Identification of novel pyrrolopyrimidine and pyrrolopyridine derivatives as potent ENPP1 inhibitors

References

• (a) Emens LA, Butterfield LH, Hodi FS, et al. Cancer immunotherapy trials: leading a paradigm shift in drug development. J Immuno Ther Cancer 2016;4:42.
   PubMed Web of Science ®Google Scholar
  (b) Sanmamed MF, Chen L. A paradigm shift in cancer immunotherapy: from enhancement to normalization. Cell 2018;175:313–26.
   PubMed Web of Science ®Google Scholar
• (a) Park JA, Cheung NV. Limitations and opportunities for immune checkpoint inhibitors in pediatric malignancies. Cancer Treat Rev 2017;58:22–33.
   PubMed Web of Science ®Google Scholar
  (b) Ottaviano M, De Placido S, Ascierto PA. Recent success and limitations of immune checkpoint inhibitors for cancer: a lesson from melanoma. Virchows Arch 2019;474:421–32.
   PubMed Web of Science ®Google Scholar
  (c) Park YJ, Kuen DS, Chung Y. Future prospects of immune checkpoint blockade in cancer: from response prediction to overcoming resistance. Exp Mol Med 2018;50:1–13.
   Web of Science ®Google Scholar
• (a) Duan Q, Zhang H, Zheng J, Zhang L. Turning cold into hot: firing up the tumor microenvironment. Trends Cancer 2020;6:605–18.
   PubMed Web of Science ®Google Scholar
  (b) Iwasaki A, Medzhitov R. Control of adaptive immunity by the innate immune system. Nat Immunol 2015;16:343–53.
   PubMed Web of Science ®Google Scholar
• (a) Motwani M, Pesiridis S, Fitzgerald KA. DNA sensing by the cGAS-STING pathway in health and disease. Nat Rev Genet 2019;20:657–74.
   PubMed Web of Science ®Google Scholar
  (b) Chen Q, Sun L, Chen ZJ. Regulation and function of the cGAS-STING pathway of cytosolic DNA sensing. Nat Immunol 2016;17:1142–9.
   PubMed Web of Science ®Google Scholar
• Carozza JA, Böhnert V, Nguyen KC, et al. Extracellular cGAMP is a cancer cell-produced immunotransmitter involved in radiation-induced anti-cancer immunity. Nat Cancer 2020;1:184–96.
   PubMedGoogle Scholar
• (a) Carozza JA, Brown JA, Böhnert V, et al. Structure-aided development of small-molecule inhibitors of ENPP1, the extracellular phosphodiesterase of the immunotransmitter cGAMP. Cell Chem Biol 2020;27:1347–58.e5.
   PubMed Web of Science ®Google Scholar
  (b) Chang L, Lee SY, Leonczak P, et al. Imidazopyridine- and purine-thioacetamide derivatives: potent inhibitors of nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1). J Med Chem 2014;57:10080–100.
   PubMed Web of Science ®Google Scholar
  (c) Forcellini E, Boutin S, Lefebvre CA, et al. Synthesis and biological evaluation of novel quinazoline-4-piperidinesulfamide derivatives as inhibitors of NPP1. Eur J Med Chem 2018;147:130–49.
   PubMed Web of Science ®Google Scholar
  (d) Lee SY, Sarkar S, Bhattarai S, et al. Substrate-dependence of competitive Nucleotide Pyrophosphatase/Phosphodiesterase1 (NPP1) inhibitors. Front Pharmacol 2017;8:54.
   PubMed Web of Science ®Google Scholar
  (e) Lee SY, Perotti A, De Jonghe S, et al. Thiazolo[3,2-a]benzimidazol-3(2H)-one derivatives: Structure-activity relationships of selective nucleotide pyrophosphatase/phosphodiesterase1 (NPP1) inhibitors. Bioorg Med Chem 2016;24:3157–65.
   PubMed Web of Science ®Google Scholar
  (f) Lefebvre CA, Forcellini E, Boutin S, et al. Synthesis of novel substituted pyrimidine derivatives bearing a sulfamide group and their in vitro cancer growth inhibition activity. Bioorg Med Chem Lett 2017;27:299–302.
   PubMed Web of Science ®Google Scholar
  (g) Ullah S, El-Gamal MI, Zaib S, et al. Synthesis, biological evaluation, and docking studies of new pyrazole-based thiourea and sulfonamide derivatives as inhibitors of nucleotide pyrophosphatase/phosphodiesterase. Bioorg Chem 2020;99:103783.
   PubMed Web of Science ®Google Scholar
  (h) Patel SD, Habeski WM, Cheng AC, et al. Quinazolin-4-piperidin-4-methyl sulfamide PC-1 inhibitors: alleviating hERG interactions through structure based design. Bioorg Med Chem Lett 2009;19:3339–43.
