Abstract
The one-pot, three component and facile synthesis of diethyl ((4-isopropylphenyl) (substitutedphenylamino)methyl)phosphonate 4a–4j has been achieved from the reaction of 4-isopropylbenzaldehyde 1 with various substituted amines 2a–2j and diethyl phosphite 3 using Kabachnik–Fields reaction under room temperature and solvent free conditions using nano Cu2O as a stable, noncorrosive, low-cost, recyclable, eco-friendly heterogeneous catalyst. Furthermore, melting point, IR, NMR, and mass spectra were used to interpret this new series of compounds. The newly synthesized formulations were evaluated in vitro for antioxidant and antimicrobial activity, and they executed well when compared to the standard.
Similar content being viewed by others
REFERENCES
Ali Khan, M., Rahman, A.A., Islam, S., Khandokhar, P., Shahnaj Parvin, S., Islam, M.B., Hossain, M., Rashid, M., Sadik, G., Nasrin, S., Mollah, M.N.H., and Khurshid, A.H.M., BMC Res. Notes, 2013, vol. 6, no. 24, p. 1. https://doi.org/10.1186/1756-0500-6-24
WHO Methods and Data Sources for Global Burden of Disease Estimates 2000–2011. WHO, Geneva, Switzerland: 2013.
Gupta, M., Sharma, R., and Kumar, A., Orient. Pharm. Exp. Med., 2019, vol. 19, no. 1, p. 259. https://doi.org/10.1007/s13596-019-00359-z
WHO Antimicrobial Resistance: Global Report on Surveillance. WHO, Geneva, Switzerland: 2014.
Baym, M., Stone, L.K., and Kishony, R., Science, 2016, vol. 351, no. 6268, p. 3292. https://doi.org/10.1126/science.aad3292
Cadez, T., Kolic, D., Sinko, G., and Kovarik, Z., Sci. Rep., 2021, vol. 11, no. 21486, p. 1. https://doi.org/10.1038/s41598-021-00953-9
Carraminana, V., Retana, A.M.O., and Palacios, F., Molecules, 2021, vol. 26, no. 2, p. 426. https://doi.org/10.3390/molecules26020426
Al Quntar, A.A.A., Dweik, H., and Dembitsky, V., Russ. J. Org. Chem., 2020, vol. 56, no. 1, p. 139. https://doi.org/10.1134/S1070428020010212
Smolobochkin, A.V., Turmanov, R.A., Gazizov, A.S., Kuznetsova, E.A., Burilov, A.R., and Pudovik, M.A., Russ. J. Org. Chem., 2020, vol. 56, no. 6, p. 1119. https://doi.org/10.1134/s107042802006024
Engel, R., Chem. Rev., 1977, vol. 77, no. 3, p. 349. https://doi.org/10.1021/cr60307a003
Hiratake, J. and Oda, J., Biosci., Biotech. Biochem., 1997, vol. 61, no. 2, p. 211. https://doi.org/10.1271/bbb.61.211
Moonen, K., Laureyn, I., and Stevens, C.V., Chem. Rev., 2004, vol.104, no. 12, p. 6177. https://doi.org/10.1021/cr030451c
Palacios, F., Alonso, C., and De los Santos, J.M., Curr. Org. Chem., 2004, vol. 8, no. 15, p.1481. https://doi.org/10.2174/1385272043369863
Schug, K.A. and Lindner, W., Chem. Rev., 2005, vol. 105, no. 1, p. 67. https://doi.org/10.1021/cr040603j
Smolobochkin, A.V., Gazizov, A.S., Doszhanova, K.A., Kuandykova, A.B., Jiyembayev, B.Z., Burilov, A.R., and Cherkasov, R.A., Russ. J. Gen. Chem., 2020, vol. 90, no. 6, p. 1100. https://doi.org/10.1134/s1070363220060274
Baylis, E.K., Campbell, C.D., and Dingwall, J.G., J. Chem. Soc., Perkin Trans., 1984, vol. 1, p. 2845. https://doi.org/10.1039/P19840002845
Sonar, S.S., Sadaphal, S.A., Labade, V.B., Shingate, B.B., and Shingare, M.S., Phosphor. Sulfur Silicon Rel. Elem., 2010, vol. 185, no. 1, p. 65. https://doi.org/10.1080/10426500802713259
Kumar, B.S., Sankar, A.U.R., Suresh Reddy, C., Nayak, S.K., and Naga Raju, C., Arkivoc, 2007, vol. 3, no. 13, p. 155.
