- A novel dehydroabietic acid-based AIE-active fluorescent probe for rapid detection of Hg2+ and its environmental and biological applications
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A highly sensitive AIE fluorescent probe (DBAQ) containing quinoxaline moiety was designed based on the natural diterpene dehydroabietic acid. This probe was synthesized and manifested via the analysis of FT-IR, 1H NMR, 13C NMR, and ESI-MS spectra. The probe DBAQ was utilized to selectively recognize Hg2+ against other competitive metal ions with the detection limit of 10.3 nM in MeCN/H2O solution (v/v = 1/9, pH = 7.5). In particular, DBAQ (λex/em = 425/600 nm) possessed a large Stokes shift (175 nm), short response time (10 s), and a wide pH range for Hg2+ detection (5 ~ 10). Job's plot method was used to determine the stoichiometry ratio of DBAQ-Hg2+ complexes as 1:2, which was confirmed by FT-IR. The binding mechanisms of DBAQ with Hg2+ were confirmed by 1H NMR titration. Meanwhile, DBAQ exhibited satisfied detection performance in seafood and environmental water samples. Furthermore, DBAQ revealed the considerably low cytotoxic effects to MCF-7 cells (IC50 > 100 μM), and it could be utilized as an outstanding imaging agent for the determination of Hg2+ both in living cells and zebrafish.
- Chen, Lin-lin,Gu, Wen,Liu, Qing-song,Sun, Lu,Sun, Xue-bao,Sun, Yue,Wang, Zhong-long,Yang, Zi-hui
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- Synthesis and antitumor evaluation of (aryl)methyl-amine derivatives of dehydroabietic acid-based B ring-fused-thiazole as potential PI3K/AKT/mTOR signaling pathway inhibitors
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Abstract: In an attempt to search for new natural product-based antitumor agents, a series of novel (aryl)methyl-amine derivatives of dehydroabietic acid-based B ring-fused-thiazole were designed and synthesized. The primary bioassay showed that compounds
- Chen, Nai-Yuan,Xie, Yu-Lan,Lu, Guo-Dong,Ye, Fang,Li, Xin-Yu,Huang, Yu-Wen,Huang, Ming-Li,Chen, Tie-Yu,Li, Cui-Ping
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p. 967 - 979
(2020/04/24)
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- A novel dehydroabietic acid-based turn-on fluorescent probe for the detection of bisulfite and its application in live-cell and zebrafish imaging
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In this paper, a turn-on fluorescent probe (DBE) was designed and synthesized for probing bisulfite (HSO3?) by coupling dehydroabietic acid-based benzimidazole derivatives with ethyl cyanoacetate moiety. The structure of the compound was characterized using its UV-Vis,1H-NMR,13C-NMR and HRMS spectra. The probe showed significant selectivity and sensitivity towards HSO3?compared to other analytes in DMF/PBS buffer (3/7, v/v, 10 mM, pH = 7.4), and exhibited a detection limit at the nanomolar level (3.2 nM), fast response time (140 s) and good pH stability (6-10) in living systems. Furthermore, this probe was successfully utilized for the fluorescence imaging of HSO3?in living zebrafish and MCF-7 cells with remarkable lysosome-targeting properties.
- Li, A-Liang,Wang, Zhong-Long,Wang, Wen-Yan,Liu, Qing-Song,Sun, Yue,Gu, Wen
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p. 16822 - 16832
(2021/09/28)
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- Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction
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The first synthesis of C-18- and C-19-bifunctionalized abietane diterpenoids, bodinieric (or callicapoic) acids, via an aldol reaction has been developed. This key aldol reaction was very sensitive to steric hindrance. This fact has been studied by deuterium exchange experiments and DFT methods. Optimization of this reaction led to the synthesis of anti-inflammatory bodinieric acids A and B, starting from abietic acid.
- González-Cardenete, Miguel A.,Zaragozá, Ramón J.
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p. 15015 - 15022
(2020/04/27)
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- Synthesis, cytotoxicity and apoptosis-inducing activity of novel 1H-benzo[d]imidazole derivatives of dehydroabietic acid
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With the expectation of finding new and effective antitumor drugs, a series of novel N-(1H-benzo[d]imidazole-2-yl)-benzamide/benzenesulfonamide derivatives of dehydroabietic acid were synthesized and evaluated for cytotoxic activity against three human ca
- Li, A-Liang,Yang, Ya-Qun,Wang, Wen-Yan,Liu, Qing-Song,Sun, Yue,Gu, Wen
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p. 1668 - 1678
(2020/07/30)
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- Synthesis and anticancer evaluation of novel 1H-benzo[d]imidazole derivatives of dehydroabietic acid as PI3Kα inhibitors
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Phosphatidylinositol 3-kinase (PI3K) is one of the most attractive therapeutic targets for cancer treatment. In this study, a series of new 2-arylthio- and 2-arylamino-1H-benzo[d]imidazole derivatives of dehydroabietic acid were designed, synthesized and characterized by 1H NMR, 13C NMR, IR and MS spectra analyses. In the in vitro anticancer assay, some title compounds showed significant inhibitory activities against four cancer cell lines (HCT-116, MCF-7, HeLa and HepG2). Among them, compound 9g exhibited the most potent activity with IC50 values of 0.18 ± 0.03, 0.43 ± 0.05, 0.71 ± 0.08 and 0.63 ± 0.09 μM against four cancer cell lines, and considerably lower cytotoxicity to human gastric mucosal cell line Ges-1 (IC50: 21.95 ± 0.73 μM). Besides, compound 9g displayed a certain selective activity to PI3Kα (IC50 = 0.012 ± 0.002 μM) over PI3Kβ, γ and δ, and meanwhile, it can remarkably decrease the expression level of p-Akt (Ser473). In addition, compound 9g could increase intracellular reactive oxygen species level, decrease mitochondrial membrane potential, upregulate Bax and cleaved caspase-3/9 levels, downregulate Bcl-2 level and thus induce the apoptosis of HCT-116 cells in a dose-dependent manner. The results suggested that compound 9g could be considered as a promising PI3Kα inhibitor.
