Keywords
How to Cite
Abstract
This article describes a semi-empirical study on the thermodynamics involved in the synthesis of three novel ortho, meta and para, potentially intercalatingphenoxazine 1 derivatives o-(6), m-(7) and p-(8). Quantum chemical calculations at the semi-empirical PM3 method were used in order to evaluate conformational states of the molecules, as well as to predict thermodynamic properties and equilibrium constants. The more favourable product was found to be the compound with the methoxy group in ortho-position. The methoxy group in para-position hinders the reaction by steric factor, which is reflected from the small constant, Kp.
References
Angyal SJ, Bullock E, Hanger WC, Havell J. Actinomycin. Part III. The reaction of actinomycin with alcali. J Chem Soc. 1957; 1592-602. http://dx.doi.org/10.1039/jr9570001592
Mueller W, Crothers DM. Studies of the binding of actinomycin related compounds to DNA. J Mol Biol. 1968; 35:251-90 http://dx.doi.org/10.1016/S0022-2836(68)80024-5
Vogler K, Lanz P. Synthesen in der polymyxin-reihe. 1. Miteilung. Synthese eines pentapeptid-fragmentes. Helv Chim Acta. 1960; 43: 270-9. http://dx.doi.org/10.1002/hlca.19600430136
Ionescu M, Mantsch H, Katritzky AR, Boulton AJ. Advances in Heterocyclic Chemistry. 1967.Academic Press, New York, USA.
Sainsbury M. The Chemistry of Carbon Compounds. 2nd ed. Amsterdam; Coffey Elsevier 1978.
Gilmand H, Moore LO. The metalation of phenoxazine and some of its derivatives. J Am Chem Soc. 1958; 80: 2195-7. http://dx.doi.org/10.1021/ja01542a040
Gilmand H, Shirley DA, Van Ess PR. Metalation of phenotiazine. J Am Chem Soc. 1944; 66: 625-7. http://dx.doi.org/10.1021/ja01232a035
Weintein B, Crews O, Baker M, Goodman B. Potential anticancer agents LXX. Some simple derivatives of the actinomycins. J Org Chem. 1962; 27 (4): 1389-95. http://dx.doi.org/10.1021/jo01051a064
Sheehan JG, Goodman M, Hess GP. Peptide derivatives containing hydroxyamino acids. J Am Chem Soc. 1956; 78: 1367-9. http://dx.doi.org/10.1021/ja01588a029
Goldberg HI, Rabinowitz M. Actinomycin D inhibitich of desoxiribonucleic acid-dependent synthesis of ribonucleic acid. Science 1962; 136 (3513): 315-6. http://dx.doi.org/10.1126/science.136.3513.315
Reich E, Shatkin F. Effect of actinomycin D on cellular nucleic acid synthesis and virus production. Science. 1961; 134: 556-7. http://dx.doi.org/10.1126/science.134.3478.556
Jensen F. Introduction to Computational Chemistry. New York; John Wiley and Sons 1999.
Young D. Computational Chemistry. New York; John Wiley and Sons 2000.
Stewart JJP. Optimization of parameter for semiempirical methods. I. 1. Method. J Comp Chem. 1989; 10: 209-20 http://dx.doi.org/10.1002/jcc.540100208
Halgren TA, Nachbar RB. Merch molecular force field. IV conformational energy and geometry for MMFF94. J Comput Chem. 1996;17: 587-615. http://dx.doi.org/10.1002/(SICI)1096-987X(199604)17:5/6<587::AID-JCC4>3.0.CO;2-Q
Jian FF, Zhang PS, Zheng Z. Ab initio and experimental studies on dibenzothiazyl disulfide. Bull Korean Chem Soc. 2006; 27: 1048-52. http://dx.doi.org/10.5012/bkcs.2006.27.7.1048
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
Copyright (c) 2013 Journal of Basic & Applied Sciences