Synthesis of Novel Gabapentin Scaffold Derived Hydrazide-hydrazones for Potential Antimicrobial agents and Antioxidants
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ORIGINAL ARTICLE
Synthesis of Novel Gabapentin Scaffold Derived Hydrazide‑hydrazones for Potential Antimicrobial agents and Antioxidants Ramya Krishna Pallapati1 · Baby Ramana Mutchu1 · Bala Murali Krishna Khandapu1 · Umamaheswara Rao Vanga2 · Ravi Varala3 · Hari Babu Bollikolla1 Received: 28 July 2020 / Accepted: 7 September 2020 © The Tunisian Chemical Society and Springer Nature Switzerland AG 2020
Abstract Twelve new analogues of gabapentin (GBP) derived hydrazide-hydrazone scaffolds were produced by using various electronically and structurally divergent aromatic aldehydes. All the hydrazones were obtained in moderate to good yields (66–82%) by heating the GBP hydrazide with respective aldehydes to a temperature of 45–65 °C for 4–7 h. Further, the compounds were explored for their antimicrobial activity on three different Gram positive (Micrococcus luteus, Streptococcus mutans, Enterococcus faecalis) and Gram negative bacterial strains (Salmonella enterica, Alcaligenes faecalis, Pseudomonas aeruginosa). The antibacterial results obtained were found to be good against Gram positive bacteria when compared to Gram negative bacteria. Moreover, the compounds were also screened for antioxidant activity at four different concentrations using the DPPH method and the results showed that some of the compounds were moderately active. Keywords Gabapentin · Hydrazide-hydrazone · Antioxidant · Antimicrobial · DPPH method
1 Introduction Gabapentin (GBP) is a structural analogue of the inhibitory neurotransmitter γ-amino-butyric acid (GABA) and chemically called as 1-(aminomethyl) cyclohexane acetic acid (Fig. 1) [1]. It is available with the trade name Neurontin and other available brands include Horizant and Gralise. It was first approved by the Medicines and Healthcare products Regulatory Agency (MHRA) in 1993 as an oral add-on therapy for the treatment of partial seizures and later in 2000 for peripheral neuropathy.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s42250-020-00184-x) contains supplementary material, which is available to authorized users. * Hari Babu Bollikolla [email protected] 1
Department of Chemistry, Acharya Nagarjuna University, Nnagar, Guntur, Andhra Pradesh 522510, India
2
Department of Botany & Microbiology, Acharya Nagarjuna University, Nnagar, Guntur, Andhra Pradesh 522510, India
3
Scrips Pharma, Mallapur, Hyderabad, Telangana 500076, India
It is probably one of the most effective agents of the newer generation of antiepileptics used for the treatment of neuropathic pain [2, 3]. The analogues of gabapentin were studied for various other purposes such as nitric oxide release derivative [4] and as a cisplatin-induced neuropathic pain model [5]. This was the recently developed derivative of gabapentin for neuropathic pain model and involves the reaction of amine functionality of gabapentin with salicylaldehyde [5]. Schwarz et al. [6] have synthesized novel cyclopropyl β-amino acid analogues of gabapentin which target the
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