molecules Article Fluorinated Analog NMR s of Organosulfur Compounds from Garlic (Allium sativum): Synthesis, Chemistry and Anti-Angiogenesis and Antithrombotic Studies Eric Block 1,* ID , Benjamin Bechand 1, Sivaji Gundala 1, Abith Vattekkatte 1, Kai Wang 1, Shaymaa S. Mousa 2, Kavitha Godugu 2, Murat Yalcin 2,3 and Shaker A. Mousa 2,* ID 1 Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222, USA;
[email protected] (B.B.);
[email protected] (S.G.);
[email protected] (A.V.);
[email protected] (K.W.) 2 The Pharmaceutical Research Institute, Albany College of Pharmacy and Health Sciences, Rensselaer, NY 12144, USA;
[email protected] (S.S.M.);
[email protected] (K.G.);
[email protected] (M.Y.) 3 Department of Physiology, Veterinary Medicine Faculty, Uludag University, Bursa 16059, Turkey * Correspondence:
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[email protected] (S.A.M.); Tel.: +1-518-442-4459 (E.B.); +1-518-694-7397 (S.A.M.) Received: 6 October 2017; Accepted: 24 November 2017; Published: 28 November 2017 Abstract: We 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.