Synthesis of spirooxindolocarbamates based on Betti reaction: antibacterial, antifungal and antioxidant activities
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ORIGINAL ARTICLE
Synthesis of spirooxindolocarbamates based on Betti reaction: antibacterial, antifungal and antioxidant activities Venkata Bharat Nishtala1 · Chityala Mahesh2 · G. Bhargavi3 · Vijay Kumar Pasala2 · Srinivas Basavoju1 Received: 20 July 2019 / Accepted: 11 November 2019 © Springer Nature Switzerland AG 2019
Abstract A series of new spirooxindolocarbamates 4a–l and 6a–d were synthesized by using the Betti reaction. All the target compounds were well characterized by IR, NMR and mass spectrometry. The structures of the compounds 4a and 4e were confirmed by the single crystal X-ray diffraction. The in vitro antibacterial activity results revealed that the compounds 4f exhibited excellent antibacterial activity against E. coli with MIC value 7.5 µg/mL when compared with the standard drug ciprofloxacin with MIC value 9.25 µg/mL. The compounds 4l and 6c exhibit significant inhibiting activity against E. Coli with MIC values 10.5 µg/mL and 9.5 µg/mL, respectively. The compounds 4c and 4e showed significant activity against S. aureus with MIC value 10.5 µg/mL. The compounds 4a and 4f were exhibited moderate antifungal activity against A. niger with MIC values 17.5 µg/mL and 18.0 µg/mL, respectively. The compounds 4f and 4l exhibited the potent antioxidant activity with IC50 values 9.12 ± 0.01 µM and 7.06 ± 0.78 µM, respectively. Graphic abstract
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11030-019-10017-w) contains supplementary material, which is available to authorized users. Extended author information available on the last page of the article
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Molecular Diversity
Keywords Spirooxindolocarbamates · Betti reaction · Antibacterial activity · Antifungal activity · Antioxidant activity
Introduction In recent years, the multi-drug resistant (MDR) microbial infections became a major global concern for public health [1]. In this regard, design and synthesis of novel, efficient and safe antibiotics is the main objective to the chemists. Multi-component reactions (MCRs) are the best tools to synthesize diverse drug-like molecules because MCRs allow minimum three components to produce polyfunctional complex scaffolds in one-pot without isolation of intermediates [2–5]. Even though there are several multi-component approaches for the synthesis of the spirooxindoles [6, 7], the development of new synthetic strategies for the construction of these moieties by using MCRs is quite interesting. Spirooxindoles are versatile and pre-eminent structural units, which are most commonly present in a several biologically active natural products. Some of the biologically active spirooxindoles are shown in Fig. 1 [8, 9]. Organic carbamates have gained much attention from the chemists, because of their vital role in various fields like medicinal, agro, polymer chemistry etc., [10–14]. Particularly, in medicinal chemistry, the peptide-based drug-like molecules are modified by replacing with some unnatural linkages like carbamates to increase the
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