organic compounds
(E)-4-Methoxy-N′-(4-methylbenzylidene)benzohydrazide
aDepartment of Chemistry, Saranathan College of Engineering, Tiruchirappalli, Tamilnadu, India, bPG and Research Department of Chemistry, Periyar EVR College, Tiruchirappalli, Tamilnadu, India, and cDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai-603 203 Tamil Nadu, India
*Correspondence e-mail: swaroopapranav@gmail.com, phdguna@gmail.com
In the title compound, C16H16N2O2, the dihedral angle between the methoxyphenyl ring and the methylbenzylidene ring is 60.43 (5)°. In the crystal, molecules are linked via N—H⋯O hydrogen bonds, reinforced by C—H⋯O hydrogen bonds, forming chains propagating along the c-axis direction. Inversion-related chains are linked via C—H⋯π interactions, forming ribbons propagating along the c-axis direction.
Keywords: crystal structure; hydrazide; benzohydrazide; N—H⋯O hydrogen bonding..
CCDC reference: 1465282
Structure description
et al., 2016), medicine (Velezheva et al., 2016) and catalysis (Selvamurugan et al., 2016). Hydrazone derivatives exhibit antimicrobial (Pieczonka et al., 2013), anti-proliferation (Yadagiri et al., 2014) and antiplatelet (Mashayekhi et al., 2013) activities.
have attracted interest due to their versatile applications in various fields, such as biology (IbrahimThe geometric parameters of the title molecule (Fig. 1) agree well with those reported for similar structures (Maheswari et al., 2016; Nair et al., 2012). The dihedral angle between the methoxyphenyl ring and the methylbenzylidene ring is 60.43 (5)°.
The crystal packing is controlled by N—H⋯O and C—H⋯O hydrogen bonds (Fig. 2 and Table 1), which result in the formation of chains along [001]. Inversion-related chains are linked via C—H⋯π interactions, forming ribbons propagating along [001].
Synthesis and crystallization
A few drops of conc. HCl were added to a mixture of 4-methoxybenzohydrazide (1.7 g, 0.01 mol) and p-methyl benzaldehyde (1.2 ml, 0.01 mol) in ethanol (15 ml). The reaction mixture was refluxed for 3 h. The precipitate that formed was filtered and washed with petroleum ether and dried in a vacuum desiccator. The crude solid was recrystallized from DMSO giving colourless block-like crystals (yield 96%).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1465282
10.1107/S2414314616004314/su4020sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616004314/su4020Isup2.hkl
A few drops of conc. HCl were added to a mixture of 4-methoxybenzohydrazide (1.7 g, 0.01 mol) and p-methyl benzaldehyde (1.2 ml, 0.01 mol) in ethanol (xx ml) how much??. The reaction mixture was refluxed for 3 h. The precipitate that formed was filtered and washed with petroleum ether and dried in a vacuum desiccator. The crude solid was recrystallized from DMSO giving colourless block-like crystals (yield 96%).
Hydrazones have attracted interest due to their versatile applications in various fields, such as biology (Ibrahim et al., 2016), medicine (Velezheva et al., 2016) and catalysis (Selvamurugan et al., 2016). Hydrazone derivatives exhibit antimicrobial (Pieczonka et al., 2013), anti-proliferation (Yadagiri et al., 2014) and antiplatelet (Mashayekhi et al., 2013) activities.
The geometric parameters of the title molecule (Fig. 1) agree well with those reported for similar structures (Maheswari et al., 2016; Nair et al., 2012). The dihedral angle between the methoxyphenyl ring and the methylbenzylidene ring is 60.43 (5)°.
The crystal packing is controlled by N—H···O and C—H···O hydrogen bonds (Fig. 2 and Table 1), which result in the formation of chains along [001]. Inversion-related chains are linked via C—H···π interactions, forming ribbons propagating along [001].