- Chen, Hao,Gu, Wen,Liu, Qing-Song,Sun, Yue,Yang, Ya-Qun
-
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- The synthesis of a DHAD/ZnAlTi-LDH composite with advanced UV blocking and antibacterial activity for skin protection
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Skin wounds are particularly vulnerable and susceptible to bacterial infection. Unfortunately, the abuse of antibiotics has resulted in the emergence of a number of multidrug-resistant bacteria in the past few decades. Moreover, secondary damage of the fragile new tissue around the wound caused by high-energy ultraviolet (UV) radiation has been rarely noticed. To address these problems, herein, we present an alternative strategy to overcome drug-resistant bacteria and UV damage by taking advantage of dehydroabietic acid derivatives (DHADs) and layered double hydroxides (LDHs). DHAD, synthesized from dehydroabietic acid (DHA) through a series of reactions, was assembled with ZnAlTi-LDH to obtain a DHAD/ZnAlTi-LDH composite. The results showed that DHAD/ZnAlTi-LDH has a prominent reactive oxygen species (ROS) production capacity, and both Gram-negative and positive bacteria can be killed under visible light irradiation. At the same time, it can effectively shield the skin from UV rays. In vitro and vivo experiments confirmed that the composite has great promise for bactericidal applications, UV blocking and wound healing.
- Duan, Wengui,Hu, Tingting,Liang, Ruizheng,Lin, Guishan,Liu, Xinlong,Wang, Xiu,Wei, Min,Zhu, Yu
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p. 9786 - 9790
(2020/03/23)
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- Dehydroabietic acid-based 2,4-diarylbenzimidazole fluorescent probe for ferric ions and mercury ions, and preparation method and application thereof
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The invention discloses a dehydroabietic acid-based 2,4-diarylbenzimidazole fluorescent probe for ferric ions and mercury ions, and a preparation method and application thereof. The preparation methodcomprises the following steps: subjecting dehydroabieti
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Paragraph 0030-0035
(2020/09/30)
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- Dehydroabietic acid benzimidazole thioether heterocycle derivative with anti-tumor activity and preparation method and application thereof
-
The invention discloses a type of dehydroabietic acid benzimidazole thioether heterocycle derivatives with anti-tumor activity and a preparation method and application thereof. The invention relates to a dehydroabietic acid benzimidazole thioether heteroc
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Paragraph 0070-0072
(2019/02/25)
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- Dehydroabietic-based fluorescent compound and preparation method thereof
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The invention relates to the technical field of dehydroabietic-based compounds, in particular to a dehydroabietic-based fluorescent compound and a preparation method thereof. The compound is dehydroabietic-based-salicylaldehyde Schiff base or dehydroabiet
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Paragraph 0037-0039
(2019/04/17)
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- Synthesis and Antibacterial Activity of Benzenesulfonylhydrazone Derivatives of Methyl Dehydroabietate
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Six benzenesulfonylhydrazone derivatives of methyl dehydroabietate are synthesized via esterification, benzylic oxidation, condensation with hydrazine hydrate, and following nucleophilic substitution reaction with a variety of substituted benzenesulfonyl chloride. The structures of the synthesized compounds are characterized by 1H NMR and MS spectra. Antibacterial activity of the target compounds is evaluated by disk diffusion method against E. coli, S. aureus, and B. subtilis. The results demonstrate that benzenesulfonylhydrazone derivatives of methyl dehydroabietate exhibit inhibitory activity. Among the six compounds, p-fluorobenzenesulfonylhydrazone of methyl dehydroabietate exhibits the highest antibacterial activity with the zone of inhibition of 17.3 mm against B. subtilis and 16.5 mm against S. aureus.
