338
SRINIVAS, KRUPADANAM
3.8 Hz, 1H, H5ʹa), 4.98–5.07 m (3H, H5,2ʹ), 6.63 d.d (J =
6.8, 1.7 Hz, 1H, H7ʹ), 6.85 q (J = 8.1 Hz, 2H, H5ʹ,6ʹ),
7.22 d (J = 7.9 Hz, 1H, H3″,5″), 7.37 s (1H, H4ʹ), 7.58 d
form of UGC-SRF and Head of Department of
Chemistry, Osmania University, Hyderabad, India for
providing laboratory facilities and CFRD, O.U,
Hyderabad, India for providing spectral data.
13
(J = 8.0 Hz, 2H, H2″,6″). C NMR spectrum, δ, ppm:
21.46 (C4″a), 37.38 (C4), 56.10 (C9ʹ), 64.58 (C2ʹ), 65.61
(C5ʹa), 77.94 (C5), 114.71 (C7), 121.04 (C8ʹa), 121.41
(C5ʹ), 121.47 (C6ʹ), 121.74 (C2″,6″), 126.28 (C1″), 126.68
(C3″,5″), 129.54 (C3ʹ), 134.51 (C4ʹ), 140.63 (C4″), 144.13
(C8ʹa), 147.90 (C8ʹ), 156.18 (C3), 164.18 (C3ʹa). ESI-
MS: m/z 380.1 [M + H]+, 381.1 [M + H + 1]+.
REFERENCES
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4. Lago, J.H.G., Ramos, C.S., Casanova, D.C.C., Moran-
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doi 10.1021/np030530j
[3-(4-Chlorophenyl)-4,5-dihydroisoxazol-5-yl]-
methyl-8-methoxy-2H-chromene-3-carboxylate (8o).
White solid, yield 75%, mp 130–134°C. IR spectrum,
ν, cm–1: 1712–1740 (C=O), 1579–1595 (C=N). 1H NMR
spectrum, δ, ppm: 3.19 d.d (J = 16.7, 6.7 Hz, 1H, H4),
3.49 d.d (J = 16. 7, 10.9 Hz, 1H, H4), 3.87 s (3H, H9ʹ),
4.34 d.d (J = 11.9, 5.2 Hz, 1H, H5ʹa), 4.43 d.d (J = 11.9,
3.8 Hz, 1H, H5ʹa), 5.01 s (1H, H2ʹ), 5.07 m (1H, H5),
6.65 d.d (J = 6.4, 2.3 Hz, 1H, H7ʹ), 6.88 t (J = 6.4 Hz,
1H, H6ʹ, 5ʹ), 7.36–7.43 m (3H, H4ʹ,3″,5″), 7.62 d (J =
13
8.5 Hz, 2H, H2″,6″). C NMR spectrum, δ, ppm: 37.09
(C4), 56.10 (C9ʹ), 64.55 (C2ʹ), 65.41 (C5ʹa), 78.43 (C5),
114.76 (C7ʹ), 120.99 (C4ʹa), 121.35 (C5ʹ), 121.56 (C6ʹ),
121.65 (C2″,6″), 127.62 (C1″), 127.95 (C3″,5″), 129.13
(C3ʹ), 134.60 (C4ʹ), 136.34 (C4″), 144.12 (C8ʹa), 147.92
(C8), 155.31 (C3), 164.12 (C3ʹa). ESI-MS: m/z 400.0
[M + H]+, 402.0 [M + H + 2]+. 3 : 1 ratio.
[3-(4-Benzyloxyphenyl)-4,5-dihydroisoxazol-5-
yl]methyl-8-methoxy-2H-chromene-3-carboxylate
(8p). White solid, yield 70%, mp 126–128°C. IR
spectrum, ν, cm–1: 1740 (C=O), 1694 (C=N). 1H NMR
spectrum, δ, ppm: 3.18 d.d (J = 16.6, 6.6 Hz, 1H, H4),
3.48 d.d (J = 16.6, 10.8 Hz, 1H, H4), 3.87 s (3H, H9ʹ),
4.32 d.d (J = 11.8, 5.4 Hz, 1H, H5ʹa), 4.40 d.t (J = 16.7,
8.3 Hz, 1H, H5ʹa), 4.96–5.07 m (3H, H5,2ʹ), 5.10 s (2H,
H1‴a), 6.66 d.d (J = 6.9, 1.9 Hz, 1H, H7ʹ), 6.82–6.90 m
(2H, H5ʹ,6ʹ), 7.00 d (J = 8.8 Hz, 2H, H3″,5″), 7.32–7.45 m
5. Bernard, C.B., Krishnamurty, H.G., Chauret, D., Durst, T.,
Philogene, B.J.R., Sanchez Vindas, P., Hasbun, C.,
Poveda, L., San Roman, L., and Arnason, J.T., J. Chem.
Ecol., 1995, vol. 21, p. 801. doi 10.1007/BF02033462
13
(6H, H4ʹ,2‴,3‴,4‴,5‴,6‴), 7.63 d (J = 8.8 Hz, 1H, H2″,6″). C
6. (a) Engler, T.A., La Tessa, K.O., Iyengar, R., Chai, W.,
and Agrios, K., Bioorg. Med. Chem., 1996, vol. 4,
p. 1755. doi 10.1016/0968-0896(96)00192-7;
(b) Kashiwada, Y., Yamazaki, K., Ikeshiro, Y.,
Yamagishi, T., Fujioka, T., Mihashi, K., Mizuki, K.,
Cosentino, L.M., Fowke, K., Morris Natschke, S., and
Lee, K.H., Tetrahedron, 2001, vol. 57, p. 1559. doi
10.1016/S0040-4020(00)01144-3
7. (a) Skommer, J., Wlodkowic, D., Mvtt, M., et al.,
Leukemia Res., 2006, vol. 30, p. 322. doi 10.1016/
j.leukres.2005.08.022; (b) Kemnitzer, W., Drewe, J.,
Jiang, S., et al., J. Med. Chem., 2004, vol. 47, p. 6299.
doi 10.1021/jm049640t; (c) Kasibhatla, S., Gourdeau, H.,
Meerovitch, K., et al., Mol. Cancer Ther., 2004, vol. 3,
NMR spectrum, δ, ppm: 37.51 (C4), 56.11 (C9), 64.60
(C2ʹ), 65.58 (C1‴a), 70.10 (C5ʹa), 77.86 (C5), 114. 70
(C4″,5″), 115 .16 (C7), 121.05 (C4ʹa), 121.43 (C5ʹ),
121.49 (C6ʹ), 121.77 (C1″), 121.90 (C2‴,5‴), 127.46 (C4‴),
128.17 (C2″,5″), 128.31 (C3‴,5‴), 128.68 (C3ʹ), 134.53
(C4ʹ), 136.44 (C1‴), 144.15 (C8ʹa), 147.92 (C8), 155.74
(C3), 160.42 (C4″), 164.20 (C3ʹa). ESI-MS: m/z: 472.1
[M + H]+, 473.1 [M + H+1]+.
ACKNOWLEDGMENTS
One of the authors (B. Srinivas) is thankful to the
UGC-New Delhi, India for financial support in the
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 2 2017