Studies On Steroidal Compounds Of The Soft Coral Nephthea Sp. And Exploring Synthesis Of (1R,2S)-2-Fluorocyclopropylamine

This dissertation focus on the isolation and structural identification of steroidal compoundsof the soft coral Nephthea sp. we collected from Naozhou Island, Zhanjiang, China. By usingmodern isolation techniques,16compounds were isolated from the soft coral Nephthea sp.including12steroids. All16structures were established by spectroscopic analysis (1H NMR,13CNMR, DEPT,1H-1H COSY, HSQC, HMBC, HRMS) and comparisons of their spectral data withthose of related compounds. The16compounds are as follow:4-hydroxybenzoic acid (1), batilol(2),5-proyl-5-hydroxy-3,4-dimethylfuran-2(5H)-one (3),5-hydroxy-3,4-dimethyl-5-pentyl-furan-2(5H)-one (4),(17α)-progesterone (5),(20S)-pregnan-1,4-diene-3-oxo-20-carboxylic acidmethyl ester (6), pregnan-4-ene-3,6,20-trione (7),(20R)-pregnan-4,16-diene-20-hydroxy-3-one (8), pregnan-15β-hydroxy-4,6-diene-3,20-dione (9), pregnan-4,6-diene-3,20-dione (10),3β-O-palmitoyl-pregnan-20-one (11),(22E)-3β,6α-dihydroxy-11-acetyloxy-9,11-secocholesta-7,22-diene-9-one (12), pregnan-4-ene-14α-hydroxy-3,20-dione (13),8β-methyltestolactone (14),(22R)-18,22-diacetoxy-cholesta-1,4-diene-3-one (15),(20R,22R)-20-hydroxy-22-acetoxy-cholesta-1,4-diene-3-one (16). Among these16compounds, compound15and16were isolatedand identified for the first time. Evidence of bioactive experiments also shows compound15and16exhibited cytotoxic activity against HeLa cells with IC50values8.29±0.42μg/mL and17.25±0.61μg/mL, respectively.Sitafloxacin shows significant curative effect in RTI and UTI treatments. Evidence ofclinical trails shows the drug can reduce adverse drug reactions due to itscis-2-fluorocyclopropylamine subtituent. We tried to explore a synthesis method of (1R,2S)-2-fluorocyclopropylamine in this dissertation and accomplished the synthesis of its precursorcompound benzyl N-(1-phenylethyl)-N-vinylcarbamate on a massive scale.