2,540
Views
0
CrossRef citations to date
0
Altmetric
Research Article

Synthesis biological evaluation and molecular docking of isatin hybrids as anti-cancer and anti-microbial agents

, , , , &
Article: 2288548 | Received 28 Sep 2023, Accepted 22 Nov 2023, Published online: 11 Dec 2023

References

  • Sartori A, Portioli E, Battistini L, Calorini L, Pupi A, Vacondio F, Arosio D, Bianchini F, Zanardi F. Synthesis of novel c(Amp-RGD)-sunitinib dual conjugates as molecular tools targeting the αβ integrin/VEGFR2 couple and impairing tumor-associated angiogenesis. J Med Chem. 2017;60(1):248–262.
  • Chiyanzu I, Hansell E, Gut J, Rosenthal PJ, McKerrow JH, Chibale K. Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain. Bioorg Med Chem Lett. 2003;13(20):3527–3530.
  • Vine KL, Matesic L, Locke JM, Ranson M, Skropeta D. Cytotoxic and anticancer activities of isatin and its derivatives: a comprehensive review from 2000–2008. Anticancer Agents Med Chem. 2009;9(4):397–414.
  • Raj AA, Raghunathan R, SrideviKumari MR, Raman N. Synthesis, antimicrobial and antifungal activity of a new class of spiro pyrrolidines. Bioorg Med Chem. 2003;11(3):407–419.
  • Mathur G, Nain S. Recent advancement in synthesis of isatin as anticonvulsant agents: a review. Med Chem. 2014;4(4):417–427.
  • Rakesh KP, Ramesh S, Kumar HM, Chandan S, Gowda DC. Quinazolinones linked amino acids derivatives as a new class of promising antimicrobial, antioxidant and anti-inflammatory agents. Eur J Chem. 2015;6(3):254–260.
  • Zhang X, Marichannegowda MH, Rakesh KP, Qin H-L. Master mechanisms of Staphylococcus aureus: consider its excellent protective mechanisms hindering vaccine development! Microbiol Res. 2018;212–213:59–66.
  • Verma R, Verma SK, Rakesh KP, Girish YR, Ashrafizadeh M, Sharath Kumar KS, Rangappa KS. Pyrazole-based analogs as potential antibacterial agents against methicillin-resistance Staphylococcus aureus (MRSA) and its SAR elucidation. Eur J Med Chem. 2021;212:113134.
  • Moku B, Ravindar L, Rakesh KP, Qin H-L. The significance of N-methylpicolinamides in the development of anticancer therapeutics: synthesis and structure–activity relationship (SAR) studies. Bioorg Chem. 2019;86:513–537.
  • Ravindar L, Bukhari SNA, Rakesh KP, Manukumar HM, Vivek HK, Mallesha N, Xie Z-Z, Qin H-L. Aryl fluorosulfate analogues as potent antimicrobial agents: SAR, cytotoxicity and docking studies. Bioorg Chem. 2018;81:107–118.
  • Rakesh KP, Darshini N, Manukumar HM, Vivek HK, Eissa MYH, Prasanna DS, Mallesha N. Xanthone conjugated amino acids as potential anticancer and DNA binding agents: molecular docking, cytotoxicity and SAR studies. Anticancer Agents Med Chem. 2018;18(15):2169–2177.
  • Ullas BJ, Rakesh KP, Shivakumar J, Gowda CD, Chandrashekar PG. Multi-targeted quinazolinone-Schiff’s bases as potent bio-therapeutics. Results Chem. 2020;2:100067.
  • Wang S, Zhao Y, Zhang G, Lv Y, Zhang N, Gong P. Design, synthesis and biological evaluation of novel 4-thiazolidinones containing indolin-2-one moiety as potential antitumor agent. Eur J Med Chem. 2011;46(8):3509–3518.
  • Singh A, Kaur H, Arora S, Singh Bedi PM. Design, synthesis, and biological evaluation of novel morpholinated isatin–quinoline hybrids as potent anti-breast cancer agents. Arch Pharm. 2021;355(2):e2100368.
  • Heer S, Kaur K, Gulati HK, Kumar N, Sharma A, Singh J, Bhagat K, Kaur G, Kaur K, Singh H, et al. Design, synthesis, and biological evaluation of isatin-indole-3-carboxaldehyde hybrids as a new class of xanthine oxidase inhibitors. Arch Pharm. 2022;355(6):e2200033.
  • Singh A, Kaur K, Kaur H, Mohana P, Arora S, Bedi N, Chadha R, Bedi PMS. Design, synthesis and biological evaluation of isatin–benzotriazole hybrids as new class of anti-Candida agents. J Mol Struct. 1274;1274:134456.
  • Zhai X, He Y, Yang Z, Gong P. Syntheses and antiproliferative activities of novel diarylthiosemicarbazide derivatives. Chem Res Chin Univ. 2013;29(1):62–66.
  • Majumder A, Gupta R, Mandal M, Babu M, Chakraborty D. Air-stable palladium(0) phosphine sulfide catalysts for Ullmann-type C–N and C–O coupling reactions. J Organomet Chem. 2015;781:23–34.
