{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,10]],"date-time":"2026-08-10T18:45:50Z","timestamp":1786387550710,"version":"build-2736575974"},"reference-count":47,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2022,7,1]],"date-time":"2022-07-01T00:00:00Z","timestamp":1656633600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2022,7,1]],"date-time":"2022-07-01T00:00:00Z","timestamp":1656633600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2022,7,1]],"date-time":"2022-07-01T00:00:00Z","timestamp":1656633600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2022,7,1]],"date-time":"2022-07-01T00:00:00Z","timestamp":1656633600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2022,7,1]],"date-time":"2022-07-01T00:00:00Z","timestamp":1656633600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2022,7,1]],"date-time":"2022-07-01T00:00:00Z","timestamp":1656633600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2022,7,1]],"date-time":"2022-07-01T00:00:00Z","timestamp":1656633600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic Chemistry"],"published-print":{"date-parts":[[2022,7]]},"DOI":"10.1016\/j.bioorg.2022.105857","type":"journal-article","created":{"date-parts":[[2022,5,10]],"date-time":"2022-05-10T00:15:32Z","timestamp":1652141732000},"page":"105857","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":10,"special_numbering":"C","title":["Ultrasound assisted one-pot synthesis of rosuvastatin based novel azaindole derivatives via coupling\u2013cyclization strategy under Pd\/Cu-catalysis: Their evaluation as potential cytotoxic agents"],"prefix":"10.1016","volume":"124","author":[{"given":"Jetta Sandeep","family":"Kumar","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gangireddy Sujeevan","family":"Reddy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Raghavender","family":"Medishetti","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kazi","family":"Amirul Hossain","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"B.","family":"Thirupataiah","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jhansi","family":"Edelli","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shilpak","family":"Dilip Bele","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rebecca","family":"Kristina Edwin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alex","family":"Joseph","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gautham G.","family":"Shenoy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"C.","family":"Mallikarjuna Rao","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Manojit","family":"Pal","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.bioorg.2022.105857_b0005","doi-asserted-by":"crossref","first-page":"19935","DOI":"10.3390\/molecules191219935","article-title":"The azaindole framework in the design of kinase inhibitors","volume":"19","author":"Merour","year":"2014","journal-title":"Molecules"},{"key":"10.1016\/j.bioorg.2022.105857_b0010","doi-asserted-by":"crossref","first-page":"727","DOI":"10.2174\/1389557518666180928154004","article-title":"7-Azaindole analogues as bioactive agents and recent results","volume":"19","author":"Sharma","year":"2019","journal-title":"Mini-Rev. Med. Chem."},{"issue":"24","key":"10.1016\/j.bioorg.2022.105857_b0015","doi-asserted-by":"crossref","first-page":"115830","DOI":"10.1016\/j.bmc.2020.115830","article-title":"Azaindole therapeutic agents","volume":"28","author":"Motati","year":"2020","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bioorg.2022.105857_b0020","doi-asserted-by":"crossref","first-page":"112506","DOI":"10.1016\/j.ejmech.2020.112506","article-title":"The importance of indole and azaindole scaffold in the development of antitumor agents","volume":"203","author":"Han","year":"2020","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2022.105857_b0025","doi-asserted-by":"crossref","first-page":"869","DOI":"10.3892\/ijo.2015.3306","article-title":"Akt inhibitors in cancer treatment: The long journey from drug discovery to clinical use (Review)","volume":"48","author":"Nitulescu","year":"2016","journal-title":"Int. J. Oncol."