Synthesis, cytotoxicity, Pan-HDAC inhibitory activity and docking study of new N-(2-aminophenyl)-2-methylquinoline-4-carboxamide and (E)-N-(2-aminophenyl)-2-styrylquinoline-4-carboxamide derivatives as anticancer agents

Ouyang Y, Li J, Chen X, Fu X, Sun S, Wu Q. Chalcone derivatives: role in anticancer therapy. Biomolecules. 2021;11:894.

Article  CAS  Google Scholar 

Ramaiah MJ, Tangutur AD, Manyam RR. Epigenetic modulation and understanding of HDAC inhibitors in cancer therapy. Life Sci. 2021;277:119504.

Article  CAS  Google Scholar 

Routholla G, Pulya S, Patel T, Adhikari N, Amin SA, Paul M, et al. Design, synthesis and binding mode of interaction of novel small molecule o-hydroxy benzamides as HDAC3-selective inhibitors with promising antitumor effects in 4T1-Luc breast cancer xenograft model. Bioorg Chem. 2021;117:105446.

Article  CAS  Google Scholar 

Xiang Y-F, Qian C-W, Xing G-W, Hao J, Xia M, Wang Y-F. Anti-herpes simplex virus efficacies of 2-aminobenzamide derivatives as novel HSP90 inhibitors. Bioorg medicinal Chem Lett. 2012;22:4703–6.

Article  CAS  Google Scholar 

Mabkhot YN, Al-Majid AM, Barakat A, Al-Showiman SS, Al-Har MS, Radi S, et al. Synthesis and biological evaluation of 2-Aminobenzamide derivatives as antimicrobial agents: Opening/Closing pharmacophore site. Int J Mol Sci. 2014;15:5115–27.

Article  Google Scholar 

McClarty B, Rodriguez G, Dong H. Dose effects of histone deacetylase inhibitor tacedinaline (CI-994) on antipsychotic haloperidol-induced motor and memory side effects in aged mice. Front Neurosci. 2021;15:674745.

Article  Google Scholar 

Iaconelli J, Xuan L, Karmacharya R. HDAC6 modulates signaling pathways relevant to synaptic biology and neuronal differentiation in human stem cell-derived neurons. Int J Mol Sci. 2019;20:1605.

Article  CAS  Google Scholar 

Hamblett CL, Methot JL, Mampreian DM, Sloman DL, Stanton MG, Kral AM, et al. The discovery of 6-amino nicotinamides as potent and selective histone deacetylase inhibitors. Bioorg Med Chem Lett. 2007;17:5300–9.

Article  CAS  Google Scholar 

Routholla G, Pulya S, Patel T, Amin SA, Adhikari N, Biswas S, et al. Synthesis, biological evaluation, and molecular docking analysis of novel linker-less benzamide based potent and selective HDAC3 inhibitors. Bioorg Chem. 2021;114:105050.

Article  CAS  Google Scholar 

Omidkhah N, Eisvand F, Hadizadeh F, Zarghi A, Ghodsi R. synthesis, cytotoxicity, Pan-HDAC inhibitory activity and docking study of N-(2-Aminophenyl)-2-arylquinoline-4- and N-(2-Aminophenyl)-2-arylbenzo[h]quinoline-4-carboxamides**. ChemistrySelect. 2022;7(29):e202201239.

Omidkhah N, Hadizadeh F, Abnous K, Ghodsi R. Synthesis, structure activity relationship and biological evaluation of a novel series of quinoline–based benzamide derivatives as anticancer agents and histone deacetylase (HDAC) inhibitors. J Mol Struct. 2022;1267:133599. https://doi.org/10.1016/j.molstruc.2022.133599.

Article  CAS  Google Scholar 

Omidkhah N, Ghodsi R. NO-HDAC dual inhibitors. Eur J Med Chem. 2022;227:113934.

Article  CAS  Google Scholar 

Omidkhah N, Hadizadeh F, Ghodsi R. Dual HDAC/BRD4 inhibitors against cancer. Med Chem Res. 2021;30:1822–36.

Article  CAS  Google Scholar 

Tang C, Wang X, Jin Y, Wang F. Recent advances in HDAC-targeted imaging probes for cancer detection. Biochim Biophys Acta (BBA)-Rev Cancer. 2022;1877(5):188788.

