Synthesis, kinetic studies and in-silico investigations of novel quinolinyl-iminothiazolines as alkaline phosphatase inhibitors

References

• Straus DS, Glass CK. Anti-inflammatory actions of PPAR ligands: new insights on cellular and molecular mechanisms. Trends Immunol. 2007;28(12):551–558.
   PubMed Web of Science ®Google Scholar
• Chang TC, Wang JK, Hung MW, Chiao CH, Tsai LC, Chang GG. Regulation of the expression of alkaline phosphatase in a human breast-cancer cell line. Biochem J. 1994;303(1):199–205.
   PubMedGoogle Scholar
• al‐Rashida M, Iqbal J. Therapeutic potentials of ecto‐nucleoside triphosphate diphosphohydrolase, ecto‐nucleotide pyrophosphatase/phosphodiesterase, ecto‐5′‐nucleotidase, and alkaline phosphatase inhibitors. Med Res Rev. 2014;34(4):703–743.
   PubMed Web of Science ®Google Scholar
• Ali AT, Penny CB, Paiker JE, Psaras G, Ikram F, Crowther NJ. The effect of alkaline phosphatase inhibitors on intracellular lipid accumulation in preadipocytes isolated from human mammary tissue. Ann Clin Biochem. 2006;43(Pt 3):207–213.
   PubMedGoogle Scholar
• Llinas P, Stura EA, Ménez A, Kiss Z, Stigbrand T, Millán JL, Le Du MH. Structural studies of human placental alkaline phosphatase in complex with functional ligands. J Mol Biol. 2005;350(3):441–451.
   PubMed Web of Science ®Google Scholar
• Sundström B, Johansson B, Hietala SO, Stigbrand T. Radio-immunolocalization in nude mice using anticytokeratin monoclonal antibodies. Tumour Biol. 1990;11(3):158–166.
   PubMedGoogle Scholar
• Orsaria M, Londero AP, Marzinotto S, Di Loreto C, Marchesoni D, Mariuzzi L. Placental type alkaline phosphatase tissue expression in ovarian serous carcinoma. Cancer Biomark. 2016;17(4):479–486.
   PubMed Web of Science ®Google Scholar
• Hanschkow M, Boulet N, Kempf E, Bouloumié A, Kiess W, Stein R, Körner A, Landgraf K. Expression of the adipocyte progenitor markers MSCA1 and CD36 is associated with adipose tissue function in children. J Clin Endocrinol Metab. 2022;107(2):e836–e851.
   PubMed Web of Science ®Google Scholar
• Tuin A, Poelstra K, de Jager-Krikken A, Bok L, Raaben W, Velders MP, Dijkstra G. Role of alkaline phosphatase in colitis in man and rats. Gut. 2009;58(3):379–387.
   PubMed Web of Science ®Google Scholar
• Su F, Brands R, Wang Z, Verdant C, Bruhn A, Cai Y, Raaben W, Wulferink M, Vincent JL. Beneficial effects of alkaline phosphatase in septic shock. Crit Care Med. 2006;34(8):2182–2187.
   PubMed Web of Science ®Google Scholar
• Alam SN, Yammine H, Moaven O, Ahmed R, Moss AK, Biswas B, Muhammad N, Biswas R, Raychowdhury A, Kaliannan K, et al. Intestinal alkaline phosphatase prevents antibiotic-induced susceptibility to enteric pathogens. Ann Surg. 2014;259(4):715–722.
   PubMed Web of Science ®Google Scholar
• Anderson HC. The role of matrix vesicles in physiological and pathological calcification. Curr Opin Orthop. 2007;18(5):428–433.
   Google Scholar
• van der Heijde D, Kivitz A, Schiff MH, Sieper J, Dijkmans BAC, Braun J, Dougados M, Reveille JD, Wong RL, Kupper H, ATLAS Study Group, et al. Efficacy and safety of adalimumab in patients with ankylosing spondylitis: results of a multicenter, randomized, double-blind, placebo-controlled trial. Arthritis Rheum. 2006;54(7):2136–2146.
