{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,3]],"date-time":"2026-08-03T22:41:07Z","timestamp":1785796867807,"version":"3.56.0"},"reference-count":47,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2024,9,1]],"date-time":"2024-09-01T00:00:00Z","timestamp":1725148800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2024,9,1]],"date-time":"2024-09-01T00:00:00Z","timestamp":1725148800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2024,6,25]],"date-time":"2024-06-25T00:00:00Z","timestamp":1719273600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000054","name":"National Cancer Institute","doi-asserted-by":"publisher","award":["507275896"],"award-info":[{"award-number":["507275896"]}],"id":[{"id":"10.13039\/100000054","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100006492","name":"National Institute of Allergy and Infectious Diseases Division of Intramural Research","doi-asserted-by":"publisher","award":["ZIA BC 006538"],"award-info":[{"award-number":["ZIA BC 006538"]}],"id":[{"id":"10.13039\/100006492","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["STE 3140\/1-1"],"award-info":[{"award-number":["STE 3140\/1-1"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["494832089"],"award-info":[{"award-number":["494832089"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["GRK2873"],"award-info":[{"award-number":["GRK2873"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic &amp; Medicinal Chemistry Letters"],"published-print":{"date-parts":[[2024,9]]},"DOI":"10.1016\/j.bmcl.2024.129858","type":"journal-article","created":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T06:05:38Z","timestamp":1719209138000},"page":"129858","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":5,"special_numbering":"C","title":["Revisiting the antiangiogenic mechanisms of fluorinated thalidomide derivatives"],"prefix":"10.1016","volume":"110","author":[{"given":"Johannes","family":"Sievers","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rabea","family":"Voget","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Feiteng","family":"Lu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kathleen M.","family":"Garchitorena","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuen Lam Dora","family":"Ng","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cindy H.","family":"Chau","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christian","family":"Steinebach","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"William D.","family":"Figg","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jan","family":"Kr\u00f6nke","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"G\u00fctschow","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.bmcl.2024.129858_h0005","doi-asserted-by":"crossref","first-page":"310","DOI":"10.1038\/nrclinonc.2018.9","article-title":"Improving immunotherapy outcomes with anti-angiogenic treatments and vice versa","volume":"15","author":"Khan","year":"2018","journal-title":"Nat Rev Clin Oncol"},{"key":"10.1016\/j.bmcl.2024.129858_h0010","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1016\/j.mvr.2008.08.003","article-title":"The anti-cancer drug lenalidomide inhibits angiogenesis and metastasis via multiple inhibitory effects on endothelial cell function in normoxic and hypoxic conditions","volume":"77","author":"Lu","year":"2009","journal-title":"Microvasc Res"},{"key":"10.1016\/j.bmcl.2024.129858_h0015","doi-asserted-by":"crossref","first-page":"198","DOI":"10.1038\/s41392-023-01460-1","article-title":"Angiogenic signaling pathways and anti-angiogenic therapy for cancer","volume":"8","author":"Liu","year":"2023","journal-title":"Signal TransductTargeted Ther"},{"key":"10.1016\/j.bmcl.2024.129858_b0010","doi-asserted-by":"crossref","first-page":"4082","DOI":"10.1073\/pnas.91.9.4082","article-title":"Thalidomide is an inhibitor of angiogenesis","volume":"91","author":"D'Amato","year":"1994","journal-title":"PNAS"},{"key":"10.1016\/j.bmcl.2024.129858_b0015","doi-asserted-by":"crossref","first-page":"11395","DOI":"10.1096\/fj.201903060RR","article-title":"Role of cereblon in angiogenesis and in mediating the antiangiogenic activity of immunomodulatory drugs","volume":"34","author":"Beedie","year":"2020","journal-title":"FASEB J"},{"key":"10.1016\/j.bmcl.2024.129858_b0020","first-page":"3189","article-title":"Antiangiogenic activity of N-substituted and