Struct Chem (2012) 23:209–217
217
´
16. Dimmock JR, Zello GA, Oloo EO, Quail JW, Kraatz H-B, Perjesi
Conclusions
P, Aradi F, Takacs-Novak K, Allen TM, Santos CL, Balzarini J,
de Clercq E, Stables JP (2002) J Med Chem 45:3103
´
17. Levai A, Schag JB (1979) Pharmazie 34:749
18. Levai A, Dinya Z, Schag JB, Toth G, Szollosy A (1981) Phar-
1
Complete H and 13C NMR chemical shift assignments of
´
´
seven homoisoflavonoids and six thiohomoisoflavonoids
together with four structurally close compounds are reported
based on two-dimensional homo- and heteronuclear NMR
chemical shift correlation maps. Seven single crystal X-ray
structures are also reported. The crystallographic structures
were not found congruent with the ones previously obtained
by molecular modeling. In the molecular level the structures
in present study resemble well the previously known struc-
tures of (E)-3-benzylidene-4-chromanone derivatives, but
the crystal packing is different. We wish that these data are
useful also for other researchers working with these phar-
macologically important compounds.
´
´
´
¨
}
mazie 36:465
19. Poisson T, Dalla V, Marsais F, Dupas G, Oudeyer S, Levacher V
(2007) Angew Chem Int Ed 46:7090 (Supporting Information)
20. Yee SW, Jarno L, Gomaa MS, Elford C, Ooi L-L, Coogan MP,
McClelland R, Nicholson RI, Evans BAJ, Brancale A, Simons C
(2005) J Med Chem 48:7123
21. Hurd RE, John BK (1991) J Magn Reson 91:648
22. Rance M, Sørensen OW, Bodenhausen G, Wagner G, Ernst RR,
Wu¨thrich K (1983) Biochem Biophys Res Commun 117:479
23. Derome A, Williamson M (1990) J Magn Reson 88:117
24. Bax A, Griffey RH, Hawkins BL (1983) J Magn Reson 55:301
25. Bax A, Subramanian S (1986) J Magn Reson 67:565
26. Bax A, Summers MF (1986) J Am Chem Soc 108:2093
27. Otwinowski Z, Minor W (1997) Methods in enzymology, vol.
276: macromolecular crystallography, part A. Academic Press,
New York, pp 307–326
Acknowledgments The authors express their thanks to Dr. Tibor
Mezei (EGIS Pharmaceuticals, Budapest, Hungary) for his generous
contribution to the synthetic works. The corresponding author grate-
fully acknowledges Academy Professor Kari Rissanen from Univer-
28. Burla MC, Camalli M, Carrozzini B, Cascarano GL, Giacovazzo
C, Polidori G, Spagna R (2003) J Appl Crystallogr 36:1103
29. Sheldrick GM (2008) Acta Crystallogr A64:112
30. Spek AL (2009) Acta Crystallogr D65:148
¨
¨
sity of Jyvaskyla and the Academy of Finland (project No. 122350)
for financial support. The University of Jyvaskyla and the Faculty of
¨
¨
31. Farrugia LJ (1997) J Appl Crystallogr 30:565
´
Medicine of University of Pecs (AOK-KA 34039-12/2009) is also
acknowledged for supporting this work.
32. Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P,
Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood
PA (2008) J Appl Crystallogr 41:466
˚
33. Toth G, Szollosy A, Levai A, Oszbach G, Dietrich W, Kuhne H
´
´
(1991) Magn Reson Chem 29:801
¨ ¨
¨
34. Pivnenko NS, Orlov VD, Nodel0man OA, Mikhed0kina EI,
Lavrushin VF (1980) Zh Org Khim 16:1945
35. Katrusiak A, Ratajczak-Sitarz M, Kałuski Z, Orlov VD (1987)
Acta Crystallogr C43:103
References
1. Kirkiacharian BS, Gomis M, Tongo HG, Mahuteau J, Brion JD
(1984) Org Magn Reson 22:106
36. Augustine APT, Vithiya SM, Ramkumar V, Kanakam CC (2008)
Acta Crystallogr E64:o2080
37. Marx A, Manivannan V, Suresh R, Kanagam CC, Sridhar B
(2008) Acta Crystallogr E64:o328
38. Marx A, Suresh R, Kanakam CC, Manivannan V, Vasam CS
(2008) Acta Crystallogr E64:o27
¨
39. Marx A, Suresh R, Kanagam CC, Manivannan V, Bu¨yu¨kgu¨ngor
O (2007) Acta Crystallogr E63:o4530
40. Suresh R, Kanagam CC, Umarani PR, Manivannan V,
´
J Ethnopharm 81:381
´ ´ ´
2. Miadokova E, Masterova I, Vlckova V, Duhova V, Toth J (2002)
´
´
3. Masterova I, Suchy V, Uhrin D, Ubik K, Grancaiova Z,
Bobovnicky B (1991) Phytochemistry 30:713
4. Koorbanally C, Crouch NR, Langlois A, du Toit K, Mulholland
DA, Drewes SE (2006) S Afr J Bot 72:428
5. Rao VM, Damu GLV, Sudhakar D, Siddaiah V, Rao CV (2008)
ARKIVOC (xi):285
¨
Bu¨yu¨kgu¨ngor O (2007) Acta Crystallogr E63:o4387
6. Maheswara M, Siddaiah V, Rao CV (2006) Chem Pharm Bull
54:1193
7. Ye G, Ye M, Guo D, Huang C (2005) Chromatographia 61:121
8. Chang J-M, Shen C–C, Huang Y-L, Chien M-Y, Ou J-C, Shieh
B-J, Chen C-C (2002) J Nat Prod 65:1731
9. Mutanyatta J, Matapa B, Shushu D, Abegaz B (2003) Phyto-
chemistry 62:797
10. Tait S, Salvati AL, Desideri N, Fiore V (2006) Antiviral Res
72:252
¨
41. Marx A, Manivannan V, Suresh R, Kanagam CC, Bu¨yu¨kgu¨ngor
O (2007) Acta Crystallogr E63:o4383
42. Suresh R, Kanagam CC, Umarani PR, Manivannan V,
¨
Bu¨yu¨kgu¨ngor O (2007) Acta Crystallogr E63:o4248
43. Chantrapromma S, Boonsri S, Fun H-K, Anjum S, Kanjana-opas
A (2006) Acta Crystallogr E62:o1254
44. Boonsri S, Chantrapromma S, Fun H-K, Karalai C, Kanjana-opas
A, Anjum S (2005) Acta Crystallogr E61:o3930
45. Allen FR (2002) Acta Crystallogr B58:380 (CSD, version 5.32,
February 2011 update)
46. Molm D, Florke U, Risch N (1998) Eur J Org Chem 2185
47. Hauer B, Bickley JF, Massue J, Pena PCA, Roberts SM,
Skidmore J (2002) 80:546
48. Zhou J-X, Wanga X-S, Shi D-Q (2007) Acta Crystallogr
E63:o2082
´
11. Levai A (2004) ARKIVOC (vii):15
12. Perjesi P, Das U, de Clercq E, Balzarini J, Kawase M, Sakagami
´
¨
¨
H, Stables JP, Lorand T, Rozmer Z, Dimmock JR (2008) Eur J
Med Chem 43:839
}
13. Perjesi P, Perjessy A, Kolehmainen E, Osz E, Samalikova M,
´
Virtanen E (2004) J Mol Struct 697:41
}
14. Perjesi P, Linnanto J, Kolehmainen E, Osz E, Virtanen E (2005)
49. Rong L-C, Li X-Y, Yao C-S, Wang H-Y, Shi D-Q (2006) Acta
Crystallogr E62:o35
´
J Mol Struct 740:81
´
50. Oloo EO, Quail JW, Perjesi P, Dimmock JR (2002) Acta Crys-
tallogr E58:o582
15. Dimmock JR, Kandepu NM, Nazarali AJ, Kowalchuk TP, Mot-
aganahalli N, Quail JW, Mykytiuk P, Audette GF, Prasad L,
51. Kałuski Z, Skrzypczak-Jankun E, Orlov VD, Borovoi IA (1978)
Bull Acad Pol Sci Ser Sci Chim 26:869
´
Perjesi P, Allen TM, Santos CL, Szydlowski J, de Clercq E,
Balzarini J (1999) J Med Chem 42:1358
123