- Zhou, Zhi,Wang, Xiang,Zhou, Tingting
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p. 819 - 823
(2019/06/27)
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- Synthesis and biological evaluation of novel N-(piperazin-1-yl)alkyl-1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid as potential MEK inhibitors
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In this paper, a series of novel 1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid bearing different N-(piperazin-1-yl)alkyl side chains were designed, synthesised and evaluated for their in vitro anticancer activities against three human hepato
- Chen, Hao,Qiao, Chao,Miao, Ting-Ting,Li, A-Liang,Wang, Wen-Yan,Gu, Wen
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p. 1544 - 1561
(2019/08/28)
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- Dehydroabietic acid arylamine benzimidazole derivative with anti-tumor activity, and preparation method and applications thereof
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The invention discloses a dehydroabietic acid arylamine benzimidazole derivative with anti-tumor activity, and a preparation method and applications thereof, and more specifically discloses the dehydroabietic acid arylamine benzimidazole derivative with a
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Paragraph 0075-0077
(2019/02/13)
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- Synthesis and Biological Studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and Representative Analogues: SAR Studies
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The first semisynthesis and biological profiling of the new abietane diterpenoid (+)-liquiditerpenoic acid A (abietopinoic acid) (7) along with several analogues are reported. The compounds were obtained from readily available methyl dehydroabietate (8), which was derived from (-)-abietic acid (1). Biological comparison was conducted according to the different functional groups, leading to some basic structure-activity relationships (SAR). In particular, the ferruginol and sugiol analogues 7 and 10-16 were characterized by the presence of an acetylated phenolic moiety, an oxidized C-7 as a carbonyl, and a different functional group at C-18 (methoxycarbonyl, carboxylic acid, and hydroxymethyl). The biological properties of these compounds were investigated against a panel of six representative human tumor solid cells (A549, HBL-100, HeLa, SW1573, T-47D, and WiDr), five leukemia cellular models (NALM-06, KOPN-8, SUP-B15, UoCB1, and BCR-ABL), and four Leishmania species (L. infantum, L. donovani, L. amazonensis, and L. guyanensis). A molecular docking study pointed out some targets in these Leishmania species. In addition, the ability of the compounds to modulate GABAA receptors (α1β2γ2s) is also reported. The combined findings indicate that these abietane diterpenoids offer a source of novel bioactive molecules with promising pharmacological properties from cheap chiral-pool building blocks.
- Hamuli?, Damir,Stadler, Marco,Hering, Steffen,Padrón, José M.,Bassett, Rachel,Rivas, Fatima,Loza-Mejía, Marco A.,Dea-Ayuela, M. Auxiliadora,González-Cardenete, Miguel A.
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supporting information
p. 823 - 831
(2019/03/19)
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- Late-stage C-H amination of abietane diterpenoids
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This study aims at highlighting the synthetic versatility of the rhodium-catalyzed C-H amination reactions using iodine(iii) oxidants for the late-stage functionalization of natural products. Inter-and intramolecular nitrene insertions have been performed from various abietane diterpenoids, leading to the amination of the C-3, C-6, C-7, C-11 and C-15 positions. Ca. 20 aminated compounds have been isolated with yields of up to 86% and high levels of regio-, chemo-and stereoselectivities.
- Lapuh, María Ivana,Dana, Alejandro,Di Chenna, Pablo H.,Darses, Benjamin,Durán, Fernando J.,Dauban, Philippe
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supporting information
p. 4736 - 4746
(2019/05/24)
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- Synthesis and biological evaluation of 2-aryl-benzimidazole derivatives of dehydroabietic acid as novel tubulin polymerization inhibitors
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A series of novel 2-aryl-benzimidazole derivatives of dehydroabietic acid were synthesized and characterized by IR, 1H NMR, 13C NMR, MS and elemental analyses. All the target compounds were evaluated for their in vitro cytotoxic activity against SMMC-7721, MDA-MB-231, HeLa and CT-26 cancer cell lines and the normal hepatocyte cell line QSG-7701 through MTT assays. Among them, compound 6j displayed the most potent cytotoxic activity with IC50 values of 0.08 ± 0.01, 0.19 ± 0.04, 0.23 ± 0.05 and 0.42 ± 0.07 μM, respectively, and substantially reduced cytotoxicity against QSG-7701 cells (5.82 ± 0.38 μM). The treatment of SMMC-7721 cells with compound 6j led to considerable inhibition of cell migration ability. The influence of compound 6j on cell cycle distribution was assessed on SMMC-7721 cells, exhibiting a cell cycle arrest at the G2/M phase. Moreover, tubulin polymerization assays and immunofluorescence assays elucidated that compound 6j could significantly inhibit tubulin polymerization and disrupt the intracellular microtubule network. A molecular docking study provided insight into the binding mode of compound 6j in the colchicine site of tubulin. In addition, compound 6j was found to induce apoptosis of SMMC-7721 cells, an increase of intracellular ROS level and a loss of mitochondrial membrane potential in a dose-dependent manner. These findings provided new molecular scaffolds for the further development of novel antitumor agents targeting tubulin polymerization.
- Miao, Ting-Ting,Tao, Xu-Bing,Li, Dong-Dong,Chen, Hao,Jin, Xiao-Yan,Geng, Yi,Wang, Shi-Fa,Gu, Wen
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p. 17511 - 17526
(2018/05/29)
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- Discovery of 12-Thiazole Abietanes as Selective Inhibitors of the Human Metabolic Serine Hydrolase hABHD16A
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Screening of an in-house library of compounds identified 12-thiazole abietanes as a new class of reversible inhibitors of the human metabolic serine hydrolase. Further optimization of the first hit compound lead to the 2-methylthiazole derivative 18, with an IC50 value of 3.4 ± 0.2 μM and promising selectivity. ABHD16A has been highlighted as a new target for inflammation-mediated pain, although selective inhibitors of hABHD16A (human ABHD16A) have not yet been reported. Our study presents abietane-type diterpenoids as an attractive starting point for the design of selective ABHD16A inhibitors, which will contribute toward understanding the significance of hABHD16A inhibition in vivo.
