30905-83-0

Usage

Uses

Used in Organic Synthesis:
(1R,4aS,10aR)-methyl 6-bromo-1,2,3,4,4a,9,10,10a-octahydro-7-isopropyl-1,4a-dimethylphenanthrene-1-carboxylate is used as a precursor in organic synthesis for the creation of various biologically active molecules.
Used in Pharmaceutical Research:
In Pharmaceutical Research, (1R,4aS,10aR)-methyl 6-bromo-1,2,3,4,4a,9,10,10a-octahydro-7-isopropyl-1,4a-dimethylphenanthrene-1-carboxylate is used as a starting material for the synthesis of new drugs, given its unique chemical structure and properties.

Upstream product

• 1235-74-1 Methyl dehydroabietate 
• 186581-53-3 diazomethane 
• 1740-19-8 dehydroabietic acid 
• 22478-66-6 dehydroabietic acid chloride 

Downstream Products

• 1235-74-1 Methyl dehydroabietate 

Relevant academic research and scientific papers

A novel dehydroabietic acid-based AIE-active fluorescent probe for rapid detection of Hg2+ and its environmental and biological applications

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.

A novel dehydroabietic acid-based turn-on fluorescent probe for the detection of bisulfite and its application in live-cell and zebrafish imaging

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.

Synthesis and anticancer evaluation of novel 1H-benzo[d]imidazole derivatives of dehydroabietic acid as PI3Kα inhibitors

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.

Synthesis, cytotoxicity and apoptosis-inducing activity of novel 1H-benzo[d]imidazole derivatives of dehydroabietic acid

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

Dehydroabietic acid-based 2,4-diarylbenzimidazole fluorescent probe for ferric ions and mercury ions, and preparation method and application thereof

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

Dehydroabietic-based fluorescent compound and preparation method thereof

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

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

Synthesis and biological evaluation of 2-aryl-benzimidazole derivatives of dehydroabietic acid as novel tubulin polymerization inhibitors

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.

Synthesis and in vitro cytotoxic evaluation of new 1H-benzo[d]imidazole derivatives of dehydroabietic acid

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.

Photoresponsive Foams Generated by a Rigid Surfactant Derived from Dehydroabietic Acid

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