Tiyadiazol Halkası İçeren‘‘5-(2-Kloro-6-Florobenziltiyo)-1,3,4-Tiyadiazol- 2-Amin’’ TekKristalinin Moleküler YapısınınDeneysel ve Teorik Yöntemlerle İncelenmesi
Bu çalışmada, tiyadiazol halka içeren5-(2-kloro-6-florobenziltiyo)-1,3,4-tiyadiazol-2-amin tek kristalisentezlenmiştir. Sentezlenen kristalin yapısı, 1 H-NMR, 13 C-NMR ve X-ışını analiz teknikleri ileaydınlatılmıştır. Deneysel sonuçlara destek olması amacıyla da teorik hesaplamalar yapılmıştır. Bununiçinde bileşiğin geometrik parametreleri gaussian 09paket programı kullanılarak, yoğunluk fonksiyonelteorisi (DFT) B3LYP/6-31G(d) metodu ile optimize edildi ve yapısal parametreleri (bağ açıları, bağuzunlukları ve dihedral açıları), 1 H- ve 13 C-NMR spektrumları vesınır moleküler orbitalleri (HOMO-LUMO)teorik olarak hesaplanmıştır. Son olarak, sentezlenen tek kristalin inhibitör aktivite çalışması için, 2WQYreseptör hedef yapısını inhibe etmek amacıyla moleküler doking simülasyonu yapılmıştır.
Investigation of The Crystal and Molecular Structure Of ‘‘5-(2-Chloro-6- Fluorobenzylthio)-1,3,4-Thiadiazol-2-Amine’’ Single Crystal Containing ThiadiazolRingby Experimental and Theoretical Methods
In this work, a single crystal of 5-(2-chloro-6-fluorobenzylthio)-1,3,4-thiadiazol-2-aminecontaining thiadiazole ring was synthesized. The structure of the synthesized crystal was confirmed by 1 H-NMR, 13 C-NMR and X-ray analysis techniques. Theoretical calculations have been made in order to support experimental results. In this, the geometric parameters of the compound were optimized by the density functional theory(DFT) B3LYP/6-31G(d) method using the gaussian 09 packet program and structural parameters (bond angles, bond lengths and dihedral angles), 1 H- and 13 C-NMR spectra and frontier molecular orbitals (HOMO-LUMO) of the single crystal have been calculatedtheoretically. Finally, the molecular doking simulation was carried out to inhibit the 2WQY receptor target structure for inhibitor activity study of the synthesized single crystal.
___
- Atkins P.W., 1992. The elements of physical
chemistry (Oxford University Press Oxford
United Kingdom).
- Becke
A.D.,
1993.
Density‐functional
thermochemistry. III. The role of exact
exchange, The Journal of Chemical Physics,
98, 5648-52.
B
ruker A., 2008. APEX2, V2008. 6, SADABS
V2008/1, SAINT V7. 60A, SHELXTL V6. 14,
Bruker AXS Inc., Madison, Wisconsin, USA.
- Dennington R., Keith, T. and Millam, J., 2009.
GaussView, version 5, Semichem Inc.,
Shawnee Mission, KS.
- Ditchfield R., 1972. Molecular orbital theory of
magnetic
shielding
and
magnetic
susceptibility, The Journal of Chemical
Physics, 56, 5688-91.
- Dolomanov O.V., Bourhis, L.J., Gildea, R.J., Howard,
J.A. and Puschmann, H., 2009. OLEX2: a
complete structure solution, refinement
and analysis program, Journal of Applied
Crystallography, 42, 339-41.
- Er M., Işıldak G., Tahtaci H. and Karakurt T., 2016.
Novel 2-amino-1,3,4-thiadiazoles and their
acyl
derivatives:
Synthesis,structural
characterization, molecular docking studies
and comparison of experimental and
computational results, Journal of Molecular
Structure, 1110, 102-13.
- Er M., Ergüven B., Tahtaci H., Onaran A., Karakurt T.
and
Ece
A.,
2017.
Synthesis,
characterization, preliminary SAR and
molecular docking study of some novel
substituted imidazo [2, 1-b][1, 3, 4]
thiadiazole derivatives as antifungal agents,
Medicinal Chemistry Research, 26, 615-30.
- Er M., Şahin A. and Tahtaci H., 2014. Synthesis and
characterization of novel 1,3-thiazole and
2-amino-1,3,4-thiadiazole
derivatives,
Macedonian Journal of Chemistry and
Chemical Engineering, 33, 189-98.
- Fan S.-H., Zhang, A.-G., Ju, C.-C., Gao, L.-H. and
Wang, K.-Z., 2010. A Triphenylamine-
grafted
imidazo
[4,
5-f][1,
10]
phenanthroline ruthenium (II) complex:
Acid− base and photoelectric properties,
Inorganic Chemistry, 49, 3752-63.
