Theoretical Study of Some Nitrososulfamide Compounds with Antitumor Activity

Khatmi, Djameleddine; Soumeya, Seridi; Fatiha, Madi

doi:10.3390/91000883

Cited by 2 publications

(1 citation statement)

References 10 publications

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“…N-nitroso-N'-(2-chloroethyl)-N'-sulfamide piperidine (CENS) (Fig. 1) constitutes a new compound exhibiting an antitumoral activity and which is capable to replace chloroethylnitrosourea (CENU) [45][46][47][48][49][50][51][52]. Recently, it was shown that CENS have some instability and low solubility in water.…”

Section: Introductionmentioning

confidence: 99%

Molecular model of CENS piperidine β-CD inclusion complex: DFT study

Fatiha

Khatmi

Dhaoui

et al. 2009

Comptes Rendus. Chimie

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Structural aspects of the complexation of N-nitroso-N'-(2-chloroethyl)-N'-sulfamide piperidine (CENS) with b-cyclodextrin (b-CD) were investigated using standard B3LYP and MPW1PW91 Density Functional Theory (DFT) calculations. Two orientations of the incoming CENS inside b-CD were considered to determine the lowest energy complex, namely the head (ring first) and tail (chain first) orientations. The calculations confirm that the tail orientation is more favorable than the head one by 5.9 kcal/mol (B3LYP) and 5.9-6.1 kcal/mol (MPW1PW91) the driving factor being the deformation energy undergone by b-CD. This preference is also due to the fact that the complexation with tail orientation of CENS occurs with a favourable anti-parallel disposition of the dipole moments of b-CD and CENS. The computed structure for the CENS -b-CD complex is in good agreement with mass and 15 N NMR spectroscopy observations. Moreover, this complexation mode leads to the formation of four intermolecular H-bonds between CENS and CD, i.e. two conventional H-bonds, one between N atom (N136) of the NO bond of CENS and H-6-O atom (H129) of b-CD and the other one between O atom (O137) of CENS SO 2 group and H-6-O (H120) and two weak (C-H. . .O) bonds. These interactions were investigated using the Natural Bond Orbital (NBO) approach. To cite this article: F.

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Section: Introductionmentioning

confidence: 99%

Molecular model of CENS piperidine β-CD inclusion complex: DFT study

Fatiha

Khatmi

Dhaoui

et al. 2009

Comptes Rendus. Chimie

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Theoretical Study on Internal Rotation of Nitrosoureas and Toxicological Analysis

Cui

Zhao

Liu

et al. 2007

J. Theor. Comput. Chem.

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A theoretical study has been carried out for internal rotation of nitrosoureas at the B3LYP/6-311G* level of theory. For each nitrosourea compound, two ground state structures have been found and the E isomer is predicted to be more stable than the Z isomer. Two transition state conformations for the isomerization have also been obtained and the calculated results show that the isomerization through TS1 is easier than that through TS2. The relationship between energy barrier and toxicity has also been investigated. It is concluded that the carcinogenic potency increases along with the decrease of rotational energy barrier.

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Theoretical Study of Some Nitrososulfamide Compounds with Antitumor Activity

Cited by 2 publications

References 10 publications

Molecular model of CENS piperidine β-CD inclusion complex: DFT study

Molecular model of CENS piperidine β-CD inclusion complex: DFT study

Theoretical Study on Internal Rotation of Nitrosoureas and Toxicological Analysis

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