Article  CAS  Google Scholar 

Su M, Gong X, Liu F. An update on the emerging approaches for histone deacetylase (HDAC) inhibitor drug discovery and future perspectives. Expert Opin Drug Discov. 2021;16:745–61.

Article  CAS  Google Scholar 

De Filippis B, Ammazzalorso A, Fantacuzzi M, Giampietro L, Maccallini C, Amoroso R. Anticancer activity of stilbene‐based derivatives. ChemMedChem. 2017;12:558–70.

Article  Google Scholar 

Khan ZA, Iqbal A, Shahzad SA. Synthetic approaches toward stilbenes and their related structures. Mol Diversity. 2017;21:483–509.

Article  Google Scholar 

Teka T, Lele Z, Xiaoyan G, Li Y, Lifeng H, Xiaohui Y. Stilbenes: Source plants, chemistry, biosynthesis, pharmacology, application and problems related to their clinical Application-A comprehensive review. Phytochemistry. 2022;197:113128.

Article  CAS  Google Scholar 

Penthala NR, Janganati V, Bommagani S, Crooks PA. Synthesis and evaluation of a series of quinolinyl trans-cyanostilbene analogs as anticancer agents. MedChemComm. 2014;5:886–90.

Article  CAS  Google Scholar 

Srivastava V, Lee H. Synthesis and bio-evaluation of novel quinolino-stilbene derivatives as potential anticancer agents. Bioorg Med Chem. 2015;23:7629–40.

Article  CAS  Google Scholar 

Hussain M, Singh DK, Singh A, Asad M, Ansari M, Shameem M, et al. A novel benzocoumarin-stilbene hybrid as a DNA ligase I inhibitor with in vitro and in vivo anti-tumor activity in breast cancer models. Sci Rep. 2017;7:1–14.

Article  Google Scholar 

Banik K, Ranaware AM, Harsha C, Nitesh T, Girisa S, Deshpande V, et al. Piceatannol: A natural stilbene for the prevention and treatment of cancer. Pharmacol Res. 2020;153:104635.

Article  CAS  Google Scholar 

Parida PK, Mahata B, Santra A, Chakraborty S, Ghosh Z, Raha S, et al. Inhibition of cancer progression by a novel trans-stilbene derivative through disruption of microtubule dynamics, driving G2/M arrest, and p53-dependent apoptosis. Cell Death Dis. 2018;9:1–18.

Article  CAS  Google Scholar 

Giardina GA, Sarau HM, Farina C, Medhurst AD, Grugni M, Raveglia LF, et al. Discovery of a novel class of selective non-peptide antagonists for the human neurokinin-3 receptor. 1. Identification of the 4-quinolinecarboxamide framework. J Med Chem. 1997;40:1794–807.

Article  CAS  Google Scholar 

Omidkhah N, Ghodsi R. Synthesis of novel 2-methyl-4-carboxyquinolines, the new by-products of the Doebner reaction. Synth Commun. 2021;51:1947–55.

CAS  Google Scholar 

Pashaei H, Rouhani A, Nejabat M, Hadizadeh F, Mirzaei S, Nadri H, et al. Synthesis and molecular dynamic simulation studies of novel N-(1-benzylpiperidin-4-yl) quinoline-4-carboxamides as potential acetylcholinesterase inhibitors. J Mol Struct. 2021;1244:130919.

Article  CAS  Google Scholar 

Namballa HK, Anchi P, Manasa KL, Soni JP, Godugu C, Shankaraiah N, et al. β-Carboline tethered cinnamoyl 2-aminobenzamides as class I selective HDAC inhibitors: Design, synthesis, biological activities and modelling studies. Bioorg Chem. 2021;117:105461.

Article  CAS  Google Scholar 

Zhang B, Zhang Q, Liu Z, Wang N, Jin H, Liu F, et al. Synthesis and anticancer research of N‐(2‐aminophenyl) benzamide acridine derivatives as dual topoisomerase I and isoform‐selective HDAC inhibitors. ChemistrySelect. 2020;5:8311–8.

