Research Article
BibTex RIS Cite

Synthesis and Characterization of New Series Benzothiazole-Dithiocarbamate Derivatives As Potential Antifungal Agents

Year 2022, Volume: 24 Issue: 70, 105 - 110, 17.01.2022

Derya Osmaniye Begüm Nurpelin Saglik

https://doi.org/10.21205/deufmd.2022247011

Abstract

Invasive fungal infections (IFIs) have been and will continue to be a great threat to human. Nowadays the aim of many medical research is to discover new safer and more effective antifungal agents. Benzothiazole compounds are important fragments in medicinal chemistry because of their wide range of biological activities. Furthermore, dithiocarbamate compounds have become important for many activities due to their chemical structure. In this study, it was aimed to determine being antifungal agents capacity of newly synthesized benzothiazole compounds including dithiocarbamate moiety. The structures of the obtained compounds were elucidated using by 1H-NMR, 13C-NMR and mass spectroscopy.

Keywords

Benzothiazole Dithiocarbamate NMR Antifungal activity

References

  • Lino, C. I., de Souza, I. G., Borelli, B. M., Matos, T. T. S., Teixeira, I. N. S., Ramos, J. P., ... & de Oliveira, R. B. 2018. Synthesis, molecular modeling studies and evaluation of antifungal activity of a novel series of thiazole derivatives: European Journal of Medicinal Chemistry, vol. 151, pp. 248-260. DOI: 10.1016/j.ejmech.2018.03.083
  • Łukowska-Chojnacka, E., Kowalkowska, A., Gizińska, M., Koronkiewicz, M., Staniszewska, M. 2019. Synthesis of tetrazole derivatives bearing pyrrolidine scaffold and evaluation of their antifungal activity against Candida albicans: European journal of medicinal chemistry, vol. 164, pp, 106-120. DOI: 10.1016/j.ejmech.2018.12.044
  • Zhao, L., Tian, L., Sun, N., Sun, Y., Chen, Y., Wang, X., Zhao, S., Su, X., Zhao, D., Cheng, M. 2019. Design, synthesis, and structure-activity relationship studies of l-amino alcohol derivatives as broad-spectrum antifungal agents: European journal of medicinal chemistry, vol. 177, pp. 374-385. DOI: 10.1016/j.ejmech.2019.05.047
  • Li, B., Wang, K., Zhang, R., Li, B., Shen, Y., Ji, Q. 2019. Design, synthesis and biological evaluation of novel diazaspiro [4.5] decan-1-one derivatives as potential chitin synthase inhibitors and antifungal agents: European journal of medicinal chemistry, vol. 182, pp. 111669. DOI: 10.1016/j.ejmech.2019.111669
  • El Shehry, M. F., Ghorab, M. M., Abbas, S. Y., Fayed, E. A., Shedid, S. A., Ammar, Y. A. 2018. Quinoline derivatives bearing pyrazole moiety: Synthesis and biological evaluation as possible antibacterial and antifungal agents: European journal of medicinal chemistry, vol. 143, pp. 1463-1473. DOI: doi.org/10.1016/j.ejmech.2017.10.046
  • Chandrika, N. T., Dennis, E. K., Shrestha, S. K., Ngo, H. X., Green, K. D., Kwiatkowski, S., ... & Garneau-Tsodikova, S. 2019. N, N′-diaryl-bishydrazones in a biphenyl platform: Broad spectrum antifungal agents: European journal of medicinal chemistry, vol. 164, pp. 273-281. DOI: 10.1016/j.ejmech.2018.12.042
  • Wang, L. L., Battini, N., Bheemanaboina, R. R. Y., Zhang, S. L., Zhou, C. H. 2019. Design and synthesis of aminothiazolyl norfloxacin analogues as potential antimicrobial agents and their biological evaluation: European journal of medicinal chemistry, vol. 167, pp. 105-123. DOI: 10.1016/j.ejmech.2019.01.072
  • Nalawade, J., Shinde, A., Chavan, A., Patil, S., Suryavanshi, M., Modak, M., ... & Mhaske, P. C. 2019. Synthesis of new thiazolyl-pyrazolyl-1, 2, 3-triazole derivatives as potential antimicrobial agents: European Journal of Medicinal Chemistry, vol. 179, pp. 649-659. DOI: 10.1016/j.ejmech.2019.06.074