},{"issue":"2","key":"10.1016\/j.bioorg.2022.105857_b0030","doi-asserted-by":"crossref","first-page":"360","DOI":"10.1158\/1535-7163.MCT-10-0760","article-title":"Preclinical pharmacology, antitumor activity, and development of pharmacodynamic markers for the novel, potent AKT inhibitor CCT128930","volume":"10","author":"Yap","year":"2011","journal-title":"Mol. Cancer Ther."},{"key":"10.1016\/j.bioorg.2022.105857_b0035","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1182\/blood-2020-141012","article-title":"An azaindole-based small molecule Hzx-02-059 induces methuosis in B-cell acute lymphoblastic leukemia through the PI3K\/AKT axis","volume":"136","author":"Lu","year":"2020","journal-title":"Blood"},{"issue":"5","key":"10.1016\/j.bioorg.2022.105857_b0040","doi-asserted-by":"crossref","first-page":"484","DOI":"10.2183\/pjab.86.484","article-title":"A historical perspective on the discovery of statins","volume":"86","author":"Endo","year":"2010","journal-title":"Proc. Japan Acad. Ser. B Phys. Biol. Sci."},{"key":"10.1016\/j.bioorg.2022.105857_b0045","doi-asserted-by":"crossref","first-page":"248","DOI":"10.1186\/gb-2004-5-11-248","article-title":"The 3-hydroxy-3-methylglutaryl coenzyme-A (HMG-CoA) reductases","volume":"5","author":"Friesen","year":"2004","journal-title":"Genome Biol."},{"issue":"1","key":"10.1016\/j.bioorg.2022.105857_b0050","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1002\/ijc.24536","article-title":"Incidence of cancer and statin usage - Record linkage study","volume":"126","author":"Haukka","year":"2010","journal-title":"Int. J. Cancer."},{"issue":"19","key":"10.1016\/j.bioorg.2022.105857_b0055","doi-asserted-by":"crossref","first-page":"1792","DOI":"10.1056\/NEJMoa1201735","article-title":"Statin use and reduced cancer-related mortality","volume":"367","author":"Nielsen","year":"2012","journal-title":"N. Engl. J. Med."},{"issue":"1","key":"10.1016\/j.bioorg.2022.105857_b0060","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1038\/bjc.2016.149","article-title":"Statin use and all-cancer survival: Prospective results from the Women\u2019s Health Initiative","volume":"115","author":"Wang","year":"2016","journal-title":"Br. J. Cancer."},{"key":"10.1016\/j.bioorg.2022.105857_b0065","doi-asserted-by":"crossref","first-page":"28813","DOI":"10.1371\/journal.pone.0028813","article-title":"Differential effects of pravastatin and simvastatin on the growth of tumor cells from different organ sites","volume":"6","author":"Menter","year":"2011","journal-title":"PLoS One"},{"key":"10.1016\/j.bioorg.2022.105857_b0070","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1038\/srep07593","article-title":"Statin-induced mevalonate pathway inhibition attenuates the growth of mesenchymal-like cancer cells that lack functional E-cadherin mediated cell cohesion","volume":"4","author":"Warita","year":"2014","journal-title":"Sci. Rep."},{"issue":"17","key":"10.1016\/j.bioorg.2022.105857_b0075","doi-asserted-by":"crossref","first-page":"8707","DOI":"10.1158\/0008-5472.CAN-05-4061","article-title":"Breast cancer growth prevention by statins","volume":"66","author":"Campbell","year":"2006","journal-title":"Cancer Res."},{"key":"10.1016\/j.bioorg.2022.105857_b0080","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1158\/1055-9965.EPI-07-0531","article-title":"Statin induces apoptosis and cell growth arrest in prostate cancer cells","volume":"17","author":"Hoque","year":"2008","journal-title":"Cancer Epidemiol. Biomarkers Prev."