Bioactivity and characterization of exudates from Cryptomeria japonica bark

Efficient Synthesis of the N‐(buta‐2,3‐dienyl)carboxamide of Isopimaric Acid and the Potential of This Compound towards Heterocyclic Derivatives of Diterpenoids

“…To avoid the formationo fc ompounds 14 and 15 and also to improvet he selectivity,w es tudied the reactionb etweent erpenoid allene 3 and 2-iodophenol (10)i nm ore detail.F irst, we studied the effect of the palladium source in the catalytic system on the yield of the cyclization product ( Table 2, entries [3][4][5][6]. The reactiono fa llene 3 with 10 under the conditions [18b] of Pd 2 (dba) 3 ·CHCl 3 (dba = dibenzylideneacetone) as the palladium source and (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene [(R)-(+ +)-BINAP] as the ligand in acetonitrile with heating at 80 8Cf or 50 hl ed to am ixture of diterpenoid 2H-chromenes 11 a/11 b (isolated in an overall yield of 48 %) and benzofuran derivatives 12 a/12 b/13 (overall yield of 8%) ( Table 2, entry 3).…”

“…60-75 8C) were used after distillation. 1652,1606,1500,1438,1384,1330,1297,1257,1236,1166,1128,1097,1074,1056,991,910,806,754,696 -2-[(1R,4aR,4bS,7S,10aR)-1,4a,7-trimethyl-7-vinyl-1,2, 3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthren-1-yl 40 (m, 4H,2H-11, 12), 1.42-1.49 (m, 2H,2H-12), 1.51-1.78 (m, 12 H, 2H-11, 2, 3, 2, 6, 9), 1.80-1.84 (m, 4H,2H-14, 5), 1.86-2.01 (m, 8H,2H-14, 6, 3, 1), 3.52 (dd,J = 14.0,7.2 Hz,1H,3.55 (dd,J = 14.0,8.2 Hz,1H,4.85 (dd,J = 10.9,1.6 Hz,1H,4.87 (dd,J = 10.9,1.6 Hz,1H,4.91 (dd,J = 17.7,1.6 Hz,1H,4.92 (dd,J = 17.7,1.6 Hz,1H,4H,5'), 5.30 (br s, 1H, =CH 2 ), 5.37 (br s, 2H, =CH 2 ), 5.37 (s, 1H, =CH 2 ), 2H,[2][3][4][5][6][7][8]…”

“…25, 60.32 (2 C-4'), 79.50, 79.61 (2 C-5'), 109.08 (2 C-16), 111.79, 112.11( 2C-7'), 120.91, 121.06 (2 C-7), 126.36, 126.36 (4 C-2'',6''), 127.84 (2 C-4''), 128.32 (4 C-3'',5''), 135.43 (2 C-8), 137.81, 137.91 (2 C-6'), 147.18 (2 C-1''), 150.16 (2 C-15), 173.97, 174.12 ppm (2 C-2');IR: ñ = 2927IR: ñ = , 2869IR: ñ = , 2850IR: ñ = , 1650IR: ñ = , 1500IR: ñ = , 1384IR: ñ = , 1234IR: ñ = , 1139IR: ñ = , 1105IR: ñ = , 1031 4aR,4bS,7S,10aR) -1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10, (m, 10 H, 2H-11, 6, 2, 12, 2), 1. 68-1.78 (m, 4H,2 H-6, 9),1.79-2.03 (m, 10 H, 2H-1, 14, 14, 3, 5) 2869, 2846, 1648, 1598, 1500, 1461, 1436, 1384, 1292, 1247, 1240, 1182, 1139, 1126, 1095, 1047, 1027, 985, 912, 870, 754 cm (1R,4aR,4bS,7S,10aR) 4a,2,3,4,4a,4b,5,6,7,8,10, (m, 2H,2H-11), 1.32 (s, 3H,C 19 H 3 ), 1.34 (s, 3H,C 19 H 3 ), 1.31-1.39 (m, 2H,2H-12), 1.44-1.49 (m, 2H,2H-12), 1.52-1.68 (m, 10 H, 2H-11, 2, 3, 2, 6), 1.70-1.78 (m, 4H,2H-6, 9), 1.82-2.01 (m, 10 H, 2H-1, 14, 14, 3, 5) 6 Hz,1H,4.91 (dd,J = 17.7,1.6 Hz,1H,4.92 (dd,J = 17.7,1.6 Hz,1H,4H,5'), 5.32 (s, 2H, =CH 2 ), 5.34 (s, 2H, =CH 2 ), 5.36 (s, 1H, =CH 2 ), 5.76 (dd,…”

“…For example,i sopimaric acid (1)i sareadily available and versatile tricyclic diterpenoid that is well represented in the resin of conifers of the genera Pinus, Larix,a nd Picea. [3,4] The attraction of compound 1 as ab iorenewable compound and its interesting biological and pharmaceutical properties, whichi nclude anti-bacterial, [5][6][7] antiviral, [8] anda nti-inflammatory [9] activities, has stimulated the development of av ariety of chemistries for functionality,i ncluding oxidative [10][11][12] and isomeric [13] transformations, in addition to several modificationso ft he carboxyl group. [14,15] The number of examples in the literature detailing the functionalization of isopimaric acid is limited,a nd they do not result in the generation of evolvable libraries of compounds for structure-activity relationship studies.…”

Synthesis and Bioactivity Evaluation of Acylthiourea Derivatives Based on Isopimaric Acid

“…其次, 异海松酸对 结核病毒具有显著的疗效 [6] , 并对爱博斯坦巴尔病毒 也显示出抑制效果 [7] . 此外, 异海松酸对 12-O-佛波酯- [8] 、 5-脂氧酶(5-LOX, 一种催化产生炎症的媒 介) [9] 、鼠尾草种子发芽 [10] 、棉红铃虫幼虫生长 [11] 及多种 细菌、真菌 [12,13] 等具有明显的抑制作用, 并对舞毒蛾觅 食表现出阻碍作用 [14] . 因异海松酸本身具有广泛的生 物活性, 且异海松酸的化学结构中含有可反应的官能团 羧基及双键, 因此可将其作为化工中间体或以其骨架结 构作为药理活性中心, 开发具有生物活性的新型异海松 酸类衍生物.…”