- Ahonen, Tiina J.,Savinainen, Juha R.,Yli-Kauhaluoma, Jari,Kalso, Eija,Laitinen, Jarmo T.,Moreira, Vania M.
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p. 1269 - 1273
(2018/12/11)
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- Synthesis and in vitro cytotoxic evaluation of new 1H-benzo[d]imidazole derivatives of dehydroabietic acid
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A series of new 1H-benzo[d]imidazole derivatives of dehydroabietic acid were designed and synthesized as potent antitumor agents. Structures of the target molecules were characterized using MS, IR, 1H NMR, 13C NMR and elemental analyses. In the in vitro cytotoxic assay, most compounds showed significant cytotoxic activities against two hepatocarcinoma cells (SMMC-7721 and HepG2) and reduced cytotoxicity against noncancerous human hepatocyte (LO2). Among them, compound 7b exhibited the best cytotoxicity against SMMC-7721 cells (IC50: 0.36?±?0.13?μM), while 7e was most potent to HepG2 cells (IC50: 0.12?±?0.03?μM). The cell cycle analysis indicated that compound 7b caused cell cycle arrest of SMMC-7721 cells at G2/M phase. Further, compound 7b also induced the apoptosis of SMMC-7721 cells in Annexin V-APC/7-AAD binding assay.
- Gu, Wen,Miao, Ting-Ting,Hua, Da-Wei,Jin, Xiao-Yan,Tao, Xu-Bing,Huang, Chao-Bo,Wang, Shi-Fa
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p. 1296 - 1300
(2017/06/19)
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- Photoresponsive Foams Generated by a Rigid Surfactant Derived from Dehydroabietic Acid
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Innovation in the structure of surfactants is crucial to the construction of a surfactant-based system with intriguing properties. With dehydroabietic acid as a starting material, a nearly totally rigid azobenzene surfactant (R-azo-Na) was synthesized. Th
- Lei, Lan,Xie, Danhua,Song, Binglei,Jiang, Jianzhong,Pei, Xiaomei,Cui, Zhenggang
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p. 7908 - 7916
(2017/08/21)
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- 12 - oxime ether dehydroabietic acid compound and its synthesis method
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The invention relates to a 12-oxime ether dehydroabietic acid compound and a synthetic method thereof. A structural formula of the compound is as shown in the specification, wherein R1 is H, aromatic substituent or C1-C3 straight chain or branched chain alkyls; R2 is H, C1-C8 straight chain or branched chain or ring alkyls, unsaturated alkenyl, unsaturated alkynyl or aromatic substituent. The invention relates to an efficient and concise method for preparing 12-oxime ether dehydroabietic acid derivatives. The compound, and pharmaceutically acceptable salts, hydrates, solvates, crystal forms, diastereoisomers, prodrugs or mixtures and the like thereof are especially applied to treatment of diseases related to large-conductance calcium activated potassium channels.
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Paragraph 0009; 0043; 0058; 0074; 0090; 0106; 0122-0536
(2017/08/25)
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- Ir-Catalyzed Enantioselective, Intramolecular Silylation of Methyl C-H Bonds
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We report highly enantioselective intramolecular, silylations of unactivated, primary C(sp3)-H bonds. The reactions form dihydrobenzosiloles in high yields with excellent enantioselectivities by functionalization of enantiotopic methyl groups u
- Su, Bo,Hartwig, John F.
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supporting information
p. 12137 - 12140
(2017/09/12)
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- Click chemistry-based synthesis and anticancer activity evaluation of novel C-14 1,2,3-triazole dehydroabietic acid hybrids
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A concise and efficient synthetic approach has been established to readily access a series of novel C-14 1,2,3-triazole-tethered dehydroabietic acid derivatives in moderate to high yields. In vitro antiproliferative activity evaluation indicated that most of the hybrids exhibited potent inhibitory activities in a variety of cancer cell lines with low micromolar to submicromolar IC50 values. Further studies demonstrated that some of these analogues such as 20, 21, and 24 were also effective against adriamycin-resistant MCF-7 clone at low concentrations in a dose-dependent manner. Notably, the most potent compound 24, which possesses a 3-(tert-butoxycarbonylamino)phenyl-substituted triazole moiety, not only exhibited obviously improved IC50 values ranging from 0.7 to 1.2 μM against a panel of tested cancer cells, but also showed very weak cytotoxicity on normal cells. Preliminary mechanism studies indicated that compound 24 could induce apoptosis in MDA-MB-231 cells and was worth developing into a novel natural product-like anticancer lead by proper structure modification.
- Hou, Wei,Luo, Zhi,Zhang, Guanjun,Cao, Danhui,Li, Di,Ruan, Haoqiang,Ruan, Benfang Helen,Su, Lin,Xu, Hongtao
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p. 1042 - 1052
(2017/08/02)
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- Methyl esterification method of low-toxicity rosin-resin acid
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The invention discloses a methyl esterification method of low-toxicity rosin-resin acid, comprising the following steps: mixing rosin-resin acid and methyl esterification reagent dimethyl carbonate, dissolving in an organic solvent, and reflux reacting at 68-110 DEG C in the presence of a base catalyst for 24-72 h to obtain methyl rosinate-resinate. The methyl rosinate-resinate prepared by the method has yield up to 99.6%, the method has the advantages that materials are easy to obtain, the preparation process is safe, the materials are low in toxicity, and reacting is easy to control and post-treatment is simple and easy.
