Liu Z, Zhang B, Xia S, Fang L, Gou S. ROS-responsive and multifunctional anti-Alzheimer prodrugs: tacrine-ibuprofen hybrids via a phenyl boronate linker. Eur J Med Chem. 2021;212:112997.

CAS  PubMed  Article  Google Scholar 

Zheng H, Fridkin M, Youdim M. New approaches to treating Alzheimer’s disease. Perspect Med Chem. 2015;7:S13210.

Article  Google Scholar 

Morphy R, Rankovic Z. Designed multiple ligands. An emerging drug discovery paradigm. J Med Chem. 2005;48:6523–43.

CAS  PubMed  Article  Google Scholar 

Asghar A, Yousuf M, Mubeen H, Nazir R, Haruna K, Onawole AT, et al. Synthesis, spectroscopic characterization, molecular docking and theoretical studies (DFT) of N-(4-aminophenylsulfonyl)-2-(4-isobutylphenyl) propanamide having potential enzyme inhibition applications. Bioorg Med Chem. 2019;27:2397–404.

CAS  PubMed  Article  Google Scholar 

Okulik N, Jubert AH. Theoretical study on the structure and reactive sites of three non-steroidal anti-inflammatory drugs: ibuprofen, naproxen and tolmetin acids. J Mol Struct THEOCHEM. 2006;769:135–41.

CAS  Article  Google Scholar 

Meunier B. Hybrid molecules with a dual mode of action: dream or reality? Acc Chem Res. 2008;41:69–77.

CAS  PubMed  Article  Google Scholar 

Asghar A, Yousuf M, Fareed G, Nazir R, Hassan A, Maalik A, et al. Synthesis, acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) activities, and molecular docking studies of a novel compound based on combination of flurbiprofen and isoniazide. RSC Adv. 2020;10:19346–52.

CAS  PubMed  PubMed Central  Article  Google Scholar 

Manolov S, Ivanov I, Bojilov D, Voynikov Y. Evaluation of antioxidant, anti-inflammatory and anti-arthritic activity of new ibuprofen derivatives. Bulg Chem Commun. 2021;66–71.

Weinheimer EM, Jemiolo B, Carroll CC, Harber MP, Haus JM, Burd NA, et al. Resistance exercise and cyclooxygenase (COX) expression in human skeletal muscle: implications for COX-inhibiting drugs and protein synthesis. Am J Physiol Regul Integr Comp Physiol. 2007;292:R2241–R8.

CAS  PubMed  Article  Google Scholar 

Amir M, Kumar S. Synthesis and evaluation of anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation properties of ibuprofen derivatives. Acta Pharm. 2007;57:31.

CAS  PubMed  Article  Google Scholar 

Kaufman DW, Kelly JP, Wiholm B-E, Laszlo A, Sheehan JE, Koff RS, et al. The risk of acute major upper gastrointestinal bleeding among users of aspirin and ibuprofen at various levels of alcohol consumption. Am J Gastroenterol. 1999;94:3189–96.

CAS  PubMed  Article  Google Scholar 

Bhandari SV, Bothara KG, Raut MK, Patil AA, Sarkate AP, Mokale VJ. Design, synthesis and evaluation of antiinflammatory, analgesic and ulcerogenicity studies of novel S-substituted phenacyl-1, 3, 4-oxadiazole-2-thiol and Schiff bases of diclofenac acid as nonulcerogenic derivatives. Bioorg Med Chem. 2008;16:1822–31.

CAS  PubMed  Article  Google Scholar 

Ahmadi A, Khalili M, Olama Z, Karami S, Nahri-Niknafs B. Synthesis and study of analgesic and anti-inflammatory activities of amide derivatives of ibuprofen. Mini Rev Med Chem. 2017;17:799–804.

