Design, synthesis and biological evaluation of 2-((4-sulfamoylphenyl)amino)-pyrrolo[2,3-d]pyrimidine derivatives as CDK inhibitors

References

• Khalaf N, El-Serag HB, Abrams HR, Thrift AP. Burden of pancreatic cancer: from epidemiology to practice. Clin Gastroenterol Hepatol. 2021;19(5):876–884.
   PubMed Web of Science ®Google Scholar
• Hajatdoost L, Sedaghat K, Walker EJ, Thomas J, Kosari S. Chemotherapy in pancreatic cancer: a systematic review. Medicina. 2018;54(3):48.
   PubMedGoogle Scholar
• Malone ER, Oliva M, Sabatini PJB, Stockley TL, Siu LL. Molecular profiling for precision cancer therapies. Genome Med. 2020;12(1):8.
   PubMed Web of Science ®Google Scholar
• Lakkakula BVKS, Farran B, Lakkakula S, Peela S, Yarla NS, Bramhachari PV, Kamal MA, Saddala MS, Nagaraju GP. Small molecule tyrosine kinase inhibitors and pancreatic cancer-Trials and troubles. Semin Cancer Biol. 2019;56:149–167.
   PubMed Web of Science ®Google Scholar
• Siegel RL, Miller KD, Fuchs HE, Jemal A. Cancer Statistics. CA Cancer J Clin. 2021;71(1):7–33.
   PubMed Web of Science ®Google Scholar
• Spadi R, Brusa F, Ponzetti A, Chiappino I, Birocco N, Ciuffreda L, Satolli MA. Current therapeutic strategies for advanced pancreatic cancer: a review for clinicians. World J Clin Oncol. 2016;7(1):27–43.
   PubMedGoogle Scholar
• Malumbres M. Cyclin-dependent kinases. Genome Biol. 2014;15(6):122.
   PubMed Web of Science ®Google Scholar
• Malumbres M, Barbacid M. To cycle or not to cycle: a critical decision in cancer. Nat Rev Cancer. 2001;1(3):222–231.
   PubMed Web of Science ®Google Scholar
• Panagiotou E, Gomatou G, Trontzas IP, Syrigos N, Kotteas E. Cyclin-dependent kinase (CDK) inhibitors in solid tumors: a review of clinical trials. Clin Transl Oncol. 2022;24(2):161–192.
   PubMed Web of Science ®Google Scholar
• Spring LM, Wander SA, Andre F, Moy B, Turner NC, Bardia A. Cyclin-dependent kinase 4 and 6 inhibitors for hormone receptor-positive breast cancer: past, present, and future. Lancet. 2020;395(10226):817–827.
   PubMed Web of Science ®Google Scholar
• Kazi A, Chen L, Xiang S, Vangipurapu R, Yang H, Beato F, Fang B, Williams TM, Husain K, Underwood P, et al. Global phosphoproteomics reveal CDK suppression as a vulnerability to KRas addiction in pancreatic cancer. Clin Cancer Res. 2021;27(14):4012–4024.
   PubMed Web of Science ®Google Scholar
• Ma Y, Sender S, Sekora A, et al. Inhibitory response to CK II inhibitor silmitasertib and cdks inhibitor dinaciclib is related to genetic differences in pancreatic ductal adenocarcinoma cell lines. Int J Mol Sci. 2022;23(8):4409.
   PubMed Web of Science ®Google Scholar
• Garcia-Reyes B, Kretz AL, Ruff JP, et al. The emerging role of Cyclin-Dependent Kinases (CDKs) in pancreatic ductal adenocarcinoma. Int J Mol Sci. 2018;19(10):3219.
   PubMed Web of Science ®Google Scholar
• Pecoraro C, Parrino B, Cascioferro S, et al. A new oxadiazole-based topsentin derivative modulates cyclin-dependent kinase 1 expression and exerts cytotoxic effects on pancreatic cancer cells. Molecules. 2021;27(1):19.
   PubMed Web of Science ®Google Scholar
• Wijnen R, Pecoraro C, Carbone D, et al. Cyclin Dependent Kinase-1 (CDK-1) inhibition as a novel therapeutic strategy against Pancreatic Ductal Adenocarcinoma (PDAC). Cancers. 2021;13(17):4389.