   PubMed Web of Science ®Google Scholar
• Brandt J, Khariouzov A, Listing J, Haibel H, Sörensen H, Grassnickel L, Rudwaleit M, Sieper J, Braun J. Six‐month results of a double‐blind, placebo‐controlled trial of etanercept treatment in patients with active ankylosing spondylitis. Arthritis Rheum. 2003;48(6):1667–1675.
   PubMed Web of Science ®Google Scholar
• van der Heijde D, Dijkmans B, Geusens P, Sieper J, DeWoody K, Williamson P, Braun J, Ankylosing Spondylitis Study for the Evaluation of Recombinant Infliximab Therapy Study Group. Efficacy and safety of infliximab in patients with ankylosing spondylitis: results of a randomized, placebo‐controlled trial (ASSERT). Arthritis Rheum. 2005;52(2):582–591.
   PubMed Web of Science ®Google Scholar
• Antoni C, Krueger GG, de Vlam K, Birbara C, Beutler A, Guzzo C, Zhou B, Dooley LT, Kavanaugh A, IMPACT 2 Trial Investigators. Infliximab improves signs and symptoms of psoriatic arthritis: results of the IMPACT 2 trial. Ann Rheum Dis. 2005;64(8):1150–1157.
   PubMed Web of Science ®Google Scholar
• Li L, Chang L, Pellet-Rostaing S, Liger F, Lemaire M, Buchet R, Wu Y. Synthesis and evaluation of benzo [b] thiophene derivatives as inhibitors of alkaline phosphatases. Bioorg Med Chem. 2009;17(20):7290–7300.
   PubMed Web of Science ®Google Scholar
• Narisawa S, Harmey D, Yadav MC, O'Neill WC, Hoylaerts MF, Millán JL. Novel inhibitors of alkaline phosphatase suppress vascular smooth muscle cell calcification. J Bone Miner Res. 2007;22(11):1700–1710.
   PubMed Web of Science ®Google Scholar
• Maslat AO, Abussaud M, Tashtoush H, Al-Talib M. Synthesis, antibacterial, antifungal and genotoxic activity of bis-1, 3, 4-oxadiazole derivatives. Pol J Pharmacol. 2002;54(1):55–59.
   PubMedGoogle Scholar
• Barsu N, Sen M, Premkumar JR, Sundararaju B. Cobalt (iii) catalyzed C–8 selective C–H and C–O coupling of quinoline N-oxide with internal alkynes via C–H activation and oxygen atom transfer. Chem Commun (Camb)). 2016;52(7):1338–1341.
   PubMed Web of Science ®Google Scholar
• Baird JK, Rieckmann KH. Can primaquine therapy for vivax malaria be improved? Trends Parasitol. 2003;19(3):115–120.
   PubMed Web of Science ®Google Scholar
• Hargrave KD, Hess FK, Oliver JT. N-(4-Substituted-thiazolyl) oxamic acid derivatives, new series of potent, orally active antiallergy agents. J Med Chem. 1983;26(8):1158–1163.
   PubMed Web of Science ®Google Scholar
• Fisher RS, van Emde Boas W, Blume W, Elger C, Genton P, Lee P, Engel J. Epileptic seizures and epilepsy: definitions proposed by the International League Against Epilepsy (ILAE) and the International Bureau for Epilepsy (IBE). Epilepsia. 2005;46(4):470–472.
   PubMed Web of Science ®Google Scholar
• El-Ansary SL, Hassan GS, Abdel Rahman DE, Farag NA, Hamed MI, Baset MA. Design, synthesis and biological evaluation of some new succinimide, 2-iminothiazoline and oxazine derivatives based benzopyrone as anticonvulsant agents. Int J Pharm Pharm Sci. 2016;8(4):222–228.
   Google Scholar
• Larik FA, Saeed A, Faisal M, Hamdani S, Jabeen F, Channar PA, Mumtaz A, Khan I, Kazi MA, Abbas Q, et al. Synthesis, inhibition studies against AChE and BChE, drug-like profiling, kinetic analysis and molecular docking studies of N-(4-phenyl-3-aroyl-2 (3H)-ylidene) substituted acetamides. J Mol Struct. 2020;1203:127459.
   Web of Science ®Google Scholar
• Sharma PK, Sawhney SN, Gupta A, Singh GB, Bani S. Synthesis and antiinflammatory activity of some 3-(2-thiazolyl)-1, 2-benzisothiazoles. Indian J Chem B. 1998;37:376–381.