},{"key":"10.1016\/j.bioorg.2022.105857_b0085","doi-asserted-by":"crossref","first-page":"1139","DOI":"10.1093\/carcin\/22.8.1139","article-title":"Cerivastatin, an inhibitor of HMG-CoA reductase, inhibits the signaling pathways involved in the invasiveness and metastatic properties of highly invasive breast cancer cell lines: an in vitro study","volume":"22","author":"Denoyelle","year":"2001","journal-title":"Carcinogenesis"},{"issue":"6","key":"10.1016\/j.bioorg.2022.105857_b0090","doi-asserted-by":"crossref","first-page":"1214","DOI":"10.1002\/ijc.23242","article-title":"Differences in antitumor effects of various statins on human pancreatic cancer","volume":"122","author":"Gbelcov\u00e1","year":"2008","journal-title":"Int. J. Cancer."},{"issue":"19","key":"10.1016\/j.bioorg.2022.105857_b0095","doi-asserted-by":"crossref","first-page":"1461","DOI":"10.1093\/jnci\/djr291","article-title":"Statin prescriptions and breast cancer recurrence risk: A Danish nationwide prospective cohort study","volume":"103","author":"Ahern","year":"2011","journal-title":"J. Natl. Cancer Inst."},{"issue":"3","key":"10.1016\/j.bioorg.2022.105857_b0100","doi-asserted-by":"crossref","first-page":"573","DOI":"10.1007\/s10549-007-9683-8","article-title":"Post-diagnosis statin use and breast cancer recurrence in a prospective cohort study of early stage breast cancer survivors","volume":"109","author":"Kwan","year":"2008","journal-title":"Breast Cancer Res. Treat."},{"issue":"102","key":"10.1016\/j.bioorg.2022.105857_b0105","doi-asserted-by":"crossref","first-page":"100487","DOI":"10.1039\/C6RA20148B","article-title":"Cu-Catalyzed ligand-free synthesis of rosuvastatin based novel indole derivatives as potential anticancer agents","volume":"6","author":"Kumar","year":"2016","journal-title":"RSC Adv."},{"key":"10.1016\/j.bioorg.2022.105857_b0110","doi-asserted-by":"crossref","first-page":"112335","DOI":"10.1016\/j.ejmech.2020.112335","article-title":"Rosuvastatin based novel 3-substituted isocoumarins \/ 3-alkylidenephthalides: Ultrasound assisted synthesis and identification of new anticancer agents","volume":"201","author":"Kumar","year":"2020","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2022.105857_b0115","doi-asserted-by":"crossref","first-page":"130574","DOI":"10.1016\/j.molstruc.2021.130574","article-title":"Sonochemical synthesis of rosuvastatin based novel 3-methyleneisoindolin-1-one derivatives as potential anticancer agents","volume":"1240","author":"Kumar","year":"2021","journal-title":"J. Mol. Struc."},{"issue":"25","key":"10.1016\/j.bioorg.2022.105857_b0120","doi-asserted-by":"crossref","first-page":"4814","DOI":"10.1016\/j.tet.2009.04.054","article-title":"A highly effective synthesis of 2-alkynyl-7-azaindoles: Pd\/C-mediated alkynylation of heteroaryl halides in water","volume":"65","author":"Layek","year":"2009","journal-title":"Tetrahedron"},{"issue":"6","key":"10.1016\/j.bioorg.2022.105857_b0125","doi-asserted-by":"crossref","first-page":"478","DOI":"10.1039\/c1md00029b","article-title":"Alkynylation of N-(3-iodopyridin-2-yl)sulfonamide under Pd\/C-Cu catalysis: A direct one pot synthesis of 7-azaindoles and their pharmacological evaluation as potential inhibitors of sirtuins","volume":"2","author":"Layek","year":"2011","journal-title":"Med. Chem. Commun."