  • Sari, S., Kart, D., Öztürk, N., Kaynak, F. B., Gencel, M., Taşkor, G., ... & Dalkara, S. 2019. Discovery of new azoles with potent activity against Candida spp. and Candida albicans biofilms through virtual screening: European journal of medicinal chemistry, vol. 179, pp. 634-648. DOI: 10.1016/j.ejmech.2019.06.083
  • Elias, R., Benhamou, R. I., Jaber, Q. Z., Dorot, O., Zada, S. L., Oved, K., ... & Fridman, M. 2019. Antifungal activity, mode of action variability, and subcellular distribution of coumarin-based antifungal azoles: European journal of medicinal chemistry, vol. 179, pp. 779-790. DOI: 10.1016/j.ejmech.2019.07.003
  • Ji, Q., Deng, Q., Li, B., Li, B., & Shen, Y. 2019. Design, synthesis and biological evaluation of novel 5-(piperazin-1-yl) quinolin-2 (1H)-one derivatives as potential chitin synthase inhibitors and antifungal agents: European journal of medicinal chemistry, vol. 180, pp. 204-212. DOI: 10.1016/j.ejmech.2019.07.035
  • Zhao, S., Zhao, L., Zhang, X., Liu, C., Hao, C., Xie, H., ... & Cheng, M. 2016. Design, synthesis, and structure-activity relationship studies of benzothiazole derivatives as antifungal agents: European journal of medicinal chemistry, vol. 123, pp. 514-522. DOI: 10.1016/j.ejmech.2016.07.067
  • Catalano, A., Carocci, A., Defrenza, I., Muraglia, M., Carrieri, A., Van Bambeke, F., ... & Franchini, C. 2013. 2-Aminobenzothiazole derivatives: search for new antifungal agents: European journal of medicinal chemistry, vol. 64, pp. 357-364. DOI: 10.1016/j.ejmech.2013.03.064
  • Singh, M. K., Tilak, R., Nath, G., Awasthi, S. K., Agarwal, A. 2013. Design, synthesis and antimicrobial activity of novel benzothiazole analogs: European journal of medicinal chemistry, vol. 63, pp. 635-644. DOI: 10.1016/j.ejmech.2013.02.027
  • Payaz, D. Ü., Küçükbay, F. Z., Küçükbay, H., Angeli, A., Supuran, C. T. 2019. Synthesis carbonic anhydrase enzyme inhibition and antioxidant activity of novel benzothiazole derivatives incorporating glycine, methionine, alanine, and phenylalanine moieties: Journal of enzyme inhibition and medicinal chemistry, vol. 34(1), pp. 343-349. DOI: 10.1080/14756366.2018.1553040.
  • Durmaz, R., Köroğlu, M., Küçükbay, H. A. S. A. N., Temel, I., Ozer, M. K., Refiq, M., Cetinkaya, E., Cetinkaya, B., Yoloğlu, S. 1998. Investigation of serum minimal inhibitory concentrations of some benzimidazole, imidazole and benzothiazole derivatives and their effects on liver and renal functions. Arzneimittel-forschung, vol. 48(12), pp. 1179-1184.
  • Küçükbay, H. , Durmaz, B. 1997. Antifungal activity of organic and organometallic derivatives of benzimidazole and benzothiazole. Arzneimittel-forschung, vol. 47(5), pp. 667-670.
  • Mangasuli, S. N., Hosamani, K. M., Managutti, P. B. 2019. Synthesis of novel coumarin derivatives bearing dithiocarbamate moiety: An approach to microwave, molecular docking, Hirshfeld surface analysis, DFT studies and potent anti-microbial agents: Journal of Molecular Structure, vol. 1195, pp. 58-72. DOI: 10.1016/j.molstruc.2018.12.049
  • Rodriguez-Tudela, J.L., Barchiesi, F. 2008. Subcommittee on Antifungal Susceptibility Testing (AFST). EUCAST Definitive Document EDef 7.1: Method for the determination of broth dilution MICs of antifungal agents for fermentative yeast: Clinical Microbiology and Infection, vol. 14(4), pp. 398-405. DOI: /10.1111/j.1469-0691.2007.01935.x
  • Karaburun, A., Acar Çevik, U., Osmaniye, D., Sağlık, B., Kaya Çavuşoğlu, B., Levent, S., Ozkay, Y., Koparal, A.S., Behcet, M., Kaplancıklı, Z. 2018. Synthesis and Evaluation of New 1, 3, 4-Thiadiazole Derivatives as Potent Antifungal Agents, Molecules, vol. 23(12), pp. 3129. DOI: 10.3390/molecules23123129
  • Osmaniye, D., Kaya Cavusoglu, B., Saglik, B. N., Levent, S., Acar Cevik, U., Atli, O., Ozkay, Y., Kaplancikli, Z. A. 2018. Synthesis and anticandidal activity of new imidazole-chalcones: Molecules, 23(4), 831. DOI: 10.3390/molecules23040831