   Google Scholar
• Saeed A, Al-Masoudi NA, Pannecouque C. In-vitro anti-HIV activity of new thiazol-2-ylidene substituted benzamide analogues. Der Pharma Chem. 2012;4(1):106–115.
   Google Scholar
• Sondhi SM, Singh N, Lahoti AM, Bajaj K, Kumar A, Lozach O, Meijer L. Synthesis of acridinyl-thiazolino derivatives and their evaluation for anti-inflammatory, analgesic and kinase inhibition activities. Bioorg Med Chem. 2005;13(13):4291–4299.
   PubMed Web of Science ®Google Scholar
• Tsuji K, Ishikawa H. Synthesis and anti-pseudomonal activity of new 2-isocephems with a dihydroxypyridone moiety at C-7. Bioorg Med Chem Lett. 1994;4(13):1601–1606.
   Web of Science ®Google Scholar
• Saeed S, Hussain R, Ali M. Synthesis and Antimicrobial Activity of N‐[(2 Z)‐3‐(4, 6‐Substitutedpyrimidin‐2‐yl)‐4‐phenyl‐1, 3‐thiazol‐2 (3 H)‐ylidene]‐3, 5‐dinitrobenzamide Analogues. J Heterocyclic Chem. 2013;50(2):237–243.
   Web of Science ®Google Scholar
• Rokach J, Girard Y, Hamel P, Reader G, Rooney CS, Mandel LR, Cragoe EJ, Zacchei AG. Inhibitors of indoleethylamine N-methyltransferase. Derivatives of 3-methyl-2-thiazolidinimine. In vitro, in vivo, and metabolic studies. J Med Chem. 1980;23(7):773–780.
   PubMed Web of Science ®Google Scholar
• Saeed A, Rafique H. Synthesis of new N-[3-(Benzo [d] thiazol-2-yl)-4-methylthiazol-2 (3H)-ylidene] substituted benzamides. Turk J Chem. 2013;37(6):909–916.
   Web of Science ®Google Scholar
• Tomizawa M, Cowan A, Casida JE. Analgesic and toxic effects of neonicotinoid insecticides in mice. Toxicol Appl Pharmacol. 2001;177(1):77–83.
   PubMed Web of Science ®Google Scholar
• Hosseinimehr SJ, Shafiee A, Mozdarani H, Akhlagpour S. Radioprotective effects of 2-iminothiazolidine derivatives against lethal doses of gamma radiation in mice. J Radiat Res. 2001;42(4):401–408.
   PubMed Web of Science ®Google Scholar
• Chowdhury R, Candela-Lena JI, Chan MC, Greenald DJ, Yeoh KK, Tian YM, McDonough MA, Tumber A, Rose NR, Conejo-Garcia A, et al. Selective small molecule probes for the hypoxia inducible factor (HIF) prolyl hydroxylases. ACS Chem Biol. 2013;8(7):1488–1496.
   PubMed Web of Science ®Google Scholar
• Manaka A, Ishii T, Takahashi K, Sato M. 2-Acylimino-3-alkyl-3H-thiazoline derivatives: one-pot, three-component condensation synthesis of novel β-turn mimics. Tetrahedron Lett. 2005;46(3):419–422.
   Web of Science ®Google Scholar
• Kim DS, Jeong YM, Park IK, Hahn HG, Lee HK, Kwon SB, Jeong JH, Yang SJ, Sohn UD, Park KC, et al. A new 2-imino-1, 3-thiazoline derivative, KHG22394, inhibits melanin synthesis in mouse B16 melanoma cells. Biol Pharm Bull. 2007;30(1):180–183.
   PubMed Web of Science ®Google Scholar
• Pietrancosta N, Moumen A, Dono R, Lingor P, Planchamp V, Lamballe F, Bähr M, Kraus JL, Maina F. Imino-tetrahydro-benzothiazole derivatives as p53 inhibitors: discovery of a highly potent in vivo inhibitor and its action mechanism. J Med Chem. 2006;49(12):3645–3652.