CAS  PubMed  Article  Google Scholar 

Akgun H, Tozkoparan B, Ertan M, Aksu F, Inan S. Synthesis of some 2-arylpropionic acid amides as prodrugs. Arzneimittel-Forschung/Drug Res. 1996;46:91–4.

Cocco MT, Congiu C, Onnis V, Morelli M, Cauli O. Synthesis of ibuprofen heterocyclic amides and investigation of their analgesic and toxicological properties. Eur J Med Chem. 2003;38:513–8.

PubMed  Article  Google Scholar 

Bushra R, Aslam N. An overview of clinical pharmacology of ibuprofen. Oman Med J. 2010;25:155.

PubMed  PubMed Central  Article  Google Scholar 

Farooqi SI, Arshad N, Channar PA, Perveen F, Saeed A, Larik FA, et al. Synthesis, theoretical, spectroscopic and electrochemical DNA binding investigations of 1, 3, 4-thiadiazole derivatives of ibuprofen and ciprofloxacin: cancer cell line studies. J Photochem Photobiol B Biol. 2018;189:104–18.

CAS  Article  Google Scholar 

Channar PA, Saeed A, Larik FA, Bolte M, Erben MF. Ibuprofen-thiadiazole hybrid compounds: synthesis, vibrational analysis and molecular structure of 5-(1-(4-isobutylphenyl) ethyl)-1, 3, 4-thiadiazol-2-amine hydrochloride. J Mol Struct. 2019;1179:11–7.

CAS  Article  Google Scholar 

Elaridi J. Preparation and biological evaluation of novel acylhydrazide derivatives of 2, 3-dichloronaphthoquinone. 2017.

Mousa EF, Jassim IK. Preparation and characterization of oxadiazoles derived from ibuprofen. J Pharm Sci Res. 2018;10:2297–304.

CAS  Google Scholar 

Carey JS, Laffan D, Thomson C, Williams MT. Analysis of the reactions used for the preparation of drug candidate molecules. Org Biomol Chem. 2006;4:2337–47.

CAS  PubMed  Article  Google Scholar 

Habekost A. The analgesic metamizole (dipyrone) and its related products antipyrine, 4-aminoantipyrine and 4-methylaminoantipyrine. Part 1: mass spectrometric and electrochemical detection. World J Chem Educ. 2018;6:134–44.

CAS  Article  Google Scholar 

Kang AJ, Brown AK, Wong CS, Yuan Q. Removal of antibiotic sulfamethoxazole by anoxic/anaerobic/oxic granular and suspended activated sludge processes. Bioresour Technol. 2018;251:151–7.

CAS  PubMed  Article  Google Scholar 

Sakthivel M, Ramaraj S, Chen S-M, Dinesh B. Synthesis of rose like structured LaCoO3 assisted functionalized carbon nanofiber nanocomposite for efficient electrochemical detection of anti-inflammatory drug 4-aminoantipyrine. Electrochim Acta. 2018;260:571–81.

CAS  Article  Google Scholar 

Aiad IA, Tawfik SM, El-Shafie M, Rhman ALA. 4-Aminoantipyrine derived cationic surfactants: synthesis, characterization, surface activity and screening for potential antimicrobial activities. Egypt J Pet. 2018;27:327–34.

Article  Google Scholar 

Drillia P, Dokianakis S, Fountoulakis M, Kornaros M, Stamatelatou K, Lyberatos G. On the occasional biodegradation of pharmaceuticals in the activated sludge process: the example of the antibiotic sulfamethoxazole. J Hazard Mater. 2005;122:259–65.

CAS  PubMed  Article  Google Scholar 

Reddyrajula R, Dalimba U. The bioisosteric modification of pyrazinamide derivatives led to potent antitubercular agents: synthesis via click approach and molecular docking of pyrazine-1, 2, 3-triazoles. Bioorg Med Chem Lett. 2020;30:126846.