Potansiyel Antifungal Ajanlar Olarak Yeni Benzotiyazol-Ditiyokarbamat Türevlerinin Sentezi ve Karakterizasyonu

Year 2022, Volume: 24 Issue: 70, 105 - 110, 17.01.2022

Derya Osmaniye Begüm Nurpelin Saglik

https://doi.org/10.21205/deufmd.2022247011

Abstract

İnvaziv mantar enfeksiyonları (IFI'lar) insan için büyük bir tehdit olmuştur ve olmaya devam edecektir. Günümüzde birçok tıbbi araştırmanın amacı yeni daha güvenli ve daha etkili antifungal ajanlar bulmaktır. Benzotiyazol bileşikleri, çok çeşitli biyolojik aktiviteleri nedeniyle farmasötik kimyada önemli bir farmakofor yapıdır. Ayrıca, ditiyokarbamat bileşikleri kimyasal yapıları nedeniyle birçok aktivite için önemli hale gelmiştir. Bu çalışmada, yeni sentezlenen benzotiyazol-ditiyokarbamat bileşiklerinin antifungal etkinliklerinin belirlenmesi amaçlanmıştır. Elde edilen bileşiklerin yapıları, 1H-NMR, 13C-NMR ve kütle spektroskopisi kullanılarak aydınlatılmıştır.

