{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T17:42:48Z","timestamp":1788370968227,"version":"build-2803163510"},"reference-count":30,"publisher":"Springer Science and Business Media LLC","issue":"3","license":[{"start":{"date-parts":[[2021,8,6]],"date-time":"2021-08-06T00:00:00Z","timestamp":1628208000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.springer.com\/tdm"},{"start":{"date-parts":[[2021,8,6]],"date-time":"2021-08-06T00:00:00Z","timestamp":1628208000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/www.springer.com\/tdm"}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Mol Divers"],"published-print":{"date-parts":[[2022,6]]},"DOI":"10.1007\/s11030-021-10290-8","type":"journal-article","created":{"date-parts":[[2021,8,6]],"date-time":"2021-08-06T08:02:48Z","timestamp":1628236968000},"page":"1621-1633","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["A Dimroth rearrangement approach for the synthesis of selenopheno[2,3-e][1,2,4]triazolo[1,5-c]pyrimidines with cytotoxic activity on breast cancer cells"],"prefix":"10.1007","volume":"26","author":[{"given":"Omid","family":"Kohandel","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Seddigheh","family":"Sheikhi-Mohammareh","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fatemeh","family":"Oroojalian","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Toktam","family":"Memariani","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joel","family":"Mague","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5736-6287","authenticated-orcid":false,"given":"Ali","family":"Shiri","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2021,8,6]]},"reference":[{"key":"10290_CR1","doi-asserted-by":"publisher","first-page":"731","DOI":"10.1016\/0040-4020(77)80183-X","volume":"33","author":"J Liebscher","year":"1977","unstructured":"Liebscher J, Hartmann H (1977) Ein einfacher zugang zu neuartigen selenopyron-bzw. Selenopyrylium-derivaten aus \u03b2-chlor-propenyliden-immoniumsalzen und selen-nucleophilen. Tetrahedron 33:731\u2013734","journal-title":"Tetrahedron"},{"key":"10290_CR2","doi-asserted-by":"publisher","first-page":"1971","DOI":"10.1016\/j.ejmech.2007.12.006","volume":"43","author":"SH Abdel-Hafez","year":"2008","unstructured":"Abdel-Hafez SH (2008) Selenium containing heterocycles: synthesis, anti-inflammatory, analgesic and anti-microbial activities of some new 4-cyanopyridazine-3 (2H) selenone derivatives. Eur J Med Chem 43:1971\u20131977","journal-title":"Eur J Med Chem"},{"key":"10290_CR3","doi-asserted-by":"publisher","first-page":"281","DOI":"10.1016\/j.brainresbull.2009.03.006","volume":"79","author":"EA Wilhelm","year":"2009","unstructured":"Wilhelm EA, Jesse CR, Bortolatto CF et al (2009) Anticonvulsant and antioxidant effects of 3-alkynyl selenophene in 21-day-old rats on pilocarpine model of seizures. Brain Res Bull 79:281\u2013287","journal-title":"Brain Res Bull"},{"key":"10290_CR4","doi-asserted-by":"publisher","first-page":"20","DOI":"10.1016\/j.yexmp.2009.03.004","volume":"87","author":"EA Wilhelm","year":"2009","unstructured":"Wilhelm EA, Jesse CR, Roman SS et al (2009) Hepatoprotective effect of 3-alkynyl selenophene on acute liver injury induced by D-galactosamine and lipopolysaccharide. Exp Mol Pathol 87:20\u201326","journal-title":"Exp Mol Pathol"},{"key":"10290_CR5","doi-asserted-by":"publisher","first-page":"1395","DOI":"10.1016\/j.ejmech.2009.12.039","volume":"45","author":"L-C Chou","year":"2010","unstructured":"Chou L-C, Huang L-J, Hsu M-H et al (2010) Synthesis of 1-benzyl-3-(5-hydroxymethyl-2-furyl) selenolo [3, 2-c] pyrazole derivatives as new anticancer agents. Eur J Med Chem 45:1395\u20131402","journal-title":"Eur J Med Chem"},{"key":"10290_CR6","doi-asserted-by":"publisher","first-page":"419","DOI":"10.1016\/j.pbb.2009.06.003","volume":"93","author":"EA Wilhelm","year":"2009","unstructured":"Wilhelm EA, Jesse