Block, EricBechand, BenjaminGundala, SivajiVattekkatte, AbithWang, KaiMousa, Shaymaa SGodugu, KavithaMousa, Shaker A.2022-12-292022-12-292017-11-24Block, E. vd. (2017). ''Fluorinated analog NMR s of organosulfur compounds from garlic (allium sativum): Synthesis, chemistry and anti-angiogenesis and antithrombotic studies''. Molecules, 22(12).https://doi.org/10.3390/molecules22122081https://www.mdpi.com/1420-3049/22/12/20811420-3049http://hdl.handle.net/11452/30161We describe the synthesis, reactivity, and antithrombotic and anti-angiogenesis activity of difluoroallicin (S-(2-fluoroallyl) 2-fluoroprop-2-ene-1-sulfinothioate) and S-2-fluoro-2-propenyl-l-cysteine, both easily prepared from commercially available 3-chloro-2-fluoroprop-1-ene, as well as the synthesis of 1,2-bis(2-fluoroallyl)disulfane, 5-fluoro-3-(1-fluorovinyl)-3,4-dihydro-1,2-dithiin, trifluoroajoene ((E,Z)-1-(2-fluoro-3-((2-fluoroallyl)sulfinyl)prop-1-en-1-yl)-2-(2-fluoroallyl)disulfane), and a bis(2-fluoroallyl)polysulfane mixture. All tested organosulfur compounds demonstrated effective inhibition of either FGF or VEG-mediated angiogenesis (anti-angiogenesis activity) in the chick chorioallantoic membrane (CAM) or the mouse Matrigel (R) models. No embryo mortality was observed. Difluoroallicin demonstrated greater inhibition (p < 0.01) versus organosulfur compounds tested. Difluoroallicin demonstrated dose-dependent inhibition of angiogenesis in the mouse Matrigel (R) model, with maximal inhibition at 0.01 mg/implant. Allicin and difluoroallicin showed an effective antiplatelet effect in suppressing platelet aggregation compared to other organosulfur compounds tested. In platelet/fibrin clotting (anti-coagulant activity), difluoroallicin showed concentration-dependent inhibition of clot strength compared to allicin and the other organosulfur compounds tested.eninfo:eu-repo/semantics/openAccessBiochemistry & molecular biologyChemistry2-fluoroallyl sulfur compoundsAjoeneAllicinAngiogenesisAnti-angiogenesisAnti-thromboticCoagulationDifluoroallicinGarlicPlateletThrombosisTrifluoroajoeneVinyl dithiinsIn-vitroAllicinEfficacyPolymerizationDerivativesAntagonistsDynamicsStressAcidAngiogenesis inhibitorsAnimalsDose-response relationship, drugFibrinolytic agentsHalogenationMiceModels, molecularMolecular conformationNeovascularization, physiologicOrganic chemicalsSulfur compoundsGarlicArticle0004192424000512-s2.0-85035354617221229182588Biochemistry & molecular biologyChemistry, multidisciplinaryAllicin; Garlic; Diallyl TrisulfideAngiogenesis inhibitorFibrinolytic agentOrganic compoundSulfur derivativeAngiogenesisAnimalChemistryConformationDose responseDrug effectGarlicHalogenationMolecular modelMouseSynthesis