   PubMed Web of Science ®Google Scholar
  (i) Shayhidin EE, Forcellini E, Boulanger MC, et al. Quinazoline-4-piperidine sulfamides are specific inhibitors of human NPP1 and prevent pathological mineralization of valve interstitial cells. Br J Pharmacol 2015;172:4189–99.
   PubMed Web of Science ®Google Scholar
• (a) Barth M, Contal S, Junien J, et al. Inventiva. Preparation of [4-[[(1,1-dioxo-1,2-benzothiazol-3-yl)hydrazono]methyl]phenyl]boronic acids and derivatives as inhibitors of YAP/TAZ-TEAD interaction and their use in the treatment of cancer, particularly malignant mesothelioma, Patent WO 2020070181; 2020.
   Google Scholar
  (b) Arcari JT, Beebe JS, Berliner MA, et al. Discovery and synthesis of Novel 4-aminopyrrolopyrimidine Tie-2 kinase inhibitors for the treatment of solid tumors. Bioorganic Med Chem Lett 2013;23:3059–63.
   PubMedGoogle Scholar
• (a) Chan DMT, Monaco KL, Wang RP, Winters MP. New N- and O-Arylations with phenylboronic acids and cupric acetate. Tetrahedron Lett 1998;39:2933–6.
   Web of Science ®Google Scholar
  (b) Duan W, Geng M, Wang W, et al. Compound having AXL inhibitory activity, preparation method therefor and use thereof. Patent WO2018121228 2018.
   Google Scholar
• Pudlo JS, Nassiri MR, Kern ER, et al. Synthesis, antiproliferative, and antiviral activity of certain 4-substituted and 4,5-disubstituted 7-[(1,3-dihydroxy-2-propoxy)methyl]pyrrolo[2,3-d]pyrimidines. J Med Chem 1990;33:1984–92.
   PubMed Web of Science ®Google Scholar
• (a) Gallatin WM, Odingo J, Dietsch GN, et al. Mavupharma, Inc. Preparation quinolinyl and quinazolinyl benzenesulfamides and analogs as ectonucleotide pyrophosphatase-phosphodiesterase 1 (ENPP-1) inhibitors as antitumor antiviral, Patent WO2019046778; 2019.
   Google Scholar
  (b) Horatscheck A, Andrijevic AT, Nchinda A, et al. Identification of 2,4-disubstituted imidazopyridines as hemozoin formation inhibitors with fast-killing kinetics and in vivo efficacy in the plasmodium falciparum NSG mouse model. J Med Chem 2020;63:13013–30.
   PubMed Web of Science ®Google Scholar
• (a) Abell A, Polyak S, Tieu W, et al. University of Adelaide. Preparation of biotin derivatives as antibiotics, Patent WO2020087122; 2020
   Google Scholar
  (b) Winum J-Y, Toupet L, Barragan V, et al. tert-Butoxycarbonyl)-N-[4- (dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl]azanide: a new sulfamoylating agent. structure and reactivity toward Amines. Organic Lett 2001;3:2241–3.
   PubMed Web of Science ®Google Scholar
  (c) Esteve C, Vidal B. Solid-phase synthesis of sulfamides. Tetrahedron Letters 2002;43:1019–21.
   Web of Science ®Google Scholar
• Badescu VO, Filla SA, Gallagher PT, Whatton MA, Eli Lilly and Company. Preparation of pyrazole derivatives as 5-HT7 receptor antagonists, Patent WO2009048765; 2009.
   Google Scholar
• Gangar M, Goyal S, Raykar D, et al. Design, synthesis and biological evaluation studies of novel small molecule ENPP1 inhibitors for cancer immunotherapy. Bioorganic Chem 2022;119:105549.
   PubMed Web of Science ®Google Scholar
• Li J, Duran MA, Dhanota N, Chatila WK, et al. Metastasis and immune evasion from extracellular cGAMP hydrolysis. Cancer Discovery 2021;11:1213–27.
   Google Scholar
• O’Boyle NM, Banck M, James CA. J Cheminform Open Babel: an open chemical toolbox. 2011;3:33.
   PubMed Web of Science ®Google Scholar
• Abagyan R, Totrov M, Kuznetsov D. J Comput Chem ICM?A new method for protein modeling and design: applications to docking and structure prediction from the distorted native conformation. 1994;15:488–506.
   Web of Science ®Google Scholar
• Berman HM, Westbrook J, Feng Z, et al. Nucleic Acids Res The Protein Data Bank. 2000;28:235–42.
   PubMed Web of Science ®Google Scholar
• Laskowski RA, Swindells MB. LigPlot+: multiple ligand-protein interaction diagrams for drug discovery. J Chem Inf Model. 2011;51:2778–86.
   PubMed Web of Science ®Google Scholar
• Salentin S, Schreiber S, Haupt VJ, et al. PLIP: fully automated protein-ligand interaction profiler. Nucleic Acids Res 2015;43:W443–W447.
   PubMed Web of Science ®Google Scholar