   PubMed Web of Science ®Google Scholar
• Heravi MM, Moghimi S. An efficient synthesis of thiazol-2-imine derivatives via a one-pot, three-component reaction. Tetrahedron Lett. 2012;53(4):392–394.
   Web of Science ®Google Scholar
• Assis DB, Aragão Neto HC, da Fonsêca DV, de Andrade HHN, Braga RM, Badr N, Maia MDS, Castro RD, Scotti L, Scotti MT, et al. Antinociceptive activity of chemical components of essential oils that involves docking studies: a review. Front Pharmacol. 2020;11:777.
   PubMed Web of Science ®Google Scholar
• Chang L, Duy DL, Mébarek S, Popowycz F, Pellet-Rostaing S, Lemaire M, Buchet R. Synthesis and evaluation of thiophenyl derivatives as inhibitors of alkaline phosphatase. Bioorg Med Chem Lett. 2011;21(8):2297–2301.
   PubMed Web of Science ®Google Scholar
• Azarakhshi F, Khaleghian M, Farhadyar N. DFT study and NBO analysis of conformational properties of 2-substituted 2-Oxo-1, 3, 2-dioxaphosphorinanes and their dithia and diselena analogs. Lett Org Chem. 2015;12(7):516–522.
   Web of Science ®Google Scholar
• Frisch M, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, et al. Gaussian 09, Revision B. 01. Wallingford (CT): Gaussian, Inc; 2009.
   Google Scholar
• Al-Rashida M, Iqbal J. Inhibition of alkaline phosphatase: an emerging new drug target. Mini Rev Med Chem. 2015;15(1):41–51.
   PubMed Web of Science ®Google Scholar
• Channar SA, Channar PA, Saeed A, Alsfouk AA, Ejaz SA, Ujan R, Noor R, Bilal MS, Abbas Q, Hussain Z, et al. Exploring thiazole-linked thioureas using alkaline phosphatase assay, biochemical evaluation, computational analysis and structure–activity relationship (SAR) studies. Med Chem Res. 2022;31(10):1792–1802.
   Web of Science ®Google Scholar
• Bauernschmitt R, Häser M, Treutler O, Ahlrichs R. Calculation of excitation energies within time-dependent density functional theory using auxiliary basis set expansions. Chem Phys Lett. 1997;264(6):573–578.
   Web of Science ®Google Scholar
• Calais JL. Orthonormalization and symmetry adaptation of crystal orbitals. Int J Quantum Chem. 2009;28(S19):655–667.
   Google Scholar
• Weigend F, Ahlrichs R. Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy. Phys Chem Chem Phys. 2005;7(18):3297–3305.
   PubMed Web of Science ®Google Scholar
• Hossen J, Ali MA, Reza S. Theoretical investigations on the antioxidant potential of a non-phenolic compound thymoquinone: a DFT approach. J Mol Model. 2021;27(6):1–11.
   Web of Science ®Google Scholar
• Parr RG, Yang W. Density functional theory of atoms and molecules. New York (NY): Oxford University Press; 1989: p. 1989.
   Google Scholar
• Schäfer A, Huber C, Ahlrichs R. Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr. J Chem Phys. 1994;100(8):5829–5835.
   Web of Science ®Google Scholar
• Bartolotti LJ, Flurchick K. An introduction to density functional theory. Rev Comput Chem. 1996;7:187–260.
   Google Scholar
• Thanikaivelan P, Subramanian V, Raghava Rao J, Unni Nair B. Application of quantum chemical descriptor in quantitative structure activity and structure property relationship. Chem Phys Lett. 2000;323(1–2):59–70.
   Web of Science ®Google Scholar
• Dennington R, Keith T, Millam J, Eppinnett K, Hovell WL, Gilliland R. GaussView v.5.0.9 visualizer and builder. Wallingford (CT): Gaussian Inc; 2009.
   Google Scholar
• Iqbal Z, Ashraf Z, Hassan M, Abbas Q, Jabeen E. Substituted phenyl [(5-benzyl-1, 3, 4-oxadiazol-2-yl) sulfanyl] acetates/acetamides as alkaline phosphatase inhibitors: synthesis, computational studies, enzyme inhibitory kinetics and DNA binding studies. Bioorg Chem. 2019;90:103108.
