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Bioorganic and Medicinal Chemistry

Volumn 10, Issue 4, 2002, Pages 1019-1024

Molecular structure and stereoelectronic properties of herbicide sulphonylureas

(4) Galeazzi, R a Marucchini, C b Orena, M a Zadra, C b

a UNIVERSITÀ POLITECNICA DELLE MARCHE (Italy)

b UNIVERSITY OF PERUGIA (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOLACTATE SYNTHASE; HERBICIDE; SULFONYLUREA DERIVATIVE;

ARTICLE; DRUG STRUCTURE; ENZYME INHIBITION; QUANTUM CHEMISTRY; STEREOCHEMISTRY; THEORY;

ACETOLACTATE SYNTHASE; ELECTROCHEMISTRY; HERBICIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONYLUREA COMPOUNDS;

EID: 0036172629 PISSN: 09680896 EISSN: None Source Type: Journal
DOI: 10.1016/S0968-0896(01)00357-1 Document Type: Article

Times cited : (17)

References (50)

1
- 0008387266
- Levitt, G. In Pesticide Chemistry: Human Welfare and Environment; Miymato, J.; Kearney, P. C, Eds.; Pergamon: New York, 1983; Vol. 1, p. 243.

2
- 0008332028
- Sauers, R. F., Levitt, G. In Pesticide Synthesis Through Rational Approaches; Magee, P. S., Kohn, G. K., Mean, J. J., Eds.; American Chemical Society: Washington, 1984; p 21.

3
- 0008330566
- Beyer, E. M.; Duffy, M. J.; Hay, J. V.; Schlueter, D. D. In Sulphonylurea Herbicides in Herbicides: Chemistry, Degradation and Mode of Action Vol. 3; Kearney, P. C., Kaufman, D. D., Eds.; Marcel Dekker: New York, 1988; Chapter 3, pp 117

4
- 0029818907
- (1996) Environm. Toxicol. Chem. , vol.15 , pp. 1500
- Berger, B.M.¹ Wolfe, N.L.²

5
- 33751392206
- (1992) J. Agric. Food Chem. , vol.40 , pp. 513
- Shalaby, L.M.¹ Bramble, F.Q.J.² Lee, P.W.³

6
- 0031899517
- (1998) Pestic. Sci. , vol.53 , pp. 29
- Strek, H.J.¹

7
- 0030845996
- (1997) Pestic. Sci. , vol.51 , pp. 56
- Bray, L.D.¹ Heard, N.E.² Overman, M.C.³ Vargo, J.D.⁴ King, D.L.⁵ Lawrence, L.J.⁶ Phelps, A.W.⁷

8
- 33751386486
- (1993) J. Agric. Food Chem. , vol.41 , pp. 2404
- Schneiders, G.E.¹ Koeppe, M.K.² Naidu, M.V.³ Horne, P.⁴ Brown, A.M.⁵ Mucha, C.F.⁶

9
- 0030798467
- (1997) Pestic. Sci. , vol.51 , pp. 102
- Marucchini, C.¹ Luigetti, R.²

10
- 0001728908
- (1996) Chem. Rev. , vol.96 , pp. 1027
- Karelson, M.¹ Lobanov, V.S.² Katritsky, A.R.³

11
- 0008380593
- Franke, R. Theoretical Drug Design Methods; Elsevier: Amsterdam, 1984, p 115.

12
- 0013602932
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 5720
- Zhou, Z.¹ Parr, R.G.²

13
- 0000103764
- (1985) J. Chromatogr. , vol.346 , pp. 53
- Osmialowski, K.¹ Halkiewicz, J.² Radecki, A.³ Kaliszan, R.⁴

14
- 0027503975
- (1993) Quant. Struct. Act. Relat. , vol.12 , pp. 251
- Nakayama, A.¹ Hagiwara, K.² Hashimoto, S.³ Shimoda, S.⁴

15
- 4243183749
- (1996) Science in China (Series B) , vol.39 , pp. 78
- Lu, R.¹ Yang, H.² Shang, Z.³ Wang, W.⁴ Pan, Y.⁵ Zhao, X.⁶

16
- 0028801561
- (1995) Weed Sci. , vol.43 , pp. 175
- Guttieri, M.J.¹ Eberlein, C.V.² Thill, D.³

17
- 0029189132
- (1995) Weed Sci. , vol.43 , pp. 578
- Currie, R.S.¹ Kwon, C.S.² Penner, D.³

18
- 0028155068
- (1994) Weed Sci. , vol.42 , pp. 327
- Mekki, M.¹ Leroux, G.D.²

19
- 0043162336
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 4379
- Chang, G.¹ Guida, W.C.² Still, W.C.³

20
- 0344110495
- (a) We chose as descriptors HOMO-LUMO energy gap, their topology, the frontier electron density (directly related to the measure of proton affinity), the heat of formation, the reactivity index, partial charges and MEPs because these are the most significant quantum chemistry descriptors to understanding the mechanism of binding with the enzyme, as it was already proved in studies of both other classes of ALS herbicides and other bioactive compounds. For significant examples, see:
- (1998) Bioorg. Med. Chem. , vol.6 , pp. 1745
- López-Romero, E.¹ Evrard, G.² Durant, F.³ Sevrin, M.⁴ George, P.⁵

21
- 0033917401
- (2000) Bioorg. Med. Chem. , vol.8 , pp. 1741
- Werbovets, K.A.¹ Bhattacharjee, K.A.² Brendle, J.J.³ Scovill, J.P.⁴

22
- 0008294786
- (c)Ref. 15. The heat of formation can be considered instead of total energy since the conformational analysis was carried out by using a semiempirical method since we could not use ab initio methods in order to calculate these properties. Eventually, the molecular volume and surface are still important, but especially in helping to choose the most active conformers of a compound and will be considered in a further study aimed to develop a receptor model of this class of herbicide.

