Abstract
Looking at the importance of thiazine derivatives as biologically active compounds, herein we describe the synthesis of 4,6-diaryl-2-hydrazinyl-1,3-thiazines from the corresponding chalcones and thiosemicarbazide in the presence of sodium hydroxide on heating. The synthesized compounds were tested for their larvicidal activity against saltwater shrimp eggs (Artemia cysts), and some of the compounds showed good to excellent activities. Their in silico drug likeness was estimated.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Fu, P. and MacMillan, J.B., J. Nat. Prod., 2015, vol. 78, no. 3, p. 548. https://doi.org/10.1021/np500929z
Subba Reddy, B.V., Anji Babu, R., Ramana Reddy, M., Jagan Mohan Reddy, B., and Sridhar, B., RSC Adv., 2014, vol. 4, p. 44629. https://doi.org/10.1039/c4ra08208g
Dong, J.-L., Wei, P.-Sh., Yu, L.-S.-H., and Xie, J.-W., J. Org. Chem., 2018, vol. 83, p. 2219. https://doi.org/10.1021/acs.joc.7b03120
Oguma, T., Anan, K., Suzuki, Sh., Hisakawa, Sh., Takada, A., Ogawa, M., and Kusakabe, K.-i., J. Org. Chem., 2019, vol. 84, no. 8, p. 4893. https://doi.org/10.1021/acs.joc.8b02179
Wen, L.-R., Yuan, W.-K., and Li, M., J. Org. Chem., 2015, vol. 80, no. 10, p. 4942. https://doi.org/10.1021/acs.joc.5b00288
Wang, W., Zeng, F., Bie, Q., Dai, Ch., Chen, Ch., Tong, Q., Liu, J., Wang, J., Zhou, Y., Zhu, H., and Zhang, Y., Org. Lett., 2018, vol. 20, no. 21, p. 6817. https://doi.org/10.1021/acs.orglett.8b02942
Pouwer, R.H., Deydier, S.M., Phuc Van Le, Schwartz, B.D., Franken, N.C., Davis, R.A., Coster, M.J., Charman, S.A., Edstein, M.D., Skinner-Adams, T.S., Andrews, K.T., Jenkins, I.D., and Quinn, R.J., ACS Med. Chem. Lett., 2014, vol. 5, no. 2, p. 178. https://doi.org/10.1021/ml400447v
Li, Ch.-Sh., Ding, Y., Yang, B.-J., Miklossy, G., Yin, H.-Q., Walker, L.A., Turkson, J., and Cao, Sh., Org. Lett., 2015, vol. 17, p. 3556. https://doi.org/10.1021/acs.orglett.5b01650
Kalirajan, R., Gaurav, K., Pandiselvi, A., Gowramma, B., and Sankar, S., Anti-Cancer Agents Med Chem., 2019, vol. 19, no. 11, p. 1350. https://doi.org/10.2174/1871520619666190408134224
Sousa, J.R., Silva, F.A., Targanski, S.K., Fazolo, B.R., Souza, J.M., Campos, M.G., Vieira, L.C.C., de Oliveira Mendes, T.A., and Soares, M.A., J. Appl. Entomol., 2019, vol. 143, no. 10, p. 1172. https://doi.org/10.1111/jen.12685
Pisutthanana, S., Plianbangchang, P., Pisutthanana, N., Ruanruaya, S., and Muanrita, O., Naresuan Univ. J.: Sci. Technol., 2004, vol. 12, p. 13.
ACKNOWLEDGMENTS
The authors thank Dr. C. Purushottham Reddy (Chancellor), Prof. B. Prasanna (Late) (Chiatanya Deemed to be University, Warangal), and Prof. P.V. Srilakshmi (National Institute of Technology, Warangal) for their encouragement and suggestions in the research work.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflict of interest.
Supplementary information
Rights and permissions
About this article
Cite this article
Velidandi, A., Kannuri, R. & Thupurani, M.K. Synthesis, In Silico Studies, and Larvicidal Activity of Novel Hydrazinyl 1,3-Thiazine Derivatives. Russ J Org Chem 58, 814–819 (2022). https://doi.org/10.1134/S1070428022060094
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428022060094