   PubMed Web of Science ®Google Scholar
• Lièvre A, Bachet J-B, Le Corre D, Boige V, Landi B, Emile J-F, Côté J-F, Tomasic G, Penna C, Ducreux M, et al. KRAS mutation status is predictive of response to cetuximab therapy in colorectal cancer. Cancer Res. 2006;66(8):3992–3995.
   PubMed Web of Science ®Google Scholar
• Gautschi O, Huegli B, Ziegler A, Gugger M, Heighway J, Ratschiller D, Mack PC, Gumerlock PH, Kung HJ, Stahel RA, et al. Origin and prognostic value of circulating KRAS mutations in lung cancer patients. Cancer Lett. 2007;254(2):265–273.
   PubMed Web of Science ®Google Scholar
• Slebos RJ, Kibbelaar RE, Dalesio O, Kooistra A, Stam J, Meijer CJ, Wagenaar SS, Vanderschueren RG, van Zandwijk N, Mooi WJ, et al. K-ras oncogene activation as a prognostic marker in adenocarcinoma of the lung. N Engl J Med. 1990;323(9):561–565.
   PubMed Web of Science ®Google Scholar
• Almoguera C, Shibata D, Forrester K, Martin J, Arnheim N, Perucho M. Most human carcinomas of the exocrine pancreas contain mutant c-K-ras genes. Cell. 1988;53(4):549–554.
   PubMed Web of Science ®Google Scholar
• Kanda M, Matthaei H, Wu J, Hong S-M, Yu J, Borges M, Hruban RH, Maitra A, Kinzler K, Vogelstein B, et al. Presence of somatic mutations in most early-stage pancreatic intraepithelial neoplasia. Gastroenterology. 2012;142(4):730–733 e739.
   PubMed Web of Science ®Google Scholar
• Downward J. RAS synthetic lethal screens revisited: still seeking the elusive prize? Clin Cancer Res. 2015;21(8):1802–1809.
   PubMed Web of Science ®Google Scholar
• Kaelin WG. Jr. The concept of synthetic lethality in the context of anticancer therapy. Nat Rev Cancer. 2005;5(9):689–698.
   PubMed Web of Science ®Google Scholar
• Shi X, Quan Y, Wang Y, Wang Y, Li Y. Design, synthesis, and biological evaluation of 2,6,7-substituted pyrrolo[2,3-d]pyrimidines as cyclin dependent kinase inhibitor in pancreatic cancer cells. Bioorg Med Chem Lett. 2021;33:127725.
   PubMed Web of Science ®Google Scholar
• Wang X, Yu C, Wang C, Ma Y, Wang T, Li Y, Huang Z, Zhou M, Sun P, Zheng J, et al. Novel cyclin-dependent kinase 9 (CDK9) inhibitor with suppression of cancer stemness activity against non-small-cell lung cancer. Eur J Med Chem. 2019;181:111535.
   PubMed Web of Science ®Google Scholar
• Toogood PL, Harvey PJ, Repine JT, Sheehan DJ, VanderWel SN, Zhou H, Keller PR, McNamara DJ, Sherry D, Zhu T, et al. Discovery of a potent and selective inhibitor of cyclin-dependent kinase 4/6. J Med Chem. 2005;48(7):2388–2406.
   PubMed Web of Science ®Google Scholar
• Frame S, Saladino C, MacKay C, Atrash B, Sheldrake P, McDonald E, Clarke PA, Workman P, Blake D, Zheleva D, et al. Fadraciclib (CYC065), a novel CDK inhibitor, targets key pro-survival and oncogenic pathways in cancer. PLoS One. 2020;15(7):e0234103.
   PubMed Web of Science ®Google Scholar
• Hole AJ, Baumli S, Shao H, Shi S, Huang S, Pepper C, Fischer PM, Wang S, Endicott JA, Noble ME, et al. Comparative structural and functional studies of 4-(thiazol-5-yl)-2-(phenylamino)pyrimidine-5-carbonitrile CDK9 inhibitors suggest the basis for isotype selectivity. J Med Chem. 2013;56(3):660–670.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibitors: an update on experimental agents for the treatment and imaging of hypoxic tumors. Expert Opin Investig Drugs. 2021;30(12):1197–1208.
   PubMed Web of Science ®Google Scholar