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines (see Table 1). |
C16H16N2O2 | F(000) = 568 |
Mr = 268.31 | Dx = 1.271 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.7678 (7) Å | Cell parameters from 3517 reflections |
b = 13.0072 (7) Å | θ = 1.9–28.4° |
c = 9.9025 (6) Å | µ = 0.09 mm−1 |
β = 112.371 (2)° | T = 296 K |
V = 1401.66 (14) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.13 × 0.11 mm |
Bruker Kappa APEXII CCD diffractometer | 3517 independent reflections |
Radiation source: fine-focus sealed tube | 2752 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 0 pixels mm-1 | θmax = 28.4°, θmin = 1.9° |
ω and φ scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −17→17 |
Tmin = 0.987, Tmax = 0.991 | l = −13→12 |
13430 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0794P)2 + 0.199P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
3517 reflections | Δρmax = 0.21 e Å−3 |
184 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00 |
C16H16N2O2 | V = 1401.66 (14) Å3 |
Mr = 268.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.7678 (7) Å | µ = 0.09 mm−1 |
b = 13.0072 (7) Å | T = 296 K |
c = 9.9025 (6) Å | 0.15 × 0.13 × 0.11 mm |
β = 112.371 (2)° |
Bruker Kappa APEXII CCD diffractometer | 3517 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2752 reflections with I > 2σ(I) |
Tmin = 0.987, Tmax = 0.991 | Rint = 0.025 |
13430 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.21 e Å−3 |
3517 reflections | Δρmin = −0.18 e Å−3 |
184 parameters |
x | y | z | Uiso*/Ueq | ||
C16 | 0.5536 (2) | 0.86088 (13) | 0.1367 (3) | 0.0842 (6) | |
H16A | 0.6252 | 0.9031 | 0.1805 | 0.126* | |
H16B | 0.5046 | 0.8633 | 0.1952 | 0.126* | |
H16C | 0.5062 | 0.8858 | 0.0404 | 0.126* | |
O2 | 0.76856 (10) | 0.20548 (7) | 0.35951 (9) | 0.0538 (3) | |
N2 | 0.70263 (10) | 0.37061 (7) | 0.17516 (11) | 0.0427 (3) | |
C8 | 0.77468 (11) | 0.19967 (8) | 0.23869 (12) | 0.0385 (3) | |
C5 | 0.82056 (11) | 0.10506 (8) | 0.19119 (11) | 0.0376 (3) | |
N1 | 0.74327 (10) | 0.27769 (7) | 0.14161 (10) | 0.0431 (3) | |
H1 | 0.7485 | 0.2697 | 0.0580 | 0.052* | |
C6 | 0.79284 (11) | 0.07902 (9) | 0.04612 (12) | 0.0401 (3) | |
H6 | 0.7425 | 0.1221 | −0.0273 | 0.048* | |
O1 | 0.96488 (10) | −0.16261 (7) | 0.09212 (12) | 0.0629 (3) | |
C7 | 0.83872 (12) | −0.00995 (9) | 0.00857 (13) | 0.0440 (3) | |
H7 | 0.8183 | −0.0267 | −0.0892 | 0.053* | |
C2 | 0.91488 (12) | −0.07376 (9) | 0.11683 (14) | 0.0451 (3) | |