Ouimette, D. and Coffey, M., Phytopathology, 1989, vol. 79, no. 1, p. 761. https://doi.org/10.1094/Phyto-79-761
Yang, S., Gao, X.W., and Diao, C.L., Chin. J. Chem., 2006, vol. 24, no. 11, p. 1581. https://doi.org/10.1002/cjoc.200690296
Xu, Y., Yan, K., Song, B., Xu, G., Song, Y., Wei, X., Deyu, H., Ping, L., Guiping, O., Linhong, J., and Zhuo, C., Molecules, 2006, vol. 11, no. 9, p. 666. https://doi.org/10.3390/11090666
Bloemink, M.J., Diederen, J.J.H., Dorenbos, J.P., Heetebrij, R.J., Keppler, B.K., and Reedijk, J., Eur. J. Inorg. Chem., 1999, vol. 1999, no. 10, p. 1655. https://doi.org/10.1002/(SICI)1099-0682(199910)1999:10<1655::AID-EJIC1655>3.0.CO;2-5
Jin, L., Song, B., Zhang, G., Xu, R., Zhang, S., Gao, X., Hu, D., and Yang, S., Bio. Med. Chem. Lett., 2006, vol. 16, p. 1537. https://doi.org/10.1016/j.bmcl.2006.07.048
Rao, X., Song, Z., and He, L. Het. Chem., 2008, vol. 19, p. 512. https://doi.org/10.1002/hc.20471
Disale, S.T., Kale, S.R., Kahandal, S.S., Srinivasan, T.G., and Jayaram, R.V., Tetrahedron Lett., 2012, vol. 53, no. 18, p. 2277. https://doi.org/10.1016/j.tetlet.2012.02.054
Thirumurugan, P., Nandakumar, A., Priya, N.S., Muralidaran, D., and Perumal, P., Tetrahedron Lett., 2010, vol. 51, no. 43, p. 5708. https://doi.org/10.1016/j.tetlet.2010.08.066
Reddy, P.S., Reddy, M.V.K., and Reddy, P.V.G., Chin. Chem. Lett., 2016, vol.27, no. 6, p. 943. https://doi.org/10.1016/j.cclet.2016.01.046
Tillu, V., Dumbre, D., Wakharkar, R., and Choudhary, V., Tetrahedron Lett., 2011, vol. 52, no. 8, p. 863. https://doi.org/10.1016/j.tetlet.2010.11.105
Taran, J., Ramazani, A., Aghahosseini, H., Gouranlou, F., Tarasi, R., Khoobi, M., and Joo, S.W., Phosphorus Sulfur Silicon Relat. Elem., 2017, vol. 192, no. 6, p. 776. https://doi.org/10.1080/10426507.2017.1290631
Rezaei, Z., Firouzabadi, H., and Iranpoor, N., Eur. J. Med. Chem., 2009, vol. 44, no. 11, p. 4266. https://doi.org/10.1016/j.ejmech.2009.07.009
Rezaei, Z., Khabnadideh, S., Zomorodian, K., Pakshir, K., Nadali, S., Mohtashami, N., and Mirzaei1, E.F., Int. J. Med. Chem., 2011, vol. 2011, no. 678101, p. 1, https://doi.org/10.1155/2011/678101
Hosseini-Sarvari, M., Tetrahedron, 2008, vol. 64, no. 23, p. 5459. https://doi.org/10.1016/j.tet.2008.04.016
Varga, P.R. and Keglevich, G.. Molecules, 2021, vol. 26, no. 9, p. 2511. https://doi.org/10.3390/molecules26092511
Abhinav, K.V., Rao, R.V.K., Karthik, P.S., and Singh, S.P., RSC Adv., 2015, vol. 5, no. 79, p. 63985. https://doi.org/10.1039/C5RA08205F
Hassani, H. and Jahani, Z., Russ. J. Org. Chem., 2020, vol. 56, no. 3, p. 485. https://doi.org/10.1134/s1070428020030185
Siripala, W., Ivanovskaya, A., Jaramillo, T.F., Sung, H., and McFarland, E.W., Sol. Energy Mater. Sol. Cells, 2003, vol. 77, no. 3, p. 229. https://doi.org/10.1016/S0927-0248(02)00343-4
Rao, C.N.R., Kulkarni, G.U., Thomas, P.J, and Edwards, P.P., Chem. Eur. J., 2002, vol. 8, no. 1, p. 28. https://doi.org/10.1002/1521-3765(20020104)8:1<28::AID-CHEM28>3.0.CO;2-B
White, R.J., Luque, R., Budarin, V.L., Clark, J.H., and Macquarrie, D., J. Chem. Soc. Rev., 2009, vol. 38, no. 2, p. 481. https://doi.org/10.1039/B802654H
Poizot, P., Laruelle, S., Grugeon, S., Dupont, L., and Tarascon, J.M., Nature, 2000, vol. 407, no. 1, p. 496. https://doi.org/10.1038/35035045
Alam, M.N., Bristi, N.J., and Rafiquzzaman, M., Saudi Pharm. J., 2013, vol. 21, no. 2, p. 143. https://doi.org/10.1016/j.jsps.2012.05.002
Choi, C.W., Kim, S.C., Hwang, S.S., Choi, B.K., Ahn, H.J., Lee, M.Y., Park, S.H., and Kim, S.K., Plant Sci., 2002, vol. 163, no. 6, p. 1161.
Yen, G.C. and Chen, H.Y., J. Agri. Food Chem., 1995, vol. 43, no. 1, p. 27.
Shirwaiker, A., Rajendran, K., and Dinesh kumar, C., Indian J. Exp. Biol., 2004, vol. 42, no. 8, p. 803.
Balouiri, M., Sadiki, M., and Ibnsouda, S.K., J. Pharm. Anal., 2016, vol. 6, no. 2, p. 71. https://doi.org/10.1016/j.jpha.2015.11.005
Funding
This work was financially supported by DST, New Delhi, India, for providing financial support to Sarva Santhisudha through Woman Scientist Scheme-A (WOS-A) (F. nos.: SR/WOS-A/CS-104/2018, Dated: 14-09-2020).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Rights and permissions
About this article
Cite this article
Sarva, S., Gundluru, M. & Cirandur, S.R. Facile Synthesis, Antioxidant and Antimicrobial Activities of Diethyl((4-isopropylphenyl)(substituted phenylamino)methyl)phosphonates. Russ J Gen Chem 92, 2108–2118 (2022). https://doi.org/10.1134/S1070363222100243
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363222100243