},{"issue":"52","key":"10.1016\/j.bioorg.2022.105857_b0130","doi-asserted-by":"crossref","first-page":"151326","DOI":"10.1016\/j.tetlet.2019.151326","article-title":"Ultrasound assisted one-pot synthesis of 1,2-diaryl azaindoles via Pd\/C-Cu catalysis: Identification of potential cytotoxic agents","volume":"60","author":"Venkateshwarlu","year":"2019","journal-title":"Tetrahedron Letters"},{"issue":"5","key":"10.1016\/j.bioorg.2022.105857_b0135","doi-asserted-by":"crossref","first-page":"e0197422","DOI":"10.1371\/journal.pone.0197422","article-title":"Lipophilic statins limit cancer cell growth and survival, via involvement of Akt signaling","volume":"13","author":"Beckwitt","year":"2018","journal-title":"PloS one"},{"key":"10.1016\/j.bioorg.2022.105857_h0140","doi-asserted-by":"crossref","first-page":"234","DOI":"10.2174\/1568009611313030002","article-title":"Diverse mechanisms of AKT pathway activation in human malignancy","volume":"13","author":"Cheung","year":"2013","journal-title":"Curr. Cancer Drug Targets."},{"key":"10.1016\/j.bioorg.2022.105857_h0145","first-page":"317186","article-title":"The role of the dysfunctional akt-related pathway in cancer: establishment and maintenance of a malignant cell phenotype, resistance to therapy and future strategies for drug development","author":"Romano","year":"2013","journal-title":"Scientifica (Cairo)"},{"key":"10.1016\/j.bioorg.2022.105857_b0145","doi-asserted-by":"crossref","first-page":"1355","DOI":"10.1517\/13543784.2010.520701","article-title":"Akt inhibitors in clinical development for the treatment of cancer","volume":"19","author":"Pal","year":"2010","journal-title":"Expert Opin. Investig. Drugs."},{"key":"10.1016\/j.bioorg.2022.105857_b0150","doi-asserted-by":"crossref","first-page":"299","DOI":"10.1038\/s41586-019-1730-1","article-title":"A view on drug resistance in cancer","author":"Vasan","year":"2019","journal-title":"Nature 575"},{"key":"10.1016\/j.bioorg.2022.105857_b0155","doi-asserted-by":"crossref","first-page":"2673","DOI":"10.3390\/molecules23102673","article-title":"Metal-catalyzed cross-coupling reactions on azaindole synthesis and functionalization","volume":"23","author":"Santos","year":"2018","journal-title":"Molecules"},{"key":"10.1016\/j.bioorg.2022.105857_b0160","doi-asserted-by":"crossref","first-page":"11749","DOI":"10.1039\/D0CC04264A","article-title":"Recent advances in the global ring functionalization of 7-azaindoles","volume":"56","author":"Kannaboina","year":"2020","journal-title":"Chem. Commun."},{"key":"10.1016\/j.bioorg.2022.105857_b0165","doi-asserted-by":"crossref","first-page":"1120","DOI":"10.1039\/b607868k","article-title":"Organometallic methods for the synthesis and functionalization of azaindoles","volume":"36","author":"Song","year":"2007","journal-title":"Chem. Soc. Rev."},{"key":"10.1016\/j.bioorg.2022.105857_h0175","doi-asserted-by":"crossref","first-page":"443","DOI":"10.1039\/cs9972600443","article-title":"Ultrasound in synthetic organic chemistry","volume":"26","author":"Mason","year":"1997","journal-title":"Chem. Soc. Rev."},{"key":"10.1016\/j.bioorg.2022.105857_h0180","doi-asserted-by":"crossref","DOI":"10.1016\/j.ultsonch.2021.105683","article-title":"Ultrasound-assisted synthesis of pyrimidines and their fused derivatives: A review","volume":"79","author":"Mittersteiner","year":"2021","journal-title":"Ultrasonics Sonochemistry"},{"key":"10.1016\/j.bioorg.2022.105857_h0185","doi-asserted-by":"crossref","first-page":"771","DOI":"10.1007\/s11030-019-09964-1","article-title":"Ultrasound-assisted synthesis of heterocyclic compounds","volume":"24","author":"Ziarani","year":"2020","journal-title":"Mol. Divers"},{"key":"10.1016\/j.bioorg.2022.105857_b0175","first-page":"165","article-title":"Cell sensitivity assays: the MTT assay","volume":"88","author":"Plumb","year":"2004","journal-title":"Methods Mol. Med."},{"issue":"4","key":"10.1016\/j.bioorg.2022.105857_b0180","doi-asserted-by":"crossref","first-page":"873","DOI":"10.1158\/1535-7163.MCT-11-0824-T","article-title":"Preclinical pharmacology of AZD5363, an inhibitor of AKT: pharmacodynamics, antitumor activity, and correlation of monotherapy activity with genetic background","volume":"11","author":"Davies","year":"2012","journal-title":"Mol. Cancer Ther."