C4 | 0.89715 (14) | 0.03958 (10) | 0.29838 (13) | 0.0517 (3) | |
H4 | 0.9164 | 0.0553 | 0.3962 | 0.062* | |
C9 | 0.70520 (12) | 0.44398 (9) | 0.09164 (13) | 0.0446 (3) | |
H9 | 0.7339 | 0.4308 | 0.0179 | 0.054* | |
C10 | 0.66494 (11) | 0.54833 (9) | 0.10661 (12) | 0.0423 (3) | |
C3 | 0.94501 (15) | −0.04806 (10) | 0.26235 (14) | 0.0559 (4) | |
H3 | 0.9975 | −0.0900 | 0.3356 | 0.067* | |
C13 | 0.59258 (13) | 0.75127 (10) | 0.12739 (16) | 0.0541 (3) | |
C11 | 0.58724 (12) | 0.57071 (10) | 0.17829 (15) | 0.0482 (3) | |
H11 | 0.5589 | 0.5179 | 0.2207 | 0.058* | |
C12 | 0.55146 (13) | 0.67065 (11) | 0.18738 (18) | 0.0561 (4) | |
H12 | 0.4985 | 0.6840 | 0.2350 | 0.067* | |
C1 | 0.93554 (16) | −0.19275 (12) | −0.0552 (2) | 0.0667 (4) | |
H1A | 0.8487 | −0.2048 | −0.1015 | 0.100* | |
H1B | 0.9792 | −0.2547 | −0.0576 | 0.100* | |
H1C | 0.9589 | −0.1392 | −0.1062 | 0.100* | |
C15 | 0.70586 (16) | 0.62896 (11) | 0.04561 (18) | 0.0595 (4) | |
H15 | 0.7576 | 0.6156 | −0.0036 | 0.071* | |
C14 | 0.67073 (16) | 0.72906 (11) | 0.05695 (19) | 0.0636 (4) | |
H14 | 0.7002 | 0.7822 | 0.0165 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C16 | 0.0873 (12) | 0.0478 (9) | 0.1117 (16) | 0.0202 (8) | 0.0314 (11) | −0.0069 (9) |
O2 | 0.0900 (7) | 0.0450 (5) | 0.0398 (5) | −0.0012 (4) | 0.0399 (5) | −0.0007 (4) |
N2 | 0.0585 (6) | 0.0357 (5) | 0.0368 (5) | 0.0042 (4) | 0.0215 (4) | −0.0034 (4) |
C8 | 0.0520 (6) | 0.0355 (6) | 0.0326 (5) | −0.0045 (5) | 0.0213 (5) | −0.0017 (4) |
C5 | 0.0510 (6) | 0.0325 (5) | 0.0322 (5) | −0.0032 (4) | 0.0192 (5) | 0.0006 (4) |
N1 | 0.0666 (6) | 0.0358 (5) | 0.0329 (5) | 0.0059 (4) | 0.0258 (4) | −0.0008 (4) |
C6 | 0.0505 (6) | 0.0366 (6) | 0.0323 (5) | 0.0033 (5) | 0.0145 (5) | 0.0014 (4) |
O1 | 0.0764 (7) | 0.0416 (5) | 0.0668 (7) | 0.0149 (5) | 0.0228 (5) | −0.0052 (4) |
C7 | 0.0552 (7) | 0.0401 (6) | 0.0354 (6) | 0.0009 (5) | 0.0159 (5) | −0.0056 (4) |
C2 | 0.0537 (7) | 0.0322 (6) | 0.0495 (7) | 0.0008 (5) | 0.0197 (5) | −0.0010 (5) |
C4 | 0.0775 (9) | 0.0442 (7) | 0.0309 (6) | 0.0032 (6) | 0.0176 (6) | 0.0032 (5) |
C9 | 0.0617 (7) | 0.0391 (6) | 0.0381 (6) | 0.0040 (5) | 0.0245 (5) | −0.0016 (5) |
C10 | 0.0526 (7) | 0.0369 (6) | 0.0370 (6) | 0.0030 (5) | 0.0165 (5) | −0.0019 (4) |
C3 | 0.0772 (9) | 0.0417 (7) | 0.0410 (7) | 0.0117 (6) | 0.0137 (6) | 0.0095 (5) |
C13 | 0.0533 (7) | 0.0416 (7) | 0.0604 (8) | 0.0082 (5) | 0.0137 (6) | −0.0043 (6) |
C11 | 0.0495 (7) | 0.0439 (7) | 0.0546 (7) | −0.0022 (5) | 0.0235 (6) | −0.0017 (5) |
