Novel 1,3,4-thiadiazole compounds derived from 4- phenylbutyric acid: Synthesis, characterization and DFT studies

Abstract

In this study; new 1,3,4-thiadiazole compounds were synthesized and their structural characterization were carried out by using FT-IR, ¹H-NMR, ¹³C-NMR spectroscopic methods, and elemental analysis. Furthermore, the absorption properties of the synthesized compounds were also studied with UV-Vis. spectrophotometer. In addition, molecular conformation, electronic properties and UV-vis analysis of synthesized 1,3,4-thiadiazole compounds were theoretically investigated by using density functional theory (DFT), and how F, Cl and methoxy isomers affected the molecular configuration was analyzed.

Keywords

• 134-thiadiazole
• butyric acid
• absorption
• DFT

Yeni 4-fenilbütirik asit türevi 1,3,4-tiyadiazol bileşikleri: Sentezi, karakterizasyonu ve DFT çalışmaları

Abstract

Bu çalışmada; literatürde daha önce sentezlenmemiş 1,3,4-tiyadiazol bileşikleri sentezlendi. Sentezlenen bu bileşiklerin FT-IR, ¹H-NMR, ¹³C-NMR spektroskopik yöntemleri ve elementel analiz kullanılarak yapı tayini gerçekleştirildi. Daha sonra UV-vis. spektrofotometre cihazı kullanılarak elde edilen bileşiklerin absorpsiyon özellikleri de incelendi. Ayrıca, yoğunluk fonksiyonel teorisi (DFT) kullanılarak, sentezlenen 1,3,4-tiyadiazol bileşiklerinin moleküler konformasyonu, elektronik konfigürasyonu ve UV-vis analizleri teorik olarak yapılmış, F, Cl ve metoksi izomerlerinin moleküler konfigürasyonu nasıl etkilediği analiz edildi.

Keywords

• 134-thiadiazole
• butirik asit
• absorpsiyon
• DFT

References

1. Goerdeler, J., Ohm, J., and Tegtmeyer, O., Darstellung und Eigenschaften des 1,2,4‐und des 1,3,4‐Thiodiazols. Chemische Berichte, 89, 1534-1543, (1956).
2. Foroumadi, A., Soltani, F., Moshafi, M.H., and Ashraf-Askari, R., Synthesis and in vitro antibacterial activity of some N-(5-aryl-1,3,4-thiadiazole-2-yl)piperazinyl quinolone derivatives. II Farmaco, 58, 10, 1023-1028 (2003).
3. Chen, C.J., Song, B.A., Yang, S., Xu, G.F., Bhadury, P.S., Jin, L.H., Hu, D.Y., Li, Q.Z., Liu, F., Xue, W., Lu, P., and Chen Z., Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives. Bioorganic and Medicinal Chemistry, 15, 3981-3989 (2007). Kolavi, G., Hegde, V., Khazi, I.A., and Gadad P., Synthesis and evaluation of antitubercular activity of imidazo[2,1-b][1,3,4]thiadiazole derivatives. Bioorganic and Medicinal Chemistry, 14, 3069-3080 (2006).
4. Poorrajab, F., Ardestani, S.K., Emani, S., Behrouzi- Fardmoghadam, M., Shafiee, A., and Foroumadi, A., Nitroimidazolyl-1,3,4-thiadiazole-based anti-leishmanial agents: Synthesis and in vitro biological evaluation. European Journal of Medicinal Chemistry, 44, 1758-1762 (2009).
5. Hafez, H.N., Hegab, M.I., Ahmed-Farag, I.S., and El-Gazzar A.B.A., A facile regioselective synthesis of novel spiro-thioxanthene and spiro-xanthene-9′,2-[1,3,4]thiadiazole derivatives as potential analgesic and anti-inflammatory agents. Bioorganic and Medicinal Chemistry, 18, 4538-4543 (2008).
6. Yusuf, M., Khan, R.A., and Ahmed, B., Syntheses and anti-depressant activity of 5-amino-1, 3, 4-thiadiazole-2-thiol imines and thiobenzyl derivatives. Bioorganic and Medicinal Chemistry, 16, 8029-8034 (2008).
7. Kaur H., Kumar S., Vishwakarma P., Sharma M., Saxena K.K. and Kumar A., Synthesis and antipsychotic and anticonvulsant activity of some new substituted oxa/thiadiazolylazetidinonyl/thiazolidinonylcarbazoles. European Journal of Medicinal Chemistry, 45, 2777-2783 (2010).
8. Jatav, V., Mishra, P., Kashaw, S., and Stables J.P., CNS depressant and anticonvulsant activities of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones. European Journal of Medicinal Chemistry. 43,1945-1954 (2008).

