Supplementary MaterialsIENZ_1375483_Supplementary_Materials. (6aCm The monoindolizine 5 (1?mmol, 1 equiv., 0.37?g 5a, 0.40?g 5?b, 0.45?g 5c, 0.38?g 5d, 0.40?g 5e) and bromacetophenone derivative (or/and substituted, 2?mmol, 2 equiv.) was suspended in anhydrous acetone (20?ml) and magnetically stirred instantly at reflux. The resulting precipitate was collected by filtration and washed with acetone then. All products had been purified by crystallisation (CHCl3:MeOH 1:1, v:v). (6a). Orange natural powder (0.52?g, 89% produce), mp?=?279C282?C. 1H-NMR (400?MHz, DMSO-d6): 1.36 (t, 14.3 C12, 21.3 CH3, 60.1 C11, 65.5 C22, 108.1 C1, 113.7 C6, 118.8 C8, 123.0 C3, 124.6 2??C19, 127.9 C2, 128.3 C25, C29, 128.6 2??C15, 128.7 2??C16, 129.1 C5, 129.6 C26, C28, 131.0 C24, 132.1 C17, C7, 137.8 C9, 138.7 C14, 145.4 C27, 146.6 2??C20, 152.3 C18, 162.6 C10, 184.9 C13, 190.1 C23. IR (KBr, (6b). Yellowish natural powder (0.53?g, 89% produce), mp 255C256?C. 1H-NMR (400?MHz, DMSO-d6): 1.37 (t, 14.2 C12, 55.6 OCH3, 60.1 C11, 65.7 C22, 108.1 C1, 112.9 C29, 113.6 C6, 118.8 C8, 120.5 C27, 120.6 C25, 123.0 C3, 124.6 2??C19, 127.8 C2, 128.6 2??C15, 128.7 2??C16, 129.1 C5, 130.4 C26, 134.8 C24, 132.0 C17, 132.1 C7, 137.7 C9, 138.6 C14, 146.5 2??C20, 152.2 C18, 159.5 C28, 162.6 C10, 184.9 C13, 190.6 C23. IR (KBr, (6c). Yellowish natural powder (0.59?g, Arranon cell signaling 93% produce), mp 288?C. 1H-NMR (400?MHz, DMSO-d6): 1.36 (t, 14.3 C12, 55.9 OCH3, 60.3 C11, 65.4 C22, 108.3 C1, 113.9 C6, 114.5 C26, C28, 118.9 C8, 122.9 C3, 124.7 2??C19, 126.3 C24, 128.0 C2, 128.8 2??C16, 129.3 C5, 130.8 2??C15, C25, C29, 132.3 C7, 137.0 C17, 137.4 C14, 138.0 C9, 146.7 2??C20, 152.3 C18, HDAC10 162.7 C10, 164.3 C27, 183.7 C13, 189.0 C23. IR (KBr, (6d). Yellowish natural Arranon cell signaling powder (0.46?g, 73% produce), mp 252C254?C. 1H-NMR (400?MHz, DMSO-d6): 1.36 (t, 14.3 C12, 55.6 OCH3, 60.2 C11, 65.8 C22, 108.3 C1, 113.0 C29, 113.8 C6, 118.9 C8, 120.5 C25, 120.7 C27, 123.0 C3, 124.7 2??C19, 128.0 C2, 128.8 2??C16, 129.3 C5, 130.4 C26, 130.7 2??C15, 132.3 C7, 134.9 C24, 137.0 C17, 137.0 C14, 138.0 C9, 146.6 2??C20, 152.4 C18, 159.6 C28, 162.7 C10, 183.7 C13, 190.6 C23. IR (KBr, (6e). Orange natural powder (0.55?g, 89% produce), mp 307C310?C. 1H-NMR (400?MHz, DMSO-d6): 1.37 (t, 14.3 C12, 60.2 C11, 65.5 C22, 108.2 C1, 113.8 C6, 116.3 (d, C26, C28, J=?22?Hz), 118.8 C8, 122.9 C3, 124.7 2??C19, 127.9 C2, 128.7 2??C16, 129.2 C5, 130.3 (d, C24, J=?3.0?Hz), 130.7 2??C15, 131.4 (d, C25, C29, J=?10.0?Hz), 132.2 C7, 137.0 C17, 137.3 C14, 137.9 C9, 146.6 2??C20, 152.3 C18, 162.6 C10, 165.7 (d, C27, J=?253?Hz), 183.6 C13, 189.4 C23. IR (KBr, (6f). Orange natural powder (0.61?g, 92% produce), mp 283C284?C. 1H-NMR (400?MHz, DMSO-d6): 1.37 (t, 14.4 C12, 21.4 CH3, 60.3 C11, 65.6 C22, 108.3 C1, 113.9 C6, 118.9 C8, 122.9 C3, 124.7 2??C19, 126.1 C17, 128.1 C2, 128.4 C25, C29, 129.3 C5, 129.7 C26, C28, 130.9 2??C16, 131.1 C24, 131.8 2??C15, 132.4 C7, 137.8 C14, 138.0 C9, 145.6 C27, 146.7 2??C20, 152.4 C18, 162.7 C10, 183.9 C13, 190.2 C23. IR (KBr, (6g). Orange natural powder (0.56?g, 82% produce), mp 277C278?C. 1H-NMR (400?MHz, DMSO-d6): 1.36 (t, 14.3 C12, 55.8 OCH3, 60.2 C11, 65.3 C22, 108.2 C1, 113.8 C6, 114.4 C26, C28, 118.8 C8, 122.8 C3, 124.9 2??C19, 126.0 C17, 126.2 C24, 127.9 C2, 129.2 C5, 130.7 C25, C29, 130.8 2??C16, 131.6 2??C15, 132.2 C7, 137.6 C14, 137.9 C9, 146.6 2??C20, 152.2 C18, 162.6 C10, 164.2 C27, 183.7 C13, Arranon cell signaling 188.9 C23. IR (KBr, (6h). Yellowish natural powder (0.67?g, 99% produce), mp 256C259?C. 1H-NMR (400?MHz, DMSO-d6): 1.37 (t, 14.3 C12, 55.6 OCH3, 60.2 C11, 65.8 C22, 108.3 C1, 113.0 C29, 113.8 C6, 118.8 C8, 120.5 C27, 120.7 Arranon cell signaling C25, 122.9 C3, 124.7 2??C19, 126.0 C17, 128.0 C2, 129.2 C5, 130.4 C26, 130.8 2??C16, 131.7 2??C15, 132.3 C7, 134.8 C24, 137.7 C14, 137.9 C9, 146.6 2??C20, 152.3 C18, 159.6 C28, 162.7 C10, 183.8 C13, 190.6 C23. IR (KBr, (6m). Yellowish natural powder (0.35?g, 56% produce), mp 265C267?C. 1H-NMR (400?MHz, DMSO-d6): 1.37 (t, 14.3 C12,.