4th EucheMs chemistry congress

Poster Session 1
s883
chem. Listy 106, s587–s1425 (2012)
Poster session 1 - Physical, theoretical chemistry
P - 1 0 1 6
APPArent or reAL wAter exChAnGe
reACtionS on [zn(h o) (L)] 2 4 2 + 2h o 2
B. ALzouBi 1 , M. wALther 1 , r. PuChtA 1 ,
r. vAn eLdiK 1
1 Friedrich-Alexander-University Erlangen-Nuremberg, chemie
and pharmacy, Erlangen, Germany
The exchange of a second coordination sphere water
molecule in [Zn(H O) (L)] 2 4 2 +·2H O (L = N-donor Ligand) 2 [1-3]
against a coordinated water molecule in the first coordination
sphere was studied by quantum chemical calculations
(RB3LYP/6-311+G**). The complete reaction consists of an
associative binding of one H O from the second coordination
2
sphere leading to a six-coordinate intermediate, followed by the
dissociation of a water molecule to reach the product state
[Zn(H O) (L)] 2 4 2 +·2H O. For a real water exchange reaction to
2
occur two different transition states have to be included, otherwise
only an apparent water exchange reaction takes place. For the
water exchange reaction in [Zn(H O) (L)] 2 4 2 +·2H O nearly
2
iso-energetic cis- and trans-orientated transition states are crossed.
The basicity (described as the gas-phase proton affinity) of L
shows instructive correlations with structural parameters and
energy gaps for the investigated reactions.
references:
1. B. M. Alzoubi, R. Puchta, R. van Eldik, Aust. J. Chem.
2010, 63, 236.
2. B. M. Alzoubi, R. Puchta, R. van Eldik, Eur. J. Chem.
2010, 16, 7300.
3. B. M. Alzoubi, M. Walther, R. Puchta, R. van Eldik,
Dalton Trans. 2012, 41, 6932.
Keywords: Calculated water exchange reactions;
4 th EucheMs chemistry congress
P - 0 0 4 8
CytotoxiCity of new
thiAdiAzoLo[2,3-A]Pyridine BenzAMide
derivAtiveS on five CAnCer CeLL LineS
f. AdhAMi 1
1 Islamic Azad University Shahr-Ray Branch, Chemistry,
Tehran, Iran
Cancer is a serious clinical problem which can develop in
almost any organ or tissue, but they are classified by the type of
cell that is initially affected such as the skin, bone, lung, colon,
breast and nerve cancer.
There are some therapy options like surgery, chemotherapy,
endocrine and radiation therapy in the treatment of cancer.
Chemotherapy is an important treatment for cancers. However,
toxicity and poor tolerance to current chemotherapeutic agents are
dose-limiting factors. Therefore, discovery and development of
apoptosis inducers as new chemotherapeutic agents is a promising
approach. [1]
In this study, three derivatives of Thiadiazolo[2,3-a]Pyridine
Benzamide were synthesized in two steps. First step,
reaction between three derivatives of 2-aminopyridine and
benzoylisothiocyanate formed three thiourea derivatives;
a) N-Benzoyl-N-(2-Pyridyl)Thiourea (PyTuBenzo), b) N-Benzoyl-
-N-(4-Methyl-2-Pridyl)Thiourea (4PicTuBenzo) and c) N-Benzoyl-
-N-(6-Methyl-2-Pyridyl)Thiourea (6PicTuBenzo). Second step,
three thiourea derivatives were oxidized by Cu2+ . The oxidized
products were Thiadiazolo[2,3-a]Pyridine Benzamide derivatives
as a second group; a`) N`-(2H-[1,2,4]-Thiadiazolo[2,3-a]Pyridine-
-2-Ylidne)Benzamide (2HThPyBenza), b`) N`-(7-Methyl-
-2H-[1,2,4]Thiadiazolo[2,3-a]Pyridine-2-Ylidne)Benzamide
(7MeThPyBenza) and 3`)N`-(5-Methyl-2H-[1,2,4]Thiadiazolo[2,3-
-a]Pyridine-2-Ylidne)Benzamide (5MeThPyBenza). The products
in two steps were characterized by FTIR, 1HNMR and 13CNMR spectroscopies and their crystal structures were determined.
In vitro cytotoxic activity of the six products were studied
by five human cell lines include Breast cancer cell line
MDA-MB-231, Prostate adenocarcinoma cell line LNCap,
Neuroblastoma cell line SK-N-MC, Nasopharyngeal epidermoid
carcinoma cell line KB and Liver cancer cell line HEPG-2.
The results were compared with Doxorubicin using MTT-dye
reduction assay.
In vitro results suggested that the second group inhibited the
growth of cancer cell lines. Among these Benzamide derivatives
in this group, 7MeThPyBenza showed the best results for four
human cell lines than the other derivatives.
references:
1. N.I. Wenzel, et al., J. Med. Chem. 53 (2010) 3214.
Keywords: Thiadiazolo Benzamide; Cytotoxicity; Cancer cell
line; [2,3-a]Pyridine Benzamide;
AUGUst 26–30, 2012, PrAGUE, cZEcH rEPUbLIc