tetrafluorinated thalidomide analogues","volume":"63","author":"Ng","year":"2003","journal-title":"Cancer Res"},{"key":"10.1016\/j.bmcl.2024.129858_h0035","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1016\/j.bmc.2003.11.007","article-title":"Thalidomide analogues demonstrate dual inhibition of both angiogenesis and prostate cancer","volume":"12","author":"Capitosti","year":"2004","journal-title":"Bioorg Med Chem"},{"key":"10.1016\/j.bmcl.2024.129858_h0040","doi-asserted-by":"crossref","first-page":"2080","DOI":"10.1002\/cmdc.201800263","article-title":"Synthesis, structural characterization, and antiangiogenic activity of polyfluorinated benzamides","volume":"13","author":"Steinebach","year":"2018","journal-title":"ChemMedChem"},{"key":"10.1016\/j.bmcl.2024.129858_h0045","doi-asserted-by":"crossref","first-page":"2219","DOI":"10.1021\/jm0304820","article-title":"Comparative molecular field analysis and comparative molecular similarity indices analysis of thalidomide analogues as angiogenesis inhibitors","volume":"47","author":"Lepper","year":"2004","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmcl.2024.129858_h0050","doi-asserted-by":"crossref","first-page":"2228","DOI":"10.1158\/1535-7163.MCT-15-0320","article-title":"Anticancer properties of a novel class of tetrafluorinated thalidomide analogues","volume":"14","author":"Beedie","year":"2015","journal-title":"Mol Cancer Ther"},{"key":"10.1016\/j.bmcl.2024.129858_h0055","doi-asserted-by":"crossref","first-page":"2621","DOI":"10.1002\/cmdc.201600496","article-title":"Synthesis and antiangiogenic properties of tetrafluorophthalimido and tetrafluorobenzamido barbituric acids","volume":"11","author":"Ambro\u017cak","year":"2016","journal-title":"ChemMedChem"},{"key":"10.1016\/j.bmcl.2024.129858_b0035","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1146\/annurev-pharmtox-022123-104147","article-title":"From thalidomide to rational molecular glue design for targeted protein degradation","volume":"64","author":"Oleinikovas","year":"2024","journal-title":"Annu Rev Pharmacol Toxicol"},{"key":"10.1016\/j.bmcl.2024.129858_h0065","doi-asserted-by":"crossref","first-page":"5","DOI":"10.1016\/j.ddtec.2019.02.002","article-title":"A critical evaluation of the approaches to targeted protein degradation for drug discovery","volume":"31","author":"Chopra","year":"2019","journal-title":"Drug Discov Today Technol"},{"key":"10.1016\/j.bmcl.2024.129858_h0070","first-page":"2202300351","article-title":"A degron blocking strategy towards improved CRL4CRBN recruiting PROTAC selectivity","volume":"24","author":"Bouguenina","year":"2023","journal-title":"ChemBioChem"},{"key":"10.1016\/j.bmcl.2024.129858_h0075","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1126\/science.1244851","article-title":"Lenalidomide causes selective degradation of IKZF1 and IKZF3 in multiple myeloma cells","volume":"343","author":"Kr\u00f6nke","year":"2014","journal-title":"Science"},{"key":"10.1016\/j.bmcl.2024.129858_h0080","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1126\/science.1244917","article-title":"The myeloma drug lenalidomide promotes the cereblon-dependent destruction of Ikaros proteins","volume":"343","author":"Lu","year":"2014","journal-title":"Science"},{"key":"10.1016\/j.bmcl.2024.129858_h0085","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1038\/nature14610","article-title":"Lenalidomide induces ubiquitination and degradation of CK1\u03b1 in Del(5q) MDS","volume":"523","author":"Kr\u00f6nke","year":"2015","journal-title":"Nature"},{"key":"10.1016\/j.bmcl.2024.129858_h0090","doi-asserted-by":"crossref","first-page":"252","DOI":"10.1038\/nature18611","article-title":"A novel cereblon modulator recruits GSPT1 to the CRL4(CRBN) ubiquitin ligase","volume":"535","author":"Matyskiela","year":"2016","journal-title":"Nature"},{"key":"10.1016\/j.bmcl.2024.129858_b0050","doi-asserted-by":"crossref","first-page":"981","DOI":"10.1038\/s41589-018-0129-x","article-title":"SALL4 mediates teratogenicity as a thalidomide-dependent cereblon substrate","volume":"14","author":"Matyskiela","year":"2018","journal-title":"Nat Chem Biol"},{"key":"10.1016\/j.bmcl.2024.129858_h0100","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1186\/s12935-023-02985-9","article-title":"SALL4 promotes angiogenesis in gastric cancer by regulating VEGF expression and targeting SALL4\/VEGF pathway