Methyl 2-methoxy-7-(4-methylbenzoyl)-4-oxo-6-p-tolyl-4Hfuro[3,2-c] pyran-3-carboxylate: A combined experimental and theoretical investigation

Journal of Molecular Modeling

Volumn 15, Issue 10, 2009, Pages 1193-1201

  Özdemir, Namik ^a   Dinçer, Muharrem ^a   Koca, Irfan ^b   Yildirim, Ismail ^c   Büyükgüngör, Orhan ^a  

^a ONDOKUZ MAYIS UNIVERSITY   (Turkey)

^b BOZOK UNIVERSITY   (Turkey)

^c ERCIYES UNIVERSITY   (Turkey)

Author keywords

Ab initio calculation; AM1 and PM3 semi empirical methods; B3LYP; Conformational analysis; Hartree Fock; Vibrational assignment; X ray structure determination

Indexed keywords

METHYL 2 METHOXY 7 (4 METHYLBENZOYL) 4 OXO 6 P TOLYL 4H FURO[3,2 C]PYRAN 3 CARBOXYLATE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; CRYSTALLIZATION; DRUG CONFORMATION; DRUG DETERMINATION; DRUG IDENTIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; EXPERIMENTAL STUDY; GEOMETRY; INFRARED RADIATION; MATHEMATICAL COMPUTING; MOLECULAR MODEL; PRIORITY JOURNAL; THEORETICAL STUDY; THERMODYNAMICS; VIBRATION; X RAY DIFFRACTION;

CRYSTALLIZATION; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; PYRANS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMODYNAMICS;

EID: 68949186015     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-009-0479-0     Document Type: Article

References (34)

1. Mo S, Wang S, Zhou G, Yang Y, Li Y, Chen X, Shi J (2004) J Nat Prod 67:823-828
2. Kim JP, Yun B-S, Shim YK, Yoo ID (1999) Tetrahedron Lett 40:6643-6644
3. Dinçer M, Yildirim I, Koca I, Özdemir N (2004) Acta Cryst E60:0207-0209
4. Florey HW, Chain E, Headley NG, Jennings M, Sanders AG, Abraham ED, Florey ME (1949) Antibiotics, 2 vols. Oxford Univ Press, London
5. Woordward RB, Singh G (1950) J Am Chem Soc 72(3):1428
6. Suarez M, Salfran E, Verdecia Y, Ochoa E, Alba L, Martin N, Martinez R, Quinteiro M, Seoane C, Novoa H, Blaton N, Peeters OM, De Ranter C (2002) Tetrahedron 58:953-960
7. Kemnitzer W, Drewe J, Jiang S, Zhang H, Wang Y, Zhao J, Jia S, Herich J, Labreque D, Storer R, Meerovitch K, Bouffard D, Rej R, Denis R, Blais C, Lamothe S, Attardo G, Gourdeau H, Tseng B, Kasibhatla S, Cai SX (2004) J Med Chem 47:6299-6310
8. Zhang H-Z, Kasibhatla S, Kuemmerle J, Kemnitzer W, Ollis-Mason K, Qiu L, Crogan-Grundy C, Tseng B, Drewe J, Cai SX (2005) J Med Chem 48:5215-5223
9. Andreani LL, Lapi E (1960) Boll Chim Farm 99:583-587
10. Bonsignore L, Loy G, Secci D, Calignano A (1993) Eur J Med Chem 28:517-519
11. Kojima K, Ohno T, Inoue M, Mizukami H, Nagatsu A (2008) Chem Pharm Bull 56(2):173-175
12. Armetso D, Horspool WM, Martin N, Ramos A, Seaone C (1989) J Org Chem 54:3069-3072
13. Hatakeyama S, Ochi N, Numata H, Takano S (1988) J Chem Soc Chem Commun 17:1202-1204
14. Gonzalez R, Martin N, Seoane C, Marco JL, Albert A, Cano FH (1992) Tetrahedron Lett 33:3809-3812
15. Madhushaw RJ, Li CL, Shen KH, Hu CC, Liu RS (2001) J Am Chem Soc 123(30):7427-7428
16. Shen KH, Lush SF, Chen TL, Liu RS (2001) J Org Chem 66:8106-8111
17. Snider BB, Roush DM, Killinger TA (1979) J Am Chem Soc 101:6023-6027
18. Fuhrer C, Messer R, Häner R (2004) Tetrahedron Lett 45:4297-4300
19. Takano S, Satoh S, Ogasawara K, Aoe K (1990) Heterocycles 30:583-605
20. Ziegler E, Eder M, Belegratis C, Prewedourakis E (1967) Monatsh Chem 98:2249-2251
21. Yildirim I, Koca I (2005) Kuwait J Sci Eng 32(1):49-60
22. Yildirim I, Koca I, Dinçer M (2008) J Chem Soc Pak 30(1):134-141
23. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785-789
24. Becke AD (1993) J Chem Phys 98:5648-5652
25. Ditchfield R, Hehre WJ, Pople JA (1971) J Chem Phys 54:724-728
26. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03. Revision E.01. Gaussian Inc., Wallingford CT
27. Foresman JB, Frisch A (1996) Exploring chemistry with electronic structure methods, 2nd edn. Gaussian Inc, Pittsburgh
28. Dennington R II, Keith T, Millam J (2007) GaussView, Version 4.1.2. Semichem Inc, Shawnee Mission, KS
29. Farrugia LJ (1997) J Appl Crystallogr 30:565
30. Bucourt R (1974) In: Eliel EL, Allinger N (eds) Topics in Stereochemistry, vol 8. John Wiley, New York, pp 159-224
31. Bruno G, Nicoló F, Rotondo A, Foti F, Risitano F, Grassi G, Bilardo C (2001) Acta Cryst C57:493-494
32. Bernstein J, Davis RE, Shimoni L, Chang N-L (1995) Angew Chem Int Ed Engl 34:1555-1573
33. Allen FH (2002) Acta Cryst B58:380-388
34. Bruno IJ, Cole JC, Edgington PR, Kessler M, Macrae CF, McCabe P, Pearson J, Taylor R (2002) Acta Cryst B58:389-397