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Paragraph 0054; 0055; 0056; 0057; 0058; 0059-0064
(2016/12/01)
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- Dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives with anti-tumor activity and preparation method therefor and application thereof
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The invention discloses dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives with anti-tumor activity and a preparation method therefor and an application thereof. The invention discloses a dehydroabietic acid benzimidazole Schiff base heterocyclic derivative which has a structure shown in a formula I and pharmaceutically acceptable salt thereof (the formula is shown in the description), wherein the formula is shown in the description. The dehydroabietic acid benzimidazole Schiff base heterocyclic derivative and the pharmaceutically acceptable salt thereof have remarkable anti-tumor activity. Pharmacological experiments show that the dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives have remarkable inhibitory effect on human liver cancer cells HepG2 and SMMC-7721 and the effect of the derivatives is equivalent to positive control etoposide. The derivatives and salt thereof have the potential of developing anti-tumor drugs.
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Paragraph 0047-0049
(2017/01/23)
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- A kind of dehydroabietic acid the use of the indole derivatives
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The invention relates to the fields of organic synthesis and medicinal chemistry and in particular relates to an application of dehydroabietic acid indole derivatives in preparation of antitumor drugs. The pharmacology experiment proves that the dehydroabietic acid indole derivatives have obvious inhibition effects on seven kinds of tumor cells, such as human hepatoma cells (Hep-1, Huh7), cervical cancer cells (HeLa), breast cancer cells (MCF7), colon cancer cells (Caco-2), gastric cancer cells (HGC-27) and lung carcinoma cells (HCC827) and have values of developing antitumor drugs.
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Paragraph 0022; 0023
(2016/12/01)
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- Synthesis and antifeedant activities of rosin-based esters against Armyworm
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A series of rosin based esters have been synthesized from dehydroabietic acid and maleopimaric acid, respectively. Their structures were confirmed by FT-IR, 1H NMR, 13C NMR and single crystal X-ray diffraction. Their antifeedant activities against armyworm were examined by leaf plate method. Methyl ester of dehydroabietic acid and maleopimaric acid were crystallized in orthorhombic system with cell dimensions of a = 26.352 [5] ?, b = 6.1020 [12] ?, c = 11.812 [2] ? and a = 7.9216 [11] ?, b = 11.9912 [16] ?, c = 23.425 [3] ?, respectively. They contained classic tricyclic hydrophenanthrene skeleton. The antifeedant results indicated that most rosin-based esters exhibited significant antifeedant activities at a concentration of 0.01 g mL-1. Their feeding deterrence values were above 70% after 24h. The antifeedant activities for rosin-based esters increased with the growth of chain length of alcohol except (Ia). Some armyworm were found dead during the antifeedant activity test, by which we speculated that these synthetic rosinbased esters had stomach poison activities against armyworm.
- Li, Liu,Xinyan, Yan,Yanqing, Gao,Xiao-Ping, Rao
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p. 193 - 199
(2016/05/09)
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- Indole derivatives dehydroabietic acid, preparation method and its use
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The invention relates to the field of the organic synthesis and medicinal chemistry, and in particular relates to a dehydroabietic acid indole derivative, a preparation method of the dehydroabietic acid indole derivative and application of the dehydroabietic acid indole derivative in preparing anti-tumor medicaments. Pharmacology experiments show that the dehydroabietic acid indole derivative disclosed by the invention has a significant inhibiting effect on seven strains of tumor cells such as human liver cancer cells (Hep-1, Huh7), cervical cancer cells (HeLa), breast cancer cells (MCF7), colon cancer cells (Caco-2), gastric cancer cells (HGC-27) and lung cancer cells (HCC827), and has the values of developing the anti-tumor medicaments.
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Paragraph 0010; 0011; 0028; 0029
(2018/07/10)
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- Use of 12-dehydroabietic acid oxime ether derivative
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The invention relates to a use of a 12-dehydroabietic acid oxime ether derivative. The 12-dehydroabietic acid oxime ether derivative has good inhibition activity on Staphylococcus aureus newman strains, and also has certain inhibition activity on some drug-resistant strains, such as NRS-1 strains ( aminoglycoside antibiotic and tetracycline resistant Staphylococcus aureus), NRS-70 strains (erythromycin and spectinomycin resistant Staphylococcus aureus), NRS-100 strains (oxacillin and tetracycline resistant Staphylococcus aureus), NRS-108 strains (gentamycin resistant Staphylococcus aureus) and NRS-271 strains (methicillin and linezolid resistant Staphylococcus aureus).
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Paragraph 0041; 0043
(2016/12/22)
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- Iodine, a Mild Reagent for the Aromatization of Terpenoids
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Efficient procedures based on the use of iodine for the aromatization of a series of terpenoids possessing diene and homoallylic or allylic alcohol functionalities are described. Different examples are reported as a proof-of-concept study. Furthermore, iodine also proved to mediate the dehydrogenation of testosterone.
- Domingo, Victoriano,Prieto, Consuelo,Silva, Lucia,Rodilla, Jess M. L.,Qulez Del Moral, Jos F.,Barrero, Alejandro F.