  • Jain R, Bansal M. A facile synthesis and central nervous system activities of fluorine-containing spiro-[3H-indole-3,4′(4H)-pyran]-2(1H)ones. Pharmazie. 1995;50:224–225.
  • Friedel M, Marko ND, Tang W. Inhibition of cyclin-dependent kinase 1 (CDK1) by indirubin derivatives in human tumour cells. Nat Cell Biol. 1999;1:60.
  • Eldehna WM, Altoukhy A, Mahrous H, Abdel-Aziz HA. Design, synthesis and QSAR study of certain isatin–pyridine hybrids as potential anti-proliferative agents. Eur J Med Chem. 2015;90:684–694.
  • Vintonyak VV, Warburg K, Kruse H, Grimme S, Hübel K, Rauh D, Waldmann H. Identification of thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of the Mycobacterium tuberculosis protein tyrosine phosphatase B. Angew Chem Int Ed Engl. 2010;49(34):5902–5905.
  • Bari A, Grenier D, Azelmat J, Syed SA, Al-Obaid AM, Hosten EC. Synthesis and anti-inflammatory activity of diversified heterocyclic systems. Chem Biol Drug Des. 2019;94(4):1750–1759.
  • Bari A, Ghani U, Syed SA, Riazullah  . Thiosemicarbazide binds with the dicopper center in the competitive inhibition of mushroom tyrosinase enzyme: synthesis and molecular modeling of theophylline analogues. Bioorg Med Chem Lett. 2021;36:127826.
  • Ragavendran JV, Sriram D, Patel SK, Reddy IV, Bharathwajan N, Stables J, Yogeeswari P. Design and synthesis of anticonvulsants from a combined phthalimide–GABA–anilide and hydrazone pharmacophore. Eur J Med Chem. 2007;42(2):146–151.
  • Mologni L, Rostagno R, Brussolo S, Knowles PP, Kjaer S, Murray-Rust J, Rosso E, Zambon A, Scapozza L, McDonald NQ, et al. Synthesis, structure–activity relationship and crystallographic studies of 3-substituted indolin-2-one RET inhibitors. Bioorg Med Chem. 2010;18(4):1482–1496.
  • Liang Z, Zhang D, Ai J, Chen L, Wang H, Kong X, Zheng M, Liu H, Luo C, Geng M, et al. Identification and synthesis of N′-(2-oxoindolin-3-ylidene)hydrazide derivatives against c-Met kinase. Bioorg Med Chem Lett. 2011;21(12):3749–3754.
  • Refer to supplementary data for complete details.
  • Refer to supplementary data for antimicrobial procedures and sample preparations.
  • Poustforoosh A, Hashemipour H, Tüzün B, Azadpour M, Faramarz S, Pardakhty A, Mehrabani M, Nematollahi MH. The impact of D614G mutation of SARS-COV-2 on the efficacy of anti-viral drugs: a comparative molecular docking and molecular dynamics study. Curr Microbiol. 2022;79(8):241.
  • Kekeçmuhammed H, Tapera M, Tüzün B, Akkoç S, Zorlu Y, Sarıpınar E. Synthesis, molecular docking and antiproliferative activity studies of a thiazole-based compound linked to hydrazone moiety. ChemistrySelect. 2022;7(26):e202201502.
  • Lipinski CA. Lead-and drug-like compounds: the rule-of-five revolution. Drug Discov Today Technol. 2004;1(4):337–341.
  • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Delivery Rev. 1997;23(1–3):3–25.
  • Jorgensen WJ, Duffy EM. Prediction of drug solubility from structure. Adv Drug Deliv Rev. 2002;54(3):355–366.
  • Schrödinger Release 2021-3: Maestro. New York (NY): Schrödinger, LLC; 2021.
  • Singh A, Sharma S, Arora S, Attri S, Kaur P, Kaur Gulati H, Bhagat K, Kumar N, Singh H, Vir Singh J, et al. New coumarin–benzotriazole based hybrid molecules as inhibitors of acetylcholinesterase and amyloid aggregation. Bioorg Med Chem Lett. 2020;30(20):127477.
  • Singh A, Kaur H, Singh H, Singh B, Bedi PMS, Kaur S. Ameliorative effects of Grewia asiatica leaves in animal models of pain and inflammation. J Herbs Spices Med Plants. 2022;29(1):63–72.
  • Schrödinger Release 2021-3: protein preparation wizard. New York (NY)/New York (NY)/New York (NY): Epik, Schrödinger, LLC/Impact, Schrödinger, LLC/Prime, Schrödinger, LLC; 2021.
  • Schrödinger Release 2021-3: LigPrep. New York (NY): Schrödinger, LLC; 2021.
  • Shahzadi I, Zahoor AF, Tüzün B, Mansha A, Anjum MN, Rasul A, Irfan A, Kotwica-Mojzych K, Mojzych M. Repositioning of acefylline as anti-cancer drug: synthesis, anticancer and computational studies of azomethines derived from acefylline tethered 4-amino-3-mercapto-1,2,4-triazole. PLOS One. 2022;17(12):e0278027.
  • Schrödinger Release 2021-3: QikProp. New York (NY): Schrödinger, LLC; 2021.