inhibits cancer progression","volume":"23","author":"Abouelnazar","year":"2023","journal-title":"Cancer Cell Int"},{"key":"10.1016\/j.bmcl.2024.129858_h0105","doi-asserted-by":"crossref","first-page":"104","DOI":"10.1186\/s13046-020-01609-8","article-title":"VHL mutation-mediated SALL4 overexpression promotes tumorigenesis and vascularization of clear cell renal cell carcinoma via Akt\/GSK-3\u03b2 signaling","volume":"39","author":"Sun","year":"2020","journal-title":"J Exp Clin Cancer Res"},{"key":"10.1016\/j.bmcl.2024.129858_h0110","doi-asserted-by":"crossref","first-page":"4578","DOI":"10.1038\/s41467-020-18488-4","article-title":"Structural bases of IMiD selectivity that emerges by 5-hydroxythalidomide","volume":"14","author":"Furihata","year":"2020","journal-title":"Nat Commun"},{"key":"10.1016\/j.bmcl.2024.129858_h0115","doi-asserted-by":"crossref","first-page":"4683","DOI":"10.1038\/s41467-023-40385-9","article-title":"Lenalidomide derivatives and proteolysis-targeting chimeras for controlling neosubstrate degradation","volume":"14","author":"Yamanaka","year":"2023","journal-title":"Nat Commun"},{"key":"10.1016\/j.bmcl.2024.129858_b0065","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/j.bbrc.2020.11.117","article-title":"On the correlation of cereblon binding, fluorination and antiangiogenic properties of immunomodulatory drugs","volume":"534","author":"Heim","year":"2021","journal-title":"Biochem Biophys Res Commun"},{"key":"10.1016\/j.bmcl.2024.129858_b0070","doi-asserted-by":"crossref","first-page":"14513","DOI":"10.1021\/acs.jmedchem.3c00851","article-title":"Leveraging ligand affinity and properties: discovery of novel benzamide-type cereblon binders for the design of PROTACs","volume":"66","author":"Steinebach","year":"2023","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmcl.2024.129858_b0075","doi-asserted-by":"crossref","first-page":"1085","DOI":"10.1002\/1520-6017(200008)89:8<1085::AID-JPS13>3.0.CO;2-N","article-title":"Rapid-gradient HPLC method for measuring drug interactions with immobilized artificial membrane: comparison with other lipophilicity measures","volume":"89","author":"Valko","year":"2000","journal-title":"J Pharm Sci"},{"key":"10.1016\/j.bmcl.2024.129858_b0080","unstructured":"IAM chromatography was performed with a Regis IAM.PC.DD2 column (100 \u00d7 4.6 mm, 10 \u03bcm, 300 \u00c5) equipped with a guard cartridge at 25 \u00b0C as described.14 Mobile phase A was 50 mM NH4OAc, pH 7.4, mobile phase B was MeCN. The retention times were determined with a gradient of 0 to 95% MeCN from 0 to 6 min, which was kept at 95% until 6.5 min, then dropped to 0% from 6.5 to 7 min, and finally kept at 0% until 9 min. The mobile phase flow rate was 1.5 mL\/min. A calibration was performed by plotting the retention times of paracetamol, acetanilide, acetophenone, propiophenone, butyrophenone, valerophenone, and octanophenone against their literature CHI values.15."},{"key":"10.1016\/j.bmcl.2024.129858_b0085","unstructured":"Metabolic stability analyses in human liver microsomes were performed by Pharmacelsus (Saarbr\u00fccken, Germany) as described.14."},{"key":"10.1016\/j.bmcl.2024.129858_b0090","unstructured":"HUVEC cells were cultured as described.13 MM1.S cells (RRID:CVCL_8792; American Type Culture Collection, Manassas, VA) were grown in RPMI-1640 medium (Life Technologies, Carlsbad, CA) with 10% FBS and 1% Pen\/Strep. All cell lines were cultured in 5% CO2 and 95% air at 37 \u00b0C and underwent routine cell line authentication and mycoplasma testing through ATCC."},{"key":"10.1016\/j.bmcl.2024.129858_b0095","unstructured":"For the cell proliferation assay, HUVEC (15,000 cells\/well) and MM1.S (20,000 cells\/well) cells were seeded in a 96-well plate in 50 \u00b5L\/well and allowed to incubate overnight at 37 \u00b0C in 5% CO2. An equal amount of treatment media containing the vehicle (0.5% DMSO), or the test compound was then plated on top of the seeded for 48 hours (HUVEC) or 72 hours (MM1.S). Cell proliferation was evaluated by adding 10 \u00b5L of Cell Counting Reagent-8 (CCK-8; Dojindo Laboratories, Rockville, MD) to each well and incubated for 2 hours. Plates were read at absorbance of 450 nm on a microplate reader (SpectraMax iD3, Molecular Devices, San Jose, CA)."