Keywords

Benzotiyazol Ditiyokarbamat NMR Antifungal aktivite

References

  • Lino, C. I., de Souza, I. G., Borelli, B. M., Matos, T. T. S., Teixeira, I. N. S., Ramos, J. P., ... & de Oliveira, R. B. 2018. Synthesis, molecular modeling studies and evaluation of antifungal activity of a novel series of thiazole derivatives: European Journal of Medicinal Chemistry, vol. 151, pp. 248-260. DOI: 10.1016/j.ejmech.2018.03.083
  • Łukowska-Chojnacka, E., Kowalkowska, A., Gizińska, M., Koronkiewicz, M., Staniszewska, M. 2019. Synthesis of tetrazole derivatives bearing pyrrolidine scaffold and evaluation of their antifungal activity against Candida albicans: European journal of medicinal chemistry, vol. 164, pp, 106-120. DOI: 10.1016/j.ejmech.2018.12.044
  • Zhao, L., Tian, L., Sun, N., Sun, Y., Chen, Y., Wang, X., Zhao, S., Su, X., Zhao, D., Cheng, M. 2019. Design, synthesis, and structure-activity relationship studies of l-amino alcohol derivatives as broad-spectrum antifungal agents: European journal of medicinal chemistry, vol. 177, pp. 374-385. DOI: 10.1016/j.ejmech.2019.05.047
  • Li, B., Wang, K., Zhang, R., Li, B., Shen, Y., Ji, Q. 2019. Design, synthesis and biological evaluation of novel diazaspiro [4.5] decan-1-one derivatives as potential chitin synthase inhibitors and antifungal agents: European journal of medicinal chemistry, vol. 182, pp. 111669. DOI: 10.1016/j.ejmech.2019.111669
  • El Shehry, M. F., Ghorab, M. M., Abbas, S. Y., Fayed, E. A., Shedid, S. A., Ammar, Y. A. 2018. Quinoline derivatives bearing pyrazole moiety: Synthesis and biological evaluation as possible antibacterial and antifungal agents: European journal of medicinal chemistry, vol. 143, pp. 1463-1473. DOI: doi.org/10.1016/j.ejmech.2017.10.046
  • Chandrika, N. T., Dennis, E. K., Shrestha, S. K., Ngo, H. X., Green, K. D., Kwiatkowski, S., ... & Garneau-Tsodikova, S. 2019. N, N′-diaryl-bishydrazones in a biphenyl platform: Broad spectrum antifungal agents: European journal of medicinal chemistry, vol. 164, pp. 273-281. DOI: 10.1016/j.ejmech.2018.12.042
  • Wang, L. L., Battini, N., Bheemanaboina, R. R. Y., Zhang, S. L., Zhou, C. H. 2019. Design and synthesis of aminothiazolyl norfloxacin analogues as potential antimicrobial agents and their biological evaluation: European journal of medicinal chemistry, vol. 167, pp. 105-123. DOI: 10.1016/j.ejmech.2019.01.072
  • Nalawade, J., Shinde, A., Chavan, A., Patil, S., Suryavanshi, M., Modak, M., ... & Mhaske, P. C. 2019. Synthesis of new thiazolyl-pyrazolyl-1, 2, 3-triazole derivatives as potential antimicrobial agents: European Journal of Medicinal Chemistry, vol. 179, pp. 649-659. DOI: 10.1016/j.ejmech.2019.06.074
  • Sari, S., Kart, D., Öztürk, N., Kaynak, F. B., Gencel, M., Taşkor, G., ... & Dalkara, S. 2019. Discovery of new azoles with potent activity against Candida spp. and Candida albicans biofilms through virtual screening: European journal of medicinal chemistry, vol. 179, pp. 634-648. DOI: 10.1016/j.ejmech.2019.06.083
  • Elias, R., Benhamou, R. I., Jaber, Q. Z., Dorot, O., Zada, S. L., Oved, K., ... & Fridman, M. 2019. Antifungal activity, mode of action variability, and subcellular distribution of coumarin-based antifungal azoles: European journal of medicinal chemistry, vol. 179, pp. 779-790. DOI: 10.1016/j.ejmech.2019.07.003
  • Ji, Q., Deng, Q., Li, B., Li, B., & Shen, Y. 2019. Design, synthesis and biological evaluation of novel 5-(piperazin-1-yl) quinolin-2 (1H)-one derivatives as potential chitin synthase inhibitors and antifungal agents: European journal of medicinal chemistry, vol. 180, pp. 204-212. DOI: 10.1016/j.ejmech.2019.07.035
  • Zhao, S., Zhao, L., Zhang, X., Liu, C., Hao, C., Xie, H., ... & Cheng, M. 2016. Design, synthesis, and structure-activity relationship studies of benzothiazole derivatives as antifungal agents: European journal of medicinal chemistry, vol. 123, pp. 514-522. DOI: 10.1016/j.ejmech.2016.07.067
  • Catalano, A., Carocci, A., Defrenza, I., Muraglia, M., Carrieri, A., Van Bambeke, F., ... & Franchini, C. 2013. 2-Aminobenzothiazole derivatives: search for new antifungal agents: European journal of medicinal chemistry, vol. 64, pp. 357-364. DOI: 10.1016/j.ejmech.2013.03.064
  • Singh, M. K., Tilak, R., Nath, G., Awasthi, S. K., Agarwal, A. 2013. Design, synthesis and antimicrobial activity of novel benzothiazole analogs: European journal of medicinal chemistry, vol. 63, pp. 635-644. DOI: 10.1016/j.ejmech.2013.02.027
  • Payaz, D. Ü., Küçükbay, F. Z., Küçükbay, H., Angeli, A., Supuran, C. T. 2019. Synthesis carbonic anhydrase enzyme inhibition and antioxidant activity of novel benzothiazole derivatives incorporating glycine, methionine, alanine, and phenylalanine moieties: Journal of enzyme inhibition and medicinal chemistry, vol. 34(1), pp. 343-349. DOI: 10.1080/14756366.2018.1553040.
  • Durmaz, R., Köroğlu, M., Küçükbay, H. A. S. A. N., Temel, I., Ozer, M. K., Refiq, M., Cetinkaya, E., Cetinkaya, B., Yoloğlu, S. 1998. Investigation of serum minimal inhibitory concentrations of some benzimidazole, imidazole and benzothiazole derivatives and their effects on liver and renal functions. Arzneimittel-forschung, vol. 48(12), pp. 1179-1184.
  • Küçükbay, H. , Durmaz, B. 1997. Antifungal activity of organic and organometallic derivatives of benzimidazole and benzothiazole. Arzneimittel-forschung, vol. 47(5), pp. 667-670.
  • Mangasuli, S. N., Hosamani, K. M., Managutti, P. B. 2019. Synthesis of novel coumarin derivatives bearing dithiocarbamate moiety: An approach to microwave, molecular docking, Hirshfeld surface analysis, DFT studies and potent anti-microbial agents: Journal of Molecular Structure, vol. 1195, pp. 58-72. DOI: 10.1016/j.molstruc.2018.12.049
  • Rodriguez-Tudela, J.L., Barchiesi, F. 2008. Subcommittee on Antifungal Susceptibility Testing (AFST). EUCAST Definitive Document EDef 7.1: Method for the determination of broth dilution MICs of antifungal agents for fermentative yeast: Clinical Microbiology and Infection, vol. 14(4), pp. 398-405. DOI: /10.1111/j.1469-0691.2007.01935.x
  • Karaburun, A., Acar Çevik, U., Osmaniye, D., Sağlık, B., Kaya Çavuşoğlu, B., Levent, S., Ozkay, Y., Koparal, A.S., Behcet, M., Kaplancıklı, Z. 2018. Synthesis and Evaluation of New 1, 3, 4-Thiadiazole Derivatives as Potent Antifungal Agents, Molecules, vol. 23(12), pp. 3129. DOI: 10.3390/molecules23123129
  • Osmaniye, D., Kaya Cavusoglu, B., Saglik, B. N., Levent, S., Acar Cevik, U., Atli, O., Ozkay, Y., Kaplancikli, Z. A. 2018. Synthesis and anticandidal activity of new imidazole-chalcones: Molecules, 23(4), 831. DOI: 10.3390/molecules23040831
There are 21 citations in total.

