E. Sansinenea et al. / Tetrahedron Letters 57 (2016) 2604–2607
2607
J = 7 Hz, H12); 13C NMR (125 MHz, CDCl3) d: 169.9 (C1@O), 164.8 (C7@O), 60.1
P21212, cell parameters a = 11.8825(7), b = 12.0691(7), c = 18.5436(14) Å,
(C9) 58.7 (C6), 45.0 (C3), 28.5 (C5), 28.3 (C10), 22.3 (C4), 19.1 (C11), 16.0 (C12).
Z = 8, Z0 = 2, Dc = 1.300 g cmꢀ1
Atlas, Gemini diffractometer at room temp, with the Cu
.
20,418 reflections collected on
a
Xcalibur,
IR max: 3212, 2969, 1669, 1426, 1293, 791 cmꢀ1; EI-HRMS: calculated for
Ka radiation
t
(C10H16N2O2), 196.1212; found, 196.1192.
(k = 1.54184 Å) in the range 2h = 8.742–134.146°, of which 4754 are unique
(Rint = 0.0426, Rsigma = 0.0319). 354 variables refined: R1 = 0.0399, wR2 = 0.0878
[I > 2r
(I)] and R1 = 0.0626, wR2 = 0.1024 [all data].21 The absolute configura-
19. Crystal data for 2: C10H16N2O2, M = 196.25, colorless plate, colorless prism,
mp = 165.2 °C, 0.444 ꢁ 0.128 ꢁ 0.085 mm3, orthorhombic, space group P212121,
cell parameters a = 5.7929(4), b = 10.6294(11), c = 34.938(3) Å, Z = 8, Z0 = 2,
Dc = 1.212 g cmꢀ1. 11,222 reflections collected on a Xcalibur, Atlas, Gemini
tions of C6 and C9 were assigned by analysis of anomalous dispersion of data
collected. CCDC-1439218 contains the supplementary crystallographic data for
ing The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge
CB2 1EZ, UK. Fax: +44 1223 336033.
diffractometer at rt, with the CuK
2h = 8.696–148.96°, of which 4389 are unique (Rint = 0.0275, Rsigma = 0.0297).
257 variables refined: R1 = 0.0604, wR2 = 0.1681 [I > 2 (I)] and R1 = 0.0906,
a radiation (k = 1.54184 Å) in the range
r
wR2 = 0.1988 [all data].21 The absolute configurations of C6 and C9 were assigned
by analysis of anomalous dispersion of data collected. CCDC-1439226 contains
the supplementary crystallographic data for this Letter. These data can be
data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic
Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK. Fax: +44 1223 336033.
28. 7.5 mg of the compounds were dissolved in 100
Sterile filter paper disks containing 10 L of crude extract (75 mg/mL) were
placed on plates of LB and Muller–Hinton agar seeded with 100 of
lL of distilled sterile water.
l
lL
suspensions of one day old cultures of bacteria tested. The negative control
was a sterile disk impregnated with distilled water and control positive was
the antibiotic ampicillin (150 mg/mL) for Gram negative bacteria and
vancomycin (50 mg/mL) for Gram positive bacteria. The diameters of the
zones of inhibition of growth around the disks were measured after incubation
periods of one day at 29 °C.
22. cyclo-(L-Proline-L H
-Phenylalanine) 3; extraction yield 3.32%, mp 128–131 °C; 1
NMR (500 MHz, CDCl3) d: 7.29 (5H, m, Ph), 5.60 (1H, br s, NH), 4.28 (1H, dd,
J = 10.5, 3.5 Hz, H9), 4.08 (1H, dd, J = 7.5 Hz, H6), 3.64 (1H, m, H10a), 3.62 (1H,
m, H3a), 3.57 (1H, m, H3b), 2.77 (1H, dd, J = 14.5, 10.5 Hz, H10b), 2.34 (1H, m,
H5a), 2.03 (1H, m, H5b), 1.99 (1H, m, H4a), 191 (1H, m, H4b); 13C NMR
(125 MHz, CDCl3) d: 169.3 (C1@O), 165.0 (C7@O), 135.8 (C10), 129.3 (C30, C50),
129.0 (C20,C60), 127.5 (C40), 59.1 (C6), 56.1 (C9), 45.4 (C3), 36.7 (C10), 28.3 (C5),
22.5 (C4). EI-HRMS: calculated for (C14H16N2O2), 244.1212; found, 244.1177.
29. 7.5 mg of the compounds were dissolved in 100 lL of distilled sterile water
(75 mg/mL). Fungal spore suspensions were prepared taking a small mycelial
fragment of 5 day old PDA plate cultures of each test fungal pathogen and
mixing with 6 mL of LB medium. The fraction of inoculated fungus was
disintegrated gently with the help of the handle, stirred vigorously for 30 s in a
45° angle and was left at rest in a rack to get the spores separated from hyphae
and remaining in the supernatant. The spore suspensions were adjusted to give
a concentration of approximately 106–107 spores mLꢀ1. Sterile filter paper
23. cyclo-(
L
-Proline-
L
-Tyrosine) 4; extraction yield 2.9%, [
a
]
25 = ꢀ53 (c 0.7, EtOH);
D
mp = 142–147 °C, 1H NMR (500 MHz, CDCl3) d: 7.07 (2H, d, J = 8.5 Hz, H30, H50),
6.80 (2H, d, H20, H60), 6.36 (1H, br s, OH), 5.79 (1H, br s, NH), 4.21 (1H, dd,
J = 10.5, 3.5 Hz, H9), 4.09 (1H, br t, J = 7.5 Hz, H6), 3.68 (2H, m, H3a, H3b), 3.51
(1H, dd, J = 14.5, 3.5 Hz, H10a), 2.78 (1H, dd, J = 14.5, 10.5 Hz, H10b), 2.34 (1H,
m, H5a), 2.05 (1H, m, H5b), 1.90 (2H, m, H4a, H4b); 13C NMR (125 MHz, CDCl3)
d: 169.7 C1@O), 165.1 (C7@O), 155.5 (C40), 130.2 (C30, C50), 127.1 (C10), 116.1
disks, containing 10
lL of the compounds were placed on plates of PDA agar
seeded with 100 L of spore suspensions of the fungal pathogens to be tested.
l
The negative control was a sterile disk impregnated with distilled water and
positive control was the antifungal agent miconazole (Neomicol Medix, 20 mg/
mL). The diameters of the zones of inhibition of growth around the disks were
measured after incubation periods of three days at 29 °C.
(C20,C60), 59.0 (C9), 56.1 (C6), 45.3 (C3), 35.9 (C10), 28.2 (C5), 22.5 (C4). IR
:
t
max
3292, 1632, 1514, 1433, 1227, 806 cmꢀ1
(C14H16N2O3), 260.1161; found, 260.1160.
;
EI-HRMS: calculated for
24. Crystal data for 4: C14H16N2O3, M = 260.29, colorless plate, colorless prism,
mp = 147.2 °C, 0.752 ꢁ 0.533 ꢁ 0.366 mm3, orthorhombic, space group