ORIGINAL PAPER Synthesis and bio-evaluation of quaternary centered 3-hydroxy-3-(trifluoromethyl)indolin-2-one derivatives for anticancer and antimicrobial activities Raktani Bikshapathi 1 • Parvathaneni Sai Prathima 1 • B. Yashwanth 2 • R. Pamanji 2 • G. Jagadeeshkumar 1 • R. Maheshwari 2 • J. Venkateswara Rao 2 • U. S. N. Murty 2 • V. Jayathirtha Rao 1 Received: 4 March 2016 / Accepted: 17 April 2016 Ó Springer-Verlag Wien 2016 Abstract A series of C(3)-trifluoromethylated com- pounds derived from N-substituted isatins were synthesized. The biological activity of all 3-hydroxy-3- (trifluoromethyl)indolin-2-one derivatives have been eval- uated for in vitro cytotoxic activity and antibacterial activity. The active compounds were screened against nuclear xenobiotic receptor CAR (PDB ID: 1XLS), PIM1 kinase (PDB ID: 2O65), and CDK2 kinase (PDB ID: 3QHR) by using in silico molecular docking studies to obtain lead molecules. In addition to its potential anti- cancer activity, 5-bromo-3-ethynyl-3-hydroxy-1-(prop-2- yn-1-yl)indolin-2-one also showed specific antibacterial activity against S. aureus. Graphical abstract N HO O CF 3 R 1 R = benzyl, ethyl, methyl, allyl, propargyl, phenyl R 1 = chloro, bromo, iodo R Keywords Trifluoromethyl group Á Oxindoles Á Cyototoxicity Á 3-Hydroxy-3-(trifluoromethyl)indolin-2- one derivatives Introduction Isatin scaffold binds to wide range of bioactive targets and can, therefore, be applicable to various clinical indications [1, 2]. Thus, it is reasonable to explore replacements, or modifications, to the isatin core at highly active C(3) position. Much interest has been intended for the study of 3-hydroxyoxindoles possessing substituents at their 3-po- sition due to their biological significance [3, 4]. In particular, compounds containing these structural moieties are serving as targets for drug design and synthesis with high synthetic versatility. In particular 3-substituted 3-hydroxyoxindole is a promising scaffold for drug discovery with a broad spec- trum of biological activities including antiviral, antibacterial, anti-inflammatory, antifungal, anticonvulsant and new targets for cancer chemotherapy [5]. Several pharmacologically active alkaloids such as arundaphine, CPC-1, donaxaridine, welwitindolinone C in addition to several others contain 3-hydroxyoxindole moiety [6]. Isatin derivatives have received considerable attention due to their potent anticancer activities [7]. A number of reviews have been focused on the diverse range of bio- logical activities displayed by isatin analogs obtained by derivatization of the isatin nitrogen and C(2)/C(3) carbonyl moieties [8]. Advances in the development of more potential isatin-based chemotherapeutics and selectively deliverable conjugates are highly desirable. The incorporation of fluorine or CF 3 groups has attrac- ted increasing interests in the drug design for enhancing the Electronic supplementary material The online version of this article (doi:10.1007/s00706-016-1764-0) contains supplementary material, which is available to authorized users. & Parvathaneni Sai Prathima saiprathimaiict@gmail.com & V. Jayathirtha Rao jrao@iict.res.in 1 Crop Protection Chemicals Division, Organic II, CSIR-Indian Institute of Chemical Technology (IICT), Uppal Road, Tarnaka, Hyderabad 500607, India 2 Biology Division, IICT, Hyderabad, India 123 Monatsh Chem DOI 10.1007/s00706-016-1764-0