CR, Bortolatto CF et al (2009) Antinociceptive and anti-allodynic effects of 3-alkynyl selenophene on different models of nociception in mice. Pharmacol Biochem Behav 93:419\u2013425","journal-title":"Pharmacol Biochem Behav"},{"key":"10290_CR7","doi-asserted-by":"publisher","first-page":"193","DOI":"10.1158\/1535-7163.MCT-06-0482","volume":"6","author":"S-H Juang","year":"2007","unstructured":"Juang S-H, Lung C-C, Hsu P-C et al (2007) D-501036, a novel selenophene-based triheterocycle derivative, exhibits potent in vitro and in vivo antitumoral activity which involves DNA damage and ataxia telangiectasia\u2013mutated nuclear protein kinase activation. Mol Cancer Ther 6:193\u2013202","journal-title":"Mol Cancer Ther"},{"key":"10290_CR8","doi-asserted-by":"publisher","first-page":"610","DOI":"10.1016\/j.bcp.2006.10.019","volume":"73","author":"H-S Shiah","year":"2007","unstructured":"Shiah H-S, Lee W-S, Juang S-H et al (2007) Mitochondria-mediated and p53-associated apoptosis induced in human cancer cells by a novel selenophene derivative, D-501036. Biochem Pharmacol 73:610\u2013619","journal-title":"Biochem Pharmacol"},{"key":"10290_CR9","doi-asserted-by":"publisher","first-page":"757","DOI":"10.1093\/jnci\/83.11.757","volume":"83","author":"A Monks","year":"1991","unstructured":"Monks A, Scudiero D, Skehan P et al (1991) Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. JNCI J Natl Cancer Inst 83:757\u2013766","journal-title":"JNCI J Natl Cancer Inst"},{"key":"10290_CR10","unstructured":"Grever MR, Schepartz SA, Chabner BA (1992) The National Cancer Institute: cancer drug discovery and development program. In: Seminars in oncology, pp 622\u2013638"},{"key":"10290_CR11","doi-asserted-by":"publisher","first-page":"5065","DOI":"10.1016\/j.bmcl.2010.07.034","volume":"20","author":"P-C Hong","year":"2010","unstructured":"Hong P-C, Chen L-J, Lai T-Y et al (2010) Synthesis of selenophene derivatives as novel CHK1 inhibitors. Bioorg Med Chem Lett 20:5065\u20135068","journal-title":"Bioorg Med Chem Lett"},{"key":"10290_CR12","doi-asserted-by":"publisher","first-page":"10453","DOI":"10.1016\/j.tet.2009.10.021","volume":"65","author":"D Thomae","year":"2009","unstructured":"Thomae D, Perspicace E, Henryon D et al (2009) One-pot synthesis of new tetrasubstituted thiophenes and selenophenes. Tetrahedron 65:10453\u201310458","journal-title":"Tetrahedron"},{"key":"10290_CR13","doi-asserted-by":"publisher","first-page":"13059","DOI":"10.1002\/chem.201302129","volume":"19","author":"RF Schumacher","year":"2013","unstructured":"Schumacher RF, Ros\u00e1rio AR, Leite MR, Zeni G (2013) Cyclization of Homopropargyl Chalcogenides by Copper (II) Salts: Selective Synthesis of 2, 3-Dihydroselenophenes, 3-Arylselenophenes, and 3-Haloselenophenes\/thiophenes. Chem Eur J 19:13059\u201313064","journal-title":"Chem Eur J"},{"key":"10290_CR14","doi-asserted-by":"publisher","first-page":"317","DOI":"10.1007\/s10593-009-0272-0","volume":"45","author":"VA D\u2019yakonov","year":"2009","unstructured":"D\u2019yakonov VA, Ibragimov AG, Khalilov LM et al (2009) Dzhemilev reaction in the synthesis of five-membered sulfur and selenium heterocycles. Chem Heterocycl Compd 45:317\u2013326","journal-title":"Chem Heterocycl Compd"},{"key":"10290_CR15","doi-asserted-by":"publisher","first-page":"1955","DOI":"10.1002\/zaac.201000135","volume":"636","author":"TM Klap\u00f6tke","year":"2010","unstructured":"Klap\u00f6tke TM, Krumm B, Scherr M (2010) Halogenation of Dibenzoselenophene and Dibenzo [1, 2] diselenine. Zeitschrift f\u00fcr Anorg und Allg Chemie 636:1955\u20131961","journal-title":"Zeitschrift f\u00fcr Anorg und Allg Chemie"},{"key":"10290_CR16","doi-asserted-by":"publisher","first-page":"2583","DOI":"10.1021\/jo0700023","volume":"72","author":"S Kumar","year":"2007","unstructured":"Kumar S, Johansson H, Engman L et al (2007) Regenerable chain-breaking 2, 3-dihydrobenzo [b] selenophene-5-ol antioxidants. J Org Chem 72:2583\u20132595","journal-title":"J Org Chem"},{"key":"10290_CR17","doi-asserted-by":"publisher","first-page":"403","DOI":"10.3184\/174751915X14357589569981","volume":"39","author":"S Sheikhi-mohammareh","year":"2015","unstructured":"Sheikhi-mohammareh S, Shiri A, Bakavoli M (2015) Synthesis of new derivatives of pyrazolo [4, 3- e ][1, 2, 4 ] triazolo [4, 3- c ] pyrimidine. J Chem Res 39:403\u2013406","journal-title":"J Chem Res"},{"key":"10290_CR18","doi-asserted-by":"publisher","first-page":"1231","DOI":"10.1002\/jhet.2432","volume":"53","author":"S Sheikhi-Mohammareh","year":"2016","unstructured":"Sheikhi-Mohammareh S, Shiri A, Bakavoli M, Mague J (2016) A Straightforward Approach for the Synthesis of Novel Derivatives of Benzo[b]pyrazolo[5\u2032,1\u2032:2,3]pyrimido[4,5-e][1,4]thiazine. J Heterocycl Chem 53:1231\u20131235. https:\/\/doi.org\/10.1002\/jhet.2432","journal-title":"J Heterocycl Chem"},{"key":"10290_CR19","doi-asserted-by":"publisher","first-page":"2055","DOI":"10.1002\/jhet.3242","volume":"55","author":"S Sheikhi-Mohammareh","year":"2018","unstructured":"Sheikhi-Mohammareh S, Shiri A (2018) An alternative regioselective approach for the synthesis of highly functionalized derivatives of Pyrazolo[5,1- b ]purine Scaffold. J Heterocycl Chem 55:2055\u20132060. https:\/\/doi.org\/10.1002\/jhet.3242","journal-title":"J Heterocycl Chem"},{"key":"10290_CR20","doi-asserted-by":"publisher","first-page":"963","DOI":"10.1007\/s00706-020-02617-2","volume":"151","author":"S Sheikhi-Mohammareh","year":"2020","unstructured":"Sheikhi-Mohammareh S, Shiri A, Beyzaei H, Yarmohammadi E (2020) New efficient design and synthesis of novel antioxidant and antifungal 7-imino[1,3]selenazolo[4,5-d]pyrimidine-5(4H)-thiones utilizing a base-promoted cascade addition\/cyclization sequence. Monatshefte f\u00fcr Chemie Chem Mon 151:963\u2013969. https:\/\/doi.org\/10.1007\/s00706-020-02617-2","journal-title":"Monatshefte f\u00fcr Chemie Chem Mon"},{"key":"10290_CR21","doi-asserted-by":"publisher","first-page":"1555","DOI":"10.1007\/s13738-020-01875-5","volume":"17","author":"S Sheikhi-Mohammareh","year":"2020","unstructured":"Sheikhi-Mohammareh S, Mashreghi M, Shiri A (2020) Robust approach leading to novel densely functionalized four-cyclic benzo[e]pyrazolo[5\u2032,1\u2032:2,3]pyrimido[4,5-b][1,4]diazepines with antibacterial activity toward resistant strains. J Iran Chem Soc 17:1555\u20131566. https:\/\/doi.org\/10.1007\/s13738-020-01875-5","journal-title":"J Iran Chem Soc"},{"key":"10290_CR22","doi-asserted-by":"publisher","first-page":"10060","DOI":"10.1002\/slct.202002474","volume":"5","author":"S Sheikhi-Mohammareh","year":"2020","unstructured":"Sheikhi-Mohammareh S, Shiri A, Maleki EH et al (2020) Synthesis of various derivatives of [1,3]Selenazolo[4,5-d]pyrimidine and exploitation of these heterocyclic systems as antibacterial, antifungal, and anticancer agents. ChemistrySelect 5:10060\u201310066. https:\/\/doi.org\/10.1002\/slct.202002474","journal-title":"ChemistrySelect"},{"key":"10290_CR23","doi-asserted-by":"publisher","DOI":"10.1007\/s11030-021-10203-9","author":"S Sheikhi-Mohammareh","year":"2021","unstructured":"Sheikhi-Mohammareh S, Shiri A, Mague J (2021) Dimroth rearrangement-based synthesis of novel derivatives of [1,3]selenazolo[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine as a new class of selenium-containing heterocyclic architecture. Mol Divers. https:\/\/doi.org\/10.1007\/s11030-021-10203-9","journal-title":"Mol Divers"},{"key":"10290_CR24","doi-asserted-by":"publisher","first-page":"226","DOI":"10.1002\/hc.20114","volume":"16","author":"AE Rashad","year":"2005","unstructured":"Rashad AE, Heikal OA, El-Nezhawy AOH, Abdel-Megeid FME (2005) Synthesis and isomerization of thienotriazolopyrimidine and thienotetrazolopyrimidine derivatives with potential anti-inflammatory activity. Heteroat