Abstract
By acid-catalyzed reaction of substituted isatins with Girard’s reagent T, new water-soluble isatin-3-acylhydrazones were obtained with high yields. Their antimicrobial activity was evaluated. Selective activity against Gram-positive bacteria (S. aureus 209p and B. cereus 8035) and yeast-like fungus Candida albicans 855–653 along with low hematoxicity was established.
Graphical abstract
Similar content being viewed by others
References
Singh GS, Desta ZY (2012) Chem Rev 112:6104
Musin LI, Bogdanov AV, Mironov VF (2015) Chem Heterocycl Compd 51:421
Bogdanov AV, Musin LI, Mironov VF (2015) Arkivoc 6:362
Bogdanov AV, Mironov VF (2016) Chem Heterocycl Compd 52:90
Pakravan P, Kashanian S, Khodaei MM, Harding FJ (2013) Pharmacol Rep 65:313
Sriram D, Perumal Y (2003) Curr Med Chem 10:1689
Vine KL, Matesic L, Locke JM, Ranson M, Skropeta D (2009) Anti-Cancer Agents Med Chem 9:397
Ibrahim HS, Abou-Seri SM, Tan M, Elaasser MM, Abdel-Aziz HA, Supuran CT (2015) Eur J Med Chem 103:583
Wang J, Tan H, Li Y, Ma Y, Li Zh, Guddat LW (2011) J Agric Food Chem 59:9892
Aboul-Fadl T, Bin-Jubair FAS, Aboul-Wafa O (2010) Eur J Med Chem 45:4578
Havaldar FH, Patil AR (2008) Heterocycl Commun 14:107
El-Faham A, Hozzein WN, Wadaan MAM, Khattab ShN, Ghabbour HA, Fun H-K, Siddiqui MR (2015) J Chem 2015:1
Radwan AA (2013) Med Chem Res 22:1131
Bogdanov AV, Kutuzova TA, Mironov VF (2016) Russ J Gen Chem 86:756
Bogdanov AV, Bukharov SV, Oludina YUN, Musin LI, Nugumanova GN, Syakaev VV, Mironov VF (2013) Arkivoc 3:424
Bogdanov AV, Kutuzova TA, Krivolapov DB, Dobrynin AB, Mironov VF (2016) Russ J Gen Chem 86:539
Marvel CS, Hiers GS (1971) In: Gilman H (ed) Organic syntheses collective, vol 1. Wiley, New York, p 327
Shimazawa R, Kuriyama M, Shirai R (2008) Bioorg Med Chem Lett 18:3350
Shibinskaya MO, Kutuzova NA, Mazepa AV, Lyakhov SA, Andronati SA, Zubritsky MJU, Galat VF, Lipkowski J, Kravtsov VCH (2012) J Heterocycl Chem 49:678
Nugumanova GN, Bukharov SV, Tagasheva RG, Kurapova MV, Syakaev VV, Mukmeneva NA, Gurevich PA, Burilov AR (2007) Russ J Org Chem 43:1797
National Committee for Clinical Laboratory Standards (2000) Methods for dilution antimicrobial susceptibility. Tests for bacteria that grow aerobically: approved standard, 6th edn. NCCLS, Wayne
National Committee for Clinical Laboratory Standards (1998) Reference method for broth dilution antifungal susceptibility testing of conidium-forming filamentous fungi: proposed standard, M38-P. NCCLS, Wayne
Pashirova TN, Lukashenko SS, Zakharov SV, Voloshina AD, Zhiltsova EP, Zobov VV, Souto EB, Zakharova LYA (2015) Colloid Surf B Biointerf 127:266
Becke AD (1993) J Chem Phys 98:5648
Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03 (Revision B.04). Gaussian Inc, Wallingford
Sheldrick GM (2000) SHELXTL v.6.12, Structure Determination Software Suite. Bruker AXS, Madison
Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H (2009) J Appl Cryst 42:339
Acknowledgements
The work was supported by Russian Science Foundation (Grant No. 14-50-00014).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Bogdanov, A.V., Zaripova, I.F., Voloshina, A.D. et al. Synthesis and antimicrobial activity evaluation of some novel water-soluble isatin-3-acylhydrazones. Monatsh Chem 149, 111–117 (2018). https://doi.org/10.1007/s00706-017-2049-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-017-2049-y