},{"key":"10.1016\/j.bmcl.2024.129858_b0100","unstructured":"Cell culture, cell treatment and immunoblotting was performed as described.14. The plasmid used for the reporter system was Aiolos ZF2 (AA146-168) in Cilantro 2 (Addgene plasmid #74456). In brief, the plasmid comprised the IMiD-binding zinc finger 2 (ZF2) of IKZF3 fused to eGFP with mCherry in vector backbone. MM.1S cells were lentivirally transduced with the IKZF3-ZF2 reporter and treated with respective compounds for 16 hours. Flow cytometry was performed for the quantification of eGFP and mCherry mean fluorescence intensity. The eGFP\/mCherry ratio was indicative of IKZF3-ZF2 degradation levels. Compound-treated samples were normalized to DMSO-treated samples. Data was obtained with biological replicates (n=3) and representmean\u00b1 SD."},{"key":"10.1016\/j.bmcl.2024.129858_b0105","doi-asserted-by":"crossref","first-page":"1513","DOI":"10.1182\/blood.2023021105","article-title":"Mezigdomide is effective alone and in combination with Menin inhibition in pre-clinical models of KMT2A-r and NPM1c AML","volume":"143","author":"Bourgeois","year":"2024","journal-title":"Blood"},{"key":"10.1016\/j.bmcl.2024.129858_b0110","unstructured":"The Artichoke reporter assay was performed as described.14 Briefly, HEK293T cells were transfected and virus was harvested. MM1.S cells were transduced and treated with the test compounds. Cells were measured on a Cytoflex (Beckman Coulter) flow cytometer. Live single cells expressing mCherry were gated for FITC and histograms displaying counts were plotted and quantified."},{"key":"10.1016\/j.bmcl.2024.129858_h0170","doi-asserted-by":"crossref","first-page":"775","DOI":"10.1038\/s41586-022-05333-5","article-title":"The E3 ligase adapter cereblon targets the C-terminal cyclic imide degron","volume":"610","author":"Ichikawa","year":"2022","journal-title":"Nature"},{"key":"10.1016\/j.bmcl.2024.129858_h0175","doi-asserted-by":"crossref","first-page":"66","DOI":"10.1016\/j.bbrc.2022.11.001","article-title":"Identification and structural basis of C-terminal cyclic imides as natural degrons for cereblon","volume":"637","author":"Heim","year":"2022","journal-title":"Biochem Biophys Res Commun"},{"key":"10.1016\/j.bmcl.2024.129858_h0180","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1016\/j.bbrc.2023.01.051","article-title":"Cereblon neo-substrate binding mimics the recognition of the cyclic imide degron","volume":"646","author":"Heim","year":"2023","journal-title":"Biochem Biophys Res Commun"},{"key":"10.1016\/j.bmcl.2024.129858_h0185","doi-asserted-by":"crossref","first-page":"26663","DOI":"10.1002\/anie.202108848","article-title":"Phenyl-Glutarimides: Alternative cereblon binders for the design of PROTACs","volume":"60","author":"Min","year":"2021","journal-title":"Angew Chem Int Ed"},{"key":"10.1016\/j.bmcl.2024.129858_h0190","doi-asserted-by":"crossref","first-page":"16388","DOI":"10.1021\/acs.jmedchem.3c01848","article-title":"Design and synthesis of novel cereblon binders for use in targeted protein degradation","volume":"66","author":"Norris","year":"2023","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmcl.2024.129858_b0125","doi-asserted-by":"crossref","first-page":"8858","DOI":"10.1039\/D2CC02094G","article-title":"Targeting the deubiquitinase USP7 for degradation with PROTACs","volume":"58","author":"Murgai","year":"2022","journal-title":"Chem Commun"},{"key":"10.1016\/j.bmcl.2024.129858_b0130","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1038\/nature13527","article-title":"Structure of the DDB1-CRBN E3 ubiquitin ligase in complex with thalidomide","volume":"512","author":"Fischer","year":"2014","journal-title":"Nature"},{"key":"10.1016\/j.bmcl.2024.129858_b0135","unstructured":"General procedure for the preparation of compounds 9-11: 3-Aminopiperidine-2,6-dione hydrochloride (0.25 g, 1.5 mmol) was suspended in dry CH2Cl2 (15 mL), and it was cooled to 0 \u00b0C. Et3N (0.30 g, 0.42 mL, 3.0 mmol) and the corresponding monofluoro-substituted benzoyl chloride (238 mg, 1.5 mmol) were added. After stirring for 18 h at room temperature, it was quenched by the addition of half-saturated aqueous NH4Cl solution (50 mL). The mixture was extracted with 10% MeOH in EtOAc (2 \u00d7 50 mL) and the combined organic layers were washed with H2O (50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using gradient of petroleum ether\/EtOAc 1:2 to EtOAc. For analytical details, see Table S1."