},{"key":"10.1016\/j.bioorg.2022.105857_b0185","doi-asserted-by":"crossref","first-page":"450","DOI":"10.3390\/genes9090450","article-title":"Phosphorylation-Dependent Inhibition of Akt1","volume":"9","author":"Balasuriya","year":"2018","journal-title":"Genes"},{"key":"10.1016\/j.bioorg.2022.105857_b0190","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1038\/srep42717","article-title":"SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules","volume":"7","author":"Daina","year":"2017","journal-title":"Sci. Rep."},{"issue":"4","key":"10.1016\/j.bioorg.2022.105857_b0195","doi-asserted-by":"crossref","first-page":"982","DOI":"10.1158\/1535-7163.MCT-14-0751","article-title":"The IGF-Trap: Novel Inhibitor of Carcinoma Growth and Metastasis","volume":"14","author":"Wang","year":"2015","journal-title":"Mol Cancer Ther."},{"issue":"19","key":"10.1016\/j.bioorg.2022.105857_b0200","doi-asserted-by":"crossref","first-page":"5607","DOI":"10.1016\/j.bmcl.2010.08.053","article-title":"Discovery of pyrrolopyrimidine inhibitors of Akt","volume":"20","author":"Blake","year":"2010","journal-title":"J. Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2022.105857_b0205","unstructured":"M. Westerfield, The Zebrafish Book. A Guide for the Laboratory Use of Zebrafish (Danio rerio). 4th Edition, 2000, University of Oregon Press, Eugene."},{"issue":"5","key":"10.1016\/j.bioorg.2022.105857_b0210","first-page":"382","article-title":"Morphological score assignment guidelines for the dechorionated zebrafish teratogenicity assay. Birth Defects Research Part B: Developmental and Reproductive","volume":"89","author":"Panzica-Kelly","year":"2010","journal-title":"Toxicology"},{"issue":"1","key":"10.1016\/j.bioorg.2022.105857_b0215","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1016\/j.vascn.2012.10.003","article-title":"A Zebra fish phenotypic assay for assessing drug-induced hepatotoxicity","volume":"67","author":"He","year":"2013","journal-title":"J. Pharmacol. Toxicol. Methods"},{"key":"10.1016\/j.bioorg.2022.105857_b0220","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1089\/zeb.2009.0631","article-title":"Caffeine- induced effects on heart rate in zebrafish embryos and possible mechanisms of action: an effective system for experiments in chemical biology","volume":"7","author":"Rana","year":"2010","journal-title":"Zebrafish"}],"container-title":["Bioorganic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0045206822002620?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0045206822002620?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,9,23]],"date-time":"2025-09-23T08:36:09Z","timestamp":1758616569000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0045206822002620"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,7]]},"references-count":47,"alternative-id":["S0045206822002620"],"URL":"https:\/\/doi.org\/10.1016\/j.bioorg.2022.105857","relation":{},"ISSN":["0045-2068"],"issn-type":[{"value":"0045-2068","type":"print"}],"subject":[],"published":{"date-parts":[[2022,7]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Ultrasound assisted one-pot synthesis of rosuvastatin based novel azaindole derivatives via coupling\u2013cyclization strategy under Pd\/Cu-catalysis: Their evaluation as potential cytotoxic agents","name":"articletitle","label":"Article Title"},{"value":"Bioorganic Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bioorg.2022.105857","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2022 Elsevier Inc. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"105857"}}