—H6⋯O2iv0.932.573.442 (2)155
C12—H12⋯N1v0.932.593.499 (2)165
C15—H15⋯O2iv0.932.483.2805 (19)145
C2—H2A⋯Cg3vi0.932.903.502 (2)124
N4—H4B⋯Cg2iii0.85 (2)2.67 (2)3.218 (2)123 (2)
C14—H14⋯Cg2vii0.932.833.463 (2)126

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

  5 in total

1.  A short history of SHELX.

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

2.  N-Carbethoxy-N'-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea.

Authors:  Anton V Dolzhenko; Geok Kheng Tan; Lip Lin Koh; Anna V Dolzhenko; Wai Keung Chui
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-02-06

3.  Tri-substituted triazoles as potent non-nucleoside inhibitors of the HIV-1 reverse transcriptase.

Authors:  Martha De La Rosa; Hong Woo Kim; Esmir Gunic; Cheryl Jenket; Uyen Boyle; Yung-Hyo Koh; Ilia Korboukh; Matthew Allan; Weijian Zhang; Huanming Chen; Wen Xu; Shahul Nilar; Nanhua Yao; Robert Hamatake; Stanley A Lang; Zhi Hong; Zhijun Zhang; Jean-Luc Girardet
Journal:  Bioorg Med Chem Lett       Date:  2006-06-27       Impact factor: 2.823

4.  Synthesis, cytotoxicity and effects of some 1,2,4-triazole and 1,3,4-thiadiazole derivatives on immunocompetent cells.

Authors:  Anelia Ts Mavrova; Diana Wesselinova; Yordan A Tsenov; Pavletta Denkova
Journal:  Eur J Med Chem       Date:  2008-03-25       Impact factor: 6.514

5.  Synthesis of new S-derivatives of clubbed triazolyl thiazole as anti-Mycobacterium tuberculosis agents.

Authors:  Mahendra Ramesh Shiradkar; Kiran Kumar Murahari; Hanimi Reddy Gangadasu; Tatikonda Suresh; Chakravarthy Akula Kalyan; Dolly Panchal; Ranjit Kaur; Prashant Burange; Jyoti Ghogare; Vinod Mokale; Mayuresh Raut
Journal:  Bioorg Med Chem       Date:  2007-04-06       Impact factor: 3.641
  5 in total
  1 in total

1.  N-(5-Chloro-2-meth-oxy-phen-yl)benzene-sulfonamide.

Authors:  Mehmet Akkurt; Muhammad Athar Abbasi; Islam Ullah Khan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-10-20
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.