C12 | 0.0500 (7) | 0.0554 (8) | 0.0678 (9) | 0.0057 (6) | 0.0278 (7) | −0.0081 (6) |
C1 | 0.0732 (10) | 0.0504 (8) | 0.0802 (11) | 0.0034 (7) | 0.0333 (8) | −0.0223 (7) |
C15 | 0.0824 (10) | 0.0452 (7) | 0.0675 (9) | 0.0082 (7) | 0.0470 (8) | 0.0068 (6) |
C14 | 0.0824 (10) | 0.0398 (7) | 0.0774 (10) | 0.0039 (7) | 0.0401 (9) | 0.0076 (7) |
C16—C13 | 1.5113 (19) | C4—C3 | 1.3772 (19) |
C16—H16A | 0.9600 | C4—H4 | 0.9300 |
C16—H16B | 0.9600 | C9—C10 | 1.4636 (16) |
C16—H16C | 0.9600 | C9—H9 | 0.9300 |
O2—C8 | 1.2279 (14) | C10—C15 | 1.3849 (18) |
N2—C9 | 1.2707 (15) | C10—C11 | 1.3851 (18) |
N2—N1 | 1.3860 (13) | C3—H3 | 0.9300 |
C8—N1 | 1.3491 (14) | C13—C14 | 1.380 (2) |
C8—C5 | 1.4901 (15) | C13—C12 | 1.380 (2) |
C5—C6 | 1.3886 (15) | C11—C12 | 1.3799 (18) |
C5—C4 | 1.3914 (17) | C11—H11 | 0.9300 |
N1—H1 | 0.8600 | C12—H12 | 0.9300 |
C6—C7 | 1.3864 (16) | C1—H1A | 0.9600 |
C6—H6 | 0.9300 | C1—H1B | 0.9600 |
O1—C2 | 1.3606 (15) | C1—H1C | 0.9600 |
O1—C1 | 1.421 (2) | C15—C14 | 1.384 (2) |
C7—C2 | 1.3820 (17) | C15—H15 | 0.9300 |
C7—H7 | 0.9300 | C14—H14 | 0.9300 |
C2—C3 | 1.3875 (19) | ||
C13—C16—H16A | 109.5 | N2—C9—H9 | 118.6 |
C13—C16—H16B | 109.5 | C10—C9—H9 | 118.6 |
H16A—C16—H16B | 109.5 | C15—C10—C11 | 118.12 (12) |
C13—C16—H16C | 109.5 | C15—C10—C9 | 118.58 (12) |
H16A—C16—H16C | 109.5 | C11—C10—C9 | 123.30 (11) |
H16B—C16—H16C | 109.5 | C4—C3—C2 | 120.03 (12) |
C9—N2—N1 | 113.77 (10) | C4—C3—H3 | 120.0 |
O2—C8—N1 | 123.11 (11) | C2—C3—H3 | 120.0 |
O2—C8—C5 | 121.40 (10) | C14—C13—C12 | 117.95 (12) |
N1—C8—C5 | 115.48 (9) | C14—C13—C16 | 120.30 (15) |
C6—C5—C4 | 117.96 (11) | C12—C13—C16 | 121.75 (15) |
C6—C5—C8 | 123.87 (10) | C12—C11—C10 | 120.58 (13) |
C4—C5—C8 | 118.17 (10) | C12—C11—H11 | 119.7 |
C8—N1—N2 | 120.74 (9) | C10—C11—H11 | 119.7 |
C8—N1—H1 | 119.6 | C11—C12—C13 | 121.47 (13) |
N2—N1—H1 | 119.6 | C11—C12—H12 | 119.3 |
C7—C6—C5 | 121.26 (10) | C13—C12—H12 | 119.3 |
C7—C6—H6 | 119.4 | O1—C1—H1A | 109.5 |
C5—C6—H6 | 119.4 | O1—C1—H1B | 109.5 |
C2—O1—C1 | 117.80 (11) | H1A—C1—H1B | 109.5 |
C2—C7—C6 | 119.81 (11) | O1—C1—H1C | 109.5 |
C2—C7—H7 | 120.1 | H1A—C1—H1C | 109.5 |
C6—C7—H7 | 120.1 | H1B—C1—H1C | 109.5 |
O1—C2—C7 | 124.60 (12) | C14—C15—C10 | 120.86 (14) |
O1—C2—C3 | 115.75 (11) | C14—C15—H15 | 119.6 |
C7—C2—C3 | 119.66 (11) | C10—C15—H15 | 119.6 |
C3—C4—C5 | 121.27 (11) | C13—C14—C15 | 121.01 (14) |
C3—C4—H4 | 119.4 | C13—C14—H14 | 119.5 |
C5—C4—H4 | 119.4 | C15—C14—H14 | 119.5 |