Article  CAS  Google Scholar 

Zhang GH, Gan YH. Combination of Pan-HDAC inhibitor and COX-2 inhibitor produces synergistic anticancer effects in human salivary adenoid cystic cancer cells. Chin J Dent Res. 2019;22:221–7.

Google Scholar 

Cappellacci L, Perinelli DR, Maggi F, Grifantini M, Petrelli R. Recent progress in histone deacetylase inhibitors as anticancer agents. Curr Med Chem. 2020;27:2449–93.

Article  CAS  Google Scholar 

Eckschlager T, Plch J, Stiborova M, Hrabeta J. Histone deacetylase inhibitors as anticancer drugs. Int J Mol Sci. 2017;18:1414.

Article  Google Scholar 

Lavu S, Boss O, Elliott PJ, Lambert PD. Sirtuins—novel therapeutic targets to treat age-associated diseases. Nat Rev Drug Discov. 2008;7:841–53.

Article  CAS  Google Scholar 

Ediriweera MK, Tennekoon KH, Samarakoon SR. Emerging role of histone deacetylase inhibitors as anti-breast-cancer agents. Drug Discov Today. 2019;24:685–702.

Article  CAS  Google Scholar 

Bell EW, Zhang Y. DockRMSD: an open-source tool for atom mapping and RMSD calculation of symmetric molecules through graph isomorphism. J Cheminformatics. 2019;11:1–9.

Article  CAS  Google Scholar 

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 Deliv Rev. 1997;23:3–25.

Article  CAS  Google Scholar 

Duan Y-C, Jin L-F, Ren H-M, Zhang S-J, Liu Y-J, Xu Y-T, et al. Design, synthesis, and biological evaluation of novel dual inhibitors targeting lysine specific demethylase 1 (LSD1) and histone deacetylases (HDAC) for treatment of gastric cancer. Eur J Med Chem. 2021;220:113453.

Article  CAS  Google Scholar 

Bhal SK, Kassam K, Peirson IG, Pearl GM. The rule of five revisited: applying log D in place of log P in drug-likeness filters. Mol Pharmaceutics. 2007;4:556–60.

Article  CAS  Google Scholar 

Kaboudi N, Shayanfar A. Predicting the drug clearance pathway with structural descriptors. Eur J Drug Metab Pharmacokinetics. 2022;47:363–9.

Article  CAS  Google Scholar 

Pires DE, Blundell TL, Ascher DB. pkCSM: predicting small-molecule pharmacokinetic and toxicity properties using graph-based signatures. J Med Chem. 2015;58:4066–72.

Article  CAS  Google Scholar 

Yang F, Han L, Zhao N, Yang Y, Ge D, Zhang H, et al. Synthesis and biological evaluation of thiophene-based hydroxamate derivatives as HDACis with antitumor activities. Future Med Chem. 2020;12:655–72.

Article  CAS  Google Scholar 

Li X, Inks ES, Li X, Hou J, Chou CJ, Zhang J, et al. Discovery of the first N-hydroxycinnamamide-based histone deacetylase 1/3 dual inhibitors with potent oral antitumor activity. J Med Chem. 2014;57:3324–41.

Article  CAS  Google Scholar 

Belayet JB, Beamish S, Rahaman M, Alanani S, Virdi RS, Frick DN, et al. Development of a novel, small-molecule brain-penetrant histone deacetylase inhibitor that enhances spatial memory formation in mice. J Med Chem. 2022;65:3388–403.

Article  CAS  Google Scholar 

Krieger V, Hamacher A, Gertzen CG, Senger J, Zwinderman MR, Marek M, et al. Design, multicomponent synthesis, and anticancer activity of a focused histone deacetylase (HDAC) inhibitor library with peptoid-based cap groups. J Med Chem. 2017;60:5493–506.

Article  CAS  Google Scholar 

Avelar LAA, Schrenk C, Sönnichsen M, Hamacher A, Hansen FK, Schliehe-Diecks J, et al. Synergistic induction of apoptosis in resistant head and neck carcinoma and leukemia by alkoxyamide-based histone deacetylase inhibitors. Eur J Med Chem. 2021;211:113095.

Article 

留言 (0)

沒有登入
gif