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supporting information
p. 831 - 837
(2016/05/24)
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- A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans -ozic acid
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Ozonolysis of aromatic abietane (+)-carnosic acid (4) is used to create an important intermediate in an enantiomerically pure form, resulting in a simple, concise, readily scalable, and asymmetric synthesis of (-)-antrocin (1). This strategy not only provides an efficient approach to (-)-antrocin (1) synthesis but can also be readily adopted for the syntheses of optically pure (+)-asperolide C (2) and (-)-trans-ozic acid (3) from the naturally abundant aromatic abietanes (+)-podocarpic acid (5) and (+)-dehydroabietic acid (6). The strategy presented here is an example of the use of naturally occurring aromatic abietanes as a chiral pool and offers an account of the asymmetric synthesis of terpenoids.
- Li, Fu-Zhuo,Li, Shuang,Zhang, Peng-Peng,Huang, Zhi-Hui,Zhang, Wei-Bin,Gong, Jianxian,Yang, Zhen
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supporting information
p. 12426 - 12429
(2016/10/24)
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- EIMS Fragmentation Pathways and MRM Quantification of 7α/β-Hydroxy-Dehydroabietic Acid TMS Derivatives
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EI mass fragmentation pathways of TMS derivatives οf 7α/β-hydroxy-dehydroabietic acids resulting from NaBH4-reduction of oxidation products of dehydroabietic acid (a component of conifers) were investigated and deduced by a combination of (1) low energy CID-GC-MS/MS, (2) deuterium labeling, (3) different derivatization methods, and (4) GC-QTOF accurate mass measurements. Having identified the main fragmentation pathways, the TMS-derivatized 7α/β-hydroxy-dehydroabietic acids could be quantified in multiple reaction monitoring (MRM) mode in sea ice and sediment samples collected from the Arctic. These newly characterized transformation products of dehydroabietic acid constitute potential tracers of biotic and abiotic degradation of terrestrial higher plants in the environment. [Figure not available: see fulltext.]
- Rontani, Jean-Fran?ois,Aubert, Claude,Belt, Simon T.
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p. 1606 - 1616
(2015/08/18)
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- Synthesis and biological evaluation of novel N-substituted 1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid as potential antimicrobial agents
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A series of new N-substituted 1H-dibenzo[a,c]carbazole derivatives were synthesized from dehydroabietic acid, and their structures were characterized by IR, 1H NMR and HRMS spectral data. All compounds were evaluated for their antibacterial and antifungal activities against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas fluorescens) and three fungi (Candida albicans, Candida tropicalis and Aspergillus niger) by serial dilution technique. Some of the synthesized compounds displayed pronounced antimicrobial activity against tested strains with low MIC values ranging from 0.9 to 15.6 μg/ml. Among them, compounds 6j and 6r exhibited potent inhibitory activity comparable to reference drugs amikacin and ketoconazole.
- Gu, Wen,Qiao, Chao,Wang, Shi-Fa,Hao, Yun,Miao, Ting-Ting
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p. 328 - 331
(2014/01/17)
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- Synthesis and biological evaluation of novel N-substituted 1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid as potential antimicrobial agents
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A series of new N-substituted 1H-dibenzo[a,c]carbazole derivatives were synthesized from dehydroabietic acid, and their structures were characterized by IR, 1H NMR and HRMS spectral data. All compounds were evaluated for their antibacterial and
- Gu, Wen,Qiao, Chao,Wang, Shi-Fa,Hao, Yun,Miao, Ting-Ting
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p. 328 - 331
(2015/02/05)
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- Synthesis and antiproliferative activity of some novel triazole derivatives from dehydroabietic acid
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Dehydroabietic acid (DHA) is a naturally occurring diterpene with different and relevant biological activities. Previous studies have shown that some DHA derivatives display antiproliferative activity. However, the reported compounds did not include triazole derivatives. Starting from DHA (8,11,13-abietatrien-18- oic acid), and its alcohol dehydroabietinol (8,11,13-abietatrien-18-ol), four alkyl esters were prepared. The alkyl terpenes were treated with different aromatic azides to synthesize hybrid compounds using click chemistry. Some 16 new DHA hybrids were thus synthesized and their structures were confirmed by spectroscopic and spectrometric means. The antiproliferative activity of the new compounds was assessed towards human cell lines, namely normal lung fibroblasts (MRC-5), gastric epithelial adenocarcinoma (AGS), lung cancer (SK-MES-1) and bladder carcinoma (J82) cells. Better antiproliferative effect was found for compound 5, with an IC50 of 6.1 μM and selectivity on SK-MES-1 cells. Under the same experimental conditions, the IC50 of etoposide, was 1.83 μM.