   PubMed Web of Science ®Google Scholar
• Saeed A, Saddique G, Ali Channar P, Ali Larik F, Abbas Q, Hassan M, Raza H, Fattah TA, Seo SY. Synthesis of sulfadiazinyl acyl/aryl thiourea derivatives as calf intestinal alkaline phosphatase inhibitors, pharmacokinetic properties, lead optimization, Lineweaver-Burk plot evaluation and binding analysis. Bioorg Med Chem. 2018;26(12):3707–3715.
   PubMed Web of Science ®Google Scholar
• Abbasi MA, Nazir M, Ur-Rehman A, Siddiqui SZ, Hassan M, Raza H, Shah SAA, Shahid M, Seo SY. Bi‐heterocyclic benzamides as alkaline phosphatase inhibitors: mechanistic comprehensions through kinetics and computational approaches. Arch Pharm. 2019;352(3):1800278.
   Web of Science ®Google Scholar
• Molecular Operating Environment (MOE). Montreal (QC): Chem Comput Group Inc; 2016.
   Google Scholar
• Heinzerling L, Klein R, Rarey M. Fast force field‐based optimization of protein–ligand complexes with graphics processor. J Comput Chem. 2012;33(32):2554–2565.
   PubMed Web of Science ®Google Scholar
• Al‐Hazmi GAA, Abou‐Melha KS, El‐Metwaly NM, Althagafi I, Shaaban F, Zaky R. Green synthesis approach for Fe (III), Cu (II), Zn (II) and Ni (II)‐Schiff base complexes, spectral, conformational, MOE‐docking and biological studies. Appl Organomet Chem. 2020;34(3):e5403.
   Web of Science ®Google Scholar
• Yuan S, Chan HS, Hu Z. Using PyMOL as a platform for computational drug design. Wiley Interdiscip Rev Comput Mol Sci. 2017;7(2):e1298.
   Web of Science ®Google Scholar
• Laskowski RA, Swindells MB. LigPlot+: multiple ligand–protein interaction diagrams for drug discovery. J Chem Inf Model. 2011;51(10):2778–2786.
   Google Scholar
• Zhang Y, Zhang TJ, Tu S, Zhang ZH, Meng FH. Identification of novel Src inhibitors: pharmacophore-based virtual screening, molecular docking and molecular dynamics simulations. Molecules. 2020;25(18):4094.
   PubMed Web of Science ®Google Scholar
• Shivakumar D, Williams J, Wu Y, Damm W, Shelley J, Sherman W. Prediction of absolute solvation free energies using molecular dynamics free energy perturbation and the OPLS force field. J Chem Theory Comput. 2010;6(5):1509–1519.
   PubMed Web of Science ®Google Scholar
• Martyna GJ, Tobias DJ, Klein ML. Constant pressure molecular dynamics algorithms. J Chem Phys. 1994;101(5):4177–4189.
   Web of Science ®Google Scholar
• Bowers KJ, Chow E, Xu H, Dror RO, Eastwood MP, Gregersen BA, Klepeis JL, Kolossvary I, Moraes MA, Sacerdoti FD, et al. Scalable algorithms for molecular dynamics simulations on commodity clusters. Paper presented at: SC'06. Proceedings of the 2006 ACM/IEEE Conference on Supercomputing. Tampa (FL): IEEE; 2006.
   Google Scholar
• Luty BA, Davis ME, Tironi IG, Van Gunsteren WF. A comparison of particle-particle, particle-mesh and Ewald methods for calculating electrostatic interactions in periodic molecular systems. Mol Simul. 1994;14(1):11–20.
   Web of Science ®Google Scholar
• Hospital A, Goñi JR, Orozco M, Gelpí JL. Molecular dynamics simulations: advances and applications. Adv Appl Bioinform Chem. 2015;8:37.
   PubMedGoogle Scholar
• Choudhary MI, Shaikh M, Tul-Wahab A, Ur-Rahman A. In silico identification of potential inhibitors of key SARS-CoV-2 3CL hydrolase (Mpro) via molecular docking, MMGBSA predictive binding energy calculations, and molecular dynamics simulation. PLos One. 2020;15(7):e0235030.
   PubMed Web of Science ®Google Scholar