CAS  PubMed  Article  Google Scholar 

Whitfield MG, Soeters HM, Warren RM, York T, Sampson SL, Streicher EM, et al. A global perspective on pyrazinamide resistance: systematic review and meta-analysis. PLoS ONE. 2015;10:e0133869.

PubMed  PubMed Central  Article  Google Scholar 

Maccari R, Ottanà R, Vigorita MG. In vitro advanced antimycobacterial screening of isoniazid-related hydrazones, hydrazides and cyanoboranes: part 14. Bioorg Med Chem Lett. 2005;15:2509–13.

CAS  PubMed  Article  Google Scholar 

Panda SS, Girgis AS, Mishra BB, Elagawany M, Devarapalli V, Littlefield WF, et al. Synthesis, computational studies, antimycobacterial and antibacterial properties of pyrazinoic acid–isoniazid hybrid conjugates. RSC Adv. 2019;9:20450–62.

CAS  PubMed  PubMed Central  Article  Google Scholar 

Loncle C, Brunel JM, Vidal N, Dherbomez M, Letourneux Y. Synthesis and antifungal activity of cholesterol-hydrazone derivatives. Eur J Med Chem. 2004;39:1067–71.

CAS  PubMed  Article  Google Scholar 

Obaid AK, Aowda S, Idan AH, HabeebRadhi A. Synthesis and characterization of new Isoniazid Prodrug as anticancer agent. Int J ChemTech Res. 2016;9:521–8.

CAS  Google Scholar 

Nigade G, Chavan P, Deodhar M. Synthesis and analgesic activity of new pyridine-based heterocyclic derivatives. Med Chem Res. 2012;21:27–37.

CAS  Article  Google Scholar 

Makhija D, Somani R, Chavan A. Synthesis and pharmacological evaluation of antiinflammatory mutual amide prodrugs. Indian J Pharm Sci. 2013;75:353.

CAS  PubMed  PubMed Central  Article  Google Scholar 

Gundogdu-Hizliates C, Alyuruk H, Gocmenturk M, Ergun Y, Cavas L. Synthesis of new ibuprofen derivatives with their in silico and in vitro cyclooxygenase-2 inhibitions. Bioorg Chem. 2014;52:8–15.

CAS  PubMed  Article  Google Scholar 

McKerrow JH, Lipinski CA. The rule of five should not impede anti-parasitic drug development. Int J Parasitol Drugs Drug Resist. 2017;7:248–9.

PubMed  PubMed Central  Article  Google Scholar 

Pillai RR, Karrouchi K, Fettach S, Armaković S, Armaković SJ, Brik Y, et al. Synthesis, spectroscopic characterization, reactive properties by DFT calculations, molecular dynamics simulations and biological evaluation of Schiff bases tethered 1, 2, 4-triazole and pyrazole rings. J Mol Struct. 2019;1177:47–54.

CAS  Article  Google Scholar 

Merrick JP, Moran D, Radom L. An evaluation of harmonic vibrational frequency scale factors. J Phys Chem A. 2007;111:11683–700.

CAS  PubMed  Article  Google Scholar 

Azam F, Alabdullah NH, Ehmedat HM, Abulifa AR, Taban I, Upadhyayula S. NSAIDs as potential treatment option for preventing amyloid β toxicity in Alzheimer’s disease: an investigation by docking, molecular dynamics, and DFT studies. J Biomol Struct Dyn. 2018;36:2099–117.

CAS  PubMed  Article  Google Scholar 

Frau J, Muñoz F, Glossman-Mitnik D. Application of DFT concepts to the study of the chemical reactivity of some resveratrol derivatives through the assessment of the validity of the “Koopmans in DFT”(KID) procedure. J Theor Comput Chem. 2017;16:1750006.

Article  Google Scholar 

Zhan C-G, Nichols JA, Dixon DA. Ionization potential, electron affinity, electronegativity, hardness, and electron excitation energy: molecular properties from density functional theory orbital energies. J Phys Chem A. 2003;107:4184–95.