Details

Primary Language English
Journal Section Research Article
Authors

Derya Osmaniye 0000-0002-0499-436X

Begüm Nurpelin Saglik 0000-0002-0151-6266

Publication Date January 17, 2022
Published in Issue Year 2022 Volume: 24 Issue: 70

Cite

APA Osmaniye, D., & Saglik, B. N. (2022). Synthesis and Characterization of New Series Benzothiazole-Dithiocarbamate Derivatives As Potential Antifungal Agents. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen Ve Mühendislik Dergisi, 24(70), 105-110. https://doi.org/10.21205/deufmd.2022247011
AMA Osmaniye D, Saglik BN. Synthesis and Characterization of New Series Benzothiazole-Dithiocarbamate Derivatives As Potential Antifungal Agents. DEUFMD. January 2022;24(70):105-110. doi:10.21205/deufmd.2022247011
Chicago Osmaniye, Derya, and Begüm Nurpelin Saglik. “Synthesis and Characterization of New Series Benzothiazole-Dithiocarbamate Derivatives As Potential Antifungal Agents”. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen Ve Mühendislik Dergisi 24, no. 70 (January 2022): 105-10. https://doi.org/10.21205/deufmd.2022247011.
EndNote Osmaniye D, Saglik BN (January 1, 2022) Synthesis and Characterization of New Series Benzothiazole-Dithiocarbamate Derivatives As Potential Antifungal Agents. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi 24 70 105–110.
IEEE D. Osmaniye and B. N. Saglik, “Synthesis and Characterization of New Series Benzothiazole-Dithiocarbamate Derivatives As Potential Antifungal Agents”, DEUFMD, vol. 24, no. 70, pp. 105–110, 2022, doi: 10.21205/deufmd.2022247011.
ISNAD Osmaniye, Derya - Saglik, Begüm Nurpelin. “Synthesis and Characterization of New Series Benzothiazole-Dithiocarbamate Derivatives As Potential Antifungal Agents”. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi 24/70 (January 2022), 105-110. https://doi.org/10.21205/deufmd.2022247011.
JAMA Osmaniye D, Saglik BN. Synthesis and Characterization of New Series Benzothiazole-Dithiocarbamate Derivatives As Potential Antifungal Agents. DEUFMD. 2022;24:105–110.
MLA Osmaniye, Derya and Begüm Nurpelin Saglik. “Synthesis and Characterization of New Series Benzothiazole-Dithiocarbamate Derivatives As Potential Antifungal Agents”. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen Ve Mühendislik Dergisi, vol. 24, no. 70, 2022, pp. 105-10, doi:10.21205/deufmd.2022247011.
Vancouver Osmaniye D, Saglik BN. Synthesis and Characterization of New Series Benzothiazole-Dithiocarbamate Derivatives As Potential Antifungal Agents. DEUFMD. 2022;24(70):105-10.

Dokuz Eylül Üniversitesi, Mühendislik Fakültesi Dekanlığı Tınaztepe Yerleşkesi, Adatepe Mah. Doğuş Cad. No: 207-I / 35390 Buca-İZMİR.