N2—C9—C10 | 122.80 (11) | ||
O2—C8—C5—C6 | 157.52 (12) | N1—N2—C9—C10 | 179.27 (11) |
N1—C8—C5—C6 | −23.71 (17) | N2—C9—C10—C15 | 159.59 (14) |
O2—C8—C5—C4 | −23.46 (17) | N2—C9—C10—C11 | −20.7 (2) |
N1—C8—C5—C4 | 155.32 (12) | C5—C4—C3—C2 | −1.5 (2) |
O2—C8—N1—N2 | 0.57 (19) | O1—C2—C3—C4 | −178.89 (13) |
C5—C8—N1—N2 | −178.18 (10) | C7—C2—C3—C4 | 1.3 (2) |
C9—N2—N1—C8 | 163.64 (12) | C15—C10—C11—C12 | 0.4 (2) |
C4—C5—C6—C7 | 0.69 (18) | C9—C10—C11—C12 | −179.28 (12) |
C8—C5—C6—C7 | 179.72 (11) | C10—C11—C12—C13 | −0.8 (2) |
C5—C6—C7—C2 | −0.86 (19) | C14—C13—C12—C11 | 0.3 (2) |
C1—O1—C2—C7 | −0.9 (2) | C16—C13—C12—C11 | 179.89 (15) |
C1—O1—C2—C3 | 179.30 (14) | C11—C10—C15—C14 | 0.5 (2) |
C6—C7—C2—O1 | −179.95 (12) | C9—C10—C15—C14 | −179.86 (14) |
C6—C7—C2—C3 | −0.1 (2) | C12—C13—C14—C15 | 0.6 (2) |
C6—C5—C4—C3 | 0.5 (2) | C16—C13—C14—C15 | −179.04 (16) |
C8—C5—C4—C3 | −178.61 (13) | C10—C15—C14—C13 | −1.0 (3) |
Cg1 is the centroid of the C2–C7 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.09 | 2.9280 (12) | 164 |
C6—H6···O2i | 0.93 | 2.58 | 3.3093 (14) | 136 |
C9—H9···O2i | 0.93 | 2.50 | 3.3051 (15) | 145 |
C1—H1C···Cg1ii | 0.96 | 2.77 | 3.6515 (5) | 152 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+1. |
Cg1 is the centroid of the C2–C7 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.09 | 2.9280 (12) | 164 |
C6—H6···O2i | 0.93 | 2.58 | 3.3093 (14) | 136 |
C9—H9···O2i | 0.93 | 2.50 | 3.3051 (15) | 145 |
C1—H1C···Cg1ii | 0.96 | 2.77 | 3.6515 (5) | 152 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H16N2O2 |
Mr | 268.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 11.7678 (7), 13.0072 (7), 9.9025 (6) |
β (°) | 112.371 (2) |
V (Å3) | 1401.66 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.15 × 0.13 × 0.11 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.987, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13430, 3517, 2752 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.136, 1.00 |
No. of reflections | 3517 |
No. of parameters | 184 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.18 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Acknowledgements
The authors are grateful to the authorities of Saranathan College of Engineering, Tiruchirappalli, for providing laboratory facilities, and the CAS in Crystallography and Biophysics, University of Madras, Chennai, for the data collection.
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