23
- 0842341771
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 3902
- Dewar, M.J.S.¹ Zoebish, E.G.² Healy, E.F.³ Steward, J.J.P.⁴

24
- 33845373690
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 8075
- Dewar, M.J.S.¹ Dieter, K.M.²

25
- 11644266970
- (1955) Chem. Phys. , vol.25 , pp. 1833
- Mulliken, R.J.¹

26
- 33845183253
- (1989) J. Org. Chem. , vol.54 , pp. 1423
- Pearson, R.G.¹

27
- 0001441182
- (1988) Inorg. Chem. , vol.27 , pp. 3259
- Burdett, J.K.¹ Coddens, B.A.²

28
- 0001776482
- (1989) Science , vol.245 , pp. 37
- Faust, W.L.¹

29
- 84982510159
- (1975) Bull. Soc. Chim. Belg. , vol.84 , pp. 397
- Muetterties, E.L.¹ Beier, B.F.²

30
- 0008332030
- Fukui, K. Theory of Orientation and Stereoselection; Springer: New York, 1975, p34.

31
- 0008366808
- Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: New York, 1976.

32
- 0025981233
- (1991) Mutat. Res. , vol.247 , pp. 97
- Tuppurainen, K.¹ Lotjonen, S.² Laatikainen, R.³ Vartiainen, T.⁴ Maran, U.⁵ Strandberg, M.⁶ Tamm, T.⁷

33
- 0025905132
- (1991) Drug Des. Deliv. , vol.7 , pp. 227
- Prabhakhar, Y.S.¹

34
- 0001548657
- (1995) Chem. Rev. , vol.95 , pp. 829
- Naray-Szabo, G.¹ Ferenczy, G.G.²

35
- 36849107975
- (1970) J. Chem. Phys. , vol.52 , pp. 5270
- Bonaccorsi, R.¹ Scrocco, E.² Tomasi, J.³

36
- 0003824417
- Chemical Applications of Atomic and Molecular Electrostatic Potential
- New York: Plenum
- (1981)
- Politzer, P.¹ Thrular, D.G.²

37
- 0008339741
- (1978) Adv. Quantum Chem. , vol.11 , pp. 15
- Scrocco, E.¹ Tomasi, J.²

38
- 0000254058
- (1988) J. Mol. Struct. (Theochem.) , vol.180 , pp. 161
- Murray, J.S.¹ Politzer, P.²

39
- 0002655270
- (1989) J. Mol. Struct. (Theochem.) , vol.187 , pp. 95
- Murray, J.S.¹ Politzer, P.²

40
- 0008331784
- (1986) J. Mol. Struct. (Theochem.) , vol.138 , pp. 121
- Kikuki, O.¹

41
- 0000561275
- (1987) Theor. Chim. Acta , vol.72 , pp. 507
- Murray, J.S.¹ Politzer, P.²

42
- 84990647637
- (1990) Int. J. Quantum Chem. , vol.37 , pp. 271
- Murray, J.S.¹ Evans, P.² Politzer, P.³

43
- 0008330569
- (1992) J. Mol. Struct. (Theochem.) , vol.256 , pp. 175
- Pepe, G.¹ Siri, D.² Reboul, J.P.³

44
- 0008347176
- (1992) J. Mol. Struct. (Theochem.) , vol.256 , pp. 61
- Guha, S.W.¹ Majumdar, D.² Bhattacharjee, A.K.³

45
- 0000312506
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 1544
- Sheridan, R.P.¹ Allen, L.C.²

46
- 84983967832
- (1982) Int. J. Quantum Chem. , vol.22 , pp. 575
- Naray-Szabo, G.¹

47
- 84990634585
- (1983) Int. J. Quantum Chem. , vol.23 , pp. 723
- Naray-Szabo, G.¹

48
- 0025045408
- (1990) J. Theor. Biol. , vol.145 , pp. 183
- Brasseur, J.L.¹ Dive, G.² Dehareng, D.³ Ghuysen, J.M.⁴

49
- 84987055055
- (1979) Int. J. Quantum Chem. , vol.16 , pp. 265
- Naray-Szabo, G.¹

50
- 84986437005
- MacroModel V.5.5:
- (1990) J. Comput. Chem. , vol.11 , pp. 440
- Mohamadi, F.¹ Richards, N.G.J.² Guida, W.C.³ Liskamo, R.⁴ Lipton, M.⁵ Caulfield, C.⁶ Chang, G.⁷ Hendrickson, T.⁸ Still, W.C.⁹

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