Chem An Int J Main Gr Elem 16:226\u2013234","journal-title":"Heteroat Chem An Int J Main Gr Elem"},{"key":"10290_CR25","doi-asserted-by":"publisher","first-page":"350","DOI":"10.5012\/jkcs.2010.54.3.350","volume":"54","author":"H-Y Son","year":"2010","unstructured":"Son H-Y, Song Y-H (2010) A convenient synthesis of new 2-Phenylthieno [3, 2-e][1, 2, 4] triazolo [1, 5-c] pyrimidine derivatives by Dimroth rearrangement. J Korean Chem Soc 54:350\u2013353","journal-title":"J Korean Chem Soc"},{"key":"10290_CR26","doi-asserted-by":"publisher","first-page":"442","DOI":"10.1002\/btpr.2952","volume":"36","author":"E Pishavar","year":"2020","unstructured":"Pishavar E, Oroojalian F, Ramezani M, Hashemi M (2020) Cholesterol-conjugated PEGylated PAMAM as an efficient nanocarrier for plasmid encoding interleukin-12 immunogene delivery toward colon cancer cells. Biotechnol Prog 36:442\u2013462. https:\/\/doi.org\/10.1002\/btpr.2952","journal-title":"Biotechnol Prog"},{"key":"10290_CR27","doi-asserted-by":"publisher","first-page":"716","DOI":"10.5012\/jkcs.2012.56.6.716","volume":"56","author":"M Rahimizadeh","year":"2012","unstructured":"Rahimizadeh M, Eshghi H, Shiri A et al (2012) Fe (HSO 4) 3 as an efficient catalyst for diazotization and diazo coupling reactions. J Korean Chem Soc 56:716\u2013719","journal-title":"J Korean Chem Soc"},{"key":"10290_CR28","doi-asserted-by":"publisher","first-page":"770","DOI":"10.1016\/j.msec.2017.05.068","volume":"79","author":"F Oroojalian","year":"2017","unstructured":"Oroojalian F, Rezayan AH, Mehrnejad F et al (2017) Efficient megalin targeted delivery to renal proximal tubular cells mediated by modified-polymyxin B-polyethylenimine based nano-gene-carriers. Mater Sci Eng C 79:770\u2013782","journal-title":"Mater Sci Eng C"},{"key":"10290_CR29","doi-asserted-by":"publisher","first-page":"603","DOI":"10.1007\/s11030-020-10133-y","volume":"25","author":"N Kumar","year":"2020","unstructured":"Kumar N, Gulati HK, Sharma A et al (2020) Most recent strategies targeting estrogen receptor alpha for the treatment of breast cancer. Mol Divers 25:603\u2013624","journal-title":"Mol Divers"},{"key":"10290_CR30","doi-asserted-by":"publisher","first-page":"933","DOI":"10.1007\/s11030-019-10003-2","volume":"24","author":"A Hermawan","year":"2020","unstructured":"Hermawan A, Putri H, Utomo RY (2020) Comprehensive bioinformatics study reveals targets and molecular mechanism of hesperetin in overcoming breast cancer chemoresistance. Mol Divers 24:933\u2013947","journal-title":"Mol Divers"}],"container-title":["Molecular Diversity"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s11030-021-10290-8.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/article\/10.1007\/s11030-021-10290-8\/fulltext.html","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s11030-021-10290-8.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,6,20]],"date-time":"2022-06-20T14:05:31Z","timestamp":1655733931000},"score":1,"resource":{"primary":{"URL":"https:\/\/link.springer.com\/10.1007\/s11030-021-10290-8"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,8,6]]},"references-count":30,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2022,6]]}},"alternative-id":["10290"],"URL":"https:\/\/doi.org\/10.1007\/s11030-021-10290-8","relation":{},"ISSN":["1381-1991","1573-501X"],"issn-type":[{"value":"1381-1991","type":"print"},{"value":"1573-501X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,8,6]]},"assertion":[{"value":"26 May 2021","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"28 July 2021","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"6 August 2021","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Declaration"}},{"value":"The authors have no conflicts of interest to declare that are relevant to the content of this article.","order":2,"name":"Ethics","group":{"name":"EthicsHeading","label":"Conflict of interest"}}]}}