9. Gadad, A.K., Karki, S.S., Rajurkar, V. ., and Bhongade, B. ., Synthesis and Biological Evaluation of 5-Formyl-6-arylimidazo(2,1-b)-1,3,4-thiadiazole-2-N-(dimethylaminomethino)sulfonamides as Antitumor Agents. Arzneimittelforschung / Drug Research, 49, 858-863 (1999).
10. Senff-Ribeiro, A., Echevarria, A., Silva, E.F., Franco, C.R.C., Veiga, S.S., and Oliveira M.B.M., Cytotoxic effect of a new 1,3,4-thiadiazolium mesoionic compound (MI-D) on cell lines of human melanoma. British Journal of Cancer, 91, 297-304 (2004).
11. Kumar, D., Kumar, N. .M., Chang, K.H., and Shah, K., Synthesis and anticancer activity of 5-(3-indolyl)-1,3,4-thiadiazoles. European Journal of Medicinal Chemistry., 45, 4664-4668 (2010). Asbury, R.F., Kramar, A.M.S., and Haller, D.G.M.D., Aminothiadiazole (NSC #4728) in Patients with Advanced Colon Cancer A Phase II Study of the Eastern Cooperative Oncology Group. American Journal of Clinical Oncology, 10, 380-382 (1987).
12. Elson, P.J., Kvols, L.K., Vogel, S.E., Glover, D.J., Hahn, R.G., Trump, D.L., Carbone, P. P., Earle, J.D., and Davis, T.E., Phase II trials of 5-day vinblastine infusion (NSC 49842), L-alanosine (NSC 153353), acivicin (NSC 163501), and aminothiadiazole (NSC 4728) in patients with recurrent or metastatic renal cell carcinoma. Investigation New Drugs, 6, 97-103 (1988).
13. Locker, G.Y., Kilton, L., Khandekar, J.D., Lad, T.E., Knop, R.H., Albain, K., Blough, R., French, S., and Benson, A.B., High-dose aminothiadiazole in advanced colorectal cancer. Investigatioal New Drugs, 12, 299-301 (1994). Asbury, R.M.D, Blessing, J.A., Smith, D.M.M.D., and Carson, L.F,M.D., Aminothiadiazole in the Treatment of Advanced Leiomyosarcoma of the Uterine Corpus: A Gynecologic Oncology Group Study. American Journal of Clinical Oncology 18, 397-399 (1995).
14. Balaji, K., Bhatt, P., Mallika, D., and Jha, A., Design, synthesis and antimicrobial evaluation of some mannich base derivative of 2(2-substituted)-5-amino-thiadiazoles. International Journal of Pharmacy and Pharmaceutical Sciences, 7, 145-149 (2015).
15. Mohamed, T.A., Hassan, A.E., Shaaban, I. A., Abuelela, A.M., and Zoghaib, W.M., 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, 434-441 (2017).
16. Sánchez-Bojorge, N.A., Rodríguez-Valdez, L.M., García-Cruz, I., and Flores-Holguín, N., Unexpected electron acceptor behavior of the 1,3,4-thiadiazole oligomer, a DFT study. Computational and Theoretical Chemistry, 1068, 109-116 (2015).
17. Emamian, S., Generation of a substituted 1,2,4-thiadiazole ring via the [3+2] cycloaddition reaction of benzonitrile sulfide toward trichloroacetonitrile. A DFT study of the regioselectivity and of the molecular mechanism. Comptes Rendus Chimie, 18, 1277-1283 (2015).
18. Dani, R.K., Bharty, M.K., Kushawaha, S.K., Paswan, S., Prakash, O., Singh, R. K., and Singh, N.K., Syntheses, spectral, X-ray and DFT studies of 5-benzyl-N-phenyl-1,3,4-thiadiazol-2-amine, 2-(5-phenyl-1,3,4-thiadiazol-2-yl) pyridine and 2-(5-methyl-1,3,4-thiadiazole-2-ylthio)-5-methyl-1,3,4-thiadiazole obtained by Mn(II) catalyzed reactions. Journal of Molecular Structure, 1054–1055, 251-261 (2013).
19. Romano, E., Ladetto, M.F., and Brandán, S.A., Structural and vibrational studies of the potential anticancer agent, 5-difluoromethyl-1,3,4-thiadiazole-2-amino by DFT calculations. Computational and Theoretical Chemistry, 1011, 57-64 (2013).
20. Prouillac, C., Vicendo, P., Garrigues, J.C., Poteau, R., and Rima, G., Evaluation of new thiadiazoles and benzothiazoles as potential radioprotectors: Free radical scavenging activity in vitro and theoretical studies (QSAR, DFT). Free Radical Biology and Medicine, 46, 1139-1148 (2009).
21. Gür, M., Şener, N., Muğlu, H., Çavuş, M. S., Özkan, O.E., Kandemirli, F., and Şener, İ., New 1,3,4-thiadiazole compounds including pyrazine moiety: Synthesis, structural properties and antimicrobial features. Journal of Molecular Structure, 1139,111-118 (2017).
22. Gaussian 09, Revision B.01, Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalmani G., Barone V., Mennucci B., Petersson G.A., Nakatsuji H., Caricato M., Li X., Hratchian H.P., Izmaylov A.F., Bloino J., Zheng G., Sonnenberg J.L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J.A., Jr., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.N., Staroverov V.N., Keith T., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Rega N., Millam J.M., Klene M., Knox J.E., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Martin R.L., Morokuma K., Zakrzewski V.G., Voth G.A., Salvador P., Dannenberg J.J., Dapprich S., Daniels A. D., Farkas O., Foresman J.B., Ortiz J.V., Cioslowski J., Fox D. J., Gaussian, Inc., Wallingford CT (2010).