- Pertino, Mariano Walter,Verdugo, Valery,Theoduloz, Cristina,Schmeda-Hirschmann, Guillermo
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p. 2523 - 2535
(2014/03/21)
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- Synthesis and metal ion binding activity of methyl 12-amino-13-nitro-7-oxo dehydrodeisopropylabietate derivatives
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Starting from dehydrobaietic acid with the analogous structure of carnosic acid, the intermediate methyl 12-bromo-13-nitro-7-oxo dehydrodeisopropylabietate was synthesized through methylation, bromination, carbonylation, and nitration. Subsequently, the c
- Wang, Kai,Liu, Xianxian,Yi, Xianghui,Wang, Hengshan,Zhang, Ye,Pan, Yingming
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p. 2494 - 2500
(2012/10/30)
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- Synthesis of a dehydroabietyl derivative bearing a 2-(2'-hydroxyphenyl) benzimidazole unit and its selective Cu2+ chemosensing
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A dehydroabietyl derivative 2 bearing a 2-(2'-hydroxyphenyl)benzimidazole unit was synthesized and its sensing behaviors toward metal ions were investigated by UV-Vis and fluorescence spectroscopy methods. In THF solution, compound 2 exhibited excellent s
- Wang, Ying-Chun,Liu, Lu-Zhi,Pan, Ying-Ming,Wang, Heng-Shan
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scheme or table
p. 100 - 106
(2011/03/20)
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- Synthesis and antimicrobial activities of novel 1H-dibenzo[a,c]carbazoles from dehydroabietic acid
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A series of novel 1H-dibenzo[a,c]carbazole derivatives were synthesized in good yield through reaction of methyl 7-oxo-dehydroabietate with a variety of substituted phenylhydrazines. The structures of the newly synthesized compounds were confirmed by IR, 1H NMR, MS spectral studies and elemental analysis. All compounds were investigated for their activity against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas fluorescens) and three fungi (Trichophyton rubrum, Candida albicans and Aspergillus niger). Among the compound tested, 6d, 6e, 6f and 6m exhibited pronounced antibacterial activities and 6e and 6m also showed moderate antifungal activities. Particularly, 6d exhibited stronger antibacterial activity against B. subtilis comparable to positive control.
- Gu, Wen,Wang, Shifa
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experimental part
p. 4692 - 4696
(2010/10/03)
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- Aerobic oxidation of 8,11,13-abietatrienes catalyzed by N-hydroxyphthalimide combined with 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) and its application to synthesis of naturally occurring diterpenes
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Methyl 8,11,13-abietatriene-18-oate (1b) and 7-oxo-8,11,13-abietatrienes 10 and 15 were converted into 15-hydroperoxy-7-oxo-8,11,13-abietatrienes 13 and 16 by aerobic oxidation catalyzed by N-hydroxyphthalimide (NHPI) combined with 2,2′-azobis(4-methoxy-2
- Matsushita, Yoh-ichi,Sugamoto, Kazuhiro,Iwakiri, Yoshihisa,Yoshida, Satoru,Chaen, Takehito,Matsui, Takanao
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body text
p. 3931 - 3934
(2010/08/07)
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- Synthesis and biological evaluation of dehydroabietic acid derivatives
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A series of C18-oxygenated derivatives of dehydroabietic acid were synthesized from commercial abietic acid and evaluated for their cytotoxic, antimycotic, and antiviral activities.
- Gonzalez, Miguel A.,Perez-Guaita, David,Correa-Royero, Julieth,Zapata, Bibiana,Agudelo, Lee,Mesa-Arango, Ana,Betancur-Galvis, Liliana
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experimental part
p. 811 - 816
(2010/04/26)
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- Design, synthesis, and characterization of BK channel openers based on oximation of abietane diterpene derivatives
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Oxime ether derivatives at the benzylic position of unsubstituted, dichloro, trichloro, and monobromo derivatives of the aromatic C-ring of dehydroabietic acid and podocarpic acid were synthesized and evaluated as BK channel openers in an assay system of CHO-K1 cells expressing hBKα channels. Detailed SAR analysis showed that the oximation was particularly effective in the cases of dehydroabietic acid derivatives, and some of these oxime derivatives showed more potent BK channel activities than the standard compound, NS1619. The present studies provide a new structural basis for development of efficient BK channel openers.
- Cui, Yong-Mei,Yasutomi, Eriko,Otani, Yuko,Ido, Katsutoshi,Yoshinaga, Takashi,Sawada, Kohei,Ohwada, Tomohiko
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experimental part
p. 8642 - 8659
(2011/02/25)
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- Chiral ionic liquids based on abietane
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A number of chiral ionic liquids were synthesized by reaction of 12-chloromethylabieta-8,11,13-trien-18-oic acid methyl ester with N-alkylimidazoles.
- Glushkov,Kotelev,Rudovskii,Maiorova,Tarantin,Tolstikov
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experimental part
p. 404 - 407
(2009/09/06)
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- Dehydroabietic acid esters as chiral dopants for nematic liquid crystals
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Dehydroabietic acid esters were prepared as new chiral dopants for the nematic liquid crystals. The magnitude of the helical twisting power (HTP) was good due to simple but rigid three-ring structure and two axial methyl groups. The relationship between t
- Shitara, Hiroaki,Aruga, Marie,Odagiri, Emi,Taniguchi, Kayoko,Yasutake, Mikio,Hirose, Takuji
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p. 589 - 593
(2008/02/11)
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- Regioselective routes towards 14-hydroxyabietane diterpenes. A formal synthesis of immunosuppressant (-)-triptolide from (+)-abietic acid
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Two procedures to introduce an oxygenated function into the C-14 of abietane diterpenes with complete regioselectivity have been developed. Utilizing these, the synthesis of the antileishmanial quinone (-)-12-deoxyroyleanone (1) and a formal synthesis of antitumour and immunosuppressant (-)-triptonide (7) and (-)-triptolide (8) from (+)-abietic acid (13) have been carried out.