- Frisch M., Trucks, G., Schlegel, H.B., Scuseria, G.,
Robb, M., Cheeseman, J., Scalmani, G.,
Barone, V., Mennucci, B. and Petersson, G.,
2009. Gaussian 09, revision a. 02, gaussian,
Inc., Wallingford, CT, 200.
- Kim H.S., Jadhav, J.R., Jung, S.-J. and Kwak, J.H.,
2013. Synthesis and antimicrobial activity
of imidazole and pyridine appended
cholestane-based conjugates, Bioorganic &
Medicinal Chemistry Letters, 23, 4315-18.
- Lee C., Yang, W. and Parr, R.G., 1988. Development
of the Colle-Salvetti correlation-energy
formula into a functional of the electron
density, Physical review B, 37, 785.
- Macrae C.F., Bruno, I.J., Chisholm, J.A., Edgington,
P.R., McCabe, P., Pidcock, E., Rodriguez-
Monge, L., Taylor, R., Streek, J.V. and
Wood, P.A., 2008. Mercury CSD 2.0–new
features for the visualization and
investigation of crystal structures, Journal
of Applied Crystallography, 41, 466-70.
- Mohamed T.A., Hassan A.E., Shaaban I.A., Abuelela
A.M.
and
Zoghaib
W.M.,
2017.
Conformational stability, spectral analysis
(infrared, Raman and NMR) and DFT
calculations of 2-Amino-5-(ethylthio)-1,3,4-
thiadiazole, Journal of Molecular Structure,
1130, 434-41.
- Padmavathi V., Kumara C.P., Venkatesh B.C.and
Padmaja A., 2011. Synthesis and
antimicrobial activity of amido linked
pyrrolyl and pyrazolyl-oxazoles, thiazoles
and imidazoles, European Journal of
Medicinal Chemistry, 46, 5317-26.
- Rollas S., 1981. Synthesis and spectrometric
analysis of some 1, 2, 4-triazoline-5-
thiones, J Fac Pharm Istanbul, 17, 155-63.
- Sancak K., Ünver Y. and Er M., 2007. Synthesis of 2-
Acylamino,
2-Aroylamino
and
Ethoxycarbonyl Imino-1,3,4-thiadiazoles as
Antitumor
Agents,
Turkish
Journal
Chemistry, 31, 125-34.
- Sheldrick G.M., 2015a. Crystal structure refinement
with SHELXL, Acta Crystallographica
Section C: Structural Chemistry, 71, 3-8.
- Shaaban I.A., Hassan A.E., Abuelela A.M., Zoghaib
W.M., and Mohamed T.A., 2016. Infrared,
Raman and NMR spectral analysis,
vibrational assignments,normal coordinate
analysis, and quantum mechanical
calculations of 2-Amino-5-ethyl-1,3,4-
thiadiazole, Journal of Molecular Structure,
1103, 70-81.
- Sheldrick G.M., 2015b. SHELXT–Integrated space-
group and crystal-structure determination,
Acta
Crystallographica
Section
A:
Foundations and Advances, 71, 3-8.
- Singh S.J., Rajamanickam, S., Gogoi, A., and Patel,
B.K., 2016. Synthesis of 2-amino-
substituted-1, 3, 4-thiadiazoles via 2, 3-
dichloro-5, 6-dicyano-1, 4-benzoquinone
(DDQ) mediated intramolecular C–S bond
formation
in
thiosemicarbazones,
Tetrahedron Letters, 57, 1044-47.
- Tehranchian S., Akbarzadeh, T., Fazeli, M.R.,
Jamalifar, H., and Shafiee, A., 2005.
Synthesis and antibacterial activity of 1-[1,
2, 4-triazol-3-yl] and 1-[1, 3, 4-thiadiazol-2-
yl]-3-methylthio-6, 7-dihydrobenzo [c]
thiophen-4 (5H) ones, Bioorganic &
Medicinal Chemistry Letters, 15, 1023-25.
- Trott O., and Olson, A.J., 2010. AutoDock Vina:
improving the speed and accuracy of
docking with a new scoring function,
efficient optimization, and multithreading,
Journal of Computational Chemistry, 31,
455-61.
- Wang C., Song, H., Liu, W., and Xu, C., 2016. Design,
synthesis and antifungal activity of novel
thioureas containing 1, 3, 4-thiadiazole and thioether skeleton, Chemical Research in
Chinese Universities, 32, 615-20.
- Wolinski K., Hinton, J.F., and Pulay, P., 1990.
Efficient implementation of the gauge-
independent atomic orbital method for
NMR chemical shift calculations, Journal of
the American Chemical Society, 112, 8251-
60.
- http://accelrys.com(07.12.2016)