5
3.
4.
5.
Paul, A.; Bhattacharya, S. Current Science 2012, 102, 212-231.
using structural parameters. Further biological studies for the
target compounds will be taken up in future.
Dileep, K. V.; Vijeesh, V.; Remya, C. Mol. BioSyst. 2016, 12, 860-867.
Hajian, R.; Shams, N.; Mohagheghian, M. J. Braz. Chem. Soc. 2009, 20,
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Experimental Section
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7.
Neidle, S. Natl. Prod. Rep. 2001, 18, 291–309.
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Garratt, P. J.; Neoh, S. B. J. Am. Soc. 1975, 97, 3255–3257. c) Garratt,
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General method for the preparation of 1, 2 and 3 using
Garratt Braverman Cyclization:
Bis-propargyl ether derivatives (7, 10 and 15) (0.2 mmol)
dissolved in dry DMSO (10mL), was treated with potassium
tertiarybutoxide and stirred for 30 min. at room temperature. The
reaction mixture was quenched with water and partitioned
between ethyl acetate (3×30 mL) and water (50 mL). The
combined organic layer was dried over anhydrous Na2SO4. The
solvent was evaporated under reduced pressure and the obtained
crude product was purified through column chromatography (4:1
pet ether: ethyl acetate) on silica gel with 99-100 % yield. The
pet ether used had a boiling range of 60-80 °C.
8.
9.
Basak, A.; Das, S.; Mallick, D.; Jemmis, E. D. J. Am. Soc. 2009, 131,
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9369-9386.
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4975-4978.
All compounds were characterized by NMR (400 MHz or 600
MHz for 1 H and 100 MHz or 150 MHz for 13C). Spectral data of
some selected compounds are mentioned. The data for all other
compounds are included in the SI.
11. Hopf, H.; Markopoulos, G. Beilstein J. Org. Chem. 2012, 8, 1936–
1998.
12. a) Kudoh , T.; Mori , T.; Shirahama , M.; Yamada , M.; Ishikawa , T.;
Saito, S.; Kobayashi, H. J. Am. Soc. 2007, 129, 4939–4947. b) Das, J.;
Bag, S. S.; Basak, A. J. Org. Chem. 2016, 81, 4623–4632.c) Jana, S.;
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1
Compound 1: H NMR (400 MHz, Chloroform-d): δ = 8.52 (s,
1H), 7.73 (d, J = 10.5 Hz, 2H), 5.32 (d, J = 15.7 Hz, 4H). 13C
NMR (100 MHz, Chloroform-d): δ = 138.6, 138.3, 131.7, 129.9,
126.7, 120.1, 114.3, 73.3, 73.0 ppm. HRMS: Calcd. for C18H14O2
+H+ 263.1072 found 263.1074.
13. Sirajuddin, M.; Ali, S.; Badshah, A. Journal of Photochemistry and
Photobiology B: Biology 2013, 124, 1-19.
14. Vijayalakshmi, R.; Kanthimathi, M.; Subhramanian, V.; Nair, B. U.
Biochim. Biophys. Acta. 2000, 1475, 157-162.
1
Compound 2: H NMR (400 MHz, Chloroform-d): δ = 8.53 (s,
15. a) García-Zubiri, I. X.; Burrows, H. D.; de Melo, J. S. S.; Pina, J.;
Monteserín, M.; Tapia, M. J. Photochemistry and Photobiology 2007,
83, 1455-1464. b) Bhattacharya, P.; Mandal, S. M.; Basak, A. Eur. J.
Org. Chem. 2016, 1439-1448.
2H), 8.10 (s, 2H), 5.37 (d, J = 22.1 Hz, 8H), 4.89 (s, 4H), 3.46 (s,
6H). 13C NMR (100 MHz, Chloroform-d): δ = 139.3, 138.4,
138.2, 130.9, 129.8, 126.9, 122.6, 73.6, 72.9, 69.9, 58.4 ppm.
HRMS: Calcd. for C22H22O4 +H+ 351.1596 found 351.1597.
16. a) Spillane, C. B., Smith, J. A.; Morgan, J. L.; Keene, F. R. J. Biol.
Inorg. Chem. 2007, 12, 819-824. b) Shahabadi, N.; Heidari, L.
Spectroch im. Acta Mol. Biomol. Spectrosc. 2012, 97, 406-410.
17. Duhovny, D., Nussinov, R. and Wolfson, H. J. (2002) Efficient
unbound docking of rigid molecules. In Guigo,R. and Gusfield,D.
(eds), Proceedings of the Fourth International Workshop on
Algorithms in Bioinformatics. Springer-Verlag GmbH Rome, Italy,
September 17–21, 2002, Vol. 2452, pp. 185–200.
1
Compound 3: H NMR (400 MHz, Chloroform-d): δ = 8.50(s,
2H), 7.78(s, 2H), 6.30(s, 2H), 5.34(s, 4H), 5.31(s,4H). 13C NMR
(100 MHz, Chloroform-d): δ = 138.9, 137.9, 136.9, 127.0, 120.8,
115.2, 112.0, 101.8, 73.4, 73.2 ppm. HRMS: Calcd. for C19H14O4
+H+ 307.0970 found 307.0972.
Acknowledgments
18. Hanwell, M. D.; Curtis, D. E.; Lonie, D. C.; Vandermeersch, T.;
Zurek, E.; Hutchison, G. R. Journal of Cheminformatics 2012, 4:17.
19. Lerman, L. S. J. Mol. Biol. 1961, 3, 18-30.
We thank Professor Dr. S. M. Mandal, Central Research
Facility, IIT Kharagpur, for helpful discussion and suggestion.
CSIR, Government of India, is acknowledged for funding the
project (No 02(0014)/11/EMR-II) and for the JC Bose
Fellowship to AB which supported this research. MS is grateful
to IIT Kharagpur and PB, JD and DG are grateful to CSIR,
Government of India, for research fellowships.
20. Bailly, C.; Chaires, J. B. Bioconjugate Chem. 1998, 9, 513–538.
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