- Alvarez-Manzaneda, Enrique,Chahboun, Rachid,Bentaleb, Faouzia,Alvarez, Esteban,Escobar, M. Angeles,Sad-Diki, Said,Cano, Maria José,Messouri, Ibtissam
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p. 11204 - 11212
(2008/02/13)
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- Design, synthesis, and BK channel-opening activity of hexahydrodibenzazepinone derivatives
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In order to explore new scaffolds for large-conductance Ca2+-activated K+ channel (BK channel) openers, we carried out molecular design and synthesis on the basis of the following two concepts: (1) introduction of a heteroatom into t
- Tashima, Toshihiko,Toriumi, Yoshimi,Mochizuki, Yumi,Nonomura, Taro,Nagaoka, Satoru,Furukawa, Katsuo,Tsuru, Hiromichi,Adachi-Akahane, Satomi,Ohwada, Tomohiko
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p. 8014 - 8031
(2007/10/03)
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- Synthesis and antiviral evaluation of benzimidazoles, quinoxalines and indoles from dehydroabietic acid
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Several heterocycles, such as benzimidazoles, quinoxalines and indoles incorporated into a hydrophenanthrene and naphthalene skeleton, were synthesised from two useful ortho-bromonitro precursors derived from dehydroabietic acid: methyl 12-bromo-13-nitro-deisopropyldehydroabietate and methyl 12-bromo-13,14-dinitro-deisopropyldehydroabietate. The new heterocycles were evaluated for their activity in vitro against several RNA and DNA viruses.
- Fonseca, Tatiana,Gigante, Barbara,Marques, M. Matilde,Gilchrist, Thomas L.,De Clercq, Erik
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p. 103 - 112
(2007/10/03)
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- Trimethylsilyldiazomethane - A mild and efficient reagent for the methylation of carboxylic acids and alcohols in natural products
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Esterification of various naturally occurring carboxylic acids with trimethylsilyldiazo-methane proceeds nearly quantitatively under very mild conditions. Furthermore, highly sterically hindered alcohols can be converted directly to the corresponding methyl ethers. Improved methods for the preparation and quantification of this reagent are described. Springer-Verlag 2004.
- Presser, Armin,Huefner, Antje
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p. 1015 - 1022
(2007/10/03)
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- Dehydroabietic acid derivatives as a novel scaffold for large-conductance calcium-activated K+ channel openers
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We found that the dehydroabietic acid structure is a new scaffold for chemical modulators of large-conductance calcium-activated K+ channels (BK channels). Structure-activity relationship (SAR) studies of the dehydroabietic acid derivatives and related non-aromatic compounds such as pimaric acid revealed the importance of the carboxyl functionality and an appropriate hydrophobic moiety of the molecules for BK channel-opening ability.
- Ohwada, Tomohiko,Nonomura, Taro,Maki, Keisuke,Sakamoto, Kazuho,Ohya, Susumu,Muraki, Katsuhiko,Imaizumi, Yuji
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p. 3971 - 3974
(2007/10/03)
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- Structural effects on the bioactivity of dehydroabietic acid derivatives
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The synthesis and the evaluation of the antimicrobial activity against a filamentous fungus, yeasts and bacteria of 15 hydrophenanthrene compounds derived from dehydroabietic acid, bearing different functional groups and different stereochemistry of the A/B ring junction are disclosed. The results obtained showed how their activity is dependent of the functionality at C-18, which can be increased by deisopropylation or introduction of other groups into the molecule. While the filamentous fungus tested is sensitive to almost all of the compounds under study, the aldehyde function showed to be of major importance to the inhibition of yeast. Alcohols and aldehyde C-18 derivatives also inhibit the growth of a Gram-positive bacteria, whereas Gram-negative are not sensitive.
- Gigante, Barbara,Silva, Ana M.,Marcelo-Curto, Maria Joao,Savluschinske Feio, Sonia,Roseiro, Jose,Reis, Lucinda V.
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p. 680 - 684
(2007/10/03)
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- Diels-Alder adducts of C-60 and resin acid derivatives: Synthesis, electrochemical and fluorescence properties
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New, stable and quite soluble [2+4] mono-adducts of [60]fullerene with levopimaric acid derivatives were synthesised in high yields. These adducts were also obtained directly from pine rosin. Electrochemical behaviour and fluorescence properties, including the observation of thermal delayed fluorescence, are reported.
- Gigante,Santos,Fonseca,Curto,Luftmann,Bergander,Berberan-Santos
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p. 6175 - 6182
(2007/10/03)
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- Terpenoids and flavonoids from Pseudotsuga wilsoniana
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Four new and 27 known compounds were isolated from the heartwood of Pseudotsuga wilsoniana. The structures of the new compounds, 9-oxobisabola- 1,3,5,7E-tetraen-15-oic acid methyl ester, 11-hydroxybisabola-1,3,5,9- tetraen-15-oic acid methyl ester, (S)-12-hydroxyagathic acid and 4',5- dihydroxy-7-methoxy-6-methylflavanone, were determined by chemical and spectroscopic methods.
- Hsieh, Yaw-Lung,Fang, Jim-Min,Cheng, Yu-Shia
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p. 845 - 850
(2007/10/03)
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