},{"key":"10.1016\/j.bmcl.2024.129858_b0140","unstructured":"General procedure for the preparation of compounds 12-19: The corresponding carboxylic acid (1.5 mmol) was dissolved in dry DMF (45 mL). N,N-Diisopropylethylamine (775 mg, 1.04 mL, 6 mmol) and 3-aminopiperidine-2,6-dione hydrochloride (988 mg, 6 mmol). Subsequently, the coupling reagents 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (316 mg, 1.65 mmol) and 1H-1,2,3-benzotriazol-1-ol monohydrate (253 mg, 1.65 mmol) were added and the suspension was stirred for 18 h at room temperature. The mixture was diluted with a saturated aqueous NH4Cl solution (100 mL) and extracted with EtOAc (3 \u00d7 50 mL). The combined organic layers were washed with 5% aqueous LiCl solution (3 \u00d7 100 mL) and saturated aqueous NaCl solution (100 mL), dried over Na2SO4, and filtered. The solvent was removed in vacuo. The residue was purified by preparative column chromatography, performed with an automated flash chromatography system puriFlash XS 520Plus using a gradient of 25 to 50% EtOAc in cyclohexane within 40 min. For analytical details, see Table S1."},{"key":"10.1016\/j.bmcl.2024.129858_b0145","unstructured":"For the endothelial cell tube formation assay, HUVEC cells were cultures as described.13 ECMatrix (60 \u03bcL\/well) from in vitro angiogenesis assay kit (Millipore Sigma, Rockville, MD) was plated in a 96-well plate and incubated for 30 min. HUVECs were split, plated atop the basement membrane (35,000 cells\/well), and treated with the vehicle control (0.1% DMSO), 10 \u00b5M tetrafluoro-thalidomide (2; positive control), 100 \u00b5M thalidomide (1; comparator), or test compounds at 10 \u00b5M or 100 \u00b5M. The wells were incubated for 18 hours and then imaged. Tubule formation was quantified using ImageJ based on mean mesh size. Three independent experiments were performed (with n=3-6 replicates per experiment). High dose experiments (at 100 \u00b5M) were performed once (n=3-6 replicates)."},{"key":"10.1016\/j.bmcl.2024.129858_b0150","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1016\/j.intimp.2014.05.007","article-title":"In vitro anti-proliferative and anti-angiogenic activities of thalidomide dithiocarbamate analogs","volume":"21","author":"El-Aarag","year":"2014","journal-title":"Int Immunopharmacol"},{"key":"10.1016\/j.bmcl.2024.129858_b0155","doi-asserted-by":"crossref","first-page":"2771","DOI":"10.1021\/acschembio.8b00693","article-title":"Homo-PROTACs for the chemical knockdown of cereblon","volume":"13","author":"Steinebach","year":"2018","journal-title":"ACS Chem Biol"},{"key":"#cr-split#-10.1016\/j.bmcl.2024.129858_b0160.1","unstructured":"2-(2,4-Difluorophenyl)-4,5,6,7-tetrafluoro-1H-isoindole-1,3(2H)-dione (CPS-49): (a) G\u00fctschow M, Hecker T, Thiele A, Hauschildt S, Eger K. Aza analogues of thalidomide: Synthesis and evaluation as inhibitors of tumor necrosis factor-alpha production in vitro. Bioorg Med Chem. 2001;9:1095\u22121065"},{"key":"#cr-split#-10.1016\/j.bmcl.2024.129858_b0160.2","doi-asserted-by":"crossref","unstructured":"(b) Ng SS, MacPherson GR, G\u00fctschow M, Eger K, Figg WD. Antitumor effects of thalidomide analogs in human prostate cancer xenografts implanted in immunodeficient mice. Clin Cancer Res. 2004;10:4192\u22124197.","DOI":"10.1158\/1078-0432.CCR-03-0700"}],"container-title":["Bioorganic &amp; Medicinal Chemistry Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X24002609?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X24002609?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2024,10,6]],"date-time":"2024-10-06T17:37:04Z","timestamp":1728236224000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0960894X24002609"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,9]]},"references-count":47,"alternative-id":["S0960894X24002609"],"URL":"https:\/\/doi.org\/10.1016\/j.bmcl.2024.129858","relation":{},"ISSN":["0960-894X"],"issn-type":[{"value":"0960-894X","type":"print"}],"subject":[],"published":{"date-parts":[[2024,9]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Revisiting the antiangiogenic mechanisms of fluorinated thalidomide derivatives","name":"articletitle","label":"Article Title"},{"value":"Bioorganic & Medicinal Chemistry Letters","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bmcl.2024.129858","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2024 The Authors. Published by Elsevier Ltd.","name":"copyright","label":"Copyright"}],"article-number":"129858"}}