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Computational study of the ring opening mechanism of substituted temolozolomide, TMZ-R (R = Cl, OH, CF3) in water solvent

Title
Computational study of the ring opening mechanism of substituted temolozolomide, TMZ-R (R = Cl, OH, CF3) in water solvent
Author
정회일
Keywords
Temozolomide derivatives; Transition state; Relative energy; Ring opening
Issue Date
2019-10
Publisher
ELSEVIER SCIENCE BV
Citation
CHEMICAL PHYSICS LETTERS, v. 732, article no. UNSP 136651
Abstract
MP2/6-311 + G(d,p) was employed to study the mechanism of the initial step of ring opening of temozolomide (TMZ-H) and its substituted, TMZ-R (R = Cl, OH, CF3) analogues. The study reveals that the difference formation energies of substituted MTIC acids with respect to MTIC acid are ranging between 0.44 and 1.58 kcal/mol. The ring opening of TMZ-R along pathway-2 leads to the lowest conformer (D), whereas reactions along pathway-1 give rise to lower transition states. The barrier energies of TMZ-R are 1.60-3.75 kcal/mol larger than TMZ-H. The conformational analysis reveals that intramolecular hydrogen bonds do not have a stabilizing effect in water solvent.
URI
https://www.sciencedirect.com/science/article/pii/S0009261419306323?via%3Dihubhttps://repository.hanyang.ac.kr/handle/20.500.11754/153849
ISSN
0009-2614; 1873-4448
DOI
10.1016/j.cplett.2019.136651
Appears in Collections:
COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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